Work Face
A podcast where people finally tell the truth about work. Workplace culture expert Ben Jackson hosts refreshingly honest conversations with people from all walks of life about what actually happens on the job.
Work Face
Pinball Mode (with Keith Cowing)
When was the last time your leader admitted they didn't have all the answers? With boards and investors watching every move, most executives feel pressure to project confidence, even when facing unprecedented change. But what if the most valuable thing a leader can offer their team isn't certainty about the future, but transparency about the present, and clarity about what to do next?
Keith Cowing, executive coach and product leader, shares his advice for leaders in times of rapid change: from labeling their leadership modes to communicating how decisions are made and openly calling out misaligned incentives.
(00:00) Pinball Mode
(03:59) The Disney Credit Card
(11:39) Dispelling Founder Myths
(13:51) The Power of Naming Behaviors
(16:12) Leading Through Uncertainty
(19:58) Why Transparency Is So Challenging
(23:07) Calling Out Misaligned Incentives
(27:32) Two Flavors of Honesty
(31:43) Leadership Team Mistakes During Uncertainty
(34:08) Creating Psychological Safety
(35:48) The Value of External Facilitation
Keith Cowing is an executive coach to CEOs and product leaders and a visiting lecturer at Cornell's MBA program. Previously, he served as Chief product Officer at Vesta Healthcare, VP of Product at Flatiron Health, and as a product manager at Twitter and LinkedIn.
Listen to Keith’s podcast, Executives Unplugged, follow him on LinkedIn, and read his writing on leadership at keithcowing.com.
See also:
SCARF: a brain-based model for collaborating with and influencing others, by David Rock
Boost your team’s engagement with this leadership tactic: behavior labeling, by Keith Cowing
Disagree and Commit
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Work Face is produced by Hear Me Out, a culture strategy firm for leaders with the courage to listen. We help them cultivate trust by having real conversations with employees at all levels about what’s working and what’s not.
Learn more at hearmeout.co and follow us on Instagram, Bluesky, and LinkedIn.
I remember on my first startup, I went for a taxi ride with one of the engineers, and I was asking him how things were going and, and he said, well, we're getting used to "Pinball Mode." I was like, "Pinball mode. That doesn't sound very pleasing. Tell me more about this." And to him on the team, they were bouncing back and forth between a lot of different things and it was causing whiplash.
Benjamin Jackson:What did that do for you as a CEO when you heard it put that way?
Keith Cowing:It enlightened me. It was feedback in a very crisp and understandable way that resonated of, oh, I need to fix this. It was a very, very crisp communication of how they felt in a way that I could feel it. Because, you know, stories evoke emotions, and that's a type of language that evokes emotions, Pinball Mode. If you're the ball and you're bouncing around, that ain't good.
Benjamin Jackson:When was the last time your leader admitted they didn't have all the answers? With boards and investors watching every move, most executives feel pressure to project confidence, even when facing unprecedented change. But what if the most valuable thing a leader can offer their team isn't certainty about the future, but transparency about the present, and clarity about what to do next? I'm Ben Jackson, and this is Work Face, a podcast where people finally tell the truth about work. Our guest today is Keith Cowing. Keith is an executive coach to CEOs and product leaders and a visiting lecturer at Cornell's MBA program. Previously, he served as Chief product Officer at Vesta Healthcare, VP of Product at Flatiron Health, and as a product manager at Twitter and LinkedIn. Keith Cowing, welcome to Workface.
Keith Cowing:Ben, great to be here. Thank you for having me.
Benjamin Jackson:So before we start, what do you think our audience should know about you?
Keith Cowing:Well, I've spent 10 years as a product person tinkering and building products. I spent 10 years leading product teams and organizations. And now I coach other folks that are going through those same problems and I've discovered some very specific things about CEOs and leadership teams that can make them much more successful and happy and productive, and I couldn't be happier doing anything else than getting a chance to share what I learned and talk to amazing leaders at a bunch of different companies and help them connect dots that maybe they wouldn't otherwise see.
Benjamin Jackson:Thank you. Just off the bat, I'm curious, what's the number one way that you see leaders get in their own way?
Keith Cowing:Old belief systems that no longer serve them. Things that you've assumed to be true over your career and you're underestimating when you change roles or your role changes on you. The behaviors that used to make you successful are no longer making you successful, and you have to actually rethink at a deeper level than you believe. So a founder who starts a company and then all of a sudden it's working and you raise money and you have to scale. Operating and being a CEO is a little bit different from the black art of being a founder and finding product market fit, for example. Or somebody gets promoted. I know this firsthand, I had a field promotion to go from a director to VP overnight, and all of a sudden had very different set of responsibilities and had to figure that out as I go. What made me great in the last job was sometimes actually a hindrance in the new job.
Benjamin Jackson:Mm-hmm. And what are some of the kinds of founders that you've worked with over the years?
Keith Cowing:Uh, all across the board. So my specialty is companies with zero to 500 employees. I work with venture backed startups. I work with private equity backed startups. The theme of the companies is rapid change. Either companies are going through hypergrowth or they're going through turnarounds, or they're just changing rapidly and pivoting their business model, and they're dealing with all of the pressures that come with super high demand, very limited time, very limited resources, and you gotta figure things out now and get it right and get the team aligned. So their challenges are actually fairly similar. The personalities come from all different walks of life. Engineers, salespeople, marketers. A lot of folks that are either product or engineering centric or a lot of folks that, uh, maybe had come from a sales background, I think tend to be in CEO roles.
Benjamin Jackson:Thank you. So we start every one of these episodes with the same question. What do you remember about the first time you felt insecure in the workplace?
Keith Cowing:So that'd be the first week of my first professional job. I moved to Silicon Valley for my first role, and I drove out there and I was trying to make it there honestly, with just the right amount of money, and I had a relocation package, but I didn't get it until three weeks into my first job because that's when the first paycheck came and that's when the relocation package came. So I had to relocate on my own and I had very little bankroll. I was counting out dollar bills. I drove across the country in a pickup truck with everything I owned, strapped down in a tarp in the back, and I got to Silicon Valley. I put down the security deposit. First month's rent. I was eating at Taco Bell, I was scraping by until that, that day. I remember Disney gave me an $8,000 credit line on a credit card. That Disney credit card is still a big memory for me.'cause I was like, oh my gosh, that's amazing. It's just what I need. And at the time it was huge. And the first week we went out to dinner with a bunch of folks on the team. There, 12 of us went out, had some good food, had some good drinks, had a bunch of laughs, and at the end they played this game called Credit card Roulette, where everybody threw their credit card in and they were gonna randomly select one, and that person had to pay the bill. And I was sweating it when that was happening, and they were going through the credit cards, I was like, oh no, don't be mine. Don't be mine. And of course it came up and it was mine. And I can still remember the dread in that moment of I literally cannot pay this bill, or I'm gonna go bankrupt. It's not an option. I don't wanna look like a jerk in front of these new colleagues, my first job, but there's no way I'm paying this bill. And I literally just pushed it right back and said, hell no. And it turns out it was. It was a, it was a game. It was a gimmick, and it was just a hazing technique. There was some sleight of hand where mine was guaranteed to come up because I was the new guy and I didn't have to pay the bill. if They just wanted to see my face when it came up. But it reminds me, as a leader, you gotta think about what other people are going through because it wasn't just an annoyance or a hindrance. I did not have the money and could not possibly have paid for it.
Benjamin Jackson:That is remarkable. Both for just the, the fact that hazing is part of the onboarding, and for the fact that a manager would endorse that without considering that, you know, maybe the person who just joined the company might not have the money to front dinner for every single person in the team. Did this happen with others on the team? Did you see it happen to other people after they joined?
Keith Cowing:No, I, I, I only experienced it with myself. They definitely had done it with other people. I may or may not have been the last, I'm not sure. But, uh, I didn't see anybody else go through that.
Benjamin Jackson:How did it make you feel in the moment when you saw your card come up?
Keith Cowing:I can remember it. I, I, to be honest, I think I felt defiant because I didn't have a choice. There was like, there was no money to pay for the bill, so I just pushed it back and I was like, hell no. Like, this is ridiculous. Like, I'm not paying that bill. Like I don't, I don't care what you say. Like, I don't like when you have no options, you have no options. And so, um, it was probably embarrassment mixed with defiance of like, um. I, I feel uncomfortable that you put me in the spot in front of all of these people. And, and I'm an introvert. I don't tend to be the center of attention. And my, my face likely turned a little bit red. I don't know 'cause I couldn't see myself. But, um, yeah, I would say I felt embarrassed and defiant of this. I gotta get outta this situation.
Benjamin Jackson:What kind of impression did that leave on you as a new team member about the culture that you were in?
Keith Cowing:You know, it's funny because I think back on it and I, I don't think back on it in like anger, to be honest. Uh, it's kind of funny now. At the moment, it was a, it was a wow moment. Um, I. It was in the semiconductor industry. The semiconductor industry, especially back then in 2004, is a pretty tough industry. Most of the companies went out of business, and you could only stay in business if you were rigorous and you put in the work and you were detail oriented and you pushed people hard and you were efficient and optimized. And there was a certain toughness that came from the CEO. TJ Rogers, who's, uh, very well known in Silicon Valley and, and had a big personality and, and was a tough guy. And Vince Lombardi was one of his big, uh, you know, people that he aspired to be like, who was also a famous, tough guy. And, and you kind of felt that spirit throughout the company. So to a certain extent, there was a rawness there, um, that I can actually appreciate where at times they'd kind of let your real personality come out by testing you a little bit. And then, and when you make it through the test, it's like, all right, we're we're just here to be real. We're here to be honest.
Benjamin Jackson:What do you think they were testing for in that moment?
Keith Cowing:I think there's a little bit, I mean, you see this a lot with entrepreneurs and VCs too, where they're purposely sort of poke you in the chest a few times and just see how you react. Because if you fall over and don't get back up, you're not made for the job. So I don't know if it was highly thought through or if they just thought it was funny, but I do think their culture was definitely some, let's put these people under pressure and put them in situations where they don't know the answer and they're very uncomfortable and let's see how they react. And then when they react, let's, you know, give 'em a hug and be like, Hey, it's all good, but like, you know, let's, let's get through it. It's, they, they sort of throw you in the fire a little bit. That was the mindset.
Benjamin Jackson:What were some other ways that you saw that kind of dynamic show up in your career? That let’s throw them in the fire and see what happens. Was that a theme that you saw come up again and again?
Keith Cowing:Uh, well, I end up throwing myself in the fire as an entrepreneur. As a startup CEO, you, you just, you're in the fire. There's no other choice. And so I'm probably a sucker for punishment at the end of the day. I like being challenged. I like being uncomfortable. I like sweating it out. I like being tested. I always wanna be around, you know, if I go biking, I want to go with people that are faster than me. If I wanna learn something, I want to be around people that are smarter than me. So I probably have a weird sort of brain chemistry that's a little twisted where I keep coming back for it. I've been at Goldman Sachs, I've been a startup, CEO. I've, I've been through a lot of things where, where people test you and they throw you in the fire. It hurts, but sometimes that's how you learn the fastest.
Benjamin Jackson:So how long have you been coaching for?
Keith Cowing:I've been doing coaching as part of my job as a leader of an org for 10 years. I've been doing it one-on-one as an executive coach for five years, and then I've been doing it as my sole main thing without the full-time job for two years. So it's been laddering it up. It was fairly organic I think. There's a lot of people that are thinking about making a career shift and you don't have to do it all at once. You can try something, you can get into it, you can organically figure out this is just something you love. And at a certain point it's like, all right, I'm all in. Let's go. And to me it's best job in the world. I couldn't be happier doing anything else.
Benjamin Jackson:How did you connect with your first client?
Keith Cowing:So I had developed a reputation in past jobs of being a coach and people coming to me when they were gonna make career decisions or career moves, and just asking me for advice. And I'd been doing a lot of it without thinking about it and without charging for it, but just getting practice reps and thinking about how to share what I've learned and how to ask good questions and help people discover what's gonna be best for them. You'd be amazed how often you just ask somebody when they're thinking about all these different options and things, and you just slow 'em down and pause 'em for one second and say, well, what do you want? How infrequently they have a crisp answer to that. I found it really empowering and really fun, and so I ended up one day just putting a shingle up on my website and said, Hey, I'm available for coaching. A couple people reached out there, usually people that I'd met in the past, but had come across things that I'd posted on LinkedIn or on the website or said, Hey, I'd, I'd be interested in that. And that's how it started.
Benjamin Jackson:What are the biggest myths that you end up working to dispel when you're working with founders?
Keith Cowing:Ooh, good question. I don't know if it's a myth as much, but there's, there's very frequently less clarity than they believe in what they're optimizing for and what they're trying to achieve. And then there's significantly less clarity in what the team understands of what the founder and CEO believes. And I've been through this myself, which is why I can have empathy for it. I remember on my first startup, I went for a taxi ride with one of the engineers, yellow cab in New York. And I was asking him how things were going and, and he said, well, we're getting used to "Pinball Mode." I was like, "Pinball mode. That doesn't sound very pleasing. Tell me more about this." And to him on the team, they were bouncing back and forth between a lot of different things and it was causing whiplash. And I sat down and, and really worked through it and, and talked to some folks and it realized that I wasn't being clear enough on what the objectives and the key results were and what the strategy was in communicating that to the team. Some things that I thought were obvious really were not even just how a venture-backed startup works and what the math looks like and what you have to accomplish and what you're signing up for. And so I got much, much more clear on communicating that. And then he understood the strategy and then he was free to make the tactical changes quickly on his own. And he was bouncing back and forth just as quickly between different experiments and things he was trying, but he was doing it intentionally, with the autonomy and the understanding of what he was optimizing for, and we were on the same page. And it completely changed the vibe of everything. And uh, I see that in other folks as well frequently, where the CEO has so much context or the leader of a team has so much context.'cause they're in the boardroom, they're out in the market, they're talking to customers, they're just constantly a sponge for information about what's going on. So they have a deep inner sense of where to go. And the team frequently does not have a lot of that context. And unless you tell them, unless you're really, really clear about it, then they're operating with so much less information than you. So the clarity in your communication with the team is frequently an order of magnitude less than you think it is as a leader. Uh, and it's one thing that I can help people with is getting clear and then communicating that in a crisp way to their board, to their team members, to new employees, etc.
Benjamin Jackson:I love that turn of phrase, Pinball Mode. And you know, it reminds me of something that I read while I was going through, some of your past writing. You did an article on naming behaviors, and what strikes me is that having a shorthand for that kind of feeling,"Pinball Mode." What did that do for you as a CEO when you heard it put that way?
Keith Cowing:It enlightened me. It was feedback in a very crisp and understandable way that resonated of, oh, I need to fix this. It wasn't, well, there's a couple things we're trying to figure out, or it's not clear. It was a very, very crisp communication of how they felt in a way that I could feel it. Because, you know, stories evoke emotions, and that's a type of language that evokes emotions, Pinball Mode. If you're the ball and you're bouncing around, that ain't good. And so, um. I, I think, and talking about that writing labeling behaviors is something, I actually came up when I had a conversation with Sarah Liebel, who's an excellent operator and has worked with a number of CEOs and founders and scaling companies. And, uh, we were talking about founder mode of people getting in the details or not getting in the details and where to apply that and we not to apply that. And she talks about labeling her own behaviors with her team, because if people know what to expect when you come in the room or when you join a project, or when you start a project, then they can work around that because now they know what's going on. And one of the tricky things is as CEOs, as leaders, you do frequently change modes where maybe you're gonna be commanding, maybe you're going to be just giving somebody an objective and let them run with it. Maybe you're somewhere in the middle, you're delegating, but you're monitoring and supervising and you want updates every few days. And so there's different modes that you upgraded. And that's okay. That's actually good. But what's not good is people not knowing what mode you're gonna be in and being on a different page. If they're trying to brainstorm and you're trying to cut it down. People are gonna get frustrated if they think you're gonna be in the details and you're not, and they're waiting for you, people are gonna get frustrated. If they are expecting to have the autonomy and you're in the details, people are gonna get frustrated. And so just having the same expectations as everybody is 10 times harder than folks realize. But if you can get there, and sometimes it's simple behaviors like labeling, how you're gonna act in a situation, you can really get people on the same page, and getting people on the same page is one of the most powerful high leverage things that you could do as a leader.
Benjamin Jackson:Yeah. You know the theme that's popping out to me here is that a key part of leadership is reducing uncertainty on the team. And I mean, the moment that we're in right now, the historical moment that we are in right now, is one where it, it feels like there has never been more uncertainty, in our politics, in the economy, um, just in, in, in everything that's happening around the globe right now. And that's bringing a lot of challenges for leaders and it's bringing a lot of challenges for their employees. Especially the sense of precarity, and I hear this all the time when I talk to employees at all levels, that everyone right now is worried about their job. And I'm curious, you know, has this come up with your clients? Navigating this uncertainty?
Keith Cowing:Yeah, constantly. I think it's the theme right now, which is how do you navigate uncertainty rapidly? How do you make critical decisions with limited information under pressure, quickly, while keeping your team engaged and along for the ride and supportive and understanding of what you're doing? It's a constant paradox. And on the certainty front, I frequently distinguish between certainty and clarity. I don't think you can give people certainty 'cause there isn't any. And when we work in an environment where assumptions are breaking at a faster rate than possibly ever, I work with folks a lot where people do crave certainty and frequently the leaders are people that naturally have a higher tolerance for ambiguity and uncertainty, and so they may not understand how stressful it is to have a lower feeling of certainty. And David Rock has a framework called SCARF of what people crave in the workplace. So it's S-C-A-R-F. S is for status. They want to be respected for themselves and in front of their peers. The C is for certainty. They wanna know what's coming. The A is for autonomy. They wanna own their own destiny. The R is for relatedness, which means your relationships with your coworkers. You feel like you're part of a community, and the F is for fairness. You wanna be treated the same way as other folks. And if you have those, then you feel pretty good. You crave all of them, and they come in different ways. Maybe you lose autonomy and you get frustrated, maybe you lose certainty, you get frustrated. And certainty is definitely under fire right now. And I sort of push back to be honest with people because I think pretending that you can give somebody certainty is just not being honest and that erodes trust. I would rather them be clear, And say, we're very, very clear about what we see about what we've learned about what customers have said, about what the evidence is about, why we believe this is the right move, about what feedback we've gotten from you internally, and therefore we're taking the following calculated risk. And guess what? It may not work, but we're putting a lot of reason. And process behind it. And now we're gonna make a bold decision and we're going to move and we need your support for it. And by the way, if it doesn't work, here's some mitigation techniques that we have. But this is the call and this is all the information about it. And the process by which you do that decision making of how you collect the information, how you share it transparently as you decide, And then as you share the the decision afterwards—you can't give people veto power. It just doesn't work. You can't run a company as a democracy, but you can give people input and transparency and clarity, and if you give them those things, and I think you're accomplishing as much as you can along with empathy of, we may forget how much uncertainty people have dealt with outside of their job and other parts of their life over the past five years that have sort of built up such that their tolerance is exhausted. And you just have to have empathy for this moment that people crave certainty and they can't get it. So how can we help 'em? Well, clarity and transparency and honesty are certainly some of the tools that you have complete control over.
Benjamin Jackson:Mm-hmm. I couldn't agree more You know, I find it really unfortunate how rare those qualities are in most organizations. And I'm curious, I know you can't see inside the heads of the founders that you work with or the ones that you don't, but do you have any theories as to why it is so challenging for so many founders to embrace that level of honesty and transparency and clarity with their own teams?
Keith Cowing:Two reasons that I see. One is insecurity, and I say that on behalf of people—and I've had it myself—on behalf of people that are some of the strongest leaders, some of the most impressive employees that are not insecure as humans, but. Their job is constantly getting bigger. Their job is constantly evolving. This may be the biggest leadership challenge they've ever taken on, and so you get used to something and then you get comfortable in it. But in entrepreneurship and CEOs and maybe just in life right now, every single month, the problem is harder and bigger, and so there is no. Stability, there is no plateau. So if it's constantly changing, you're constantly getting used to that next thing. And I think it's very, very difficult where leaders have to be, they have to have a lot of conviction or their team's not gonna follow them. Like you have to be the rallying cry. But on the flip side, you have to have the humility to be open to feedback, or eventually they're gonna stop following you. And how do you balance those two? And so I think there's insecurity on behalf of CEOs that think they have to have their armor on and think that they have to be right, and they're slightly afraid that they're not and they're not sure how to approach that. If you really dig under the covers... it wouldn't come out that way, but when you tease it out, I think that's one of the feelings. And then another one is that it actually takes hard work, even if you're not insecure about it. It takes extra work to go and communicate. It takes extra time and extra planning to treat a decision, like a process and say, I'm gonna collect input from these 10 people and then I'm gonna get together and then I'm gonna make a call and then I'm gonna push it out, is much different than Wednesday night saying, "Screw it. This is what we're gonna do," and send a Slack message. And so if you tease each of those apart on the insecurity side, where I work with on folks is differentiating what they have conviction in, which is you can have conviction in a great process and great assumptions and clarity. And if you have conviction in that, then you can actually go out there and be super proud of how you are approaching it.'cause you're, you're proud of the process and the decision making. And then the actual outcome, you could be humble in. This is what our bet is and we know what we're betting on. Sometimes your bet's right? Sometimes your bet is wrong. What you should never do is place a bet where you don't completely understand what the bet is. And so, I think there's opportunity there from a clarity perspective. And then on the making it easier front. I think AI is actually an excellent opportunity to make decision making more transparent. Because it's so much easier now to transcribe a call, to have the key points written out, to be able to share it to the company without it being, oh, here's an extra hour to sit down and write a document and share it and send it. That's real work. But with AI, if you have a conversation in a room and there are parts of it, you wanna sanitize it, et cetera, but there are parts of it you wanna share to the whole company to be clear about a decision that's coming up. I think that can be really, really empowering for people, and it doesn't have to be as hard as it used to be. It can actually be 10 times easier.
Benjamin Jackson:I think that's a really important point about transparency. And one of the things that I have found working with leadership teams is that oftentimes the most difficult place for people to be transparent is on a leadership team because the stakes are so high, and you may have people with competing agendas. I'm really curious to hear from you, what are some of the ways that you see transparency on leadership teams break down, and what are some of the ways that you've helped these leadership teams be more transparent with each other about what's actually going on?
Keith Cowing:A couple things come to mind. One big word is incentives, where Warren Buffett has a great quote that you could, if you own a business and you could spend 90% of your time working on incentives, that would be a good use of your time. And I think incentives frequently get in the way of transparency. But people are not open about it and don't just call it out. And so let's say there's a sales team that's incentivized to close deals this quarter and their compensation and their bonus is based on that. Their paycheck is based on closing deals this quarter. Well, what gets the deal closed this quarter? Telling the customer what they wanna hear and showing them stuff that looks good. Now you have a product and engineering team that has to support that and has a subscription problem to manage against expectations. And what are they held accountable for? Well, reliability and uptime and the velocity of new products that are in the strategy. You know, the direction of what you're trying to build, not necessarily what every customer asks for. And so you end up with this natural tension where the incentives are mismatched because what you're held accountable for are actually in tension with each other. And what I think is problematic is when people don't just literally put that on the table and say it. Um, and so if you could just say it of, say, Look, Ben, you gotta close these deals and I am set up because I have to do this over the long term. How do we make this work? Because on the surface level there's, there's gonna be this friction we have to get underneath it. And sometimes you can change the incentives. Sometimes you could say, you know what? There's some sales teams that compensate, for example, not just on getting the deal done, but on retention over the first 90 days and getting them activated and making them successful and like really following through. And so now you're aligned and, and so as a CEO, you can align incentives in a way that nobody else can. And even when you can't, or you don't, just saying it and saying. Therefore, due to this misalignment of incentives, what are we going to do about it? Maybe you can get a couple overrides a quarter where we'll do whatever it takes to get the customer deal, or it's only for million dollar deals, plus, or, you know, you come up with ways to say, because of this mismatch in incentives, we're going to have mitigation techniques. What doesn't work is people just backstabbing behind the scenes and, and it frequently happens because that is how they're incentivized if you're not careful about it. And then there's, there's another aspect of this where when you make decisions, and let's say somebody has to make a call and it's gonna impact other people positively and negatively, and it's not evenly distributed, and the leadership team is looking around figuring out what you're gonna do. Maybe you're very transparent. You show the process, then you make the call. There's a pretty common Jeff Bezosism, which is Dissent and Commit. So not everybody agrees, but you agree to support the decision because you have to.'cause if you don't do that culturally, you can never win. And so you dissent and commit. But one of the biggest risks of dissent and commit is people nod and smile and dissent and commit in the room, and then they quietly undermine it behind the scenes. And this one I really think goes all the way to the top, to the CEO, that you have to hold people accountable to an extraordinary level, that they do not dissect and commit and then quietly undermine behind the scenes. Because there's a saying that you get what you demand and you encourage what you tolerate. And I really believe it's true. If you tolerate it, you say, no, that's not good, but you don't fire the person for doing it, then you're actually encouraging it because it. It drives their own incentives. And so there, there are folks that will call that out really sharply. And obviously, like you give people a chance and, and you give them feedback and you work through it a couple of times, but if it's a pattern, then they can't be on the team anymore. And I, I think you need that level of CEO enforcement of culture. Because then people are gonna get things wrong and that's fine. You can tolerate that. What you can't tolerate is a culture that doesn't let people move with bold decisions because they're afraid of other people undermining them behind the scenes and not in an open discussion. That's harsh. But I really, really think it's it's reality of how these organizations can be successful.
Benjamin Jackson:Yeah, I, I agree. And it, it sounds like the only way to have a high functioning leadership team is to have really honest conversations. Not just honest conversations about the work, but honest meta-conversations about how the conversations themselves are shaping up.
Keith Cowing:Yeah, I totally agree. And I would say honesty, it comes in two flavors. One is, are you saying what you really think? Are you saying everything that you think? It's your job as a leader to not let things be unspoken because that causes a lot of problems. And it's, it's not just that everything comes outta your mouth is true, but if you have a thought, you share it. And it's not natural. I've been guilty of that plenty of times."This isn't the hill I'm going to die on whatever. I'm gonna choose a different battle." You really have to, you're paid to have an opinion and to share it. And that makes the whole system better. And then the other one is, I would say within honesty is also the precision of the conversation. Having people that can facilitate conversations in a way that breaks it down and makes it really precise. So if two teams, let's say marketing and product are upset about who owns pricing, because it's not clear, then somebody needs to facilitate that conversation around roles and responsibilities in a really finite, specific way. So it can be, oh, well we agree, you own naming and we agree, you own the roadmap, and there's just these three areas where we're uncertain. So now it's not fuzzy honesty about, Hey, we have a problem with who owns what. It's now really precise. We found three pain points and the other ones we're fine with, so let's solve those three pain points. So I think it's honesty. And it's precision and it's completeness of your honesty.
Benjamin Jackson:Are there any specific things that you've found helpful in working with leadership teams to help these teams become more honest and precise?
Keith Cowing:Yeah, I'll give one that can be tailored in a bunch of different ways, but I frequently see when there are different opinions. There's different levels of trust. There's different feelings in the room that if you have a conversation without an artifact—a document, an image, a spreadsheet, a budget, a roadmap, whatever it is—that a lot of times people just spin in circles and they spend 60 minutes debating and they end up right back where they started and then they leave. And there is nothing more expensive in a company than an executive team spending an hour of the most precious time in the company and not accomplishing anything. And the one of the patterns that I see is that getting people on the same page, frequently, literally involves a page. Like a one pager of, Hey, here's the strategy that we're thinking about and here are the different components. Now you can provide input and feedback, and we can be really precise about where we disagree. And yeah, you can have 12 page decks and stuff, but I, I love one pagers as much as you can when you have a key thing that you need to discuss because setting the stage for the discussion is as important as the discussion itself. And a lot of people have a fuzzy topic and they bring it, but they didn't set the stage appropriately for that discussion to be productive and healthy. And so setting the stage and facilitating the discussion is a skill and it takes work and you have to invest in that, and you have to do it.
Benjamin Jackson:You know, it sounds like so much of this is about moving conversations away from abstract ideas towards concrete feedback, concrete language, concrete next steps that people can take.
Keith Cowing:I definitely think specificity and precision in these conversations is really important. Now also, you know, there are biases out there. So I have a very analytical engineer type brain. I tend to think in, okay, let's break this problem down. There's four pieces. Let's talk about each piece. And I also think there's value. In rotating how you facilitate these conversations, so it's not always one style, one perspective, one voice. I've been in, uh, leadership teams where we actually rotated who facilitated the leadership team discussion, and I found that fascinating because there were other people that did things that I was like, oh man, like, why didn't you do it this way? But then they do other things I never would've thought of, or it never would've been my style. It's like, oh wow, that helped us see this from a different perspective. And so being able to shine lights on things from different perspectives is really important.
Benjamin Jackson:What are the mistakes that you see members of the leadership team who are not the CEO making when they're dealing with uncertainty?
Keith Cowing:Two of the most dangerous emotions that drive poor behavior and decision making are fear and anger. And usually when I see mistakes, it's driven by one of those two. And it depends mostly on the person, which one tends to creep up, but everybody has both. You know, if somebody undermines you, you're gonna be angry, and that's probably not going to breed the best decision in some complex environment instead of circumstances. And likewise, if you're afraid you're going to lose your job then, or you're just afraid of something, then maybe. You don't play to win anymore. Maybe you start playing defense. And in a world of rapid change, if you play defense, you might get trampled. And so you have to keep playing offense. And I think as leaders we have to realize that it's hard to keep playing offense and keep throwing the ball in the end zone and trying to score when people have real fear for legitimate reasons. We can't tell them, "You shouldn't be fearful for your job 'cause AI is never gonna do this stuff." We don't know that. And so I think we can be honest about where we are, but find techniques and tools to give them confidence and at least psychological safety of where they stand now and what the current environment is. And we refresh that constantly. You cannot control the certainty, but you can control those other things. I think by controlling those other things, you give the best possible fighting chance that people have enough psychological safety that they're not fearful or angry. And if they're not fearful or angry, man, that creativity is amazing. You know, that's why Pixar was so great when, and, and they still are, but they had this like almost untouchable culture in Northern California where it wasn't Hollywood and it was often this environment and they had this special way that they operated and they had talent that could tell stories and understand the technology behind animation in a way that nobody else could. But it was the culture that bred that and, and some psychological safety to try things that may not work in a way that other people weren't willing to. And, and I think that comes back again and again, and, and it may be impossible, it may be that hard that it's impossible for people to truly get rid of their fear and anger. But the more you can help reduce those emotions, the better decisions I see almost every single time.
Benjamin Jackson:And what practical steps can a CEO take to reduce those emotions, to create more psychological safety among that leadership team so that that trickles down to the rest of the organization?
Keith Cowing:I think the first step is really easy. You just ask and listen. Truly listen. What's on your mind? What could be holding you back from playing this game in the best possible way that you could play it? What could be causing you fear at work or outside of work? What could be causing you anger that's gonna get rid of the wild, creative, amazing juice that I know that's in there? Where can I help? I think it's personal and I don't think you're necessarily gonna get the full answer when you ask it once. But truly being on the lookout for that and really listening and getting feedback and understanding how people are operating and you know, that was the Pinball Mode. That was my feedback loop of, oh, this is not working for him. I didn't know that. And there are dynamics. People wanna tell the CEO certain things because their job is on the line. Of course they do. Even if they're very bold, even if they're naturally not fearful people, even if they're amazing leaders and honest and complete and precise, we're humans. And when we're humans there are dynamics. And when that person is your boss, there are dynamics. And so as the CEO, you have to work extra hard to listen and hear what's going on. And then when you really listen. You can figure out what to do about it, but I think it's the feedback loop that frequently is missing more than the action planning. The action planning is usually not that hard.
Benjamin Jackson:What do you see as the role of external facilitators, any, in making those conversations happen? We're both in the business of talking to people at work and understanding what's going on behind the scenes.
Keith Cowing:Well, so, let's take the role of a coach. There's certain tools that I have as a coach. I can listen. I can ask questions, I can help frame things for people so that they have a framework or a tool that helps them look at a problem from different lenses and maybe come up with solutions they wouldn't have otherwise come up with. I can give them support, I can hold them accountable. I can give advice. I can provide stories given my perspective of how other things are playing out in other places or historically, and they can use that as context. And within that, I think that if you help them… the CEO, let's take for example, does need to put their armor on at times and like go out to battle and not be fully transparent. Like they're out in the market, they're doing things, they're working with customers. Like it is your job to have your armor on and be that person, but they also need a place where they can take their armor off and be fully vulnerable. And it's confidential, it doesn't go anywhere and it's super safe. And then you find the blind spots, and then you find the secrets that they know, but they're suppressing that they don't want anybody else to understand. And if you're honest with yourself, not honest with other people, you're honest with yourself inside, internally, and you let that out, then we can say, okay, now we have all the pieces on the table. Let's look at what the puzzle should really look like, and then let's get you to a plan that you truly feel energized by because it's based on all of the truth, not just the truth you want the world to know about. And when you get there, I think leaders can get to the next level. So it's not about being in the room during those discussions. To me it's about being in a safe room where there's nobody else and they can let things out and you can work with a little bit and then you can help them develop a plan that they wouldn't have developed otherwise. Because you can't do it in an environment where there is any feeling of. You know, some dynamic that could hurt the company. And from that point on, it becomes, okay, we've identified what you need to do, and now I'll just hold you accountable. Hey, you, you said you were gonna have this conversation. How did it go? I expect you to have it tomorrow. And so having external accountability to run these conversations and get the feedback loop, and look the first time, is it gonna be perfect? And you iterate on it and you get better on it. But that's, that's how I approach that.
Benjamin Jackson:Keith Cowing, thank you so much for taking the time to speak with me today.
Keith Cowing:Yeah, Ben, this was a pleasure. I love what you're doing and I think you're work can help a lot of people out there. Happy to spread it.
Benjamin Jackson:Work Face is produced by Hear Me Out, a culture strategy firm for leaders with the courage to listen. Our consulting producer is Lina Misitzis. Original music composed by me, Ben Jackson. Special thanks to Rob McRae and Michelle Mattar. To learn more about Hear Me Out, visit hearmeout.co, follow us on Instagram at @hearmeout_co, or find us on LinkedIn by searching for Hear Me Out.
