Leveraging Leadership

Clarifying Requests: A Guide to Effective Stakeholder Conversations

• Emily Sander • Season 1 • Episode 255

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0:00 | 34:21

Bill Shander explains how understanding what stakeholders really need leads to better results at work, especially for roles like Chief of Staff. He shares stories about clients asking for things like blue buttons or “ballets of data,” and how asking smart questions gets everyone on the same page. The episode covers common mistakes people make when jumping too quickly into requests and why techniques like the Socratic method work for clarifying goals.


Links Mentioned:
Bill Shander’s Website

Connect with Bill Shander on LinkedIn

Bill Shander’s Book: Stakeholder Whispering



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Who Am I?
If we haven’t met 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:
01:33 The Evolution of Data Storytelling

03:15 The Inspiration Behind 'Stakeholder Whispering'

05:12 Understanding Stakeholder Dynamics

16:58 The Power of Divergent and Convergent Questions

18:49 Common Mistakes in Stakeholder Whispering

21:27 Tactical Approaches to Clarifying and Pushing Back

28:00 The Dynamics of Hierarchy and Influence

emily-sander_1_11-05-2025_130237:

My guest today is Bill Sander, not Sander Sander, and he is the author of Stakeholder Whispering. Uncovering what People Need Before Doing What They Ask. Sounds Pretty Nifty for Chief of Staff. Bill spent years of helping people and organizations communicate complex ideas, clearly teaching millions through LinkedIn learning and workshops around the world. His new book, which I have right here, tackles one of the most common challenges at work. How to truly understand what your stakeholders need before running off to execute. Bill, welcome to the show.

bill-shander--he-him-_1_11-05-2025_140237:

Thank you very much for having me. I'm excited to be

emily-sander_1_11-05-2025_130237:

Beautiful. So first of all, like quick backdrop for people. How, how does one get to be doing what you're doing now?

bill-shander--he-him-_1_11-05-2025_140237:

You know, I always start way back because I fell into my career. It kind of happened to me. So I can't claim like a strategic path to get here. Um, but essentially I studied journalism in school. Okay. Then I, I worked one job in journalism for nine months. I didn't like it, so I, then I started my company and my company was doing in the early days. things, but this was before the webs. This

emily-sander_1_11-05-2025_130237:

Okay.

bill-shander--he-him-_1_11-05-2025_140237:

CD ROMs. That's how old I am. But then, you know, along came the web and I was doing web design and development for many years, but I always had clients who had data the data was gonna be a key part of their website. Like, you know, data, interactive data experiences. And that data visualization and data storytelling became. Really all I focused on for the last 10 or 12 years, which coincided with me starting to do courses for LinkedIn Learning and the other workshops that I do, et cetera. So, you know, it was a sort of a natural progression to do the data storytelling and visualization thing. But the other thing is that in that entire time period, all 30 years, clients would always come to me and say, Hey, let's do this. And sometimes this was a great idea and sometimes this was

emily-sander_1_11-05-2025_130237:

Not good.

bill-shander--he-him-_1_11-05-2025_140237:

Yeah, it seems like maybe that's something, but let's talk about this more. And like, you know, the classic example, like in web design when I was doing that, let's make the button blue and it's like, okay, you know, why do you need a blue button? Well, it needs to be noticeable and clickable. Okay, so you need a noticeable button. Let's make a noticeable button. And by the way, it might be blue, it might end up there, but let's talk about that. And so whispering thing has been a key part of any success that I've had because. Otherwise, yeah, to your point, like, you know, someone says do something, you jump, you do it. But if it's the wrong thing, then you know what good is it?

emily-sander_1_11-05-2025_130237:

Yeah, whenever someone says data visualization, I remember this meeting. I was in room full of people, our C's up there, and he is like, I'm, I'm trying to tell a story. I'm trying to tell a story. We have these data points. I want a. Ballet of data to dance across the screen when we give this presentation. I was like, wow, okay. He's seeing something that, that the team isn't seeing, but it's true. Like, you want, you want a story to come out of that, uh, data. So yes.

bill-shander--he-him-_1_11-05-2025_140237:

sure.

emily-sander_1_11-05-2025_130237:

that. Um, so is is the book, so I've read part of this book, I'll admit, I've not read all of it, but I've read part of it. Um. What had you write this book? Was it people going, bill, you have so much information, you have so many stories, you need to make a book, or did you say, Hey, I'm gonna actually create something focused for a certain audience?

bill-shander--he-him-_1_11-05-2025_140237:

Yeah, it was a hybrid of the two. So I've been, because of my platform on LinkedIn, I get approached by publishers all

emily-sander_1_11-05-2025_130237:

Mm-hmm.

bill-shander--he-him-_1_11-05-2025_140237:

saying, Hey, you should write a book. You should write a book. Let's do a date of his book, data of his book. And I'm like, I don't wanna do a date of biz book. They're like a million of those. Um, and so I've been approached many times, and this, you know, about a year and a half ago, whenever it was, when Wiley approached me at that moment, I had just had this idea and I was like, I don't wanna do date of his book, but this book. Like, no one talks about this. No one talks about how to have these conversations. They say, oh, you should ask people questions. Great. But like, how, um, and so it just seemed like, you know, this perfect sort of synchronistic moment where, you know, a book was suggested. I didn't wanna do the other books, and this idea had been like, swirling around in my head. So, yeah. And I think there's a real need for it.

emily-sander_1_11-05-2025_130237:

Yeah. Well thank you for writing it. And then, and as you and I were talking earlier, chief of St uh, uh, sorry. Stakeholder whisper sounded like chief of staff so much to me. I was like, oh my goodness, a chief of staff needs this in their arsenal. So one of the chapters that I did read and I loved, I have it marked here. Lemme see if I can find it real quick. This is chapter 11. Peeling the stakeholder onion and I'll just, I'll, I'm gonna quote your own book back to you if you don't mind here.

bill-shander--he-him-_1_11-05-2025_140237:

sure.

emily-sander_1_11-05-2025_130237:

you say, stakeholder whispering requires identifying your stakeholders, but it also is about making sure your stakeholders identify and recognize and prioritize their stakeholders. It's a subtle distinction, but it's critical. They need to understand who they're working for and why. Can you say more about that part please?

bill-shander--he-him-_1_11-05-2025_140237:

Sure, and, and I gotta address the first part too because Yeah. You know, listen, chiefs of staff, like the closer you get to the top of an organization, right? The who, when you're dealing with the people at the top, harder it is and yet the more necessary it is, right? Because you know, your chief of staff, you're dealing with the, the senior people, person, whoever. And they know everything, right? They are the head of it all. And so they think, boom, boom, do this, do this, do this. And they're busy, right?

emily-sander_1_11-05-2025_130237:

Oh yeah.

bill-shander--he-him-_1_11-05-2025_140237:

don't have a lot of time to think everything through, and so they rely on you to say, well, okay, that's a good idea, but how about we do blah, blah, blah, blah, blah, and to really do that translation job. So, you know, especially for chiefs of staff. Um, but then, yeah, to the point, you know, the fact is that, you know, your boss asks you to do something. Okay, but is your boss really the key stakeholder for this thing that you're doing? And nine times outta 10, they're not. you know the example of your chief of staff. So the CEO says, do XI want a, a, a, a ballet of data across the screen. Sure, let's do that. And by the way, boss, um, who's gonna be watching this ballet? gonna be looking at this data and what are they supposed to do with it? Because guess what, that's the key stakeholder. That's whose needs we really have to meet. Yeah, you too. You're the boss. You're important, but you're doing this for them. Right? And so that's what it's really all about. And you know, bosses, you know, some bosses are very good at that. They recognize that they have an audience and a customer and whoever they're doing stuff for, some bosses forget whether it's their ego or other reasons. And so yeah, our job is to really remind them and help them to reorient their focus in that direction.

emily-sander_1_11-05-2025_130237:

And you talk about even taking this to kind of the nth degree. So you talk about hierarchy and everyone has someone they're answering to or reporting to, and you can do that infinitum to, you know, the CEO and the board and the sheriff. Holders and the people's, you know, spouses at home and all the way to, to this endless cycle. And while you might not prioritize all of those stakeholder needs, even thinking about it that way and really plotting out, okay, who are my stakeholders here are, there's different types of stakeholder, and you talk about that in the chapter, but, um, maybe say a little bit more about the different types of stakeholders because people hear that word and they're like, oh. End user or my boss or, but it,

bill-shander--he-him-_1_11-05-2025_140237:

Yeah.

emily-sander_1_11-05-2025_130237:

it can be those people, but it also can be some other types of people.

bill-shander--he-him-_1_11-05-2025_140237:

That's it. And so, you know, I'll give you an example from a real life project and I talked a little bit about this project. In the book. Uh, I'm working on a project, uh, putting together a giant interactive data, a ballet of data actually for this, uh, for this particular audience. And. So I was brought in by the marketing and innovation group at this company. Um, so this person was like my client. He brought me in. He's definitely a stakeholder of mine, but clearly the users of this software, this, this interactive experience, were gonna be a key stakeholder. But there were other stakeholders, you know, like the, the media. was gonna be released at this giant conference, and they wanted press coverage within this, you know, industry that was a key stakeholder. And they, they weren't like. This aims the users. We had to make sure the functionality really reached the users, but the media had to be a little bit enticed and excited about it too. And so, yeah, you know, we're gonna prioritize them. The users, number one for sure. The, the marketing team and

emily-sander_1_11-05-2025_130237:

Yeah.

bill-shander--he-him-_1_11-05-2025_140237:

were really key at the company. And then media were, were somewhere right in there. And we had like a dozen other stakeholders, you know, like the executive VPs who run this company. They were important'cause they were gonna, they could put the kibosh on it, they weren't that important in terms of like meeting their. Needs. Do you know what I mean? And so that's the constant dance is to really find, you know, as you said, the hierarchy of of stakeholders. Really prioritize'em in the right way. Recognize that some are equally important, but have different

emily-sander_1_11-05-2025_130237:

Yep.

bill-shander--he-him-_1_11-05-2025_140237:

sometimes clashing needs, uh, and do the best you can.

emily-sander_1_11-05-2025_130237:

And one of the things you call out is a mistake you made early on in your, in your career was not having the exposure or the, the time with one of the key stakeholders where you were speaking with, you know, these people, you changed their names, but Dave and Joe and I was talking to Dave and I thought like Dave and Joe were representative of like this key person and it, it wasn't. You found out

bill-shander--he-him-_1_11-05-2025_140237:

Now.

emily-sander_1_11-05-2025_130237:

I needed to be able to have conversations way upstream. Um, and that was a learning lesson from you. So for chiefs of staff listening, I think that might be relevant as well. Mm-hmm.

bill-shander--he-him-_1_11-05-2025_140237:

It is. And what's interesting is chiefs of staff are so lucky because you actually have the ear of the top of the food chain. Um, and so you're not, you don't have this, the struggle of. S whispering by proxy as I refer to it. You don't have, you know, you're, you're talking to the, the handlers and you never get to the key person. on the other hand, of course, you have to remember, you have to have empathy.'cause the people who are trying to whisper you to get to the stakeholder,

emily-sander_1_11-05-2025_130237:

yeah.

bill-shander--he-him-_1_11-05-2025_140237:

you know, you have to sort of play that game in the middle and, you know, be do as good a job, you know, communicating by proxy as you possibly can. I know that's a key thing that you do. yet also recognize that you can't be perfect at it. And to know when to, you know what? I think you should talk to the CEO next week and I can get you 22 minutes in the calendar, make it good and maybe help them prepare

emily-sander_1_11-05-2025_130237:

Yep.

bill-shander--he-him-_1_11-05-2025_140237:

cetera. Um, but yeah, it, it's such a challenge with spring bread proxy is nearly impossible, but of course it's, it's, uh, it's inevitable. And so we have to do the best we can in

emily-sander_1_11-05-2025_130237:

Yeah.

bill-shander--he-him-_1_11-05-2025_140237:

of situation.

emily-sander_1_11-05-2025_130237:

And I know chiefs of staff listening are gonna go, okay, Emily, I, I get the concept of this. I'm all on board. What happens when my CEO and my stakeholder like, does not listen? They're not, they're not wanting to listen to this message right now, but it, I, it's key to like, get this through to them.

bill-shander--he-him-_1_11-05-2025_140237:

Yeah. So I have a chapter in the book where I talk about the trouble you'll run into, and I, I list out a whole bunch of the characters, the types of. People who are more difficult to whisper. Um, and so you can sort of at least identify them, but you know, if you're a chief of staff, you know person, how whisper able they are.

emily-sander_1_11-05-2025_130237:

Yeah.

bill-shander--he-him-_1_11-05-2025_140237:

I have another chapter in the book that talks about, you know, essentially what to do about that a little bit. But the specific tactics are so contextual that it's hard to give much specific enough advice. And so the, the vague advice is honestly. Find a new boss. You know, like if your boss is truly Unw Bowl across the board, then you know, that's probably not a great place to work. It's probably very difficult to be in that role, Sometimes. Yeah. They just don't have the time. They're, they're, they got too much going on, et cetera. you do the best you can. And what I, you know, have another chapter in the book is about influence and persuasion. Some key techniques to persuade people or really to help them persuade themselves of certain things. Um, and then I also talk a lot about. When you do have limited time, or whether you're chief of staff or whether you're, you know, lowest person on the totem pole and you only get gonna get five seconds with a key person if you're lucky, at a minimum, there's always like something you can do. So, person on the totem pole or chief of staff for the most busy CEO on the Earth. On Earth. Hey, let me ask you one question and you can ask a question as basic as, tell me more about that ballet of data. And'cause then you'll get them talking a little bit and that context can be very helpful. Or maybe you can ask a question, the second level question, which is, how am I gonna measure success? Right? And that's a question we all know we're supposed to ask all the time, but it's really, it's a good question because it gives us. Sort of the, you know, the kinds of things that they're looking for. It gives that context that becomes more specifics that'll help you figure out what they really need. And obviously if you can have an hour long conversation or a three hour long conversation, all the better. But, you know, take small bites of the apple, even when that person is, is, you know, reticent to say the least.

emily-sander_1_11-05-2025_130237:

Love that. And I always tell people, start with the bottom line. So don't give'em like the context and the caveat and this, and like start with the bottom line and then backtrack into that if they wanna hear more about that. But CEOs are. Million miles a minute, got 47 things over here and 27 things over here. You gotta be to the point snappy with your, with your information. Um, I love the questions though, kind of, I always, as a coaching question, I say, if we did that or if you did that, what would you have that you don't have now? Or what would be different than it is right now? And getting them to think of like, oh, okay. Hold on. And it kind of goes to your point earlier about. The outcomes and what the actual stakeholders will use that for or will do with that end result that you have. So I think getting to some of those questions and getting your stakeholder to think about those questions and answers can can be powerful.

bill-shander--he-him-_1_11-05-2025_140237:

It is, it can be really powerful and you know. of the most important techniques that I talk in the book, in fact, the entire, entire book is kind of oriented around this, is that this is all about the Socratic method. It's all about asking questions, and the goal of the Socratic method, which people often don't remember, is you're not asking questions to learn the answer yourself. That'll happen. I mean, you are doing that, but more importantly, you're asking questions so that they learn the answer. So as you exactly as you just described, you ask a question so that they can think. literally even literally said, you know, the idea that like, oh wait, yeah, hang on. There's gonna be a moment of whoa, whoa, ha ha. And they're gonna maybe even look up at the sky because they're gonna be truly having an insight. Possibly. That's the goal of this whole process, is to get them thinking, get them having an insight, and then they will convince themselves, oh yeah, I don't need a blue button. I don't need a ballet of data. I need this. But you're helping'em get there.

emily-sander_1_11-05-2025_130237:

And I think the trap that CEOs and chiefs of staff and all of us fall into is we wanna have the answer in quotes, like the answer. And sometimes that's not the most useful thing Sometimes. Sometimes there isn't. The answer, an answer. It's like, we've got a couple options here. They've all got pros and cons. Let's talk this through. Or let's, you know what, I'm stuck in my box. I need creative thinking. So let me ask a powerful question to get us out of this.'cause we're all kind of stuck in a rut. Um, but I love your call out there on the Socratic method where it's to get them to think. And CEOs, first of all, you gotta leave like hold space and time for them to just think. Then be able to kind of create a safe space. That might not be the right word, but CEOs are like, I'm a CEO, because I have to have the answer. I'm the decider. I make the decision, boom, boom, boom, boom, boom. And it's like, Hey, sit down. Sit back. Think about this for a little bit. Yeah.

bill-shander--he-him-_1_11-05-2025_140237:

And it is a safe space.'cause yeah, like, you know, they're not, at that moment, they're not in front of the board. You're, you're the chief of staff. You are like the closest person they they have, and if they can't talk to you, boy, they can't talk to anybody. Right. And so, yeah, they should be able to actually riff a little bit. Um, but you're a hundred percent correct. Like, yeah, they're, they're used to having the answer. They expect to have the answer. And so it can be an uncomfortable feeling. To have these conversations. But I'll tell you what my favorite projects, my favorite clients, and that project that I mentioned first was one of those, they valued me across the board. They hired me every time because they're like, bill, we love the way you guide the conversation. Forget about the execution, the conversations at the beginning of the key. And so if you can work with people who value that and they get comfortable and enjoy that process, man, that's where the magic happens.

emily-sander_1_11-05-2025_130237:

What other advice would you give to chiefs of staff who are trying to unpack or un or peel back the request or the ask from their principal, from their CEO? Like, okay, they've said like, do this, uh, let me clarify. Like, how would you guide people through that questioning?

bill-shander--he-him-_1_11-05-2025_140237:

Yeah, I mean, the simplest thing I can describe is that, so I, I have a technique that I call the dance of the six of Ws in the book. Hm. And you know the six W words, who at, when, where, why, how? Right. How's an honorary W word? Um, and the magic of those words isn't just that you can bounce around between who? Tell me who, tell me when. Tell me why. Tell me who again. Like, and that's good. Like, bouncing around is key. And it's not literally just those words, but the magic of it is that some of those words are divergent words. Why? Why is a divergent question Because. The answer is endless. I could give you a 12 hour essay on why for something, right? It's literally infinite. is convergent? When? Next Thursday, right? Like so the magic of combining and bouncing back and forth between divergent and convergent questions is twofold. Divergent is endless creativity. La have to come to a decision. Conversion answers are decisions. Okay. especially like for certain people, they're gonna be much more comfortable with one or the other. Like creative people are like, oh, let me, let me ideate all day long. And they hate to come to decisions. You know, CEOs are probably the opposite. Don't, don't let me, you know, don't make me, you know, be creative and thinker. Let me get to like the 1200 decisions I need to make. Long story short, that discomfort, whichever one is more uncomfortable than the other forces, that moment of, Ooh, wait, hold on. It, it gives, it helps get them to that insightful, uh, opportunity. in addition to their own discomfort, just the fact of bouncing back and forth between the two styles just gets the brain slightly out of balance, again, leading to more opportunities for that moment of insight.

emily-sander_1_11-05-2025_130237:

I never thought of the, those types of questions like that, but yes, it's kind of this interplay of let's, let's be up in the clouds and be a visionary, creative win. Like

bill-shander--he-him-_1_11-05-2025_140237:

Yeah.

emily-sander_1_11-05-2025_130237:

why, how, like all these things. I love, I love your description of that. What, what are like the top. Mistakes you've seen people make when they try to approach stakeholder whispering, where it's like, Ooh, no, that's, that's not how you wanna do that.

bill-shander--he-him-_1_11-05-2025_140237:

Yeah. You know, it's a good question. I've made so many mistakes in my career. It's hard for me to prioritize them. Um, you know, for sure. Not recognizing who the stakeholders are, um, and not making sure you have full access to them like we talked about before. Peeling the onion. Um. I think what you just described, the idea that every feeling like you, you should already have the answer. Or that even worse, that the, the, the whole reason I wrote the book, my boss has all the answers. So not even stakeholder whispering in the first place is probably the biggest sin. You know, your boss says jump, you say how high and you start jumping.

emily-sander_1_11-05-2025_130237:

Yeah.

bill-shander--he-him-_1_11-05-2025_140237:

And so take a moment and recognize that your boss is not, you know, the all knowing right deity. They don't always know. so your job, and we're not gonna laugh at them, we're not gonna make fun of them, we're not gonna be resentful or annoyed. It's just a human condition. It's okay. So take a moment, get the clarity you need, and then work on that. I think that's probably the most important first thing. But, uh, you know, there's a bunch of things that we do and, and you know, the most important thing I would say to remind people of is, you know, you're in your job for a reason. I don't care if you're the chief of staff or if you're like, you know, the, you know that you're mopping the floors, you're there, you got that job. You know more about mopping floors or whatever it is you do than probably anybody in your organization, or at least you know enough to be in the role that you're in and your stakeholders, I don't care if they're up here or here or here, you know, they, they need you to do what you do well and to, for you to do what you do well. You know, someone says go mop the floors. Okay, sure. Should I spend extra time in the corners'cause they're a little dingy? Or should I just do it quick?'cause I know there's a meeting in 20 minutes. You know, that's a valid question and so get the clarity you need to do it right?

emily-sander_1_11-05-2025_130237:

Yeah, and one of the things that came up when you were talking is, um, I remember one of the reasons I was successful with my principal. I had worked with him before and I kind of saw through him meaning. I wasn't in awe of his title and I wasn't in a awe of his presence. I respected him for sure. He was exceptional at what he did. But I saw him as like a, a flawed person who was crazy, crazy good, like savant, like good at certain things and just fall down disaster bad at others. And he would fully admit this, um, if he was here. Uh, and, but I, I, I feel like many people get in the trap you just described, which is like, jump how high.

bill-shander--he-him-_1_11-05-2025_140237:

Yeah.

emily-sander_1_11-05-2025_130237:

you must know everything'cause you have CEO, you know, after your, after your name. So I'm wondering, do you have any tactical and practical examples of how you would clarify something or push back on something? I know it's context dependent, so you're not gonna be able to cover every scenario, but just pick a scenario you've seen and maybe share just some, some tactical takeaways if you have'em.

bill-shander--he-him-_1_11-05-2025_140237:

Yeah, I mean, so one thing is that, you know, this is, I can use the, the website Design blue button example again. You know, I am the expert in that situation. I'm a designer and I know my job is to solve my client's problems, and I, and I had to understand what the real problem was in order to get to the solution. And so, you know, I use the phrase pushback all the time. So this is not criticizing you, but I have to remind myself also, it's not really about pushing back, it's about getting clarity. And so when I'm really doing stakeholder whispering at my best. I'm asking for clarity and, and, and I'm explaining why, but I'm not pushing back on their blue button. I'm saying blue button sounds like a great idea. Tell me more about why you think a blue button is the right answer. What are you trying to accomplish when by making it a blue button? So I'm, I'm asking questions. That's the other beautiful thing about asking questions is, is you don't make'em defensive. You know, you, you're helping them bring more light to the issue. I'm trying to think of another example. Uh. You know, I've worked on a million projects, you know, speaking engagements, all the stuff that I do. Um, and actually I, I, I have another example. So like I do a lot of training companies hire me to train their people on data storytelling and visualization. And a lot of times, you know, it's sort of like I want the ballet of data as you described. Uh, you know, a company will say, oh, we need you to come in and teach our people. data visualization, data visualization, data visualization. I say, okay, cool, cool. Let's talk about your people. Tell me more about them. Who are they? What do they do? What departments are they in? How much experience do they have with data visualization, et cetera. You know, times a hundred. And usually by the end we find out really what they need is less about data visualization. Certainly not, you know, working the software. What they really need is storytelling and communication

emily-sander_1_11-05-2025_130237:

Yeah.

bill-shander--he-him-_1_11-05-2025_140237:

and so. not, I, I never say, I'm sure they don't need data visualization, but it's, it's just getting to, and I may be thinking that in my head by the way, it's getting to, you know, I, I, I guess asking leading questions, really hard balance. It's open-ended questions. Tell me more about that. And eventually, and dance at the six Ws for sure. And eventually slightly leading questions as I start to sense that. Okay. I think I might be right. I think maybe it's more about storytelling than data is. I'll start to lean into that. Do you think maybe, you know, maybe we should teach storytelling along with the visualization Oh yeah, yeah. Storytelling for sure. And then, um, you know, maybe, maybe we shouldn't teach software at all, really. Maybe it's more about the big ideas. What do you think? So, but I say that stuff to the end, you know, if you ask the leading questions at the beginning. You know, now your bias is, is introduced. You're, you're no better than the CEO who thought they had the brilliant idea. You're gonna push your brilliant idea. And now, now it's like a conflict them, get them thinking a certain way, and then at the end you can be a little bit more leading in order to make sure. And you're still clarifying, you know, it sounds like maybe storytelling you, you're still clarifying, but even though you're sort of leading the witness a little bit.

emily-sander_1_11-05-2025_130237:

No, I like that. And it's, it's, it's their idea. They, they answered the question like, oh my gosh, that's a brilliant idea. We should do more storytelling. Um,

bill-shander--he-him-_1_11-05-2025_140237:

Yeah.

emily-sander_1_11-05-2025_130237:

how do you, so we talked about CEO's time being limited, or any stakeholder might be like, you gotta be like on the point on point if you have all these questions that. Gain clarity and you kind of be leading at the end. What if you don't have that time to ask all those questions? What do you like? What do you do?

bill-shander--he-him-_1_11-05-2025_140237:

It is so hard. You know, I would say that, you know, you prepare. You're as, as best you can before the meeting. And as you, obviously, you're gonna be given hopefully, a timeframe for the meeting. So, you know, you

emily-sander_1_11-05-2025_130237:

Sure.

bill-shander--he-him-_1_11-05-2025_140237:

or 12 minutes. Um, and even if I've, if I know I've given 12 minutes, I'm gonna prepare a 30 minute conversation, but, but put the stuff that I may not get to at the bottom, and I just make sure those first two or three or four questions get to the absolute heart of the matter, as, you know, as, like you said, get to the good stuff first. Um, now that being said, it is hard to build, as I described it. When that's the situation. Yeah, sometimes you just can't do it that way.

emily-sander_1_11-05-2025_130237:

Yeah.

bill-shander--he-him-_1_11-05-2025_140237:

Sometimes, you know, if I'm given like, listen, CEO says do X, and I know that X plus Y divided by Z is probably the better approach. I may go in there and say, listen, X sounds like a great idea. You know, I was thinking you if we added Y and divided by ZI think that, and here are the three reasons why I think that might be a good idea. What's your reaction to that? You know, do you think I'm crazy or did blah, blah blah? You know, so sometimes you gotta lead the witness a little earlier. And again, that's the beauty of the chief of staff position, is that they know you and trust you. You go in the room, you have their respect. Um, and you probably allow, you can get away with a little bit more with leading the witness than the rest of us, right? Um, but even so, go in there with the tone of getting clarity. because even in that dynamic of chief of staff and the CEO, you know, I'm sure you well know everybody listening. They, you know, sometimes you know that trust can be faltered or sometimes they, they recognize your flaws and your biases, et cetera. So the more it can feel like you're asking for their brilliant input and their clarity, that then they'll never, you'll never have that defensive moment, even though you have a good, better relationship than

emily-sander_1_11-05-2025_130237:

Yeah, and I mean, I think you're hitting on it. I, we've talked about this, but clarity, it's not confrontation, it's just we're getting clear, like I'm, I'm trying to. Help me understand. I just wanna understand better so I'm clear type of thing.

bill-shander--he-him-_1_11-05-2025_140237:

Yeah.

emily-sander_1_11-05-2025_130237:

I mean, chiefs of staff, obviously their principal is their main stakeholder, but they have many others. And so you might not have the same dynamics in the relationship. You might not have the time. And so I think you know, it, it does depend and it is context dependent and sometimes it's give them like the good stuff, but make it so like, you want, like you want more of this, make'em ask for more. Like hold on. Like can we get something else on calendars to follow up on that? Absolutely.

bill-shander--he-him-_1_11-05-2025_140237:

Yeah, that's a great point. Like for sure if you, if you have these great conversations and even, even when they're, especially if you do an awesome job with a five minute meeting, yeah. They're gonna gain more trust and more trust and more trust. And before you know it, everything they do, they're gonna give you an hour.'cause they know you're bringing so much value to the

emily-sander_1_11-05-2025_130237:

Yeah, and you can still kinda lead the witness and it's not manipulative. I mean it is, but in a good way where you can even say at the end, like, and I can prepare like this, this, and this to show you for next time. Would that be helpful? Absolutely. It's like so and so get that on calendar so you can kind of position this and play this in lots of different ways.

bill-shander--he-him-_1_11-05-2025_140237:

definitely.

emily-sander_1_11-05-2025_130237:

Yeah. Gotcha. For, so you mentioned it before, but chiefs of staff also have people whispering to them, wi trying to whisper in their ear, trying to get information outta them, trying to jockey for position. If you just told them, this would be so much better. Trying to get in the room with the, on the flip side, how would you receive whispers, if that's the right way to say?

bill-shander--he-him-_1_11-05-2025_140237:

Hmm. Yeah. So yeah, sometimes you can't give him access, right? You just can't do it. There's no time. For whatever reason, know, then you know you need to be. You, you're the person. They're whispering by proxy and you do the best you can to give them the information you have. You know this, it's kind of a simple answer and that sometimes no is no right. Sometimes you just can't give them what they want and you just do the best you can to give'em what you can. Um, you know, I suppose you can always advise them, you know, if the reason you're not giving them access is'cause they're too disorganized, they don't know what they're doing, they're bad at whispering, et cetera, then you know, you can always advise them, you know. Here's the, here are the three things I would need you to do in order to give you time with so and so. Um, but that's probably like your day to day. Like, you know, I don't think I'm, I'm probably not adding much value in with that answer.

emily-sander_1_11-05-2025_130237:

No, it's, I mean, I think it's important though'cause the chief of staff role is so dynamic and, and. The chief of staff is powerful in a different way than A-C-E-O-I would say, but they're, they're so influential in their own right. And so being able to hold that and carry that weight, um, well, I think is part of your job. Uh, and by the way, there is, this is just kind of a personal thing, but the beginning of, of this one chapter, I kind of mentioned the hierarchy, but you said. There is no end to the hierarchy of power. Everyone answers to someone in some capacity. And it just struck me that, you know, our culture and in the business world, hierarchy is like ingrained in us from, you know, little kids just like school and listen to the teacher and kind of in uh, org charts and certainly in the military or all these different contexts. And I'm wondering how you just think about. Hierarchy or power dynamics or just like, I'm here to help you. I'm here to get clear. Sure. You might be the ultimate decision maker in this particular instance, but you're, no, you don't know all the answers. I'm the expert in this area. How do you kind of, what do you, what do you make of all that?

bill-shander--he-him-_1_11-05-2025_140237:

Yeah, it's so interesting'cause it is true. I mean, hierarchy is an infinite circle. It really, there is no end to it. Everybody answers to somebody and like, okay, so you know, you go all the way up the chain. The CEO may be making the decision, but yeah. The CEO has, has been arguing with his wife for the last three weeks. And so, you know, is that influencing things and might he, this might be a scheduling thing and he has to consult with his wife in order to blah, blah, blah, blah. Like there, there's always something now that she may not be your stakeholder for this context, but in a way she might be like, there might be some dynamics there. and then, yes, like I know when I'm speaking with my clients and, and it's very, in an interesting position because I am brought in as an expert. When I'm brought in to teach people data storytelling or to do project work or whatever. So I have that glow of expertise around me, lucky me, um,'cause people really listen to experts. But even if you're not an expert, um, the fact is you can leverage other people's expertise. So if you're being brought in to work on a project, on something, your boss, you know, obviously is hierarchically above you. boy, if you bring in research in your pocket and saying, well, here's the reason why we need to do it this way, this way, this way.'cause you know, this Harvard professor said, so then suddenly they're listening to the Harvard professor, but it's coming outta your mouth. And now, like the hierarchy, it's not like it's completely flipped at all, but you have a seat at the table for a reason. so yeah, hierarchy is not. Linear, you're down here, there, up there. It's far more dynamic. It's far more interesting, and that's where you know, the art of, you know, these conversations, asking good questions, getting clarity, and also a little bit of persuasion, uh, can really be really very important just to help these conversations be as productive as possible.

emily-sander_1_11-05-2025_130237:

Influence and persuasion. These are like the, the. Arsenal or the bread and butter for chief of staff.'cause I have so many chiefs of staff come to me and be like, Emily, how can I do this? I'm like, what do you mean? Like the chief of staff? But yeah, but like I don't have any direct reports and I'm like, don't have any direct authority. Um, and most of the time, not all the time, but most of the time a chief of staff will have more influence than they think. So in the same way that the title CEO will proceed, someone, it's like, it's the CEO coming into the room, that title precedes them. Same with chief of staff is coming in, but if you shrink back, then you diminish your own. Influence and powers of persuasion. So, um, yeah, I'm just really interested. This is just like a personal question of like, I've been in spots where I'm like, I feel so small in this room. Like, I am nobody. No one look at me. I'm just here to listen and learn. But, you know, I have a lot of value to, to bring to the table.

bill-shander--he-him-_1_11-05-2025_140237:

Well, it's so funny. It's like perception is everything, right? Their perception of it and your possession of, yeah, am I an assistant or am I chief of staff, right? Am I someone who's like running the whole show in a way pretty much? Or am I just sort of helping out here and there and just, yeah, the title and the way we just think about that role. Uh, and then yes, also how your colleagues actually perceive that has a huge, huge impact. There's no question.

emily-sander_1_11-05-2025_130237:

Yes, there's so much more that we could get into and maybe we'll do a round two bill. Um, but, uh, if people wanna pick up this book, which I would highly recommend, hold it up here one more time. Where can they find this? And if they're like, oh, I need to talk to Bill about storytelling or data visualization, or something else, where is the best spot for people to find you?

bill-shander--he-him-_1_11-05-2025_140237:

Yeah, you can always find me on my website, bill sander.com. I'm also of course, on LinkedIn and the book is on. What, what's the phrase everywhere where books are sold? Right, so it's on Amazon, of course, and everywhere else online. And, uh, I, I don't know where it is in stores per se, physical stores, but uh, you know, Google it, you'll find it, or just look on my web website and there's a link to it

emily-sander_1_11-05-2025_130237:

We'll have all those links in the show notes, but Bill, thank you very much.

bill-shander--he-him-_1_11-05-2025_140237:

Thank you so much, Emily.