Stop Taking Orders, Start Asking Questions: Stakeholder Whispering with Bill Shander [Full Transcript]

This is the full transcript of episode 10 of Creative Ops Compass, “Stop Taking Orders, Start Asking Questions: Stakeholder Whispering with Bill Shander.” Bill has spent 30 years in creative and technical work, specializing in data visualization and storytelling, and he's the author of a book called Stakeholder Whispering. In this conversation, we talk about why stakeholders rarely know what they actually need, how the Socratic method can guide them toward clarity, and why that skill matters even more now that AI will happily execute whatever it's asked, whether or not that's the right thing to do.

You can listen to the full episode here.

---

Intro

Jesse Krinsky: Welcome to Creative Ops Compass, your navigation system for turning creative chaos into strategic impact. My name is Jesse Krinsky. I'm a creative operations consultant and the founder of In Focus Consulting. I help in-house creative teams streamline workflows, improve stakeholder relations, and elevate their role as strategic partners.

Bill Shander: Everything is vague, and our job is to clarify requests before we do them. If you just recognize that before you jump to it and start executing on tasks, hitting pause is the first and most important lesson.

Jesse Krinsky: Today I'm talking with Bill Shander. Bill has spent 30 years in creative and technical work, specializing in data visualization and storytelling. And he's the author of a book called Stakeholder Whispering. The book deals with one of the biggest problems I see with in-house creative teams: doing what's asked, not what's needed. And that costs time, money, and credibility. Bill and I spoke about why stakeholders rarely know what they actually need, the questions that unlock better work, and how leaders can build teams that think strategically, not just execute tactically.

Why Your Stakeholders Don't Actually Know What They Need

Jesse Krinsky: Bill, thank you so much for speaking with me today. I read your book, and I'm only going to be mildly hyperbolic here. I think it's more valuable than an MBA education, and I'll get to that in a minute. But first, your book is called Stakeholder Whispering. The cover gets right to the core of it. It says “uncover what people need before doing what they ask.” Give us some more detail. Help us understand what this book is and why you wrote it.

Bill Shander: Thank you for having me, Jesse. And I really appreciate what you said. The basic idea is that, being in the creative profession for 30 years, our stakeholders often don't know what we're talking about. They're not designers, they're not technical people. I used to do web design and development, and they would come along and say, “Hey, make us a website.” I'd be like, okay, websites are hot right now, everybody needs a website, I'm not going to question that one. But then they'd say, “make the buttons blue.” And I'd say, okay, maybe you like blue, but why blue? And so we'd have these endless conversations to try to figure out why are you asking me to do the thing you just asked me to do. It's so common in design to recognize that our stakeholders just often don't know what they actually need. A good designer's job is to figure out the true need before we jump in and start doing stuff. It came very naturally when I was approached to do a book that this was the book I really wanted to write, because it's such an important topic. Not enough people really talk about it.

Jesse Krinsky: I'm so glad you did write this book. So I said a second ago that I think it's more valuable than an MBA education. Here's why. I found myself working in house, managing creative strategy at a global life sciences company. This is true for a lot of creatives who go in house for the first time. They find that they're round pegs in square holes. They're used to being in an environment like a creative agency, where creative is the center of everything. But that's not the case when you're in a corporate environment. I was constantly struggling to communicate the value of the work that I was doing and getting my stakeholders, who were obviously just Philistines, to understand why their ideas were not the right thing to do. So I went to business school. Two years later, I came out with some really valuable knowledge. But you distilled it here to the most important things.

The First and Most Important Lesson: Hit Pause

Jesse Krinsky: What do you think is the biggest takeaway that you want people to come away with?

Bill Shander: It's a good question. To your point about business school, the fact is that this book applies to all knowledge workers. It's not just for creatives, because everybody who does anything for anyone has to really think this way. I think the very first and most important lesson is that we all need to recognize that our stakeholders don't know what they need. It's not just for creatives. If you're in HR and your boss comes and says, “we got to figure out why retention is going down,” well, that's not a creative request, but it's a legitimate request, and you have to figure out what they mean by retention. And what do they mean when they want you to tell them about it? Is it a report? Is it a PowerPoint? Is it a conversation? There's so many questions. Everything is vague, and our job is to clarify requests before we do them. So the first and most important lesson is to recognize that everybody is being driven by their subconscious at all times, or they're asking you to do things which is just the normal way of doing things. “Hey, give me a report on retention.” They're not thinking it through. They're not being strategic enough themselves. So if you just recognize that first, forget about how to solve it. Recognizing that before you jump to it and start executing on tasks, hitting pause is the first and most important lesson.

Jesse Krinsky: I did some stakeholder whispering last night on a call that I had. I'm the president of a nonprofit board, and there's an event they're starting to plan. The first question I asked last night in the meeting was, “why are we doing this event?” And what do you think was the first answer?

Bill Shander: We always do it.

Jesse Krinsky: Bingo. And then I got better answers from other people, and then the person who gave me the first answer said, “those answers are good enough.” I said, “you got better as you went along, but the first answer, not good enough.” Fortunately, he had a good sense of humor that I could say that to him. But yeah, absolutely. Breaking that inertia, inertia is the most powerful force in physics. I think it's also the case for the human mind. We rely on these heuristics and these biases, not in a negative way, just the natural condition.

Bill Shander: Yeah, it's literally part of our brains. It's how they work.

Jesse Krinsky: And it is so hard for us to acknowledge our own issues, our own inertia, let alone be able to help someone else out of theirs. To be able to do that is essential for any career.

Stakeholder Whispering as Therapy: The Socratic Method

Jesse Krinsky: Could you help us understand the connection between stakeholder whispering and therapy? Because they're so clearly tied here, and there's so much value in understanding that.

Bill Shander: One of the reasons it's so much like therapy is that the process is literally like therapy. One of the techniques that I recommend people use when they are whispering their stakeholders is the Socratic method. Most people remember the term, the Socratic method, and they remember it has something to do with asking questions. But the point of asking questions in the Socratic way is literally to recognize that the questioning is teaching. The person answering the questions is the one learning. So in other words, when I go to my clients and they've assigned me something and I ask them questions, you could say I'm learning by asking the questions, I'm going to get the answers. And that happens also. But the main reason I ask the questions, kind of like you and your meeting the other night, you're asking them questions so that they can investigate it themselves. You're helping them see it in a new way. And that is what therapy is. Cognitive behavioral therapy and some of the other types of therapy, they literally use that method. When you go to the therapist, you say, “here's my childhood trauma,” and they don't say, “okay, you do 12 pushups, write in your journal three times a day, and you'll be cured.” I don't think so. What they do is they ask you a ton of questions to make you investigate yourself. You're healing yourself by thinking these things through. So that question and answer back and forth, guiding people towards an insight, is what this process looks like. And it's exactly like therapy.

Jesse Krinsky: It can be very challenging when it's most effective, right? Because people have to be willing to face truths that they weren't aware of, that they've suppressed. What's the hardest part of stakeholder whispering for you? What do you have to keep reminding yourself of now?

Bill Shander: It really depends a lot on where you are. Some clients, some bosses are very open to this idea. The culture is welcoming to these conversations. And if you're in an environment like that, it's not that hard. It's a wonderful experience, because it's not as painful as therapy, really. But in some cultures, some bosses are kind of jerks. They don't want you pushing back. They just want you to jump to it and do what they asked. So if you're in a situation like that, if you have a difficult boss, an unwhisperable boss, as I call them in the book, then that's a challenge. And there are some things you can do to address that, like as simple as just sneaking in one question. Literally the question could be as simple as, “tell me more.” You just asked me to do task X. Tell me a little bit more about that, boss. That can even help. But that can be the most challenging thing. I would say cultural and personality issues, and they're not 100% solvable to be perfectly honest, but there are some techniques to sort of try to get around them.

Why AI Can't Replace Stakeholder Whispering

Jesse Krinsky: I think there's a really interesting similarity between the book and one of the biggest challenges that we're facing, which is AI. Unless you prompt it not to, the default for AI is to give us what it thinks we want, which of course we know is not what we actually always need. And I think that's one of the critical weaknesses of AI that creative teams can absolutely exploit. How do you think that can shift the conversation about what makes human creative teams valuable?

Bill Shander: I think you hit it on the head. The fact is AI will do what you ask. That's why you have to be really good at prompting to get good results from AI, because it'll do exactly what you ask it to do. And by the way, it goes back to the point about “that's how we've always done it.” Well, how does AI do what it does? It's looking at a bazillion data points, and it's literally calculating how it's always been done. And then it regurgitates that back to you based on what you've asked. So it's literally doing everything you shouldn't be doing. So the value that humans can bring to the table is exactly this. You can read body language. You can understand out of the 47 times you've done this report, the 47 different things that happened and some of the reasons there were little gotchas. And you know that Charlie over in HR is particularly focused on this this month, times 100. And so you're going to be able to see the forest and the trees. Ask good, unexpected follow up questions, and therefore prompt better prompts from your clients, bosses, whoever they are, in order to do better work. And then yeah, you can go to AI and get the better work done. If that's about efficiency, AI isn't the problem. But this is your value as a human: it's in the ability to do what only a human can do, which is really dig out that context, be a good therapist, and guide your stakeholders towards what they actually need from you.

Jesse Krinsky: I could not agree more. And I also think that that's something that creatives who are scared right now need to understand, that they have the ability to uncover needs far better than AI can. And therefore to deliver better, more impactful creative that is actually needed and not just wanted.

Bringing Expertise to the Table

Jesse Krinsky: A lot of creatives also worry that pushing back on requests or asking probing or difficult questions can damage their relationships with their stakeholders. How do you coach people through that concern, that power imbalance?

Bill Shander: It's so hard. What you brought up earlier, especially in a corporate environment, in-house creatives have this particular challenge where, unless you're lucky enough to be an in-house creative at a company like Apple, where from the top down, creativity is literally baked into the value of the company and they get that. 99.99% of companies aren't like that. And so what you have to do is build trust over time. And it can start with, like I said before, one question, “tell me more,” which probably isn't enough in most circumstances to get to that next level. Second question I always recommend people ask is, “how are we going to measure success?” Which is such a businessy question. And people ask that all the time, but the value in that question is it starts to get towards real need. “Do X, but how are we going to measure success?” “Well, because sales are going to go up by 42%.” Okay, I can hang my hat on that. It's going to be hard to do with what you've asked me to do, but at least I can think about it, and I know what I'm sort of orienting my response towards. But there's no magic bullet in order to have these conversations when there's a power imbalance, especially in a culture where what you do isn't understood or fully valued. But all you can do is bring your expertise to the table, bring some charm if you have it, hopefully, and build trust over time. And as you do better work, obviously you're going to build more trust. And the other thing I will say, there's a chapter in the book about persuasion and influence. Robert Cialdini wrote probably the best book on persuasion of all time. And he describes six essentially categories of influence. And I honestly think one of the most important ones is expertise. And the reason I know it's so important is because there was another study that was done, which is fascinating, where you put people in an MRI machine and you're seeing where the brain is being active. And if you have someone giving that person advice, then the frontal lobe, which is where reasoning occurs, shuts down, literally flatlines. And what this is an indication of, that the researchers concluded, is essentially we don't think for ourselves when there's an expert talking to us. So what does that mean? It means that we value expertise a lot. So you, in-house creative, when you're in that meeting and you're trying to understand a little bit more about what this person is doing, why they're doing it, and make suggestions about how they might do it better, it's not just you, Joe Smith, explaining and trying to convince them. If you can say, “Listen, I was reading a research report last week that found that yellow buttons will increase e-commerce transactions by 42% over blue buttons,” “Who?” “Really? The Harvard research study said that? McKinsey said that? Who?” “All right, now I believe you, let's do it.” So you're not trying to convince them, you're bringing expertise to convince them. So that's really, really powerful. So anytime you can lean on someone else's experience and expertise, it's going to be that much more convincing when you have these meetings, especially if the culture does not welcome your opinion or if the power imbalance is that high.

Jesse Krinsky: The way that I advise my clients to do just that is, this is one of the pieces of advice that I'm constantly giving clients, which is to understand as best as you can what the environment is that you're walking into before you do. And one of the ways to do that is to have knowledge that is not necessarily directly related to creative. What do I mean by that? Well, most companies of a certain size have an annual report or a 10-K, but not very many creatives ever look at that. And why is that important? Because then they can go into these meetings and say, “As I understand it, these are the KPIs for our company right now. These are the KPIs for your department. How will this project that we're working on help meet those KPIs?” And those aren't the kind of questions that creatives are accustomed to asking. But I'm connecting this to the idea of expertise, because it shows that you are bringing in expertise, oftentimes expertise that stakeholders don't have, because they often don't know that information. They haven't read deeply into the 10-Ks to understand what their company's needs really are. So even asking those questions shows leadership.

Bill Shander: Yeah. And you know what? That's not only expertise, although it is totally that too. It's leadership thinking, right? You're the person being the strategic thinker who actually cares about the actual success of the organization writ large, not just “I'm fingers on a keyboard doing what I'm told. I'm not an order taker.” So yeah, I love that example.

Advice for Junior Creatives Navigating a Power Imbalance

Jesse Krinsky: When I was working in house, there was a stakeholder whose creative requests would be written like this: “What will the cost be for a three minute interview based video shot in North America? I need the quote in 20 minutes.”

Bill Shander: Yeah.

Jesse Krinsky: And of course, I wanted to ask follow ups. The follow ups I was thinking of were more logistic in nature. I knew that she didn't know the answers to them, because I knew that she wasn't asking her stakeholders. But I also didn't feel like I was empowered to, because my manager pushed back when I would ask critical questions. So, for people who are more junior, where the power imbalance is everywhere, what are one or two ways that they can start stakeholder whispering, to practice it, to learn the skills to improve it, and to help their career?

Bill Shander: Yeah, it's a great question, and I would start by saying, I'm touting this as being one of the most important soft skills people can and should learn to improve their career and to improve their organizations. At the same time, you can't do it all the time. If your boss says, “Hey, I'm going to stub my toe every time I walk around the corner if you don't move your desk three inches to the left,” you can probably just move your desk. You don't have to have an hour long conversation to question that task. Not everything needs to have this deep of a dive. But let's assume you are going to go down that road and you have to overcome these obstacles. It's about building trust, and it's about starting small. Whether you ask the one or two questions like the ones I mentioned before, and even in the example you just gave, give me the cost for a three minute video interview style shot in North America, man, I want to ask 800 questions, but in 20 minutes you need the estimate. You know, in the past six months, we've done 42 of those. The range of costs is from 10K to 14K. But here are the things that will influence cost: location, and so on. And you've even given the criteria. You're sort of hinting at the questions you would ask the next time around, by the way. And why not throw one question down there at the bottom? Like, “Is this for that new campaign that I heard we're working on? I was thinking about it. A social media campaign might be a really cool idea, because I saw that Nike did it last week.” If you can come up with that, even a very junior employee, answer the question quickly and efficiently, get some details in there for them to think about, and ask one good question that's strategic, man, your boss is going to be psyched, and it's not going to make them defensive. Because the question is almost like a throwaway. They're not going to feel obligated to answer, because you did give them the answer to what they asked you for. Responses like that are super, super powerful and will build trust, so that the next time you do have these conversations where you do need real answers, you're going to be more likely to get them. Or maybe, because you gave those criteria, these are the three things that affect the cost, boss, maybe they'll call you with an extra 30 or 50 or 87 minutes before the next quote, because they know you might have a couple of questions to help make the quote more accurate.

Jesse Krinsky: And something else that those kind of questions do is they show value. Actually, there's two things. They show value: the value of the junior person asking the questions, but also they offer value. In that case, the junior person who suggests that has given something for free that wasn't even asked for, but it is a little bit of value. And you talk about this in the book, it could also potentially lead to reciprocity. When we give something, people feel a sense of obligation to give back to us. Showing that you can think beyond the rote task that's being asked, and also offering value, giving somebody something that they didn't have before, is another way that, when combined with stakeholder whispering, are some skills that people who are earlier in their career could really benefit from.

Bill Shander: Yeah. And by the way, that person who asked you for that quote, they may not have been the actual one asking for it, meaning they got assigned that task possibly. And so their stakeholders don't know what the heck they're asking for either. And so when you ask them a question, now they got to go ask them a question. Recognizing that there's layers of stakeholders and hierarchy, and that the person who you're talking to may or may not be the actual person who needs to answer those questions. When you give an answer that's the answer as best you can, and ask some questions, pepper in, and give them that value that you're talking about, you're also sort of letting them off the hook a bit, because they may not be able to really help you anyway. So just always being aware of reality is very, very important.

Jesse Krinsky: And also, helping the person to understand that you understand that they are facing pressures, having empathy for their situation, is wrapped in this as well.

Building a Culture of Useful Paranoia

Jesse Krinsky: Which is essential for the North Star for large creative teams, which is to transition from being reactive order takers to strategic partners. In order to do that, you need to show that you can understand strategic thinking in general. And this is one of the ways that I always recommend that they do that. Changing the subject a little bit here: if a CMO asked you if there was one thing that you could do tomorrow to improve how a creative team operates strategically, not reactively, what would you tell them?

Bill Shander: You know, it's funny, I was trying to think of something earlier today. What if, Mr., Ms. CMO, what if you had a weekly useful paranoia session within your organization? And I don't think we've used that term yet, but useful paranoia, for everybody listening, is the basic idea that I sort of said at the very beginning when Jesse asked, “what's the most important lesson?” It's to recognize that nothing is as it seems. Your stakeholders don't know what they need, so therefore you should help them figure it out. I call that useful paranoia. At every moment, you should be a little bit paranoid about everything, but in a useful way. I'm not going to go off the deep end with my paranoia, but I'm constantly questioning everything. Critical thinking is another phrase for it. And so if you had a weekly useful paranoia session in your department, Ms. CMO, then every week, literally, it's kind of like the old standup meetings in Agile. Every week, people get together for 15 minutes and literally just say, “What's one thing that you're working on or have worked on in the past week where you had to question an underlying assumption?” Like at your meeting last night, why do we have this event every year? Well, here are the 12 actual good answer reasons why. And these three are really valuable, important. The rest of them are kind of bull, but you know what? These three are valuable enough. We probably should have that meeting. But you should be questioning those assumptions and talking about it, talking about what you're doing about it, how you're investigating it, and what the final decision should be. If people just looked at that every week, that'd be the beginning of a huge culture shift in every organization.

Jesse Krinsky: I think a CMO would need to embrace a degree of humility to be able to offer something like that, which also I think is a valuable characteristic for any leader. And it occurred to me as I was reading this book that there are aspects of this that I have done, and I've seen people do, but I haven't really had this framework that you laid out in the book. And it's given me a valuable way of thinking with more clarity about the work that I'm doing. And I want to bring that to the work that my clients do as well. So thank you for writing this. This has been fantastic. Again, I cannot recommend the book, Stakeholder Whispering, enough. I'm so glad you wrote it. I'm so glad that I read it. I'm glad that I got to talk to you about it. So thank you so much.

Bill Shander: Thank you for having me. I really appreciate your reaction and experience with the book. And hopefully we'll get another chance to talk about it at some point.

Jesse Krinsky: I love that. Thank you very much.

Bill Shander: Thank you.

Key Takeaways

Let's recap the key insights from today's conversation.

First, your stakeholders don't know what they need. They know what they want, but those are rarely the same thing. So before you jump into execution mode, hit pause. Ask questions. The person answering the questions is the one learning. You're not just gathering information, you're guiding them toward clarity about what they actually need.

Second, build trust through expertise, not just charm. When you bring external research, industry examples, or business context to the table, you're bringing authority that stakeholders can lean on. Read your company's 10-K. Understand departmental KPIs. Show that you care about organizational success, not just creative excellence. That's leadership thinking, and it's a major part of repositioning you from order taker to strategic partner.

And third, create space for useful paranoia. Fifteen minutes a week where your team questions one underlying assumption about their work. “Why are we doing this event every year?” “What's the real goal here?” That weekly practice builds a culture where strategic thinking becomes the default, not the exception.

And remember: AI is great at executing orders. It'll do exactly what you ask. But only people can read body language, understand context, and ask the unexpected questions that lead to better work. That's where your value lives. That's what makes you indispensable.

If you found value in today's episode, please subscribe and leave a comment. Let me know what creative ops challenges you're facing, and what topics would help your team work better. Reach out at jesse@infocusconsulting.net.