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June 24, 2025 23 mins

In this episode of the HR Mixtape podcast, host Shari Simpson welcomes Meg Crosby, co-founder of PeopleCap Advisors and operating partner at SSM Partners. They delve into the critical first 90 days for new leaders, emphasizing the importance of listening and understanding organizational culture during leadership transitions. This conversation is particularly timely as organizations navigate the complexities of employee experience and the integration of AI in HR, highlighting the need for inclusive leadership strategies.

Listener Takeaways:

  • Learn how to effectively support new leaders by prioritizing listening and relationship-building.

  • Discover why understanding generational dynamics can enhance team cohesion and performance.

  • Explore strategies for leveraging AI to shift focus from functional expertise to essential people management skills.

Hit “Play” to gain valuable insights on leadership development and the evolving role of HR!

Guest(s): Meg Crosby, Co-founder, PeopleCap Advisors

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:02):
You're listening to the HR Mixtape Your podcast with
the perfect mix of practical advice, thought-provoking interviews, and
stories that just hit different so that work doesn't have to feel,
well, like work. Now, your host,
Joining me today is Meg Crosby, co-founder of PeopleCap Advisors
and operating partner at SSM Partners. With

(00:24):
a background spanning organizations like Google and startups, Meg
is a trusted advisor to CEOs and governing boards, known
Meg, thank you so much for jumping on the podcast with me today. Thank
you, Shari. I'm happy to be here. So you have supported countless

(00:45):
leaders through transitions. So I thought we could start with what's maybe
one mistake that you often see organizations make in
Well, I think there are so many, but I think what I would say
is the one I see the most often is leaders jumping in with both feet
without listening to the organization, without sort of taking that

(01:06):
pause to understand where the organization is
on its growth journey, what's next, and how people are
feeling about the transition. So I think a really important first
step for new leaders in a transition is to do
I can tell you as an employee who has had more

(01:27):
than five managers over the last eight years, I know what that
feels like to have a new leader come in and start to
make changes right away without them kind of understanding the
landscape and some of the knowledge that exists with your
employees. You know, some of the unspoken rules. I
recently just moved departments, and one of the questions I asked my new manager
was, like, what skeletons are buried in this department that

(01:50):
I don't know about so that I can succeed? Same
thing for new leaders, right? That coming in and like you said, listening. How
does HR help support that? You know, I think that we get stuck
a little bit on checklists and compliance and
architecting, you know, strategic onboarding for
new leaders. But I think sometimes we miss some of the

(02:10):
more relationship stuff that we need to help them with. What
are some ways that we as HR can shift our mindset in
Sure. Well, I, let me first preface by saying, I'm giving you
how I think about HR. HR is such a broad discipline. There
are, you know, you have people looking at benefits contracts
and case, you have HRS data folks, and

(02:33):
then you have people doing talent management and recruiting and training.
And so it's a very broad discipline. So when we talk about HR,
I think about it in, in sort of, this is probably oversimplifying, but
in two buckets. There's transactional HR, which are really
the table stakes. And when companies begin, when they
are in an emerging stage and are growing, HR usually starts out

(02:54):
reporting to the CFO. It tends to be a very transactional and
defensive posture of a function in the sense that
we want to make sure that payroll is done on time. We want to make sure benefits
are in place, that we have policies and procedures and all the paperwork to
just really get people hired. And that's table stakes. But
as the company grows and talent becomes a

(03:16):
really important strategic lever for an organization, HR
begins to move into what I call the transformational side.
And this is the really strategic HR that involves talent
management, it involves change management, it involves
performance management, all of the things that really can
transform the organization in important ways. And so when

(03:38):
I think about how HR can support a leader in a transition, I'm
thinking about all sorts of ways. Obviously, we have to make sure that the
transactional side, those table stakes are still running smoothly
and that people are getting paid regularly. And if there
are any glitches and hiccups there, that can trip up a leader in
their transition. So listening to find out if people have complaints about

(03:59):
their benefits or their 401k, Those could be some quick lens
that a leader can navigate through early in a transition. But
on the transformative side, I think about HR coaching
leaders, sitting down with leaders to tell them
what's going on in the organization. They're really the pulse
check of the organization. What's going on in the organizational culture? Who

(04:22):
are the key? relationships they need to build? Who
are the key influencers in the organization? And how
do those people relate to others? What are their
working styles, their personality traits that leaders will
need to be equipped with in order to navigate those things? So those are
the kind of the things that I think about with HR support, really critical

(04:45):
I love that you mentioned working styles. I
have talked about this before in the podcast. From the HR perspective, as
you present up to your C-suite different items and
understanding your highest level, how
they like to be communicated with. You know, some leaders want you to
give them the story. Some want just the data. Some want the

(05:06):
data, then the story, and then the backup materials. But that's, you're
right, if you don't know that walking into an organization, what a great resource
for HR to be able to sit down and have that conversation or create
in your onboarding guide. You know, hey, here's the people you should meet with,
and here's a couple things you should know about them, right? They've been here 10 years.
This is how they like to be communicated with. I love all of that. I think that's

(05:27):
such good advice. As you've worked to help leaders
kind of step into these roles, how do you wrap in data from
the voice of the employee? So I'm thinking, you know, specifically if
there's a team that's getting a new leader that maybe the team
has been cohesive for a long time, and so they're getting a new leader. How
do you take into account some of the things that the

(05:49):
employees are sharing, but also with a
grain of salt. And the reason I'm saying that is because maybe you're bringing in a new leader because
the team is actually dysfunctional and you don't like their trajectory. And
Oh, without question. I think that's, uh,
so critical to the leader surveying the landscape. You

(06:11):
know, you, you've got to understand what you're dealing with when
you, um, when you walk in. So there are a couple of ways
that we do that. When we work with teams that are in transition, we often,
uh, You know, depending on the size of the team, the
more voice we can get, the better. Let me just say that. But
we start with interviews. So if it's a leadership team, we

(06:32):
want to make sure we do one-on-one interviews with each of the leadership
team members to understand what they think is working well in
the organization, what's not working well. What is the culture like?
Can they give us examples of how the culture works in the organization? What
do they see as the quick wins for the organization? What
needs to happen? These are the experts. They're on the front lines of

(06:54):
this work every day. They're the experts telling us what
they are seeing and what information needs to be related to
this new leader coming in. If we are able to, we'll survey
the entire company. We can do that online.
and get feedback from folks. And then, to your point, it's
really important to look at the themes

(07:16):
and the patterns that emerge, things that are said more than once. So,
if you have a disgruntled employee that's an outlier, it's
really easy to spot that, right? Because there's only
one person with that highly negative opinion, everybody else. has
more, maybe more measured response or is not even thinking about
that. So when we are able to get enough voices together to

(07:38):
then see the themes and patterns, things that come up multiple times, then
we're pretty confident that we can focus on things that
When you think about pipelining for leadership, what
are some of the things that you have thought about
in resetting those expectations with someone stepping

(07:59):
into a leadership role over their peers, right? There's a bajillion
books on this, right? There's Bud to Boss. I think that's one that
I hear all over and over again. But it can
be, it can be really tricky. And sometimes you, as
much as we'd love to have our pipeline ready to go, sometimes that's
not something that we've been able to do. And so you have somebody stepping

(08:20):
into a leadership role over their peers. What advice do you give
I think, for me, I lead with establishing some
strong boundaries. And that can be painful. I'll tell you a
funny story. I worked for Google in the early days
when Larry and Sergey had just brought on Eric Schmidt as the
CEO. And at the time, they had been working in an

(08:43):
office alongside a team of software engineers working
on Google's products. And the company was about to go public. It
was really In the limelight, a lot of press, there
was just a lot going on for these young executives who were
30 years old. And so one of the first things that Eric Schmidt
did was to create some pretty strong boundaries, which first

(09:05):
he took them out of that group office, gave them their own office,
and to put a an executive assistant who
was a buffer, and I called her also a bouncer for
traffic coming in and out of the office. You know, that filter to make sure
their time was spent on the things that were most important to the company and not
really wasted on hanging out with the folks that

(09:26):
they had been with before. And then that person also
began to manage their calendar, manage their email, and
filter information to them that was important for
what they were what they were doing. So I think establishing those boundaries
is important. It's hard. That's a difficult transition for especially
for those of us who had enjoyed that direct contact

(09:49):
and easy contact with them early on to
recognize that now there was someone sort of put in the way of that was
frustrating. But I think we also understood that for
the company to grow and scale and succeed, that they
had to be hyper focused on the strategy and
growth of the company, not sitting in a bullpen with

(10:09):
a bunch of distracting personalities. So
I think establishing boundaries, understanding that that is hard, but
My husband transitioned into a leader of
leaders role several years ago now. And when he made that transition,
he created a PowerPoint deck of his expectations. And

(10:32):
he's a fireman, so he held some shift meetings and went through these.
And it was interesting watching his peers react
to this different view of him. And it was there was
obviously a little bit of a transition like, hey, you used to be one of us. Now
you're in charge of us kind of stuff. But overall, when
I look at his success over the last several years, it

(10:53):
goes back to those expectations he set really early on because
it gave him common language with the people that he supports and
leads and be able to say like, hey, You know what? These are
the expectations. I'm holding you accountable to them. And when you
choose as an employee to act outside of those expectations, there's
consequences, right? Just just like anything in life. I love that

(11:15):
setting that up from the very beginning and having it be clear. And
the gatekeeper is such a good idea. If that's something that you can
afford budget-wise for somebody moving into that, that's
great. What if you can't afford that? What are some, you know, maybe
some suggestions you have for a leader stepping into that role
who doesn't have the financial backing to be able to create that kind of

(11:35):
physical buffer? What are some other buffers that you've seen work?
Yeah, I mean, I think it's just really thinking through what that
filter looks like. And, you know, if you're changing roles,
you have to set expectations for yourself as well. What
is your scorecard? What do you need to accomplish? How can
you make sure that you sharpen your focus? to be

(11:58):
exclusively focused on those things and tune out the noise. And so
some of that is just the self-discipline and the self-awareness to
understand that that is going to happen. And also create
a stop doing list. You know, I love this notion of
when you're leveling up to a new role, you can't do all
the things that you were doing before and the new role. What

(12:19):
are you going to stop doing and who's going to do those things? And be
very explicit about claiming that time and offloading
those responsibilities. I think those are some ways that, that people
can do that. You can set up email filters, use technology to
help with that as well. But I, but I think really important also
to defend your boundaries. And when people come to you who are

(12:40):
used to coming to you, but now may be jumping the chain of command to
send them back to where they're supposed to be to have those conversations. And
you can do that in a, in a thoughtful way. And eventually they'll, you
Yeah, and if they really were your peers, they should understand that.
I mean, sometimes it's difficult, like you said, but,
you know, if they really are your peers, they should understand that. You

(13:02):
know, you talked a little bit about technology. I want to dive into that a little bit.
So many times when we focus on the word innovation, we
think just about tech, right? We associate innovation with technology. I
think innovation is a much broader topic and
there's definitely the human side of leadership transition and
innovation. How have you seen that? How have you seen kind of

(13:24):
that concept of innovation brought to these leadership transition
Well, I think we are doing so much more in
the wake of a leadership transition than we ever used to. And, you know, we
talked at the top of the podcast about personality
testing and leadership style. There
are so many tools out there, so many assessments. Um,

(13:47):
so many instruments that leaders can take to understand themselves,
to, uh, to be coached, to know
what their, their preferred style is and how they lead. So
I think more than ever, I think that's been probably one of the biggest innovations
that we've had, you know, in the last 10 or 15 years is just bringing
all of these instruments to bear to help us understand how

(14:09):
we lead and how others respond to our leadership. And so
We went through a process several years ago on the HR team
where we did CliftonStrengthsFinder. And it was really, it was a
fun activity. It was a good discussion. And a lot of people in HR have taken
a lot of assessments. So, you know, you probably could ask

(14:30):
us, you know, what's our disk? What's our Enneagram? What's our, you know, CliftonStrengths? We
probably can tell you all the things. But what was great about it
is that they created these cards that sit on our desk that
are our top five strengths. And it was so great because then
we could kind of walk around and have that visual reminder of
like, oh, hey, this person's strength is strategy

(14:51):
or this person's strength is empathy. So, you know, if I need
to get a project done, how do I leverage some of
these different strengths in the room to succeed? So I
love that recommendation. I think sometimes we we focus on
those tools not in the right ways, right? We check the box or
like, hey, you You met our criteria as to how we
think leaders in our org should work, but there's so much more

(15:17):
I would add one more thing. My favorite, I always say it's
going to be on my tombstone, but my favorite quote
is structure follows strategy. And so when
we think about leadership transitions, I think
it's really important to anchor those in the strategy of the organization
or the department, depending on what kind of leadership role you're taking on

(15:37):
and thinking a lot about what kind of leader is needed
to execute on that strategy and putting the right person in
place based on those strengths. So if, you
know, if you're And getting ready to ramp up growth, you
need someone who's got some business development and sales experience.
You know, that's going to be really important. If you are looking to build out operations,

(16:00):
you need somebody who's a process-driven person. So there
are these different considerations just depending on the strategy. So
I think the strategy is the North Star. And then you layer in and
find the leader who has the strengths that can take you
Such good advice and how to think about your leadership
pipeline and succession planning a little bit differently. How

(16:24):
do you wrap in an understanding of
leaders who are coming to it that might have, they
might be in a different generation than the team, right? So you have some generational preferences
there. They might be a neurodiverse leader.
I think those are things we don't talk enough about because
they bring some unique skills to the table that unfortunately don't

(16:47):
fit kind of the mold that we think about. How do you personalize onboarding
That's a great question. As far as generations,
right now we have multiple generations in the workforce and there
has been so much change because of technology that it
is really interesting to see these generations getting

(17:09):
along. For the first time in history, if you think about the
history of work, We always worked on
sort of an apprentice model. You know, there was someone coming into
a business to learn the business from someone more senior and
more experienced and probably older as
well. And so that that model has existed for thousands of
years. And suddenly with the

(17:32):
advent of technology and our use of technology and
the internet and all the ways we use technology and systems, for
the first time in history, our more senior generations
are learning from the more junior generations. And
that's created an interesting dynamic in the workplace that's
leveled the playing field a little bit. But I think it's also,

(17:57):
It's also, we also live in an instant gratification culture.
And so some of our younger employees who
are really adept at using technology are
impatient with how long it takes to actually build expertise.
in a subject matter or to build expertise in

(18:18):
a business or to build their reputation or their credibility or
their book of business. And so I think for
the senior people, it is great
to embrace the learning that they can get from junior
folks, especially as it relates to technology. And
for the junior folks, it's really important to remember that the

(18:38):
person that you might be teaching to use this technology
has a lot of wisdom for you to draw from that
is analog, and that there's no substitute for time spent with
these folks, and you'll learn so much from them. So I think as
far as generations go, that's sort of one of the issues we're seeing. With
neurodivergence, it really is interesting. I think that just

(18:59):
goes back to what we always tell leaders, which is the
most important thing you can be is self-aware, is know
yourself. Work. And the workplace doesn't
change because you operate in one way or
another. We were just talking about work styles and everybody's got
a different work style. So I think your neurodivergence can

(19:19):
be both an asset. It certainly can be an asset, but it can also be
a hindrance. So it's just. figuring out how you can operate
in the culture, in the workplace, based on whatever
your neurodivergence is, what roles work for you,
what ways of working work well for you, and explain those to
your colleagues, ask for grace if you need to,

(19:41):
and tell them where your superpowers are with your neurodivergence and
where they should deploy those. So I think it's just being
self-aware and helping people learn how to work with you.
What doesn't work is expecting everybody to work around your
style. That doesn't work for any of us, regardless of
our style. So you've got to take the ownership of

(20:06):
I love that. And it's like you mentioned it, everybody has
to figure out that work style. So it doesn't necessarily matter your
generation or if you're neurotypical or neuro
spicy as some people like to put it. Yeah, you got to you got to figure
that out what your style is and how it fits in the organization. You
know, as we wrap our conversation, I have one last question

(20:27):
for you, and I think it's a big one. But if we fast forward,
right, 10 years, four years, five years, how
do you see the role of HR evolving as it continues
to help set leaders up for success? especially because
we have, you know, this rapid rise of AI integration
in the workplace where I think we're, we quite haven't figured

(20:49):
out in most organizations, the strategy of using AI. We're
just really trying to understand the tech and use it quickly. We
still have our hybrid models, which I think are going to exist for a while. And
who knows what the next evolution of work is going to be?
You know, I see our younger generations coming in. and
pushing in such really great ways around development and

(21:11):
opportunities for skills development. And I see that also changing
how we're thinking about roles internally, right? Can they be
a little bit more flexible? Can they lean into skills? How do we
create that gig economy inside of our own organizations? I know
I just, that was a very big, long-winded question, but I guess the
bottom line is, you know, where do you see HR in the next five years really supporting

(21:35):
Now, I think that's a great question. So I'm thinking a lot right now
about AI and how it is going to disrupt the
workforce. And the things that I'm thinking about are as
it relates to leadership and management. When you think about when you
think about taking an individual contributor, for example, and
making them into a manager, a people manager. They, there

(21:55):
are two skill sets at play there. One is, is they've been a
successful individual contributor in a particular function.
And now we've, we've added the people leadership skills onto
those folks. And what I think is going
to happen is that our functional expertise
is going to be less important because AI

(22:17):
is going to be the functional expert in everything, then that
will be less important than our people management skills, the things
that involve empathy, the ways that we help
guide people and train people to use AI. I
think that's really going to be mission critical for HR
Um, in education, we've moved to, uh,

(22:41):
we're moving to a project-based learning model. And so we
talk about, in project-based learning, we talk about, uh,
the teacher becoming not the, the old
model is the teacher as the sage on the stage. You know, you, you
have the person in front of the class giving a lecture and this new
model is the guide on the side. someone who is

(23:01):
more of a facilitator to help guide employees, help
them work with AI tools to get
to the end result. So I think we're going to see a lot more coaching leadership
style, more facilitation, and less
dependence on expertise or I'm the smartest person

(23:23):
I love that. I could not agree more. Meg, this was such a great conversation
focusing on, you know, leadership development and all the things
that we have to think of to support our pipeline and succession planning.

(23:48):
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