Leveraging Leadership

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

• Emily Sander • Season 1 • Episode 224

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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

emily-sander_1_10-01-2025_120302:

Our listener question for today is I'm a chief of staff, and right now I'm juggling three very different presentations, an internal all hands update, a customer facing pitch to a potential strategic partner, and an upcoming board meeting. I feel like I have the big, chunky stuff covered, the numbers, the updates, the basic storyline, but it all feels kind of bland. I'm struggling with how much to make each, sorry. I'm struggling with how to make each one meaningful and compelling for its specific audience instead of just repackaging the same information three different ways. What is the best approach? So this content really resonates, and this is from Carlos in Texas. Alright, Carlos, nice question here. Thank you. Um, first thing I would say is. You might repackage some information. Yes, And then I would say there's probably specific information for each one of these three scenarios. So internal all hands is more internal. There's more like, Hey, give us kind of behind the scenes what's happening. What does it mean for us as employees? Customer facing is obviously more external, and board meeting is obviously more, it's internal, external, strategic, long-term business valuation depending on your board makeup, et cetera, et cetera. So I would, um, use a lot of. Maybe the base core information as the same, and then make sure you have that specific exclusive information for each one of those audiences as well. The other thing I would say, and this is a cool trick for, not a trick, this is a cool tool or strategy to use for these three and many, many other scenarios where you're presenting to different groups. Think through the previous questions that you have gotten, you have received in each one of these three scenarios. So take an all hands meeting. So I'm not sure how long you've been chief of Staff Carlos, but let's just say you've been here long enough to have more than one all hands meeting. You probably got questions from that. Whether it was a formal qa, maybe people can submit their questions in advance. Maybe they can ask questions live. Um, if it's a in-person town hall, they grab a microphone. If it's online, maybe they drop some questions in the chat, whatever it is. But are there questions you get? Sometimes it's anecdotal kind of after the fact. You hear kind of questions in the hallways or questions that pop up when you're in different meetings, ref referencing and referring back to the all hands. So think through like take a minute, take a beat and think through, huh? What were the questions we got at the last all hands meeting? And there's gonna be obviously some very specific questions that were like, okay, yeah, that was for that specific thing that happened in that specific time period. Look for trends across the questions. Oh. Oh wow. We always tend to get this type of question. Um, we always get questions around. Pay raises. We always get questions around, is this one office shutting down?'cause that's kind of been in the back of people's minds for 12 months now. We always tend to get questions around, are we going to go after this type of customer or that type of customer? So look back and say, are there some patterns or trends on. Category designation, just type of question, how do we do this? Is it internally focused? Is it externally focused? Are people paying attention to like the, the internal office logistics internally? Are they paying attention to the customer churn externally? Are they paying attention to the industry stuff? So pick out some of those patterns and trends if you can. And then front run them. And fold them into your actual presentation this time and see if you can answer some of those things within your presentation. You or the team can answer some of those things in your presentation. Same exact thing with the, uh, customer facing pitch to a potential partner and an upcoming board meeting. So both of those things you should 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 only one presenting in either one of these scenarios, at least I hope not. So you can rely on your team and ask them, Hey, let's think through as a group, or maybe you can do it individually and we can come back as a group. Or maybe you do it individually and you send them to me individually. What questions have you received in these scenarios? Team, what questions do we tend to get in a customer facing pitch to a potential strategic partner? And they should have, you know, q and a and follow up questions and maybe RFP questions and official questions they can reference. And then like, look, I had, you know, drinks with this guy over here and he told me like, we didn't, we didn't cover this part. This was the main piece. Whatever it is, collect those data points and go, okay, again, look for patterns, look for trends. For this strategic partner, are there like strategic partners that you have presented to in the past? Are there similar types of partners that you have pitched to in the past? Can you. Weight them heavily, and you're like, oh, okay. these kinds of partners tend to ask these questions. They wanna know these things and fold that into your actual presentation front. Run that. Same thing with board meetings. You should have tons of data from your team, from being in previous board meetings yourself, If your principal is the CEO, that's great. You should have a funnel and channel of data there. Uh, CFO are usually, CFOs are usually good, good people to talk to about this as well. And then if you've sat in board meetings and or you've run point on preparing board meetings and board governance. You might have direct channels and connections to board members, in which case I would ask them specifically, Hey, thinking about what we talked about last time, and you think through the questions and think through the follow ups they ask you for, we're proposing presenting this. Does that match with what you wanna hear? Does that match with what you want to us to cover as a, as an executive team? So taking the previous questions from all of those scenarios can be really helpful and informative to bake that into the actual presentation this time. I see this as an iterative process where you start with, like you said, uh, the big chunky stuff, which is like, yep, here's the basic stuff that most 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. So you're iterating each time. So each repetition you get closer and closer and closer to what they actually want to hear. And so you have less reactive questions'cause you've preempted them. So that's a strategy that I, I've certainly used myself that I talk to people about using all the time, but really listen to questions. Um, one, one person I was just talking to. When they got questions in a presentation, they took that as bad. They took that as a negative where Emily, I failed because I didn't present the right information. And there's certain scenarios where it's like, uh, yeah, you should have prepped for that. And that was due to your lack of preparation, which was an obvious question you were gonna get. That's to one side, but there's a whole other. Realm of this where you can't possibly predict every question, but you can use every question as a learning opportunity going, oh, that's a really good question. That totally makes sense. I totally understand why you're asking and that's so interesting and that's just, let me think about that. Maybe letting me think about that out loud. Maybe let me pull some initial stats on the fly and share that. Maybe let me say, that's a great question. I'll get back to you, but questions. Can be ample fodder for future presentations. So take those as like incoming data points where they're almost a gift and this person said, I see'em as like incoming fire. I'm just being attacked and attacked by questions. And you know, there's certain scenarios where. For whatever reason, I've been in board situations where certain members are trying to do that for dramatic effect or to make themselves feel better, to push you down or whatever. So there's certain scenarios like that, those to one side for a second. Um, uh. There's lots of questions that are just like, Nope, I didn't think of that. Which is not a horrible thing, but that's a really interesting question. You care about that and maybe you ask them a follow-up question to dig into, like, why do you care about that? What are you gonna use my answer for? Or how does that help you make a decision or what, you know, what brought that question up? Anything you can do to unpack that and peel back the onion just a little bit to understand. Oh, that's how you think about it. If that's how you think about this, oh my gosh. We need to present this section like this to you. Yes. That would be amazing. Okay, so every time we come back to you board member, we're doing that like this next time. Got it. Click. One thing I wanna go back to, I said set the questions aside where they're like kind of a incoming fire situation. You can still run this process and run this thought experiment for those types of questions too. Just know there's kind of an extra layer of politics that might be in there, but they're asking for a reason. And even if you understand, oh, they wanna look good, they wanna call something out, they wanna make sure that, um. The rest of the board knows that they did that, that they brought that customer and that's why that pipeline, those pipeline numbers look so good is'cause they brought that in. Okay, good to know. Like you're kind of shooting down other members of my team'cause they aren't doing this stuff, but whatever you want credit, you want to look good in front of the rest of the board. Got it. Bake that into either your next presentation in the slides and or your talk track. And maybe they're still gonna have to say it'cause there's just, there's just those kind of people out in the world. But maybe you can front run that too. So all the questions you get are like incoming data points. Like gif. Yeah. Lucky Charms, whatever. Whatever. Like gold stars. Oh my gosh. Okay. And just use that to iterate every time you go. Okay. Let me come back to your question to make sure I answer. What is the best way to approach so the content really resonates? Yeah. Okay. So you're talking to employees, customers, and the board. So making sure it really resonates. Again, use the big chunky blocks. I think that's a good starting point. Think through what specific information each one of these groups would, um, would wanna hear about and would be relevant to them. So certainly for instance. Certain things you would say to a customer aren't relevant for an all hands, um, meeting. Same thing for like, stuff you share at the board might not be super relevant to a prospective customer or a partner. So just tailoring it in that sense and then taking the questions you've gotten in previous discussions, presentations, meetings, et cetera, and folding those in to your current presentation and really taking time to think through like, okay, let me take half an hour. To brainstorm and think through the questions. Let me throw this out to the team to see what they come back with. Uh, but I think those would be good strategies to do that. And then. You know, there's classic like surveys and follow ups and kind of official touch points with certainly, uh, your employees all hands. Certainly the board, even customers, Hey, even if we lost the deal with the customer, getting that feedback loop where it's just like, Hey, tell us what we could have done differently next time. Thank you so much. Any feedback they give you is just, thank you so much. That's, uh, that's super helpful. We're not trying to save you anymore. We're try not, not trying to negotiate anymore. We just simply want the feedback type of thing. Um. In my experience, the board will give you feedback. So you're gonna get that whether you like it or not. Uh, so you can use that as a feedback loop as well. Okay, Carlos, thank you so much for your question. Hopefully this answered it and was helpful. Feel free to follow up with, anything else you have or was top of mind for you and for everyone else listening, if you have a question, please feel free to send that in. You can drop it in the comments. You can find me on LinkedIn and DM me. Or you can email me directly at Emily at next level. Coach, and I'll catch you next time on leveraging leadership.