December 1, 2025 • 43 mins
We've all been there - That moment when you know it's time to have that conversation you've been dreading. The one that makes your stomach clench. The one you would rather run away from.
So, how do you handle these conversations? How do you keep it from becoming such a big thing in the first place?
This episode is a deep dive into what makes some conversations feel difficult: being torn between compassion and performance that some managers experience and practical strategies for saying no without burning bridges. We explore dynamics that can make these conversations even trickier for women and other minorities in tech and why it makes the biggest difference to focus your leadership approach on consistent, caring leadership instead of perfect moments.
Our guest is Nikita Rathi. Nikita has been in the tech industry for several years, transitioning from linguistics to software development, and now leading engineering teams and organizations. She has navigated the complexities of managing performance while maintaining empathy, dealt with the challenge of saying no in a people pleasing culture, and hard lessons about setting boundaries. In this episode, she shares wisdom and practical advice on having difficult conversations.
This conversation was recorded in January 2024.
Find the full episode transcript here.
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Episode Transcript
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(00:00):
I think difficult conversations are just pervasive, like they're
part of every aspect of 1's life.
But I found that most people find that there's really
stressful, ranging from like a really small conversation, like
a boundary setting one or a really hard conversation.
You know, I think everyone, thisis a universal kind of emotion
(00:23):
where there's some kind of conversation that's difficult.
We've all been there. That moment when you know that
you finally need to have that conversation that you've been
dreading for weeks, the one thatmakes your stomach clench and
the one that you would rather run away from.
Maybe that conversation is aboutgiving feedback to someone who's
(00:45):
been struggling. Maybe it's saying no to a
request when you're worried about how it will affect your
career or your relationship withyour boss.
Or maybe it's about addressing some behavior that's been
impacting your entire team, but you find it hard to balance
being kind while also holding people accountable.
This is leadership confidential,real talk on more than two hard
(01:08):
things in technology, finding community and becoming the
engineer leader you can be today.
Having difficult conversations. In my coaching and mentoring and
leadership practice, I work witha lot of leaders on their
difficult conversations every week.
What makes these conversations so difficult is by far most
(01:28):
often that the conversation happens so much later than it
should have happened, because difficult topics have this weird
habit of growing bigger exponentially the longer you
wait to bring them up. And that's when something that
could have been a quick remark or a short note suddenly turns
into this gigantic dinosaur in the room that feels impossible
(01:49):
to get under control. Or, you know, talk about.
So how do you handle the dinosaur?
Or how do you make sure that maybe the dinosaur doesn't grow
as big to begin with? That's what today's conversation
is about, a deep dive into what makes some conversations feel
difficult. Being torn between compassion
and performance that some managers experience and
(02:12):
practical strategies for saying no without burning bridges.
We also explored the dynamics that can make these
conversations even trickier for women and other minorities in
tech, and why it makes the biggest difference to focus your
leadership approach on consistent, caring leadership
instead of perfect moments. And my formidable guest today to
(02:33):
talk about all this is Nikita Rathi.
She's been in the tech industry for several years, transitioning
from linguistics to software development and now leading
engineering teams and organizations.
Nikita has navigated the complexities of managing
performance while maintaining empathy.
She's dealt with the challenge of saying no in a people
pleasing culture, which I'm very, very happy we talk about.
(02:55):
And she's learned hard lessons about setting boundaries, both
for herself and her team members.
Here's real talk on more than two hard things in technology
and difficult conversations withNikita Rafi.
(03:26):
We are here to talk about difficult conversations and I
love that you pick that topic. What made you choose that?
Yeah, I think difficult conversations are just
pervasive, like they're part of every aspect of 1's life.
But I found that most people find that they're really
stressful, ranging from like a really small conversation, like
(03:50):
a boundary setting one, or a really hard conversation.
You know, I think everyone, thisis a universe.
It's a kind of emotion where there's some kind of
conversation that's difficult. I wholeheartedly agree.
I mean, honestly, it's somethingI've really struggled with as
well over my career and still dobefore being real here.
And so I wanted to hear a littlebit from you at first.
(04:12):
What if you found makes conversations difficult for you
at work? Yeah, I was thinking about this
question and I think I've realized that when you're
talking about something that actually really matters, that's
a hard conversation. Yeah, you can find that when
things are emotionally charged, that's when you're hurt or
(04:34):
angry. That's really hard.
Cultural differences, neuro debris, perspectives.
That makes things hard. I love to or not love to, but I
have grown up sugar coating things and trying to accommodate
people's feelings. Whereas people have maybe grown
up being frank and honest and being vulnerable and sharing
(04:55):
feedback and those kinds of conversations feels hard.
Yeah. And I, I love that you called
out some aspects of what goes into kind of diversity as well,
you know, ignore divergency, different cultures.
And so I think diversity and inclusivity, that's it's non
negotiables, that's not what we're talking about, but it is a
side effect that it also means that you have many more like
(05:17):
different people with different backgrounds, upbringings,
socializations, cultural backgrounds, brains and how
brains work. And that can also lead to
tension and conflict sometimes. And that's it's ultimately I
think good and helpful, but it'salso it's part of the deal.
Yeah, absolutely. And in addition, the other thing
(05:38):
that came to mind for me is thatI think like I have, I grew up
in Germany, which is like stereotypically very direct
culture, but I didn't used to belike that.
I still I'm not I think I grew up similarly to what I heard
from you a little bit with what I'd call people pleasing
tendencies on psych, avoiding conflict and, and ensuring
harmony and everyone getting along and all that.
And so for me, difficult conversations can also be things
(06:00):
that feel more confrontative, even if it's about not even
feelings or so, but even when it's about a business case where
we just have differing opinions and need to figure out a path
forward. Also, another aspect I've
struggled with sometimes is basically when the like blast
radios of the communication or conversations I have is quite
(06:20):
large. Like when sharing larger
announcements or emails with an entire engineering organization
of several hundreds of people. Or talking about, for example,
big political events when Trump was elected.
Or when the Black Lives Matter movement really took off in the
US. Or even when George Floyd was
(06:41):
killed by a police officer. Or talking about having
conversations about me too, and the workplace and even like
outside, quote UN quote, outsideevents that obviously we're not
doing tech in isolation. And so talking about those
things with individuals, also talking about, I mean, I'm a
white person, like having conversations with people about
(07:01):
microaggressions, racism and other things that they're
experiencing. So yeah, that's, that's the
area, the direction that my brain went into as well.
It's hard stuff. Yeah, absolutely.
Yeah. And when you say the
communication to like a large blast radius, is that kind of
coming from a place of like being vulnerable and that being
(07:22):
hard? I think it's one piece of it
because of course I'll use the Black Lives Matter and protests
as an example because it's stilla topic.
But at the time when the protests really took off in the
USI was working with a team thatwas based in a lot of, you know,
cities where protests were happening.
(07:43):
We had a lot of black folks on the team.
And it's a topic where I have personal complicity just by the
fact that I'm white and this is about race and the very
complicated history of race specifically in the US, but then
also across the globe. And I want to do right by the
folks who are on our teams. And I want to acknowledge that
(08:07):
we are not working in isolation.I think there's always this
pretends the tech is apolitical,like it is very much not, but at
the same time, it's capitalism baby.
And so that also means that companies have to pretend to be
apolitical to sell to as many people as possible.
I get that. And at the same time, being a
leader in an organization, wanting people to feel like they
(08:29):
can be in a workplace, I don't think like being authentic
necessarily has to be the goal, but they can be in the
workplace. They feel like they can be there
with who they are to the degree that they're comfortable with
that. And that also does include, yes,
how do I then as like a white person leader in this
organization, talk about those things to ultimately lead to a
(08:49):
place where people feel like they can continue being in this
place? They also understand that, for
example, practical things like can they take time off or are
they just able to leave work to go to protests or shut down
their computer and take the day off if they're not feeling well
because things affect them? So I think there's a logistical
component to it, but in order to, I think, make space for the
(09:10):
logistical component and for people to be in it, there needs
to be some sort of addressing things.
And that's what I view at least is my role in this.
But it also because of who I am,because of my own background, it
does mean that for me, this is difficult and something that at
the same time, because I'm in a position of power, I view it as
(09:30):
my responsibility to honestly act, figure my shit out there.
And you know, I'm not going to go to employees and ask them for
their help in helping me work out of these topics.
I want to ask you an example of a really hard conversation that
comes to mind for you or also ask about basically which
specific types of difficult conversations you want to talk
(09:51):
about. We can also do both, but let me
know what you feel like. Yeah, I I think maybe personal
and adult adult could be an interesting one.
This is I was a new manager at this time and I was working with
somebody on the team and I was caught in a dilemma.
So I, I won't go into too many specifics, but I often had to
(10:13):
give hard feedback to this person about their performance
while they were going through something really hard in their
personal life. And I realize now that this
could be multiple things, right?Like something in their family
situation, a world event that iscausing a lot of stress.
But in this particular scenario,I often like in interviews and
(10:35):
often just like throughout my one on ones now I think like,
how could I have done this better?
It's how do you balance giving someone heartseat back because
that's the fair thing to the rest of the team, but also like,
balance, like having compassion and just empathy as a manager.
And yeah, I'm not sure, like, ifI did it right or not.
(11:00):
I think what I do know is they felt comfortable talking to me
about their personal life. And sometimes I wonder if I went
too far into that, you know, toomuch empathy and not enough good
boundaries. Then giving feedback was always
a really hard challenge. And that made the rest of the
team really suffer. Right.
(11:23):
I'd love to hear a bit more about the impact on the rest of
the team. And it sounded like you were
grappling with basically how to give that feedback and and it
sounds like basically the rest of the team existing was a
motivator for giving that feedback.
But I may have misunderstood. Tell me a bit more about that.
Yeah, so we can go and a bit more details.
(11:44):
So this person was an engineer, a senior engineer, very looked
up to a mentor to the others, and they were basically in a
point of cynicism in their life and they were very approaching
solutions, cynically shutting down ideas.
I think it's the shutting down of other people's ideas that was
the most concerning thing. And.
(12:06):
That was the setup, right? Like, the team was relatively
young in tenure, and so we were really looking to this person
for that support and silence andthen being a teacher.
And I think it's also interesting because so much of
cynicism is symptomatic of burnout and exhaustion.
(12:27):
And something else that I know about this person is that this
wasn't their behaviour, but like, this was a change in that.
So then, you know, you also start to think about, OK, are we
setting them up for success likeas a company?
Are the things around them helping them set up fast?
And obviously this glaring thinglike they were going through
(12:47):
something huge in their life. I would have probably taken time
off work, but that's not my place to tell some bad, right?
So I think that was the setup and always really tough one.
And I've seen flavors of this over and over again.
It sounds like you've been thinking about this quite a lot
since. What would you have done
(13:08):
differently in hindsight? Yeah, I've learned that they
were Speaking of different ways of processing feedback,
etcetera. I think this person would have
benefited from a lot of written feedback.
So on the one side, like we were, we had a good connection
in terms of like they were able to trust me and tell me stuff,
(13:28):
right. And like I said, maybe I went
too far. So I I think the first thing I
might have done is create betterboundaries, like maybe redirect
the people team or I refer them to the employee resources we
had, we had a partnership with atherapist organization.
So something I might have done differently now, but at the same
(13:50):
time, yeah, I think when I was is giving them feedback, it
would often become defensive thewhole commerce because maybe
they felt like they could be completely honest and free.
And that I appreciate. Yeah.
Another thing I was going to saywhen you asked me earlier, what
makes a conversation difficult is for me over and over is like
lack of preparation and being caught off guard, like that
(14:13):
conversation really difficult. So I think what I would have
done with them is given myself some space and not have it be
real time and maybe had a real time check in like after so more
people would check in but more kind of clear written
expectations and feedback. Yeah, because it also sounds to
me like you could have benefitedfrom having that space, but they
(14:37):
could have also. Absolutely.
I think, yeah, that that makes sense.
Are there things that you did there you would do the same way
as you did them back then? Yeah, I think I always want to
make space for people to be ableto talk.
So I I think the fact that I wasable to create that trust
(14:57):
between us while putting some like cards and checks for like
related boundaries. I think another thing that
worked really well there was coming up with flexible work
arrangements. This person was going through
something in their personal lifeand what they needed was they
used work as a distraction in urban there, right?
They needed work, they needed tocome to work.
(15:18):
And I think coming up with like flexible work arrangements,
their sleep was really being impacted.
So shifting things around and like being more compassionate
when it came to, yes, we can make it worth for you and change
the system. I think those are things that I
would continue to do while also making it clear these are the
outcomes or the expectations that we'll still have.
(15:40):
Honestly, that's a really interesting point because a lot
of people asked about this topic.
I did speak coaching at Lead Devjust a month ago and I think
there were three people who, separately from one another,
came to me with something like this.
And I really love the call out you just made because yes, this
is about having difficult conversations.
But I think the big question that's buried and there is
(16:02):
basically how can you be aware and take care of people and or
care for people rather and at the same time maintain a bar for
performance and then have conversations about that big,
what's the expectation towards someone who's not doing well and
(16:22):
you are aware of that and what expectation is fair towards them
as well as the rest of the team and the company that's paying
them for their time? How do you feel about that?
I, I think it's spot on like that balance, performance,
compassion dilemma. I, it's a really, it's a
tightrope and it's a really, I think nuanced thing.
(16:44):
And yeah, I think we'll get it wrong, we'll get it right.
But I have understood and learntthe benefits of having
documentations, clear expectations and then following
a people centric approach to caring and making
accommodations. I love the points you already
mentioned in terms of things youlearned from them.
(17:05):
I think this is a really good one to us.
Go back to talking about other kinds of difficult conversations
because it feels to me that basically having some sort of
shared thing can really help make a lot of difficult
conversations less difficult. If it's shared expectations,
we're all on the same page in terms of, for example, what your
job is. When we're talking about
(17:25):
performance or we have shared understanding or this we have a
shared document that outlines our strategy.
That may not mean a shared understanding, but there is one
thing that we can at least connect to or anchor in.
That seems like a really big commonality.
Yeah, that's really good points.Yeah, I'm just, you made me
think about what is the structure of every difficult
(17:49):
conversation? What's the pattern that makes it
hard? It's yeah, like you said,
probably the first thing that gets violated is that you're
just not on the same page to begin with.
So like framing around like anchoring to something either
like a common outcome. What is the future of this
conversation or relationship? But yeah, I am curious, like
(18:10):
other types of difficult conversations is there.
I know you've mentioned like some conversations that are
difficult does do any like anecdotes and that you would
definitely love to learn. There definitely are.
I was honestly, I was even thinking to some relationships
that I've had where that was a real issue, where thinking of
(18:32):
one specific person. I'm not going to talk about
details for obvious reasons, butwhere essentially at some point
we kept getting into fights about like stupid stuff, like
just silly things. And at some point you've
realized we need to remind ourselves that we actually want
to, we actually like each other and care about each other and
want to be together, reassure each other that we actually both
(18:53):
still want that. And then we can figure out the
details. And I feel like that kind of
dynamic is one that I've experienced a lot.
Actually was working just with with someone this week on a
similar topic where they've beendealing with just a lot of
communication challenges with anemployee.
And things basically were reallydifficult from the get go.
(19:15):
And they kept giving feedback and more feedback, you know,
using the SBI model for situational behaviour impact,
other frameworks. There's so many out there.
And they felt like it just wasn't landing and like both the
employee and the manager were getting more and more defensive.
And that kind of dynamic I see quite a lot.
(19:35):
And I've realized that often when that happens, the only way
out is basically to reset, to take a couple steps back.
And I do think giving some specific situational feedback
and all that is really good. Those are important tools, but
those only work if you're clear on what the point is, what
you're even talking about, and including these kinds of reset
(19:58):
conversations. You basically like zoom out.
You look at what are we doing here?
What's been making this hard? How do we want to continue with
this? Including sometimes that may
also include that someone may bebetter off in a different team
or may need a different role or things like that.
But having that zooming out conversation can.
(20:19):
Be a really good way to reconnect with what you're even
doing instead of getting lost inyet another situation where
you're arguing, here's what I perceived, here's what you
perceived and now we're stuck again and breaking through that
a little bit. I would say this is something
that comes up probably once a month at least in my coaching
now. And it's, I've experienced it a
lot as well. And it's often helped people
(20:41):
like step back and have very different conversations because
one part of it is, of course, also that there's usually some
sort of power dynamic involved. There's usually like the
employees reporting to the manager, the manager can fire
them, promote them, increase their compensation or whatnot.
And that's already not a good setup for something like this, I
(21:01):
found. But I think in figuring out a
way to take a couple steps back from the fights or discussions
about small things can sometimesbe really useful.
Yeah. Absolutely.
Just zooming out and being like what is the point of this?
I think makes a lot of sense. I'm trying to think about the
hardest conversations I've had and, you know, personal
(21:25):
conversations. I think the hardest conversation
I've had is coming out to my momand Speaking of our dynamics and
just like different dynamics. And I was trying to think of
like communication add-ons and where you fall into these
add-ons often without the ability to take a step back
(21:45):
because you have so much shared history or so much just baggage.
I don't know if this model applies to everything, but I do
know that looking back, one probably made it harder than it
was. It was hard, but it was also so
much the anticipation of the conversation is almost worse
(22:06):
than the actual conversation itself.
Yeah, I think what helped a lot was playing out different
situations, like different responses that would happen.
You're not playing or whatever. Scenario.
Play hardcore in your personal life.
Perfect. Literally, it's like, I'm going
to say this and they might say this, and I think this has
(22:28):
applied and like served me as a good tool, work in my
relationship in every other sphere of my life.
It's like just have that little mental exercise or a written
exercise or have it with someone.
But yeah. Congrats honestly like that's a
really hard conversation to haveand good for you having it.
(22:51):
Like you can be really proud of yourself.
Yeah, it was many years ago now,and it's just like a vague sort
of fan and memory. But I do know that I thought
about it for many years, just every night before sleeping.
I met my therapist because of it.
Yeah, now it's years. That easy to talk about?
(23:12):
I love that example. And another thing that it made
me think of is that one thing that makes many conversations
very difficult for people that we start imagining things and
especially for things that are going on for a longer time, we
start building up an idea of whosomeone is, what they do, how
(23:35):
they will react. And honestly, for a lot of
people, that also leads to delaying difficult
conversations. And I get that I'm not exactly a
sort of confront everything immediately person.
I often also make out, it's justthis one time, it'll not happen
again, not happen the second time.
I whatever, it's fine, it's not that bad and talk myself out of
(23:56):
addressing things head on. But that often also means that
then there's this, first of all,it usually grows and problems
kind of start piling on, which makes it increasingly harder to
talk about. And I then, yeah, realized I
developed this idea and kind of get scared, honestly, of how
someone's going to react. Like I used to have what in
hindsight, I can only describe as being bullied by an employee
(24:19):
who was reporting to me. And that person ended up having
so much power in our relationship.
I would have panic attacks before one on ones.
And a big part of that was that I got in the middle of larger
dynamics happening at the company.
But I had a really hard time even finding ways to connect
with this person at some point because it just became so scary
(24:42):
to even talk. And that's where one part I'd
want to call out is like addressing these things early
on. I speak with so many people
every week, like, ah, you know, I'm going to wait another week
and see how. No, don't wait another week.
If if the conversations feels difficult to have right now, dig
(25:02):
into what's making it feel that way and address it very early
on. And I guess you said earlier, I
pull in HR or other resources for help if you need that.
There's no shame in that. But don't delay that kind of
stuff because it just it gets messier every time and it's
going to be so much easier after, even though it in the
moment, having that conversationis hard.
(25:23):
Yeah, yeah, I think that's so spot on.
I come from a family of let's sweep things under the rug like
that. Oh, same.
Yeah, we have so many things we can't talk about.
Yeah. And I, I met my partner and she
studied communications literally.
And she, you know, works, She works at a company as a PRN
(25:44):
Commons manager. And I think a lot of her job is
to identify like good, good pat ONS of communication.
And I think just one example that stands out is like how to
apologize. I was called out many times
early in my relationship with us.
Like, you know, that's, that's not an apology.
It's like, hey, I'm sorry if youfeel that way.
Oh. Yeah, yeah.
(26:06):
Don't say that. Including in the workplace, No.
Definitely. But yeah, that sounds like a
really tough situation with yourthe person you were working with
and dreading one on ones. I have never quite felt that
extreme, but I definitely know that there are some one on ones
(26:27):
that feel harder than others. But yeah, I guess Speaking of
like working with managers, I I wanted to talk a little bit
about like managing up as well. Like I really struggled with
this. I think I'll have all of these
thoughts in my mind like these are the things I want to talk to
them about or so. And then I just, I get to that
(26:48):
moment and it's like, if I see this, will my ambition to get
that title someday be Hanford? Or should I say yes to this
request? Saying no is always hard.
Like no conversations that are so hard.
So I was, yeah. Wondering if you've thought
about that? Oh yeah, I want to call out the
(27:09):
two parts or name the two parts you mentioned or that I heard in
this. At least you let me know if that
resonates. The one part is essentially the
is it being on the other side ofthe power dynamic that we've
talked about, like basically being the employee who depends
on your boss for promotion or anything.
And the second part, the managing apart, what I heard so
far is basically just get concerns is, are things that I'm
(27:32):
going to say going to get in theway of me progressing of my
career evolving? And that's that's probably where
the saying noise. So they can make a concrete
example in a way where if you'rerefusing requests or so, that
could come back to haunt you. Absolutely.
And what have you tried so far to manage up and say no?
(27:54):
Yeah, I mean, obviously it's, I've had several managers and
it's so different based on my manager and how safe they make
me feel to really be vulnerable and honest.
And yeah, some of the best managers I've had, I haven't
even had this thought. That's the best part.
Like where I really, truly can be like, hey, actually I I just
(28:15):
don't have bandwidth to this. I spoke about people pleasing at
lead dev and a lot of the, a huge chunk of this is the my
relationship with the word no. And over time, I've definitely
learned some strategies and I have a very long list of ways to
say no. It's like someone asked me to go
(28:36):
for dinner, a friend, and sayingno is hard.
So I will say, hey, I have a loton my plate right now.
I will I have all these scripts now I.
Love that I want to see that list, but we can talk about that
later. Yeah, seriously, I think one
that I have to say a lot is at work to stakeholders, right?
(28:58):
Like teacher requirements or hey, it's So what if I tried so
far? Was your like a question, right.
I, I, I feel like employing the script, finding ways of
compromise. Like I'm always trying to find a
way of complex way of compromisebecause I found that when people
say no to me, I have an emotional response to that.
(29:19):
And I've been thinking about this a lot.
It's yes, I have respect for them that they said no to me,
something I find hard. So I really respect it.
But I also think that saying no does inevitably erode something.
No, I I don't know. Yeah.
And in, in some contexts, like it would be like, hey, listen,
(29:42):
would you be interested in doingthis task or.
Hey, can we work on this together?
And they were like, hey, no, just straight up, no.
I I will feel like taken aback. But if one says, hey, I don't
think I have bandwidth for this right now because I'm going to
want this and this like that feels like a soft of blood to
me. And I I really be objective and
really appreciate that. Yes, I've been there.
(30:03):
I appreciate you taking space and creating.
I'm angry for yourself. Yeah.
I'm also trying to find this compromise.
It does feel hard though is think of someone else's.
Right, because you also, you also have to then come up with
like compromise ideas or things that you feel will so satisfy
the original request, even if you just can't or don't want to
or whatever your reasons are. It's a lot of extra work.
(30:24):
Yeah, it is. I don't know.
How do you think about this, especially with the kind of
double bind that exists for women in the workplace.
We can be so close to being like, oh, too passive versus too
arrogant. Yeah, I do think that this word
straddles this sense, this tightrope so well.
So I'm curious, what is your experience with this been?
(30:44):
Oh boy, yeah, there is a there is a really good article that
came out. I think it's seven years pretty
much exactly. And there's I think it's the
only article where I even know that.
And the headline of it is for every yes man at work, there is
a no woman. And it has resonated with a lot
of the people I've shared with. The article came out ironic. 2
(31:06):
months or act very fittingly, rather two months after I left
the company that I Co founded after two years as a Co founder
and CEO and my Co founders perform in.
And that was basically the encapsulation of my experience.
And before that article came out, I wouldn't even have been
able to articulate why I had to leave, but at some point I just
(31:26):
knew I had to get the fuck out of there.
And that's one big thing that comes to mind for me in that
there is there are a lot of gendered dynamics where I love
the way you put this around how the word know kind of is of
almost the marker or symptomaticfor this very thin line to walk
(31:48):
between being accommodating and that guy also being someone who
gets shit done. And at the same time not being
too bossy or just refusing to dothings or not being a go getter.
I am going to share a couple more thoughts that come to mind
and then just ask you what, whatdo you think?
One other big piece that I lovedin how you described is that,
(32:12):
and we all do this. I don't mean this in any
judgmental way at all. Like we all develop these ideas
of what other people need. And we all, I think probably
spend a lifetime, even if we're very empathetic, but we spend a
lifetime learning that actually the way that we see the world is
not how other people see the world.
And the things that we think other people need aren't
(32:34):
necessarily what they actually need.
And I mentioned that because it comes up so much in these
difficult conversations. Of course, that can, if we don't
have information about what other people want or need, we're
going to have to make something up.
The only way that that often makes things even more
difficult. And the other bit that I have
also struggled with in previous leadership roles a lot is
(32:56):
basically having a perception that I'm someone who I guess
says no, who can quote, UN quote, refuses to do things.
I think there is, again, a cultural dynamic often in there
right in the US, Like it's basically better come with AI.
Think there's Oh yeah, this thing that a lot of bosses say
is don't bring me problems, bring me solutions, that kind of
(33:18):
stuff. So much bullshit.
But where I basically at some point was told that I should be
more accommodating and instead of basically refusing to
collaborate or whatnot. And so it became a big thing for
me as well. And at the same time, yeah, I
too only have so many hours in aday, even though I'd really, I
(33:41):
still want more. But so I think there's
essentially, I just want to pullout the kind of themes that I'm
seeing because I feel like it's a bunch of different ones.
I think one part is perception. How are other people going to
perceive basically the way that you manage your work, your
teams, your organization becauseof how you say no, whether you
(34:03):
say no and whatnot. Then there's the piece that you
have the gender dynamics that gointo this and where perception
can often become even trickier. Then there's of course, like
what, how we view ourselves likeI'm, I love to get stuff done.
I love to help other people. I want to be the person who will
people come to and then make stuff happen for them.
And then there's the sort of prioritization piece that comes
(34:23):
with that as well. And and how do you think about
priorities if you're in a leadership role then also
becomes about delegation and theteams that you build versus
everything relying like on you as a person and your own
schedule. Yeah, basically to say it's
really hard, even though you would think 22 letters, what
could possibly go wrong? It's just a no.
(34:48):
It's a really tough one, but I think you already pointed out
some really good tools that, youknow, I try to employ effective
delegation like prioritization. You're of your own.
What is important to me and doesthis kind of fit with my long
term goals? And if it doesn't, then I think,
(35:09):
you know, you have to think about then how much energy do
you actually want to invest in? And I'm trying to remove the
guilt of saying no things like, I just got a message before I
got on this call from somebody around, Hey, could you please
post a status update of all the bugs that are currently ongoing?
And yes, I could, but you pay mea lot of money for for this.
(35:32):
So is it also a good use of yourmoney?
I think I was like, respectfully, I think it's not
that issues are sitting with different teams and like
relating them will be a lot of just busy work.
And I have other things that I'mthinking about right now.
Yeah. And I hope that works.
I don't know. But I'm also trying to be like,
(35:54):
hey, is this a good use of the company's time?
It's a good frame. Yeah, I think, I think honestly
thinking about it as like a trade and as an as an economic
decision is a very, I found honestly very helpful because it
also depersonalizes it. Yeah.
Another thing that I've realizedit honestly works quite well is
(36:15):
to instead of saying no to like ask more questions to try and
understand what they're actuallytrying to do, especially when
it's things like busy work or just requests that seem
outrageous. And oftentimes it either turns
out that what they're looking for can be solved with much with
much lower effort, or in a different way that's already
(36:38):
accessible or whatnot. And where in the end, tech I
don't become the person who saysno, but become the person who
still helps them. But also in a way that's
actually doable for me. I find that quite elegant very
often. That's actually a really good
point. I should do that a little bit
more like just understand the request to petite.
Yeah, that's a really good point.
(36:59):
Thank you for that of. Course, yeah, I found that
basically giving people a sense that you're trying to work with
them, even if you can't, is something that kind of sticks
with folks saying, hey, you know, hey, we can't do this
exact thing. But here's another thing like
offering alternatives already, if you already understand the
(37:20):
scope really well, that can alsobe really helpful.
Or the to build on the trading thing, basically that you
mentioned saying, hey, yes, we can do that.
Here are the things that we would have to drop or stop doing
or pause in order to make that happen.
Is that worth it for you? And then basically making it
their choice can also sometimes be nice.
Yes, such a good one. I like that a lot.
(37:45):
Yeah. But what if?
Is there anything else that you found really helpful for saying
no at work? Or not saying no but still
refusing stuff. Yeah, I actually found I talked
about this in my talk as well. Like delaying helps me so much.
So stalling? What kind of delaying do you
mean? I get this is a common, I think
(38:07):
people teasing tactic as well that I use a lot.
And yeah, it's it's that in realtime moments when someone asks
you for something, you the immediate want is to say yes,
OK, let me get back to you in 24hours or more information for
you and with a definitive answer.
(38:30):
I think this just giving some time to process what do I need?
This is a simple thing that really helps the no script.
I think I've already mentioned that I also love to approach
things like you said though, like how can I make this
collaborative? Because ultimately those are the
things I value. Like I value collaboration a
lot, and I want to offer that toothers because I love when
(38:52):
people offer it to me. And yeah, it's a very small thin
line, though. It's the invisible work thing.
I've definitely been that persontoo, who does a lot of invisible
work. Like plan all the birthday
events and go like plan all the team meetings.
Like, yes, part of that is my job.
Yes, but there's also key how doI create better delegation
(39:15):
tactics like a rotation? How do we make rotations are my
favorite thing everything like. Automations, yeah.
Yeah, relations. Yeah, yeah.
It's the automation of that process stuff I I think.
Yeah, yeah. I think so too.
And yeah, so anyway, this has never been an ongoing topic in
my life. I know that.
(39:36):
It also sounds like one you've had to identify that quite early
on and you've also figured out alot of ways to cope with it,
even to the point out of difficult conversations.
Like basically a lot of things I've been hearing from US, basic
systematizing things like makingit less about having to decide
in every moment, every instance.But like with difficult
(39:59):
conversations with employees, like having clarity, written
down expectations, having regular conversations with.
Your own kind of other instancesof having to say no, like having
a list of a script, no script, or having like applying your
values, like making it more collaborative, Those are, I
think those are really good tactics.
And it sounds, even though it's probably going to stay a topic
(40:21):
in some way, you've made so muchprogress.
It's really impressive. Yeah, thank you.
And right back, actually. I think I'm sure you've felt
different kinds of challenges inevery situation that you've been
in. And yeah, I think the
self-awareness, like that's the first step, right?
Sometimes, like in hindsight, you can see the patterns and
(40:43):
tell and like, but yeah, it sounds like you knew when you
had to exit or like you knew youneeded to exit.
That obviously probably came from some deep intersection.
Yeah. So yeah, I also really
appreciate your sharing. Everyone, same to you.
This was really like wonderful. Thank you so much.
(41:03):
I love the things that you shared.
It was very unexpected and wherewe went topic wise and what came
up and so valuable. So thank you so much for
bringing this and bringing yourself and sharing so much
about this. Thank you.
Thank you so much for your time and for all the insight you
shared, Nikita. I want to emphasize a few
(41:26):
highlights from our chat and takeaways for you.
Who's listening right now. The thing that I can't emphasize
enough is that difficult conversations are rarely about
the conversation itself. They're about relationships,
power dynamics, expectations metand unmet ones, and often about
our own fears about how we'll beperceived.
(41:46):
You don't get have to have theseconversations perfect.
You just need to have them. That's probably the biggest
thing to keep in mind from this Address difficult topics early,
before problems pile up and before your own anxiety builds.
Like Nikita and I both learned, delaying these conversations
only makes them harder and harder, and it can lead to
patterns where you become afraidto even try having them.
(42:09):
So don't avoid the small, slightly uncomfortable
conversations. Have them early on instead of
kicking the can down the road. Beautiful idiom for avoiding
them. And don't let the small issues
fester and grow back. Also, create systems for caring
leadership. Whether you have a script for
yourself for saying no to things, some written
expectations for your team or peers, or regular reset
(42:32):
conversations when things get stuck, systemize the things that
are hard for you. Don't rely on having to
improvise in moments that you find difficult.
And finally, remember that effective delegation isn't just
about managing tasks, it's aboutcreating rotations and processes
so that the emotional labour doesn't always on the same
people, including you. We want to hear from you. e-mail
(42:55):
us with your difficult conversations, questions,
feedback or topic ideas at pod@lenareinhardt.com.
I can't promise that we'll always respond because this is
an unpaid side side quest, unfortunately, but I can promise
that we read every e-mail. The Leadership Confidential was
created, produced and presented by me.
Lena Reinhard. Theme, original composition and
(43:18):
mixing by Esteban Delpino. Production assistants, guest
support and social media by the formidable Sly Stark.
Thank you for listening.
I think difficult conversations are just pervasive, like they're
part of every aspect of 1's life.
But I found that most people find that there's really
stressful, ranging from like a really small conversation, like
a boundary setting one or a really hard conversation.
You know, I think everyone, thisis a universal kind of emotion
(00:23):
where there's some kind of conversation that's difficult.
We've all been there. That moment when you know that
you finally need to have that conversation that you've been
dreading for weeks, the one thatmakes your stomach clench and
the one that you would rather run away from.
Maybe that conversation is aboutgiving feedback to someone who's
(00:45):
been struggling. Maybe it's saying no to a
request when you're worried about how it will affect your
career or your relationship withyour boss.
Or maybe it's about addressing some behavior that's been
impacting your entire team, but you find it hard to balance
being kind while also holding people accountable.
This is leadership confidential,real talk on more than two hard
(01:08):
things in technology, finding community and becoming the
engineer leader you can be today.
Having difficult conversations. In my coaching and mentoring and
leadership practice, I work witha lot of leaders on their
difficult conversations every week.
What makes these conversations so difficult is by far most
(01:28):
often that the conversation happens so much later than it
should have happened, because difficult topics have this weird
habit of growing bigger exponentially the longer you
wait to bring them up. And that's when something that
could have been a quick remark or a short note suddenly turns
into this gigantic dinosaur in the room that feels impossible
(01:49):
to get under control. Or, you know, talk about.
So how do you handle the dinosaur?
Or how do you make sure that maybe the dinosaur doesn't grow
as big to begin with? That's what today's conversation
is about, a deep dive into what makes some conversations feel
difficult. Being torn between compassion
and performance that some managers experience and
(02:12):
practical strategies for saying no without burning bridges.
We also explored the dynamics that can make these
conversations even trickier for women and other minorities in
tech, and why it makes the biggest difference to focus your
leadership approach on consistent, caring leadership
instead of perfect moments. And my formidable guest today to
(02:33):
talk about all this is Nikita Rathi.
She's been in the tech industry for several years, transitioning
from linguistics to software development and now leading
engineering teams and organizations.
Nikita has navigated the complexities of managing
performance while maintaining empathy.
She's dealt with the challenge of saying no in a people
pleasing culture, which I'm very, very happy we talk about.
(02:55):
And she's learned hard lessons about setting boundaries, both
for herself and her team members.
Here's real talk on more than two hard things in technology
and difficult conversations withNikita Rafi.
(03:26):
We are here to talk about difficult conversations and I
love that you pick that topic. What made you choose that?
Yeah, I think difficult conversations are just
pervasive, like they're part of every aspect of 1's life.
But I found that most people find that they're really
stressful, ranging from like a really small conversation, like
(03:50):
a boundary setting one, or a really hard conversation.
You know, I think everyone, thisis a universe.
It's a kind of emotion where there's some kind of
conversation that's difficult. I wholeheartedly agree.
I mean, honestly, it's somethingI've really struggled with as
well over my career and still dobefore being real here.
And so I wanted to hear a littlebit from you at first.
(04:12):
What if you found makes conversations difficult for you
at work? Yeah, I was thinking about this
question and I think I've realized that when you're
talking about something that actually really matters, that's
a hard conversation. Yeah, you can find that when
things are emotionally charged, that's when you're hurt or
(04:34):
angry. That's really hard.
Cultural differences, neuro debris, perspectives.
That makes things hard. I love to or not love to, but I
have grown up sugar coating things and trying to accommodate
people's feelings. Whereas people have maybe grown
up being frank and honest and being vulnerable and sharing
(04:55):
feedback and those kinds of conversations feels hard.
Yeah. And I, I love that you called
out some aspects of what goes into kind of diversity as well,
you know, ignore divergency, different cultures.
And so I think diversity and inclusivity, that's it's non
negotiables, that's not what we're talking about, but it is a
side effect that it also means that you have many more like
(05:17):
different people with different backgrounds, upbringings,
socializations, cultural backgrounds, brains and how
brains work. And that can also lead to
tension and conflict sometimes. And that's it's ultimately I
think good and helpful, but it'salso it's part of the deal.
Yeah, absolutely. And in addition, the other thing
(05:38):
that came to mind for me is thatI think like I have, I grew up
in Germany, which is like stereotypically very direct
culture, but I didn't used to belike that.
I still I'm not I think I grew up similarly to what I heard
from you a little bit with what I'd call people pleasing
tendencies on psych, avoiding conflict and, and ensuring
harmony and everyone getting along and all that.
And so for me, difficult conversations can also be things
(06:00):
that feel more confrontative, even if it's about not even
feelings or so, but even when it's about a business case where
we just have differing opinions and need to figure out a path
forward. Also, another aspect I've
struggled with sometimes is basically when the like blast
radios of the communication or conversations I have is quite
(06:20):
large. Like when sharing larger
announcements or emails with an entire engineering organization
of several hundreds of people. Or talking about, for example,
big political events when Trump was elected.
Or when the Black Lives Matter movement really took off in the
US. Or even when George Floyd was
(06:41):
killed by a police officer. Or talking about having
conversations about me too, and the workplace and even like
outside, quote UN quote, outsideevents that obviously we're not
doing tech in isolation. And so talking about those
things with individuals, also talking about, I mean, I'm a
white person, like having conversations with people about
(07:01):
microaggressions, racism and other things that they're
experiencing. So yeah, that's, that's the
area, the direction that my brain went into as well.
It's hard stuff. Yeah, absolutely.
Yeah. And when you say the
communication to like a large blast radius, is that kind of
coming from a place of like being vulnerable and that being
(07:22):
hard? I think it's one piece of it
because of course I'll use the Black Lives Matter and protests
as an example because it's stilla topic.
But at the time when the protests really took off in the
USI was working with a team thatwas based in a lot of, you know,
cities where protests were happening.
(07:43):
We had a lot of black folks on the team.
And it's a topic where I have personal complicity just by the
fact that I'm white and this is about race and the very
complicated history of race specifically in the US, but then
also across the globe. And I want to do right by the
folks who are on our teams. And I want to acknowledge that
(08:07):
we are not working in isolation.I think there's always this
pretends the tech is apolitical,like it is very much not, but at
the same time, it's capitalism baby.
And so that also means that companies have to pretend to be
apolitical to sell to as many people as possible.
I get that. And at the same time, being a
leader in an organization, wanting people to feel like they
(08:29):
can be in a workplace, I don't think like being authentic
necessarily has to be the goal, but they can be in the
workplace. They feel like they can be there
with who they are to the degree that they're comfortable with
that. And that also does include, yes,
how do I then as like a white person leader in this
organization, talk about those things to ultimately lead to a
(08:49):
place where people feel like they can continue being in this
place? They also understand that, for
example, practical things like can they take time off or are
they just able to leave work to go to protests or shut down
their computer and take the day off if they're not feeling well
because things affect them? So I think there's a logistical
component to it, but in order to, I think, make space for the
(09:10):
logistical component and for people to be in it, there needs
to be some sort of addressing things.
And that's what I view at least is my role in this.
But it also because of who I am,because of my own background, it
does mean that for me, this is difficult and something that at
the same time, because I'm in a position of power, I view it as
(09:30):
my responsibility to honestly act, figure my shit out there.
And you know, I'm not going to go to employees and ask them for
their help in helping me work out of these topics.
I want to ask you an example of a really hard conversation that
comes to mind for you or also ask about basically which
specific types of difficult conversations you want to talk
(09:51):
about. We can also do both, but let me
know what you feel like. Yeah, I I think maybe personal
and adult adult could be an interesting one.
This is I was a new manager at this time and I was working with
somebody on the team and I was caught in a dilemma.
So I, I won't go into too many specifics, but I often had to
(10:13):
give hard feedback to this person about their performance
while they were going through something really hard in their
personal life. And I realize now that this
could be multiple things, right?Like something in their family
situation, a world event that iscausing a lot of stress.
But in this particular scenario,I often like in interviews and
(10:35):
often just like throughout my one on ones now I think like,
how could I have done this better?
It's how do you balance giving someone heartseat back because
that's the fair thing to the rest of the team, but also like,
balance, like having compassion and just empathy as a manager.
And yeah, I'm not sure, like, ifI did it right or not.
(11:00):
I think what I do know is they felt comfortable talking to me
about their personal life. And sometimes I wonder if I went
too far into that, you know, toomuch empathy and not enough good
boundaries. Then giving feedback was always
a really hard challenge. And that made the rest of the
team really suffer. Right.
(11:23):
I'd love to hear a bit more about the impact on the rest of
the team. And it sounded like you were
grappling with basically how to give that feedback and and it
sounds like basically the rest of the team existing was a
motivator for giving that feedback.
But I may have misunderstood. Tell me a bit more about that.
Yeah, so we can go and a bit more details.
(11:44):
So this person was an engineer, a senior engineer, very looked
up to a mentor to the others, and they were basically in a
point of cynicism in their life and they were very approaching
solutions, cynically shutting down ideas.
I think it's the shutting down of other people's ideas that was
the most concerning thing. And.
(12:06):
That was the setup, right? Like, the team was relatively
young in tenure, and so we were really looking to this person
for that support and silence andthen being a teacher.
And I think it's also interesting because so much of
cynicism is symptomatic of burnout and exhaustion.
(12:27):
And something else that I know about this person is that this
wasn't their behaviour, but like, this was a change in that.
So then, you know, you also start to think about, OK, are we
setting them up for success likeas a company?
Are the things around them helping them set up fast?
And obviously this glaring thinglike they were going through
(12:47):
something huge in their life. I would have probably taken time
off work, but that's not my place to tell some bad, right?
So I think that was the setup and always really tough one.
And I've seen flavors of this over and over again.
It sounds like you've been thinking about this quite a lot
since. What would you have done
(13:08):
differently in hindsight? Yeah, I've learned that they
were Speaking of different ways of processing feedback,
etcetera. I think this person would have
benefited from a lot of written feedback.
So on the one side, like we were, we had a good connection
in terms of like they were able to trust me and tell me stuff,
(13:28):
right. And like I said, maybe I went
too far. So I I think the first thing I
might have done is create betterboundaries, like maybe redirect
the people team or I refer them to the employee resources we
had, we had a partnership with atherapist organization.
So something I might have done differently now, but at the same
(13:50):
time, yeah, I think when I was is giving them feedback, it
would often become defensive thewhole commerce because maybe
they felt like they could be completely honest and free.
And that I appreciate. Yeah.
Another thing I was going to saywhen you asked me earlier, what
makes a conversation difficult is for me over and over is like
lack of preparation and being caught off guard, like that
(14:13):
conversation really difficult. So I think what I would have
done with them is given myself some space and not have it be
real time and maybe had a real time check in like after so more
people would check in but more kind of clear written
expectations and feedback. Yeah, because it also sounds to
me like you could have benefitedfrom having that space, but they
(14:37):
could have also. Absolutely.
I think, yeah, that that makes sense.
Are there things that you did there you would do the same way
as you did them back then? Yeah, I think I always want to
make space for people to be ableto talk.
So I I think the fact that I wasable to create that trust
(14:57):
between us while putting some like cards and checks for like
related boundaries. I think another thing that
worked really well there was coming up with flexible work
arrangements. This person was going through
something in their personal lifeand what they needed was they
used work as a distraction in urban there, right?
They needed work, they needed tocome to work.
(15:18):
And I think coming up with like flexible work arrangements,
their sleep was really being impacted.
So shifting things around and like being more compassionate
when it came to, yes, we can make it worth for you and change
the system. I think those are things that I
would continue to do while also making it clear these are the
outcomes or the expectations that we'll still have.
(15:40):
Honestly, that's a really interesting point because a lot
of people asked about this topic.
I did speak coaching at Lead Devjust a month ago and I think
there were three people who, separately from one another,
came to me with something like this.
And I really love the call out you just made because yes, this
is about having difficult conversations.
But I think the big question that's buried and there is
(16:02):
basically how can you be aware and take care of people and or
care for people rather and at the same time maintain a bar for
performance and then have conversations about that big,
what's the expectation towards someone who's not doing well and
(16:22):
you are aware of that and what expectation is fair towards them
as well as the rest of the team and the company that's paying
them for their time? How do you feel about that?
I, I think it's spot on like that balance, performance,
compassion dilemma. I, it's a really, it's a
tightrope and it's a really, I think nuanced thing.
(16:44):
And yeah, I think we'll get it wrong, we'll get it right.
But I have understood and learntthe benefits of having
documentations, clear expectations and then following
a people centric approach to caring and making
accommodations. I love the points you already
mentioned in terms of things youlearned from them.
(17:05):
I think this is a really good one to us.
Go back to talking about other kinds of difficult conversations
because it feels to me that basically having some sort of
shared thing can really help make a lot of difficult
conversations less difficult. If it's shared expectations,
we're all on the same page in terms of, for example, what your
job is. When we're talking about
(17:25):
performance or we have shared understanding or this we have a
shared document that outlines our strategy.
That may not mean a shared understanding, but there is one
thing that we can at least connect to or anchor in.
That seems like a really big commonality.
Yeah, that's really good points.Yeah, I'm just, you made me
think about what is the structure of every difficult
(17:49):
conversation? What's the pattern that makes it
hard? It's yeah, like you said,
probably the first thing that gets violated is that you're
just not on the same page to begin with.
So like framing around like anchoring to something either
like a common outcome. What is the future of this
conversation or relationship? But yeah, I am curious, like
(18:10):
other types of difficult conversations is there.
I know you've mentioned like some conversations that are
difficult does do any like anecdotes and that you would
definitely love to learn. There definitely are.
I was honestly, I was even thinking to some relationships
that I've had where that was a real issue, where thinking of
(18:32):
one specific person. I'm not going to talk about
details for obvious reasons, butwhere essentially at some point
we kept getting into fights about like stupid stuff, like
just silly things. And at some point you've
realized we need to remind ourselves that we actually want
to, we actually like each other and care about each other and
want to be together, reassure each other that we actually both
(18:53):
still want that. And then we can figure out the
details. And I feel like that kind of
dynamic is one that I've experienced a lot.
Actually was working just with with someone this week on a
similar topic where they've beendealing with just a lot of
communication challenges with anemployee.
And things basically were reallydifficult from the get go.
(19:15):
And they kept giving feedback and more feedback, you know,
using the SBI model for situational behaviour impact,
other frameworks. There's so many out there.
And they felt like it just wasn't landing and like both the
employee and the manager were getting more and more defensive.
And that kind of dynamic I see quite a lot.
(19:35):
And I've realized that often when that happens, the only way
out is basically to reset, to take a couple steps back.
And I do think giving some specific situational feedback
and all that is really good. Those are important tools, but
those only work if you're clear on what the point is, what
you're even talking about, and including these kinds of reset
(19:58):
conversations. You basically like zoom out.
You look at what are we doing here?
What's been making this hard? How do we want to continue with
this? Including sometimes that may
also include that someone may bebetter off in a different team
or may need a different role or things like that.
But having that zooming out conversation can.
(20:19):
Be a really good way to reconnect with what you're even
doing instead of getting lost inyet another situation where
you're arguing, here's what I perceived, here's what you
perceived and now we're stuck again and breaking through that
a little bit. I would say this is something
that comes up probably once a month at least in my coaching
now. And it's, I've experienced it a
lot as well. And it's often helped people
(20:41):
like step back and have very different conversations because
one part of it is, of course, also that there's usually some
sort of power dynamic involved. There's usually like the
employees reporting to the manager, the manager can fire
them, promote them, increase their compensation or whatnot.
And that's already not a good setup for something like this, I
(21:01):
found. But I think in figuring out a
way to take a couple steps back from the fights or discussions
about small things can sometimesbe really useful.
Yeah. Absolutely.
Just zooming out and being like what is the point of this?
I think makes a lot of sense. I'm trying to think about the
hardest conversations I've had and, you know, personal
(21:25):
conversations. I think the hardest conversation
I've had is coming out to my momand Speaking of our dynamics and
just like different dynamics. And I was trying to think of
like communication add-ons and where you fall into these
add-ons often without the ability to take a step back
(21:45):
because you have so much shared history or so much just baggage.
I don't know if this model applies to everything, but I do
know that looking back, one probably made it harder than it
was. It was hard, but it was also so
much the anticipation of the conversation is almost worse
(22:06):
than the actual conversation itself.
Yeah, I think what helped a lot was playing out different
situations, like different responses that would happen.
You're not playing or whatever. Scenario.
Play hardcore in your personal life.
Perfect. Literally, it's like, I'm going
to say this and they might say this, and I think this has
(22:28):
applied and like served me as a good tool, work in my
relationship in every other sphere of my life.
It's like just have that little mental exercise or a written
exercise or have it with someone.
But yeah. Congrats honestly like that's a
really hard conversation to haveand good for you having it.
(22:51):
Like you can be really proud of yourself.
Yeah, it was many years ago now,and it's just like a vague sort
of fan and memory. But I do know that I thought
about it for many years, just every night before sleeping.
I met my therapist because of it.
Yeah, now it's years. That easy to talk about?
(23:12):
I love that example. And another thing that it made
me think of is that one thing that makes many conversations
very difficult for people that we start imagining things and
especially for things that are going on for a longer time, we
start building up an idea of whosomeone is, what they do, how
(23:35):
they will react. And honestly, for a lot of
people, that also leads to delaying difficult
conversations. And I get that I'm not exactly a
sort of confront everything immediately person.
I often also make out, it's justthis one time, it'll not happen
again, not happen the second time.
I whatever, it's fine, it's not that bad and talk myself out of
(23:56):
addressing things head on. But that often also means that
then there's this, first of all,it usually grows and problems
kind of start piling on, which makes it increasingly harder to
talk about. And I then, yeah, realized I
developed this idea and kind of get scared, honestly, of how
someone's going to react. Like I used to have what in
hindsight, I can only describe as being bullied by an employee
(24:19):
who was reporting to me. And that person ended up having
so much power in our relationship.
I would have panic attacks before one on ones.
And a big part of that was that I got in the middle of larger
dynamics happening at the company.
But I had a really hard time even finding ways to connect
with this person at some point because it just became so scary
(24:42):
to even talk. And that's where one part I'd
want to call out is like addressing these things early
on. I speak with so many people
every week, like, ah, you know, I'm going to wait another week
and see how. No, don't wait another week.
If if the conversations feels difficult to have right now, dig
(25:02):
into what's making it feel that way and address it very early
on. And I guess you said earlier, I
pull in HR or other resources for help if you need that.
There's no shame in that. But don't delay that kind of
stuff because it just it gets messier every time and it's
going to be so much easier after, even though it in the
moment, having that conversationis hard.
(25:23):
Yeah, yeah, I think that's so spot on.
I come from a family of let's sweep things under the rug like
that. Oh, same.
Yeah, we have so many things we can't talk about.
Yeah. And I, I met my partner and she
studied communications literally.
And she, you know, works, She works at a company as a PRN
(25:44):
Commons manager. And I think a lot of her job is
to identify like good, good pat ONS of communication.
And I think just one example that stands out is like how to
apologize. I was called out many times
early in my relationship with us.
Like, you know, that's, that's not an apology.
It's like, hey, I'm sorry if youfeel that way.
Oh. Yeah, yeah.
(26:06):
Don't say that. Including in the workplace, No.
Definitely. But yeah, that sounds like a
really tough situation with yourthe person you were working with
and dreading one on ones. I have never quite felt that
extreme, but I definitely know that there are some one on ones
(26:27):
that feel harder than others. But yeah, I guess Speaking of
like working with managers, I I wanted to talk a little bit
about like managing up as well. Like I really struggled with
this. I think I'll have all of these
thoughts in my mind like these are the things I want to talk to
them about or so. And then I just, I get to that
(26:48):
moment and it's like, if I see this, will my ambition to get
that title someday be Hanford? Or should I say yes to this
request? Saying no is always hard.
Like no conversations that are so hard.
So I was, yeah. Wondering if you've thought
about that? Oh yeah, I want to call out the
(27:09):
two parts or name the two parts you mentioned or that I heard in
this. At least you let me know if that
resonates. The one part is essentially the
is it being on the other side ofthe power dynamic that we've
talked about, like basically being the employee who depends
on your boss for promotion or anything.
And the second part, the managing apart, what I heard so
far is basically just get concerns is, are things that I'm
(27:32):
going to say going to get in theway of me progressing of my
career evolving? And that's that's probably where
the saying noise. So they can make a concrete
example in a way where if you'rerefusing requests or so, that
could come back to haunt you. Absolutely.
And what have you tried so far to manage up and say no?
(27:54):
Yeah, I mean, obviously it's, I've had several managers and
it's so different based on my manager and how safe they make
me feel to really be vulnerable and honest.
And yeah, some of the best managers I've had, I haven't
even had this thought. That's the best part.
Like where I really, truly can be like, hey, actually I I just
(28:15):
don't have bandwidth to this. I spoke about people pleasing at
lead dev and a lot of the, a huge chunk of this is the my
relationship with the word no. And over time, I've definitely
learned some strategies and I have a very long list of ways to
say no. It's like someone asked me to go
(28:36):
for dinner, a friend, and sayingno is hard.
So I will say, hey, I have a loton my plate right now.
I will I have all these scripts now I.
Love that I want to see that list, but we can talk about that
later. Yeah, seriously, I think one
that I have to say a lot is at work to stakeholders, right?
(28:58):
Like teacher requirements or hey, it's So what if I tried so
far? Was your like a question, right.
I, I, I feel like employing the script, finding ways of
compromise. Like I'm always trying to find a
way of complex way of compromisebecause I found that when people
say no to me, I have an emotional response to that.
(29:19):
And I've been thinking about this a lot.
It's yes, I have respect for them that they said no to me,
something I find hard. So I really respect it.
But I also think that saying no does inevitably erode something.
No, I I don't know. Yeah.
And in, in some contexts, like it would be like, hey, listen,
(29:42):
would you be interested in doingthis task or.
Hey, can we work on this together?
And they were like, hey, no, just straight up, no.
I I will feel like taken aback. But if one says, hey, I don't
think I have bandwidth for this right now because I'm going to
want this and this like that feels like a soft of blood to
me. And I I really be objective and
really appreciate that. Yes, I've been there.
(30:03):
I appreciate you taking space and creating.
I'm angry for yourself. Yeah.
I'm also trying to find this compromise.
It does feel hard though is think of someone else's.
Right, because you also, you also have to then come up with
like compromise ideas or things that you feel will so satisfy
the original request, even if you just can't or don't want to
or whatever your reasons are. It's a lot of extra work.
(30:24):
Yeah, it is. I don't know.
How do you think about this, especially with the kind of
double bind that exists for women in the workplace.
We can be so close to being like, oh, too passive versus too
arrogant. Yeah, I do think that this word
straddles this sense, this tightrope so well.
So I'm curious, what is your experience with this been?
(30:44):
Oh boy, yeah, there is a there is a really good article that
came out. I think it's seven years pretty
much exactly. And there's I think it's the
only article where I even know that.
And the headline of it is for every yes man at work, there is
a no woman. And it has resonated with a lot
of the people I've shared with. The article came out ironic. 2
(31:06):
months or act very fittingly, rather two months after I left
the company that I Co founded after two years as a Co founder
and CEO and my Co founders perform in.
And that was basically the encapsulation of my experience.
And before that article came out, I wouldn't even have been
able to articulate why I had to leave, but at some point I just
(31:26):
knew I had to get the fuck out of there.
And that's one big thing that comes to mind for me in that
there is there are a lot of gendered dynamics where I love
the way you put this around how the word know kind of is of
almost the marker or symptomaticfor this very thin line to walk
(31:48):
between being accommodating and that guy also being someone who
gets shit done. And at the same time not being
too bossy or just refusing to dothings or not being a go getter.
I am going to share a couple more thoughts that come to mind
and then just ask you what, whatdo you think?
One other big piece that I lovedin how you described is that,
(32:12):
and we all do this. I don't mean this in any
judgmental way at all. Like we all develop these ideas
of what other people need. And we all, I think probably
spend a lifetime, even if we're very empathetic, but we spend a
lifetime learning that actually the way that we see the world is
not how other people see the world.
And the things that we think other people need aren't
(32:34):
necessarily what they actually need.
And I mentioned that because it comes up so much in these
difficult conversations. Of course, that can, if we don't
have information about what other people want or need, we're
going to have to make something up.
The only way that that often makes things even more
difficult. And the other bit that I have
also struggled with in previous leadership roles a lot is
(32:56):
basically having a perception that I'm someone who I guess
says no, who can quote, UN quote, refuses to do things.
I think there is, again, a cultural dynamic often in there
right in the US, Like it's basically better come with AI.
Think there's Oh yeah, this thing that a lot of bosses say
is don't bring me problems, bring me solutions, that kind of
(33:18):
stuff. So much bullshit.
But where I basically at some point was told that I should be
more accommodating and instead of basically refusing to
collaborate or whatnot. And so it became a big thing for
me as well. And at the same time, yeah, I
too only have so many hours in aday, even though I'd really, I
(33:41):
still want more. But so I think there's
essentially, I just want to pullout the kind of themes that I'm
seeing because I feel like it's a bunch of different ones.
I think one part is perception. How are other people going to
perceive basically the way that you manage your work, your
teams, your organization becauseof how you say no, whether you
(34:03):
say no and whatnot. Then there's the piece that you
have the gender dynamics that gointo this and where perception
can often become even trickier. Then there's of course, like
what, how we view ourselves likeI'm, I love to get stuff done.
I love to help other people. I want to be the person who will
people come to and then make stuff happen for them.
And then there's the sort of prioritization piece that comes
(34:23):
with that as well. And and how do you think about
priorities if you're in a leadership role then also
becomes about delegation and theteams that you build versus
everything relying like on you as a person and your own
schedule. Yeah, basically to say it's
really hard, even though you would think 22 letters, what
could possibly go wrong? It's just a no.
(34:48):
It's a really tough one, but I think you already pointed out
some really good tools that, youknow, I try to employ effective
delegation like prioritization. You're of your own.
What is important to me and doesthis kind of fit with my long
term goals? And if it doesn't, then I think,
(35:09):
you know, you have to think about then how much energy do
you actually want to invest in? And I'm trying to remove the
guilt of saying no things like, I just got a message before I
got on this call from somebody around, Hey, could you please
post a status update of all the bugs that are currently ongoing?
And yes, I could, but you pay mea lot of money for for this.
(35:32):
So is it also a good use of yourmoney?
I think I was like, respectfully, I think it's not
that issues are sitting with different teams and like
relating them will be a lot of just busy work.
And I have other things that I'mthinking about right now.
Yeah. And I hope that works.
I don't know. But I'm also trying to be like,
(35:54):
hey, is this a good use of the company's time?
It's a good frame. Yeah, I think, I think honestly
thinking about it as like a trade and as an as an economic
decision is a very, I found honestly very helpful because it
also depersonalizes it. Yeah.
Another thing that I've realizedit honestly works quite well is
(36:15):
to instead of saying no to like ask more questions to try and
understand what they're actuallytrying to do, especially when
it's things like busy work or just requests that seem
outrageous. And oftentimes it either turns
out that what they're looking for can be solved with much with
much lower effort, or in a different way that's already
(36:38):
accessible or whatnot. And where in the end, tech I
don't become the person who saysno, but become the person who
still helps them. But also in a way that's
actually doable for me. I find that quite elegant very
often. That's actually a really good
point. I should do that a little bit
more like just understand the request to petite.
Yeah, that's a really good point.
(36:59):
Thank you for that of. Course, yeah, I found that
basically giving people a sense that you're trying to work with
them, even if you can't, is something that kind of sticks
with folks saying, hey, you know, hey, we can't do this
exact thing. But here's another thing like
offering alternatives already, if you already understand the
(37:20):
scope really well, that can alsobe really helpful.
Or the to build on the trading thing, basically that you
mentioned saying, hey, yes, we can do that.
Here are the things that we would have to drop or stop doing
or pause in order to make that happen.
Is that worth it for you? And then basically making it
their choice can also sometimes be nice.
Yes, such a good one. I like that a lot.
(37:45):
Yeah. But what if?
Is there anything else that you found really helpful for saying
no at work? Or not saying no but still
refusing stuff. Yeah, I actually found I talked
about this in my talk as well. Like delaying helps me so much.
So stalling? What kind of delaying do you
mean? I get this is a common, I think
(38:07):
people teasing tactic as well that I use a lot.
And yeah, it's it's that in realtime moments when someone asks
you for something, you the immediate want is to say yes,
OK, let me get back to you in 24hours or more information for
you and with a definitive answer.
(38:30):
I think this just giving some time to process what do I need?
This is a simple thing that really helps the no script.
I think I've already mentioned that I also love to approach
things like you said though, like how can I make this
collaborative? Because ultimately those are the
things I value. Like I value collaboration a
lot, and I want to offer that toothers because I love when
(38:52):
people offer it to me. And yeah, it's a very small thin
line, though. It's the invisible work thing.
I've definitely been that persontoo, who does a lot of invisible
work. Like plan all the birthday
events and go like plan all the team meetings.
Like, yes, part of that is my job.
Yes, but there's also key how doI create better delegation
(39:15):
tactics like a rotation? How do we make rotations are my
favorite thing everything like. Automations, yeah.
Yeah, relations. Yeah, yeah.
It's the automation of that process stuff I I think.
Yeah, yeah. I think so too.
And yeah, so anyway, this has never been an ongoing topic in
my life. I know that.
(39:36):
It also sounds like one you've had to identify that quite early
on and you've also figured out alot of ways to cope with it,
even to the point out of difficult conversations.
Like basically a lot of things I've been hearing from US, basic
systematizing things like makingit less about having to decide
in every moment, every instance.But like with difficult
(39:59):
conversations with employees, like having clarity, written
down expectations, having regular conversations with.
Your own kind of other instancesof having to say no, like having
a list of a script, no script, or having like applying your
values, like making it more collaborative, Those are, I
think those are really good tactics.
And it sounds, even though it's probably going to stay a topic
(40:21):
in some way, you've made so muchprogress.
It's really impressive. Yeah, thank you.
And right back, actually. I think I'm sure you've felt
different kinds of challenges inevery situation that you've been
in. And yeah, I think the
self-awareness, like that's the first step, right?
Sometimes, like in hindsight, you can see the patterns and
(40:43):
tell and like, but yeah, it sounds like you knew when you
had to exit or like you knew youneeded to exit.
That obviously probably came from some deep intersection.
Yeah. So yeah, I also really
appreciate your sharing. Everyone, same to you.
This was really like wonderful. Thank you so much.
(41:03):
I love the things that you shared.
It was very unexpected and wherewe went topic wise and what came
up and so valuable. So thank you so much for
bringing this and bringing yourself and sharing so much
about this. Thank you.
Thank you so much for your time and for all the insight you
shared, Nikita. I want to emphasize a few
(41:26):
highlights from our chat and takeaways for you.
Who's listening right now. The thing that I can't emphasize
enough is that difficult conversations are rarely about
the conversation itself. They're about relationships,
power dynamics, expectations metand unmet ones, and often about
our own fears about how we'll beperceived.
(41:46):
You don't get have to have theseconversations perfect.
You just need to have them. That's probably the biggest
thing to keep in mind from this Address difficult topics early,
before problems pile up and before your own anxiety builds.
Like Nikita and I both learned, delaying these conversations
only makes them harder and harder, and it can lead to
patterns where you become afraidto even try having them.
(42:09):
So don't avoid the small, slightly uncomfortable
conversations. Have them early on instead of
kicking the can down the road. Beautiful idiom for avoiding
them. And don't let the small issues
fester and grow back. Also, create systems for caring
leadership. Whether you have a script for
yourself for saying no to things, some written
expectations for your team or peers, or regular reset
(42:32):
conversations when things get stuck, systemize the things that
are hard for you. Don't rely on having to
improvise in moments that you find difficult.
And finally, remember that effective delegation isn't just
about managing tasks, it's aboutcreating rotations and processes
so that the emotional labour doesn't always on the same
people, including you. We want to hear from you. e-mail
(42:55):
us with your difficult conversations, questions,
feedback or topic ideas at pod@lenareinhardt.com.
I can't promise that we'll always respond because this is
an unpaid side side quest, unfortunately, but I can promise
that we read every e-mail. The Leadership Confidential was
created, produced and presented by me.
Lena Reinhard. Theme, original composition and
(43:18):
mixing by Esteban Delpino. Production assistants, guest
support and social media by the formidable Sly Stark.
Thank you for listening.
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