Failing Well Beats Playing It Safe

Drew: Hello, Renegade Marketers! If this is your first time listening, welcome. If you're a regular listener, welcome back.

You're about to listen to an Expert Huddle where our flocking awesome community, CMO Huddles, gets access to experts, including the authors of some of the world's best-selling business books. In this episode, Amy Edmondson, author of Right Kind of Wrong, invites us to rethink failure — not as something to hide, but as part of how smart leaders learn. She unpacks why smart risks, psychological safety, and asking better questions matter in a world where playing it safe can become its own path to irrelevance. If you like what you hear, please subscribe to the podcast and leave a review. You'll be supporting our quest to be the number one B2B marketing podcast. All right, let's dive in.

Narrator: Welcome to Renegade Marketers Unite, possibly the best weekly podcast for CMOs and everyone else looking for innovative ways to transform their brand, drive demand, and just plain cut through, proving that B2B does not mean boring to business. Here's your host and Chief Marketing Renegade, Drew Neisser.

Drew: Hello, Huddlers. In our peer huddles, we talk a lot about what's working and occasionally about what's not, but what we rarely dive into is failure — a topic that is naturally tough to admit out loud. When most of us fail, we brace for impact, like an angry board, or a broken brand promise with a consumer, or that budget that just got cut. However, today I want to invite you to reconsider that word entirely. And to help us do that, I'm thrilled to be joined by someone who has redefined what it means to fail and fail well. Yes, that word is right — fail well. She is the author of The Right Kind of Wrong. I'm holding the hard copy, but I did listen to it. A Harvard Business School professor and world-renowned thinker on psychological safety and organizational learning. So welcome, Dr. Amy Edmondson.

Amy: Great to be here. Thanks for having me.

Drew: So, first of all, how are you and where are you this fine day?

Amy: Well, I'm fine. I'm in my office at Harvard Business School. It's a little on the chilly side here in Boston, but it's a beautiful day.

Drew: Kind of like us in New York. So let's kick things off with where things go off the rails, and especially with expectations. I'm going to bring us to marketing leaders. I know your research is much broader than that, but in this virtual room of ours right here, they all got there by performing well, avoiding screw-ups, and, yes, delivering results. So there's this paradox — how do high-achieving, results-driven leaders like these make space for intelligent failure without feeling like, well, failure?

Amy: I'm going to reframe it — not so much as a paradox, but as a challenge — because a paradox implies two things that should not or cannot be true at the same time. And truthfully, as I look at high achievers, successful people in any sphere that you name, these are not the people who have failed less often. They're the people who have failed more often than the rest of us. And that doesn't mean big, bad, ugly, embarrassing failures. It means what you said in the intro: failing well. And so it really does depend on the definition of failing well, or what I call intelligent failures. And I suspect that your listeners will agree with this premise — that if you're not taking what we might rightly call smart risks, you're not doing your job at the very highest level you could be doing it. So what's a smart risk? It's not a risk if you know exactly how it's going to turn out — that's just an action. But if it's a risk, that means there is at least a possibility that it won't work out in your preferred manner. So I define a failure as an undesired result — pretty simple. But an intelligent failure is an undesired result in new territory. And it could be new to the world or new for you. You haven't done this before, but it seems worth doing, and you've got good reason to believe what you're about to do might work out, but you're well aware that it might not. And importantly, the intelligent failure is no bigger than necessary. We don't want you to take bets that could threaten your livelihood or lead to reputational harm that you can never recover from. We want smart failures — those that are just big enough to learn and get us into new terrain, but no bigger than necessary for that learning.

Drew: We're not necessarily trying for New Coke here — a catastrophic failure.

Amy: Right. I mean, the problem with New Coke was that it was too big. Probably every other aspect of it would hit my four criteria — new territory, hadn't tried that before, in pursuit of a goal, sales excitement, some reason to believe this was what people wanted — but the size of the failure was much bigger. And we're still talking about it so many years later. So ideally, we would test that in smaller, representative settings and figure that out before we have to go live, if you will.

Drew: Yeah. You know, there used to be this thing called test marketing, and that's something you would have done that could have managed that risk. One of the things in your book — there are all sorts of stories, like the heart surgeons who failed and failed and failed until they successfully performed a pioneering transplant. That's life or death, and those are big failures. Or the Challenger failure — those are big. Those are not happening in marketing, hopefully.

Amy: Let's hope, yes.

Drew: I think it would be helpful to break down the types of failure, because you talk about basic, complex, and intelligent. Can you walk us through those?

Amy: I think that's a great idea. And I will say, just before I get there — Challenger is not a smart failure. In fact, it's almost the poster child for not-smart failure, despite the very smart people involved. The three kinds of failure that I've identified in my research are basic, complex, and intelligent. I've already described intelligent: new territory, in pursuit of a goal, with a hypothesis, no bigger than necessary. Those are the bread and butter of every great professional athlete, scientist, entrepreneur, etc. That's what they do to be great along the way. A basic failure — and yes, these are worth preventing and avoiding if humanly possible — is a preventable failure in a familiar context that has a simple, single cause, usually human error. Like: we have a recipe, but oops, we put in sugar instead of salt, and the result is lousy. With training, caution, vigilance, and teamwork, we can truly prevent those in our organizations and even in our careers. Some will slip through, but hopefully not big ones. And then complex failures are multi-causal — they're the perfect storms. They're the failures that happen when a handful of contributing factors come together in just the wrong way, and any one of those factors on its own would probably not produce the failure, but the way they came together does. Complex failures are on the rise, and often have one or more factors that might in fact be preventable — things we should have known better. So let's go back to Challenger. Challenger is the quintessential complex failure. First of all, it's a very complex activity — sending a spacecraft to orbit the Earth is a pretty complex activity with thousands and thousands of interacting parts, human ingenuity, weather, and everything else. But what shifts it from complex to a preventable complex failure was the fact that the engineers who had concerns were not listened to. So that becomes an organizational thing that we can dig into further — when and how and why it's so important for people to be listened to, because it's hard for people to speak up with concerns, questions, or dissenting views. So we have to make it easier, so that we don't get Challengers in our own lives and organizations. The open-heart surgery story — I deliberately open Chapter One of the book with it, because the early days of open-heart surgery absolutely qualify as intelligent failure. But then you might say, "Wait a minute — I get it: new territory, in pursuit of a goal, life-saving treatment, with a hypothesis, reason to believe this might work. But how do you keep it small? How on earth can you reduce the stakes, given that they're life and death, low enough to be willing to risk it?" And the answer is easy in retrospect: in those early days, you only operate on patients who literally had no other choice — they're going to die. They're going to die because of a hole in their heart or some other terrible condition. So they're either going to die in the surgery, or they're going to die soon. And so those are the ones you're willing to take this very real risk with, and hope you can save their lives, but know that if you haven't, it was a tolerable risk. It's counterintuitive, but it still fits the formula. And of course, today we take open-heart surgery absolutely for granted — a modern miracle that has saved countless lives. And we are grateful that those early pioneers in the early 1950s were willing to do the hard work of venturing into new territory.

Drew: It's so interesting. And you're absolutely right. As you're reading that, you go, "Yeah, it's so common." And you don't really go back and think about how many mistakes — or, if you will, failures — there were along the way.

Amy: Can I just jump on that? Because one of my pet peeves is the interchangeability in most of our language in business between "mistake" and "failure" — and they are not the same thing. A mistake is an unintended deviation from existing knowledge, protocol, practice, or rules. So mistakes can only happen in familiar territory, and we're fallible human beings, so we do and will make mistakes. But not all mistakes lead to failures, and not all failures are caused by mistakes. So they're really very different. A mistake is a process deviation, whereas a failure is an outcome that we much preferred not to have happened.

Drew: I can't promise I won't make that mistake.

Amy: No, nor can I — well, actually I can, but most people won't. But still, conceptually, it's fun to play with.

Drew: I hear you, and I appreciate the distinction. And as I recall from the book, a basic failure in marketing — we've all gotten the emails that say "Dear [Name]."

Amy: Yeah, right. And that's a basic failure.

Drew: The system didn't grab the name, and it still went out, and there was no way of doing it. 

Amy: And we know how, right? That's preventable.

Drew: Yes, and it's preventable. Obviously, complex failures are ones that I think CMOs actually think about a fair amount — the things that could really go wrong, particularly in situations like live events or other things where they're dependent on technology, dependent on people, dependent on all sorts of other things. I think the area that is most fruitful for us here, though, is intelligent failure and what that looks like. You've talked a little bit about psychological safety. I feel like we need to cover that, because honestly, I don't think there's a lot of psychological safety for CMOs today. There are CEOs — particularly if you're at a PE firm — where it's about the numbers. You're going to lose your job in 18 months. There's no safety. So I wonder: can you actually be a proponent of intelligent failure when you know your CEO and your board do not have your back, and there is no risk tolerance — they might say it.

Amy: I hope this is a familiar and compelling term to all of you. I think there is room for sales here. CMOs have to educate or sell people on the value of smart experiments and smart risks, because there's a way to think about this: most people, most of the time, are playing not to lose. They're finding the safe zone — setting targets lower than would be the ambitious goal, because the perceived consequences of missing are just too great to bear. So we have people playing not to lose, in their formal targets and in their interpersonal interactions. And I think we need to sell people on the value — and even occasionally the joy — of playing to win instead. Being willing to go for what you really hope and believe is possible, rather than holding yourself and your team back. But in order to do that, you have to be willing to acknowledge and talk about the very real possibility that you will fail — again, smart, small failure. I think CMOs have to sell people, including the CEO and their direct reports, on the necessity of smart risks in a constantly changing and highly uncertain world. If we're not venturing into new territory, we won't fail today, but we will fail in the longer term. We then become vulnerable to a different kind of failure — the failure of obsolescence or irrelevance as the world changes around us.

Drew: Well, here's the irony, and I'm going to throw this out there. In a world where the clock is ticking and you might only have 18 months no matter what, you might as well take your big swing. 

Amy: That's right. Go for it. Aim high.

Drew: If you don't go for it and you go down, you look back and say, "Well, I didn’t take the big swing" So — playing to win — let's get at this issue of psychological safety, and start first with the leaders who do this well, and how they build it in their teams, and what CMOs need to know about that notion.

Amy: Yes, you know, so psychological safety, again, it's gotten so much attention that it's also gotten lots of misunderstanding, which is understandable. But psychological safety refers to a climate where people believe that candor is expected. I like to think of it as a learning environment, but it's a pretty challenging environment. It's an environment where people disagree, where there's conflict, where they're speaking up, where people are willing to take the sometimes challenging interpersonal risks so as to mitigate the business risks. Because most of the business failures I've studied were utterly preventable had people been willing to speak up in a timely way. And so psychological safety describes an environment which is not the norm, but which is doable, where people just know that, yeah, we're going to expect to be a little uncomfortable, but my colleagues expect me to say what I'm really thinking here — politely, of course, with respect — but to speak up early and often so that we can have the smartest possible risks. I like to say, in an uncertain world, your success depends on high quality bets. Now, if you don't like the word bets, you can use the word decisions instead, but make no mistake, they're bets. So where do you get high quality decisions? Well, you get them from high quality conversations. And those are, in a word, candid conversations. So psychological safety is important in this conversation for two reasons. One, it really does help us avoid preventable failures, probably like New Coke, like Challenger. And secondly, it creates an environment where we're more able and willing to experiment, right, to take smart risks.

Drew: Okay, so as a CMO, a leader of a team, you have people on your team that you want to encourage to experiment, to make bets, to take risks. We talk a lot about trying to carve out parts of the budget for experimentation — 10 to 20% of it — and some are very good at getting these dollars, and in getting the CFO to understand why these dollars are necessary, because the markets are changing so quickly. But I think where they could use some guidance and help is the processes. So we say to the team, we want to innovate, we want to do new things, and it's going to be okay, you can take some big bets, right? Talk a little bit about — all right, it's a safe environment, great, now what? I mean, we want intelligent success.

Amy: Right. We do. And make no mistake, I am a fan of success. Success is first choice, and you've got to be willing to accept the other outcome as a possibility, or else you won't be brave enough, bold enough, creative enough. We love to say we value creativity, but we don't, right. We value conformity, unless you work pretty hard to create the conditions whereby creativity is really welcome, because with creativity comes the very real possibility that, oops, that was creative, but not very successful. So we have a lot of mixed messages in organizations, and I think we should be more scientific about it — just be very clear. And we can even be clear, as you were before, about the percent. If we're spending 20% of our budget on experimentation, that's a very specific number, and that helps frame it for people that, yeah, we kind of expect and hope 80% to be delivering as expected, because it's a little bit better understood, more familiar territory. But we're totally okay with the fact that the 20% is experimentation. And if all of your experiments work — sorry — if you know in advance that your experiment is going to work, it's not an experiment. Then it goes back in the 80%, right? So truly, you have to be honest. Your experiment can't be a kind of, ooh, look, here's my experiment, but it's really a playing-not-to-lose moment. If you know for sure it's going to work, you're not doing it.

Drew: And as you're talking about this, there's another sort of internal conflict. I think there is some fear among CMOs about this need to be right. And I feel like that could be crippling in this context, because I think if a junior person comes to them and says, "I'm thinking of this experiment," the CMO might very quickly say, "You know what? We tried this at my last job. It's not going to work. Here's why. I'm right, you're wrong, next." And I guess what they really sort of need to do is stop and say, "No, don't" — you know, ask the questions, make sure that you are, in fact, open to being wrong.

Amy: You've got to be open to being wrong. And I'll go back to: high quality bets depend on high quality conversations. And that was not one. If you've just had a conversation where someone says, "How about this?" and you say, "We tried that, it didn't work" — that is the poster child of not a high quality conversation, right? There was no curiosity. There was no "Ooh, tell me more, what are you thinking?" And we may have tried something like it before, but almost by definition, we haven't tried it exactly before, because it's a new moment, it's a new era, it's a new market, et cetera. So you've got to be willing to listen with curiosity. Most of us — and I include myself — we listen with judgment. And in some sense, that's how we got here, that's what made you successful, was your ability to exercise judgment. But that judgment has to be moderated by the reality that every day is truly new in some small, sometimes larger, way. So we haven't stood in this river before. So listen with curiosity. Maybe the idea is not yet fully ready for prime time, but there's a gem in there, or just a kernel of an idea that you, in that high quality conversation, can build on, can think through. Or if it's something that truly has been tried before exactly, it's okay to say so, but describe it fully. Your job as a manager is to educate that person — not to say "we did it before, doesn't work, dismissed" — but to talk through and say, "You know, here's how we were thinking, this is what we tried, this is what we concluded. What do you think? Maybe even our conclusions weren't fully right." So yes, you must overcome that desire — which we all have — to be right. You have to decide whether you're more interested in being right or more interested in being effective and being a good leader. And most of us would just say, "Oh, I want to be effective, I want to be a good leader." But then our exhibited behavior is more along the lines of, "Actually, I really want to be right."

Drew: I have found the most useful saying in my career is "I was wrong before, I'm smarter now." Yes. It just takes all the pressure off this consistent need to be right and opens up the possibility of learning. So one of the stories that you tell in the book, I think, is particularly relevant for marketers, and it's the Barbe-Nicole Veuve Clicquot story. Because in that story, I heard, oh my god, that was a whole influencer campaign — you got the celebrities to use it — and there's an expansion campaign. I'm wondering if there's some part of that story that you could share that those who haven't read the book yet would find fun and exciting and interesting.

Amy: I assumed you were going to say one of the other more familiar stories. And I love that you go to Barbe-Nicole, because it's Barbe-Nicole Ponsardin Clicquot — otherwise known as Veuve Clicquot — who essentially created an industry. The reason why I love that you went there is that the word "marketing" probably didn't even exist in the late 1700s, early 1800s. So this was truly a pioneering entrepreneur and, ultimately, business leader who was ahead of her time in many ways, engaging in the practices that you just alluded to. Why I use it — and I use it in the final chapter of the book as the opening story — is because we now look back and it's clear that Barbe-Nicole and Veuve Clicquot were — to say "success" is understating it — a remarkable success. The company was, and still is, successful. It essentially created this sort of global industry. And as you say, through influencing tactics, got people interested and associated this beverage with celebration — a little bit of luck at various points where, say, the end of a war, getting in there quickly, could be associated with that kind of celebration; or the very famous comet that people were quite interested in — particularly when an interesting astrological event was going to happen. They branded it, they made a special cork with the comet on it, and on and on it goes. But the reason I tell this story — because this all sounds pretty successful, and we know in retrospect it was — is that Barbe-Nicole's journey from becoming a young widow in her 20s, unexpectedly and devastatingly — because this was the dream, this company was the dream of her and her husband, François — this is not a story of success after success. It is truly a story of failure after failure. Technologically, marketing-wise, weather-wise, ships sinking — you almost can't get your head around the many failures that she endured along the way to ultimate, stunning success. Many entrepreneurs can identify with that. But I had not, until you asked me that question, thought of it as a marketing story.

Drew: In so many ways. First of all, creating a category is something that a lot of marketers think about. The comet thing is very much today's moment — in the moment of social, what's the zeitgeist happening, how do you grab on to that? Influencer marketing. But I also thought — what struck me so much was that women weren't supposed to be running companies. It wasn't even necessarily a legal thing.

Amy: It was only legal if you were a widow, right, so you couldn't be in that position unless you were a widow. So she capitalized on that legal opening 

Drew: And somehow convinced somebody — you know, this is the same challenge that women entrepreneurs have going to VCs and saying, "Hey, I want money." Their male counterparts find it a lot easier. So somehow she managed the equivalent of raising VC capital in the 1700s.

Amy: Absolutely. And she figured out how to make the champagne not cloudy, but clear, which is a pretty huge breakthrough — and now we wouldn't even imagine it being cloudy.

Drew: Amazing. Okay, well, that was a fun little thing, and we'll celebrate afterwards with a bottle — that is my wife's and my favorite champagne. So, yeah, I just had to get to that. These were big risks.

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Drew: You talk about this sort of manageable thing, and I want to get — this is really interesting right now, and it's probably a good transition. CMOs have been at the forefront of adopting generative AI for content creation and so forth, and they are in the moment where they could bridge and actually go to organizational transformation, because they've been using these tools earlier, more efficiently, more effectively than most other departments. But there's going to be a lot of intelligent failures — or the need for it — right, as we sort of figure out what can these things do that we could never do before? When you go into new ground like that, it's likely that not everything is going to work. So this is a moment where experimentation should be rampant. I'm just curious, as we look at it this way, in this brave new world of generative AI, I want to go back to this process of failure, of intelligent failure, and experimentation. 

Amy: I think this is,  you know, this is a lovely domain. And of course, it all started to accelerate well after the book came out. But it's fun to play with here. Gen AI, clearly, almost by definition — what most of us are doing is experimenting, right? Because we don't yet have the protocols all worked out for what we should do, shouldn't do, where it works, where it doesn't. But we're experimenting, and we're learning a lot in that experimentation. But to ensure, as a CMO, that your experimentation and your team's experimentation is intelligent — let's just think through the four criteria. New territory: well, that's a given. In pursuit of a goal: well, I hope so, yes, and there are probably opportunities to sharpen that goal, to be very clear about what we're trying to do with this experimentation. What are we hoping to gain? Not just, "okay, we're playing around with it for fun," but in fact, we want to gain efficiencies, or we want to gain more creativity, or whatever it is — be clear about it, so that people are designing the right experiments. And the third criterion is being thoughtful — your hypotheses should have good reason to believe this might work. And how do you get to the state where you have good reason to believe this might work? Usually from talking to other people. I like to say this is a team sport — it's from thinking through what do we know, what do we not know, what's worth trying. And then finally, how do we keep things no bigger than necessary? The last thing we want is some catastrophic failure that could have been avoided. So we don't want to take giant risks in new territory. We want to take small ones. And I think that too is probably subject to thoughtful conversation among colleagues.

Drew: I want to go to number two — the goal thing — because what's interesting is that a year and a half ago, when we were talking about what CMOs are doing with generative AI, it would have been just, "Hey, I got my team and they're all playing." There was a lot of experimentation, but it wasn't in pursuit of a goal.

Amy: Yeah, yeah. So now it's time to shift gears.

Drew: Yeah. And in truth, it was always time to shift gears. What's tricky with these tools is it's hard to imagine, if you don't kind of know what they can do, right? And so it was a tools-first approach, and what we're trying to get to is a strategy-first approach.

Amy: Yes, so it should be — the goal should be consistent with or in support of the overall strategy of the company, but probably the strategy of the marketing group as well. And I think fundamentally, there's sort of the goals of divergence and the goals of convergence. The goals of convergence are related to efficiency — doing what we do, but at lower cost, or maybe greater speed. And then the goals of divergence are the goals of finding new things to do that we haven't tried yet, that might yield fruit. So those are the opportunities to be more creative or more innovative, or bridge gaps that we currently don't know how to bridge. And so being clear about which — and under what conditions you're doing one versus the other — is an important first step.

Drew: I love the framing of divergence and convergence. And I think again, a lot of the emphasis has been on convergence. Yeah, we can do this faster, we can do this with fewer people, we can do more iterations of things. And so that's why the content world has been the first place that CMOs have adopted these tools. The divergence thing is so much harder, yes. And part of it is that there's some technical know-how required in order to build new things, and so it's hard to imagine — oh my gosh, we could create a whole new customer experience and tools and things — if you don't know some of the aspects of the tools you're working with and don't have somebody like an engineer on your team.

Amy: Yeah. Just — if it's a team sport, which I utterly agree it is, then think about what's the composition of that team. Is it diverse enough, or is it too homogeneous in terms of expertise and background? If you're using it to pursue other paths, be creative, be thoughtful about things we haven't tried before, then probably the composition of the team needs to reflect that goal.

Drew: Yeah, because it's funny — in pre-Gen AI days, if you said, "Hey, we want to build — we're going to have an innovation competition in our company, and you're going to get to gather a team and come up with ideas and present" — these innovation days were things that used to happen all the time. And you would try to make sure that you had an engineering person on your team, maybe even a legal person, a sales person, a marketer, and you'd create this sort of full, intelligent group — not too unwieldy, but enough that you could really brainstorm and do something interesting. I think there's a tendency now — while we can do so much with these tools, maybe we don't need all that — and that'll be an interesting part of it.

Amy: Right. Because you have virtual engineers, right? You're just grabbing their ideas and content, you know, potentially indiscriminately. But who — if that's — that's why the experimentation is so necessary. I do think and worry about — I think we need more systems thinking, more thinking about downstream consequences, right? So if, for example, as you say, and I agree, much of the experimentation has been on the convergence or efficiency side, we haven't fully thought through what that will mean, right, if we can do a lot of the tasks. And of course, the group that gets most discussed here is the sort of entry-level hires, right? So many of the tasks that they were called upon to do — the reviewing the literature, the frontline interviews, and so forth, cranking through data — are the first things to be replaceable by generative AI. But then we fail to say, okay, that's great, right? We don't need all those people now. But where do the mid-level people come from? You know, what's the future of our workforce like? And how do people develop skills and judgment and perspective without going through those experiences? We don't know the answer to a lot of these questions.

Drew: Yeah, no, there's a lot. And what's funny about some of this is that marketers were probably now spending more on it than IT does, and they also created all sorts of risk — data risks for those companies. And now the possibility of risk is even higher. So there are downstream implications on both a hiring standpoint, but also legal, ethical, and all sorts of other things they need to be thinking about. We're not going to go there. Where I want to get back to now is: let's talk about a model. As a CMO, their job is both to help deliver in the short term and have a vision for the long term, right? And that's hard. It's really, really hard. And the long term is where this experimentation comes in, because the seeds that you're planting today are going to be the oak trees tomorrow, right? So it's a hard thing, because what great CMOs do — the salesperson is thinking about the quarter, the CMO is thinking about the future of the company, both in terms of who are our new markets, who are our new products, how are we going to build a moat around our organization that will make it harder for competitors to steal our customers. All these things are in play, but experimentation is at the center of it.

Amy: Absolutely. And the first question just popped in there — it's kind of along these same lines. But the pull of the now will always win, unless we are thoughtful and mature and override it, meaning the pull of doing what is needed right now, the urgent. You know, this is the old Eisenhower matrix, where the urgent crowds out the important. So maturity, wisdom, experience, and perspective are all about insisting that we attend to the important. And the future is important, right? But it never feels important today. "I'll worry about that later. I just have to get through this agenda, these meetings," or whatever. So there isn't one best way to ensure that we attend to the future, but there are many ways not to do it, right? There are, you know, a thousand excuses and reasons to just grind through today's workload. And so I guess all I'm really saying is: you can do it, but you've got to be thoughtful and deliberate about it, and you have to make it explicit — out loud, make it a team sport. How can we ensure that we are doing today what will be needed some future date to continue to enjoy the success we're enjoying today? Right? And it is not a given. This is not a given that just because we're successful today, we'll be successful tomorrow. Nothing fails like success. We are programmed to underinvest in the future, but successful organizations find ways to get around that programming.

Drew: The person who's responsible for me reaching out to you is here with us — Amy King — and I'm going to ask Amy, if you don't mind coming on camera and joining and asking you the question that you put in chat, so that you can at least contribute to the conversation, because you were the one responsible for it. Do you mind doing that?

Amy King: Thank you, Amy. It's really great to meet you. I loved your book. We've used it across our marketing team and have really, I think, proudly built a team that is very comfortable in sharing intelligent failure and using that as a learning point. Where I think I'm struggling a little bit — and I really love the discussion on complex failures and systems thinking — is that in a modern marketing world, marketing really lives in the center of an interdepartmental system, and we're often dealing with things that don't necessarily perform to the level that we expected. But attribution can be really hard to nail down when there are so many variables that could have led to that outcome. Added to that, we often have other leaders in other departments who are somewhat skeptical — the sense that the marketing team is just asking for money. I just wondered, in that systems world, if you have recommendations on how — sometimes when we apply our "let's share our intelligent failures" approach to outside stakeholders, we get a little bit of "well, why did you spend the money and why should you get more?" So how do you work on spreading this mindset to outside stakeholders in a way that still engenders trust while not instilling doubt?

Amy: Yeah, it's hard. It's like part of your job is sort of external education — influencing other departments to embrace this mindset, which is a mindset of smart risk-taking and systems thinking, as you say. And I don't think there's one right way, but I do think you can be influential in leading a conversation. You know, education — the root of that word is to lead people toward something. And you're not trying to push it, you're trying to pull. You're trying to ask good questions, the kind of question like "what might happen if..." — helping them think it through. I used to work for a wonderful guy, Larry Wilson, who would bring senior teams together and say, "Imagine the company that, if it existed today, would put yours out of business. What do they do? What are they like? How do customers see them?" And it was just a fun, creative exercise. You fill up the flip charts with the attributes of that company. And everybody — because everybody was there — they're a little frustrated, "Yeah, we're a little bureaucratic here, we're a little slow there, we're a little stuck," and so they had fun with it, right? And then you'd say, "Okay, now be them. How do we get you there?" So it was almost like they had this emotional connection with their idealized company. And it's like, okay, you're the ones who are going to get us there. So however you do it, your job is — with warmth and respect — to engage them, because they're not stupid, right? They can see the very real risks. You can ask what happens if we don't take smart risks. What happens if we just stick with doing things the way we've always done them?

Amy King: Thank you. That's really helpful. And Drew, if it's okay, one more question. So I love the example in the book of the nurses who were afraid to report incidents. We're actually — my company is a software company for healthcare technology — and that one rang very true. I think one of the things we've struggled with a little this year, because the healthcare landscape in the US has been so uncertain, is understanding from an attribution perspective: as we do take risks, what's a behavioral problem because something's happened in the market — an intelligent failure, but one outside of our control — versus ones where maybe it was our own campaign design or the way we executed that was the problem? I'm just wondering how you help companies navigate between those kinds of determinations.

Amy: I think that's a really good question, and the answer lies in the quality of the debrief — or after-action review, failure analysis, or whatever terminology you use. I think it applies to successes and failures alike. But it is a leadership responsibility to make sure we use our own experience to teach us, to learn as much as we can. If we've invested in it, let's learn from it. Let's get the money's worth. And so a thoughtful process of understanding something that didn't go the way we truly hoped nearly always starts with "what happened?" Our temptation and instinct is "who did it?" and "what's to blame?" Stay away from that question initially. We'll get there eventually, but first we have to say what actually happened, and try to describe what happened from as many perspectives as possible. Usually — more likely than any other outcome — what we will learn is that it was a complex failure, which means there were things that we did suboptimally, and there were things outside our control in the external world that we didn't see coming and could not have seen coming. So it's a kind of mix of those things. Now, you can't change the things outside your control, but you can change your own behavior, processes, and so on. So all we can do from those learning conversations is identify the very few things that we can and are eager to improve. And then we will make those changes. With respect to the things that are absolutely out of the blue — nothing you can do about that. With respect to the things that are external but where if we'd been a little more diligent we could have known — yeah, let's get on those. Because when we look at how we contributed, some of it is sins of omission, not just commission, right? Some of it is things we did that we shouldn't have done, but a great deal of it is things we failed to do — the extra vigilance, the listening to customers, the listening to lower levels or what have you, that was really there for the asking, but we didn't do it. So it's honesty in the reflection, the soul-searching. And I don't mean to describe something that goes on and on — no, this can be very efficient indeed. But it is honest and thoughtful, and truly the goal is to find out what we can change so we can be better next time.

Drew: I love it. Well, thank you, Amy King, and I appreciate you coming on. And I appreciate you introducing the book to me. We're going to run out of time pretty quickly, Amy, but one thing that is clear: if you are lucky enough to work for a CEO who fosters a culture of innovation and experimentation, it's a beautiful thing. Is there any hope — and yes, you work for a CEO who doesn't inherently understand that notion of intelligent failure — to actually, other than handing them your book like a bottle of Geritol in the old days, any hope in your experience where a CEO sort of eventually came to understand the failures that were inherent in their inability to foster innovation in their company because of their approach?

Amy: Yes. I think there are really two possibilities if you're in that situation. One is that there are ways you can help them change and start to see things differently — and I'll come right back to that one. But the other is that you accept their limitations and resolve simply to run the absolute best possible learning-oriented department you can, including with your peers, with your direct reports, and on down. So sometimes — I don't have a magic wand — there's no guarantee that you can change them. But let's assume that that's at least a possibility. I think the best way — again, as I was talking with Amy — it's sort of through inquiry. Most CEOs got where they are because they were willing to at least take some risks. They have had experiences in their life where they kind of took a deep breath and went for it. So guiding them to see, both in their own lived experience, the valuable role of smart risks and deep learning, as well as the simple thought experiment of "what happens when we don't take enough risks?" Because there's that possibility of, you know, intelligent failure — that's always a possibility. But there's an almost certain and preventable failure that just happens later if you don't do anything differently today.

Drew: I love it. So you fight the good fight, and then when you can't, you do what you can, right?

Amy: Then buffer your people.

Drew: Exactly and build a little culture within that. So — because we're again at the last second here — one micro habit leaders can start tomorrow to foster psychological safety.

Amy: Absolutely. The one micro habit is: ask more questions. And I mean good questions. Not "how the hell did that happen?" but "thank you for that. How can I help?" or "what are you learning?" or "what are you seeing?" or "what are customers saying?" or "what are our competitors doing?" Whatever — show up as the most curious version of yourself. That creates psychological safety nearly instantaneously, if it's genuine, right? If you're asking questions and you're willing to listen to the responses, that is almost definitionally psychological safety. You've telegraphed: "I genuinely want to know what's inside your head, and I'm all ears."

Drew: Love it. Last question: is there a failure you're grateful for?

Amy: Oh yes. I think the failure I'm most grateful for — and without having time to really do this justice — was the failure of my very first research project, where I was trying to show that better teams had fewer errors. Pretty simple. I don't think that would have been a terribly interesting paper. But what ended up happening was that some teams had remarkably higher willingness to report errors. Now that was interesting. And that led me down a path I never would have thought of going on my own. So that failure — that failure to support my hypothesis — opened up an enormous and far more interesting and enriching research program.

Drew: I love it. Well, thank you, Amy, for helping us reframe failure as not something to fear, but as something to pursue with purpose. And CMOs, please go forth and fail in a very positive way — smart, small, new — right? Have at it. Amy's book, "The Right Kind of Wrong," is an essential read — or listen — especially if you're serious about innovation. And why wouldn't you be? So your homework this week: don't run from failure, but find one worth learning from. Let's give Amy a virtual round of applause! Thank you so much for joining us. 

Amy: It was great to be with you. Thank you. 

Drew: Thank you.

 

If you're a B2B CMO and you want to hear more conversations like this one, find out if you qualify to join our community of sharing, caring, and daring CMOs at cmohuddles.com.

Show Credits

Renegade Marketers Unite is written and directed by Drew Neisser. Hey, that's me! This show is produced by Melissa Caffrey, Laura Parkyn, and Ishar Cuevas. The music is by the amazing Burns Twins and the intro Voice Over is Linda Cornelius. To find the transcripts of all episodes, suggest future guests, or learn more about B2B branding, CMO Huddles, or my CMO coaching service, check out renegade.com. I'm your host, Drew Neisser. And until next time, keep those Renegade thinking caps on and strong!