Q&A: How to Delegate Without Guilt and Still Get Promoted

A Chief of Staff named Samir asks for advice about being overloaded at a startup, struggling to delegate, and never taking real breaks. Emily Sander suggests Samir update his boss on his workload, start delegating in small steps, and actually schedule and enjoy a vacation - sharing her own tips for disconnecting, including going snuba diving and ignoring email except for real emergencies. The episode highlights the importance of building a team that can function without you.

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Who Am I?
If we haven’t yet before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want.
 
Time Stamps:
00:25 Listener Question: Overwhelmed at Work
01:19 Communicating with Your Boss
02:30 The Art of Delegation
03:42 Learning from Your Role Model
04:29 Preparing for Promotion
05:19 The Importance of Taking a Break
07:38 Tips for a Successful Vacation
11:34 Final Thoughts and Recommendations

Episode Transcript

emily-sander_1_12-05-2025_0 (00:25):
All right, listener question time.
Samir asks Samir from the UAE,which is very cool, says, Hey
Emily.
I'm Samir.
I'm a chief of staff at astartup and my boss is this
super successful founder.
I really look up to, like partof me hopes I can do something
like that one day too.
Very cool.
Lately, I too become the personwho does dot, dot, dot,

(00:46):
everything.
Okay, so lately I've, I've alsobecome the person who does dot,
dot, dot, everything.
More teams, more project.
It all keeps just coming to me.
I know I should, in quotes, behanding stuff off.
Yes.
Um, but I'm really not doing it.
Hmm.
Okay.
I also don't feel like I cantell my boss about anything

(01:07):
about it, and I don't even knowwhat he actually sees of how I
work.
I haven't taken a real break ina long time and it's just
getting a lot.
Not sure what to do next.
Any thoughts?
Okay, Samir, thank you for thisquestion.
There's a lot of good stuff totalk about in here.
So the first thing I would sayis it was interesting that, I

(01:28):
don't feel like I can tell myboss.
About it.
So I would, I would tell yourboss what you're doing, not like
a blow by blow, here's this 47point list that I'm going to
just recite to you.
But it is just letting him knowin a informative, helpful,
relevant way of what types ofthings you're working on.
Sometimes I have done this whereI forget what I have given

(01:51):
someone.
I forget what my team members,I've asked of them.
And so when I say, can youplease do this thing?
And they're like, uh, yes.
Um, do you want me to do thething you just said or the thing
you said a month ago?
And I'm like, oh, oh yeah.
Or like the five other thingsthat I've said over the course
of time and I just forget.
And it's not like malicious,it's not trying to overload

(02:12):
them.
It's just, I, I have all thesethings going on and I just
happen to forget, Somethingsimilar could be happening with
your boss, where if you keep hima little bit more in tuned and
dialed into what you're doing,He might distribute that
workload a little bit more.
If he doesn't.
That's another conversationaround what's a reasonable
workload?
Okay.
The next thing is, um, I know Ishould be handing stuff off, but

(02:35):
I'm not really doing it.
Alright, so Samir, delegate,baby, delegate Away.
Do it.
You'll feel great.
They'll feel great.
It'll all be great.
one thing I wanna remind you ofis delegation is not.
Binary.
It's not on off all or nothing.
There's levels and gradients andgray areas of this thing.
So it might be, for you, itmight be more comfortable to

(02:58):
delegate a little bit ordelegate this one step or
delegate this small project.
To start with, I would rampyourself up pretty steadily
though.
Um, in some cases it might behelpful to delegate in.
Baby steps or bite-sized chunksfor your team if it's brand new.
So that could be an effectiveway to go, but I would get
yourself started with something,start something this week, and

(03:19):
then build on that over time andkeep a pretty rapid clip, um, of
how you're building that up.
Or it doesn't have to be rapid,fast, per se.
It just needs to be a deliberateand consistently steadily moving
delegation process.
You're delegating more and moreand more.
Okay.
What else?
What else?
So the other thing that.

(03:41):
Caught my attention.
Oh yes.
Was you mentioned you wanna belike your founder.
So you look up to this person,wanna be like them.
Ask yourself, does this persondelegate or do they micromanage
and take everything on?
Some founders do and theymicrowave.
Microwave.
They microwave food and theyalso micromanage sometimes,
sometimes at the same time.

(04:02):
Um, they.
We'll either be in the weeds orthey'll be like, I don't even
wanna touch that.
I'm having a vision, I'm havingan idea.
Someone else take care of that.
So you might kind of take a lookat that model that he is
presenting and say, what part ofthat works well?
What part of that doesn't?
What makes you look up to him?
There might be some of theseelements.
All of that.

(04:22):
So how is he, uh, thinking aboutworkload or where is he spending
his time and energy.
also, also if you want to belike this founder and you want
to, and or you wanna move up inthe company that you're at in
this startup as it grows, youhave to have, team in place that
can hold the work themselves.
Even if your founder wanted topromote you, but they knew the

(04:46):
work would fall down withoutyou, it's hard to do that,
right?
So they're hard pressed to belike, yeah, Samir, come over
here.
Oh no, no.
Like this stuff can't fall.
You have to keep making surethis stuff happens.
So part of putting yourself inposition to be promoted and to
become more and more like yourfounder.
Is to create a backfill or ateam that can stand on its own

(05:07):
or, um, mentor and train andguide a successor in place.
So having all that in placehelps you level up, helps you
get promoted in the long run.
Let's see here.
The, the last thing I'd say hereis, uh, take a break.
Literally go schedule a vacationRight now, just schedule, it
doesn't have to be next week,but schedule it so there's a

(05:29):
stake in the ground, and thenyou and your team can work
toward, okay, hey, I'm gonna beout for a week in, you know,
whatever, three months or sixmonths or a month, or whatever
you wanna do.
But have that be a forcingfunction.
Have that be something thateveryone's driving to.
Hey, like, Samir's gonna be out.
Okay.
Get people ready, get peoplehanded off, get people the

(05:49):
information they need.
And then this is also a reallygood test for if you've set up
your team well, a team should beable to run without you for a
week.
So, so Samir and everyonelistening, your team should be
able to run without you for aweek if you've set it up so it
falls down without you, you'venot set it up correctly.

(06:10):
I've seen a lot of people dothis intentionally.
Some, sometimes intentionally,sometimes subconsciously.
'cause their ego won't allowthem to do anything differently,
and you're, you're just setting,setting that whole thing up for
failure.
If you do that, if you are thesingle point of failure and
you're, and you wanna be in thatposition, so you're needed and
you hoard information and you doall these things, um.

(06:31):
I would, I would go a differentdirection with that because it's
not good for you, it's not goodfor your team, it's not good for
the company.
I think a far stronger and moresecure leader would say, let me
set this up for success.
Let me build the system.
Let me build up my people sothat.
I can be a human being and takea break and everything is fine
and people even get theopportunity to step up and maybe

(06:53):
for that week get to be indifferent types of meetings and
they're proxying for you or getto be in different types of
projects.
They're taking point on.
All these things are good togive people reps on your team.
So I would literally, I would goschedule a vacation.
It can be.
like a, I'm taking a plane andgoing to a different location.
It can be, Hey, I'm taking a 90minute drive and checking out a

(07:13):
cool Airbnb on the coast ofwherever, or like in a nice
little area or just a differentarea than you're used to being
in, um, something relaxing,something rejuvenating, And when
you go on vacation, actually goon vacation.
Actually be on vacation, Someaning don't just move yourself
to a different physical,geographical location and then

(07:35):
work all day long.
That's not the point, actuallygo on vacation.
And here's a few, few quick tipsfor, for doing this on vacation.
So, um, when I go on vacation, Istill check in on email once a
day.
Um, for anything critical oranything urgent, sometimes twice
a day.
But I try to be, I try to be.
Careful and deliberate withthat.
When I was working in corporate,this was really tough for me.

(07:57):
This was like, I, I, I didn'twanna go to the pool, I didn't
wanna go to this excursion, Ididn't wanna do all these things
'cause like it's taking me awayfrom the internet and from my
computer, which is like not thepoint of being on vacation.
But that's how I felt.
These other things were gettingin the way of me actually
sitting down in the hotel andworking all day long.
so what I would do is I wouldsay, I'm gonna take an hour.

(08:17):
To check email and the thingsI'm looking for are things that
are actually critical, that areactually exception cases where
this is out of the ordinary runof the mill, turn the crank
operation stuff I had set myteams up to do and I had to let
them do that even though I waslike, well, I see it and I'm,
and I'm right here so I could doit really quickly.

(08:38):
That's not the point.
That's not the point.
The filter is, are there anycritical items?
If it's truly urgent andimportant for you to do on
vacation and other people can'thandle that, like literally like
something's burning down or youare the only person who has
access level to this bank andsomething crazy has gone on with
a customer that happened once.

(08:58):
Those types of things are whatI'm talking about.
if it's, hey, like there's aclient escalation.
This is kind of urgent andimportant, but it's run of the
mill escalation, and the teamscan handle that, let that go.
Critical, urgent and importantexception cases was the filter.
I would also set a timer for 30minutes.

(09:18):
So it's like Emily, you'rehalfway through, like halfway
through and then for 50 minutes.
So like, Hey Emily, you have 10minutes left.
Wrap this stuff up.
Anything you wanna get done orhave to get done in the next 10
minutes, start doing that now'cause you're about to be done
on your time block.
So I would do that, Now I'mactually pretty good.
I will check it maybe once ortwice a day, but if I'm done in

(09:39):
10 minutes, I'm done in 10minutes.
If there's nothing urgent or outof the ordinary or critical or
whatever, I'm like, I'm donebecause.
What I wanna be doing isactually spending time with the
people I'm on vacation with orjust taking some time to walk on
a beach or go see something coolthat's historical.
All these things, that's thepoint of the vacation.
Um, oh, the other thing I woulddo is if you're like, I, I'm bad

(10:04):
at discipline.
Even if I set a where I'm notgonna do it, go do something
where you cannot be on yourphone.
So I used to go, I still go, um,suba diving with family and
friends, not scuba diving'causethat's, scary and takes
certification.
Um, but Suba with n which meansyou have the little mouthpiece.

(10:25):
And the tanks sit on, on thesurface they're like on little
floaty things on the surface ofthe water.
And there's a big cord where youcan go down, um, further than
you can snorkeling and you canstay down there.
And so it's like kind of inbetween snorkeling and scuba
diving.
It's scuba diving.
And I do this in Hawaii with,last year I went with my nephew
and we both went scuba divingand it was, um.

(10:47):
Whale mating season.
And so the whales under theirsurface were going crazy with
their like whale calls and likemating calls and like all these
different things and you couldhear them and it was amazing.
And it was so beautiful.
And you can't be checking youremails when you're scuba diving.
You can't be, you're not eventhinking about that stuff'cause
you're like, wow, I'm seeingamazing things in the ocean.

(11:07):
I'm hearing sounds, I, I neverhear on land or in the air.
And that's just.
Uh, a memory and experience withmy nephew in that way.
So you can, you can build these,build these events in or
excursions in to your time away.
Uh, you know, if you go to ahike where there's no cell
reception and they're like,there's no point in checking

(11:29):
your phone or even maybe, youknow, bringing your computer,
then, then you can structurethings like that.
So anyway, so Samir, I wouldjust thank you for, for your
message and thank you for beinghonest about this stuff.
I think that's really awesome ofyou.
I'm, I know that other peoplelistening are going through the
same or similar things as you.
Uh, so thank you for sharingand, I would, I would tell your

(11:49):
boss what you're up to.
I would start delegating, evenif it's small baby steps, I
would start setting the team upand the structure up so you can
lift out.
And when you get promoted, and Iwould go on vacation, I would go
scuba diving.
That's the point of this wholeepisode really, is to go scuba
diving and listen to whalemating calls.

(12:09):
That's my recommendation to you,Samir, and to the listeners, go,
go listen to whale calls and ifyou don't have access to an
ocean, then you can watchFinding Nemo and the scene where
Ellen DeGeneres as Dory makesthe whale sounds because that's
awesome and that will suffice aswell.
I'll catch you next week onleveraging leadership.