Listener Question: Making Presentations Pop: Tailoring Content for Employees, Customers, and the Board

A Chief of Staff struggles to make three different presentations - an internal all hands update, a customer pitch, and a board meeting - feel meaningful and tailored for each audience. Emily suggests using common core info but adding exclusive details for each group, plus using questions from past meetings to anticipate concerns and adjust content. Real examples include noticing trends in employee questions about pay raises or office changes, collecting follow-up questions from strategic partners, and asking board members what matters most to them.

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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:

01:08 Understanding Different Audiences
02:02 Leveraging Previous Questions
03:06 Identifying Patterns and Trends
04:22 Collaborating with Your Team
05:37 Handling Board Meetings
06:58 Embracing Questions as Data Points
10:31 Conclusion and Final Tips

Episode Transcript

emily-sander_1_10-01-2025_1 (00:25):
Our listener question for today is
I'm a chief of staff, and rightnow I'm juggling three very
different presentations, aninternal all hands update, a
customer facing pitch to apotential strategic partner, and
an upcoming board meeting.
I feel like I have the big,chunky stuff covered, the
numbers, the updates, the basicstoryline, but it all feels kind
of bland.

(00:46):
I'm struggling with how much tomake each, sorry.
I'm struggling with how to makeeach one meaningful and
compelling for its specificaudience instead of just
repackaging the same informationthree different ways.
What is the best approach?
So this content reallyresonates, and this is from
Carlos in Texas.
Alright, Carlos, nice questionhere.

(01:07):
Thank you.
Um, first thing I would say is.
You might repackage someinformation.
Yes, And then I would saythere's probably specific
information for each one ofthese three scenarios.
So internal all hands is moreinternal.
There's more like, Hey, give uskind of behind the scenes what's
happening.
What does it mean for us asemployees?
Customer facing is obviouslymore external, and board meeting

(01:30):
is obviously more, it'sinternal, external, strategic,
long-term business valuationdepending on your board makeup,
et cetera, et cetera.
So I would, um, use a lot of.
Maybe the base core informationas the same, and then make sure
you have that specific exclusiveinformation for each one of
those audiences as well.
The other thing I would say, andthis is a cool trick for, not a

(01:53):
trick, this is a cool tool orstrategy to use for these three
and many, many other scenarioswhere you're presenting to
different groups.
Think through the previousquestions that you have gotten,
you have received in each one ofthese three scenarios.
So take an all hands meeting.
So I'm not sure how long you'vebeen chief of Staff Carlos, but

(02:14):
let's just say you've been herelong enough to have more than
one all hands meeting.
You probably got questions fromthat.
Whether it was a formal qa,maybe people can submit their
questions in advance.
Maybe they can ask questionslive.
Um, if it's a in-person townhall, they grab a microphone.
If it's online, maybe they dropsome questions in the chat,

(02:34):
whatever it is.
But are there questions you get?
Sometimes it's anecdotal kind ofafter the fact.
You hear kind of questions inthe hallways or questions that
pop up when you're in differentmeetings, ref referencing and
referring back to the all hands.
So think through like take aminute, take a beat and think
through, huh?
What were the questions we gotat the last all hands meeting?

(02:57):
And there's gonna be obviouslysome very specific questions
that were like, okay, yeah, thatwas for that specific thing that
happened in that specific timeperiod.
Look for trends across thequestions.
Oh.
Oh wow.
We always tend to get this typeof question.
Um, we always get questionsaround.

(03:17):
Pay raises.
We always get questions around,is this one office shutting
down?
'cause that's kind of been inthe back of people's minds for
12 months now.
We always tend to get questionsaround, are we going to go after
this type of customer or thattype of customer?
So look back and say, are theresome patterns or trends on.

(03:38):
Category designation, just typeof question, how do we do this?
Is it internally focused?
Is it externally focused?
Are people paying attention tolike the, the internal office
logistics internally?
Are they paying attention to thecustomer churn externally?
Are they paying attention to theindustry stuff?
So pick out some of thosepatterns and trends if you can.

(03:59):
And then front run them.
And fold them into your actualpresentation this time and see
if you can answer some of thosethings within your presentation.
You or the team can answer someof those things in your
presentation.
Same exact thing with the, uh,customer facing pitch to a
potential partner and anupcoming board meeting.

(04:19):
So both of those things youshould have reps on or the team
should have reps on.
Let's just say for example,you're a brand new chief of
staff.
You are probably not the onlyone presenting in either one of
these scenarios, at least I hopenot.
So you can rely on your team andask them, Hey, let's think
through as a group, or maybe youcan do it individually and we
can come back as a group.
Or maybe you do it individuallyand you send them to me

(04:41):
individually.
What questions have you receivedin these scenarios?
Team, what questions do we tendto get in a customer facing
pitch to a potential strategicpartner?
And they should have, you know,q and a and follow up questions
and maybe RFP questions andofficial questions they can
reference.
And then like, look, I had, youknow, drinks with this guy over

(05:03):
here and he told me like, wedidn't, we didn't cover this
part.
This was the main piece.
Whatever it is, collect thosedata points and go, okay, again,
look for patterns, look fortrends.
For this strategic partner, arethere like strategic partners
that you have presented to inthe past?
Are there similar types ofpartners that you have pitched
to in the past?

(05:23):
Can you.
Weight them heavily, and you'relike, oh, okay.
these kinds of partners tend toask these questions.
They wanna know these things andfold that into your actual
presentation front.
Run that.
Same thing with board meetings.
You should have tons of datafrom your team, from being in
previous board meetingsyourself, If your principal is
the CEO, that's great.

(05:44):
You should have a funnel andchannel of data there.
Uh, CFO are usually, CFOs areusually good, good people to
talk to about this as well.
And then if you've sat in boardmeetings and or you've run point
on preparing board meetings andboard governance.
You might have direct channelsand connections to board
members, in which case I wouldask them specifically, Hey,

(06:05):
thinking about what we talkedabout last time, and you think
through the questions and thinkthrough the follow ups they ask
you for, we're proposingpresenting this.
Does that match with what youwanna hear?
Does that match with what youwant to us to cover as a, as an
executive team?
So taking the previous questionsfrom all of those scenarios can
be really helpful andinformative to bake that into

(06:26):
the actual presentation thistime.
I see this as an iterativeprocess where you start with,
like you said, uh, the bigchunky stuff, which is like,
yep, here's the basic stuff thatmost people cover in these
scenarios.
And then every time you do it,you wanna refine it or fine tune
it and make it a little better.

(06:46):
So you're iterating each time.
So each repetition you getcloser and closer and closer to
what they actually want to hear.
And so you have less reactivequestions'cause you've preempted
them.
So that's a strategy that I,I've certainly used myself that
I talk to people about using allthe time, but really listen to
questions.
Um, one, one person I was justtalking to.

(07:09):
When they got questions in apresentation, they took that as
bad.
They took that as a negativewhere Emily, I failed because I
didn't present the rightinformation.
And there's certain scenarioswhere it's like, uh, yeah, you
should have prepped for that.
And that was due to your lack ofpreparation, which was an
obvious question you were gonnaget.
That's to one side, but there'sa whole other.

(07:32):
Realm of this where you can'tpossibly predict every question,
but you can use every questionas a learning opportunity going,
oh, that's a really goodquestion.
That totally makes sense.
I totally understand why you'reasking and that's so interesting
and that's just, let me thinkabout that.
Maybe letting me think aboutthat out loud.

(07:53):
Maybe let me pull some initialstats on the fly and share that.
Maybe let me say, that's a greatquestion.
I'll get back to you, butquestions.
Can be ample fodder for futurepresentations.
So take those as like incomingdata points where they're almost
a gift and this person said, Isee'em as like incoming fire.
I'm just being attacked andattacked by questions.

(08:16):
And you know, there's certainscenarios where.
For whatever reason, I've beenin board situations where
certain members are trying to dothat for dramatic effect or to
make themselves feel better, topush you down or whatever.
So there's certain scenarioslike that, those to one side for
a second.
Um, uh.
There's lots of questions thatare just like, Nope, I didn't

(08:38):
think of that.
Which is not a horrible thing,but that's a really interesting
question.
You care about that and maybeyou ask them a follow-up
question to dig into, like, whydo you care about that?
What are you gonna use my answerfor?
Or how does that help you make adecision or what, you know, what
brought that question up?
Anything you can do to unpackthat and peel back the onion

(08:58):
just a little bit to understand.
Oh, that's how you think aboutit.
If that's how you think aboutthis, oh my gosh.
We need to present this sectionlike this to you.
Yes.
That would be amazing.
Okay, so every time we come backto you board member, we're doing
that like this next time.
Got it.
Click.
One thing I wanna go back to, Isaid set the questions aside

(09:20):
where they're like kind of aincoming fire situation.
You can still run this processand run this thought experiment
for those types of questionstoo.
Just know there's kind of anextra layer of politics that
might be in there, but they'reasking for a reason.
And even if you understand, oh,they wanna look good, they wanna
call something out, they wannamake sure that, um.

(09:42):
The rest of the board knows thatthey did that, that they brought
that customer and that's whythat pipeline, those pipeline
numbers look so good is'causethey brought that in.
Okay, good to know.
Like you're kind of shootingdown other members of my team
'cause they aren't doing thisstuff, but whatever you want
credit, you want to look good infront of the rest of the board.

(10:04):
Got it.
Bake that into either your nextpresentation in the slides and
or your talk track.
And maybe they're still gonnahave to say it'cause there's
just, there's just those kind ofpeople out in the world.
But maybe you can front run thattoo.
So all the questions you get arelike incoming data points.
Like gif.
Yeah.
Lucky Charms, whatever.

(10:25):
Whatever.
Like gold stars.
Oh my gosh.
Okay.
And just use that to iterateevery time you go.
Okay.
Let me come back to yourquestion to make sure I answer.
What is the best way to approachso the content really resonates?
Yeah.
Okay.
So you're talking to employees,customers, and the board.
So making sure it reallyresonates.
Again, use the big chunkyblocks.

(10:46):
I think that's a good startingpoint.
Think through what specificinformation each one of these
groups would, um, would wannahear about and would be relevant
to them.
So certainly for instance.
Certain things you would say toa customer aren't relevant for
an all hands, um, meeting.
Same thing for like, stuff youshare at the board might not be

(11:07):
super relevant to a prospectivecustomer or a partner.
So just tailoring it in thatsense and then taking the
questions you've gotten inprevious discussions,
presentations, meetings, etcetera, and folding those in to
your current presentation andreally taking time to think
through like, okay, let me takehalf an hour.
To brainstorm and think throughthe questions.

(11:27):
Let me throw this out to theteam to see what they come back
with.
Uh, but I think those would begood strategies to do that.
And then.
You know, there's classic likesurveys and follow ups and kind
of official touch points withcertainly, uh, your employees
all hands.
Certainly the board, evencustomers, Hey, even if we lost
the deal with the customer,getting that feedback loop where

(11:50):
it's just like, Hey, tell uswhat we could have done
differently next time.
Thank you so much.
Any feedback they give you isjust, thank you so much.
That's, uh, that's superhelpful.
We're not trying to save youanymore.
We're try not, not trying tonegotiate anymore.
We just simply want the feedbacktype of thing.
Um.
In my experience, the board willgive you feedback.
So you're gonna get that whetheryou like it or not.
Uh, so you can use that as afeedback loop as well.

(12:11):
Okay, Carlos, thank you so muchfor your question.
Hopefully this answered it andwas helpful.
Feel free to follow up with,anything else you have or was
top of mind for you and foreveryone else listening, if you
have a question, please feelfree to send that in.
You can drop it in the comments.
You can find me on LinkedIn andDM me.
Or you can email me directly atEmily at next level.
Coach, and I'll catch you nexttime on leveraging leadership.