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Introduction
Becky Flint: Without further ado, let’s get started with the CPO series, hosted by Dragonboat, where world-class chief product officers share their knowledge with our community. So before we get started, just a quick word about Dragonboat, who sponsors this series.
Dragonboat is an AI-native product operations platform that enables everyone in a product operating model, from CPOs to product managers, product operations, and their teams to set clear strategies, build portfolio roadmaps, and deliver products that delight customers and accelerate business outcomes. Our Product Ops co-pilot has been running in production for over 5 years for thousands of product teams, including these amazing companies, and managing very large $50 billion annual product and engineering investments. We’re excited to see how we could make an impact on a lot of product teams day to day.
And we are more than just a platform. We are your partner to achieve product operating excellence, including building a great community of product executives and product ops to share their experience, learning, and knowledge.
And with that, I’m delighted to introduce our guest today, Keith. Keith Cowing is an executive coach to CEOs and product leaders. He also advises product teams and teaches in the MBA program at Cornell. By the way, Keith and I actually met at the very beginning start of Dragonboat. So it’s a really fun story. We can talk differently later on. Previously, he was a Chief Product Officer at Vesta Healthcare, the VP of Product at Flatiron Health, acquired by Roche for $2 billion. He’s a two-time venture-backed founder and CEO. He has also worked as a product manager at Twitter and LinkedIn.
Keith grew up in a small town in New Hampshire and attended both engineering school and business school at Cornell. Outside of work, he enjoys traveling with his family and seeking new adventures. He’s a chef, an amateur mixologist, and a very amateur cyclist. Keith also has, OK, I want to make sure I said it right, a Belgian Malinois that keeps him on his toes and requires four to six miles of exercise every day.
So without further ado, welcome, Keith. And we are going to cover the topic, making and executing on critical decisions. So I’m going to stop share. And Keith, you can please go take over.
Making and Executing on Critical Decisions
Keith Cowing: Awesome. Well, thank you so much, Becky. Excited to jump in. As Becky mentioned, I’ve been a CEO, I’ve been a CPO. And now I spend a lot of my time as an executive coach working with CEOs and CPOs. One of the key sets of topics that we frequently end up focusing on is that when you get to the biggest leadership challenges that you’ve faced in your careers, a lot of times you have to reframe what you’re working on and what the real purpose of your job and your role is. And one of those is in decision-making. I spend a lot of time with folks that are making critical decisions and happy to walk through a lot of what I’ve learned and what I see people that are having a lot of success with this, how they manage it, and some really tactical tips and tricks for you so that you can manage it in your position.
And starting off with a quick story, when I was at Flatiron Health, I was interviewing a Navy SEAL for a job. And he was at The Graduate School Of Business at Stanford and was coming out and wanted to go into healthcare. The CEO and I were interviewing him, and the CEO said, “well, we understand you have all these skills and how amazing you are at what you do. What we don’t understand is how that translates to our environment. What can you do for us? Help us understand that”. And he thought about it for a second. And then he came back and said, “I am very effective at making critical decisions under pressure with limited information quickly”. And that resonated a lot with me. That is a fundamental skill that is really valuable and can go in a lot of different places.
So starting with that as a framing, and then anybody that’s in product, especially leadership knows that it comes with the corollary, which is while rallying the team and preventing a revolt.
SPADE Framework for Decisions
Keith Cowing: If you’re making a decision that impacts other people and you were going Northwest, and now you want to go Northeast, you have to rotate what other people are doing and where they’re aiming, and that part is not easy. So you have to reframe, okay, when you were an individual contributor, you worked on your judgment to make calls. And now when you’re a leader and you make a call, it’s really about the leadership piece and it’s about communication. It becomes more of a marketing problem than a problem-solving problem.
And one of the concepts here that’s really important is sunlight is the best disinfectant where if you can make a decision and actually make it out in the open, it’s your job to shine the flashlight, uncover all of the pieces of this puzzle, share it with other people in a way that they can understand so they can see the puzzle and then explain and show to them why you’re making this decision and what direction you’re going in and then involve the right people at the right time. Then when you make that decision, you execute on it, you’ll actually have the support of the troops so you can rally the team and move forward.
I’ll give you an example as a case here at Flatiron Health. We were struggling a little bit as we grew. So I was there when we were tens of millions of revenue and then grew to hundreds of millions of revenue. And Gokul Rajaram, who is an executive at Square and is on the board of Doordash and has had a really illustrious career, came and actually gave us some training on decision-making. And he has this great framework called SPADE. And we had a decision that we needed to make where we had product-market fit for small one to five doctor practices. We were an electronic health record for cancer practices. And then we also did research on the data to see what therapies were working in which types of patients and why. And we had an important decision to make where we’d been having success in the small doctor market, and now we were starting to win contracts with these large world-class research institutions that had dozens or hundreds of doctors.
We realized it was really a new market and we didn’t have product fit in that market. And we needed to dig in and figure out, hey, we have a couple of contracts where people have signed and we’re about to launch, but we know our product isn’t quite ready yet. And how are we going to handle that? We needed to decide, are we going to go enterprise now and really shift our roadmap to support these folks, or are we going to wait a year and keep working on what we’re working on and work on the small doctors because that’s our bread and butter at the moment, and we’re really good at that. It was a critical decision – It was a make or break moment. And so working with Gokul and then coming back with a team, I’ll break down this framework and how it worked for us.
So S is for “setting”. And that means really defining the decision that you’re making. At the beginning, it was, should we even go enterprise? Should we support these large institutions? And it was very clear to the CEO that we needed to because he was so deep in all of the context. But as VP of product, I was working with a lot of folks where they didn’t see all that context. And they didn’t understand why we had to go enterprise. And so I went and I did a simple Pareto chart which showed for our practices, what percent of patients do they represent? And it was a very clear 80-20 where the top 20 % of our practices covered 80 to 90 % of the patients. And we could lose our bottom 200 practices, and from a data perspective, from a business perspective, it would have very little impact. But if we lost any of the top 10, it would completely change our business and our approach. And so being able to show that visual and bring in data from different places made it clear that to accomplish our mission as a company, which was to learn from the experience of every cancer patient and then make the next treatment better, we needed to impact as many patients as possible, and when you looked at the market, that meant going with the big practices. Also, they had outsized representation of certain types of patients that didn’t go to the small practices. And so that was the “setting”.
And then you move to “people”. And people is about, who do you need to involve from an input perspective? Who do you need to communicate that needs to understand what’s happening? They don’t have to provide input in the decision, but they need to know because it impacts them, and how are you working through this. On the people side, we had three different pieces. One was strategy, folks that really understood the market so that we could color in that story and share it with people. And then the second part was operationally. If you’re launching software in a new area where it’s close and whether or not you have product-market fit, it’s really going to impact them heavily. And then the third part was emotional, where we had grown up and there is a mission-driven company, we’re trying to cure cancer, we’re working with these small practices, and a lot of folks were just all in on supporting these small practices and they never wanted to feel like we were leaving them behind. And that was incredibly important to them.
Taking all of that content, the next part is “alternatives”. Let’s define the options here, and at the beginning it was, let’s go or not go. It felt a little bit binary. We went back and forth with the team, and ultimately we got to a point where we said, well, let’s have a hybrid approach. Let’s take some of our roadmap and push it towards the big practices, specifically operational personas within the company is what we needed to focus on, and then let’s delay the go-lives. We had signed deals and we said, well, we think it’s better if we wait 6 months before we launch you so we can make you successful. And let’s change how we operate, every time we launch a practice, we’re not going to launch the next one until that one is healthy and green. So we updated our alternatives here and we’re really, really clear about that and wrote all of this in a document and shared it broadly. If you want to put input, your time is now because we’ve defined the decision. We’ve defined who’s gonna provide input, who needs to know about it. And here are our alternatives and we’re gonna make a decision at the moment.
Once you go through that, then you can go and “decide” and you make a call, which direction that you’re going in. And what’s even more important to that afterwards is “explaining” and then executing on that decision where, again, if you’re going Northwest, and you want the team to rotate Northeast, you’re gonna be working on slightly different things and getting slightly different pressures. You need them to understand why. And this is why that marketing component comes in of earlier in your career, you make a decision. It’s about your judgment. It’s about making the call and it’s about moving.
Building Trust and Communication
Keith Cowing: Later in your career, your decisions impact a lot of people and to get them bought in, you have to think about whether or not they trust the decision that you’re making. If you break trust down, psychologically, there’s four components of trust. There’s integrity. Are you honest and just generally a good human? There’s intentions. What are you optimizing for here? In our case, we had to think about our mission on helping patients. We had to think about our business and profit and be really clear and honest about that. Then there’s your competence and your job and your consistency. Consistency means can people predict what you’re about to do and know what’s coming next? Because if they can’t, they’re trying to read your mind and that drives them crazy. And so as a leader, I’ll just assume that you have these top two, integrity and intentions, but the bottom one’s competence and consistency. This is where the people are going to judge you and know whether or not they feel good following the path that you’re setting forth with them.
The process of turning a decision from a problem-solving thing into a marketing thing is about helping people understand the story and really being able to articulate it to them in a way where they can participate at the right time and saying, “Hey, we got two weeks. We’re going to collect these inputs, then we’re going to make a decision and then we’re going to roll it out”. And you can make the exact same decision, but if you do it in a different way with that transparency and manage it like a project, then at the end of the day, you can get people to trust you because they can see the consistency and they can see your competence.
And not only that, but as a leader, it actually trains them to make decisions well if you share this process with them, because especially in a hybrid world with Zoom, there’s less folks in the room sometimes with senior folks that are working through these decisions. So telegraphing what you’re doing is incredibly powerful as a technique and can help you as a leader and as a company make the right call and then rally the team to support the right call. 10% of your job is making the decision, the other 90% is running the persistent internal marketing campaign to get everybody rallied behind it.
Balancing Conviction & Humility
Keith Cowing: And when you think about balancing conviction and humility in this process, this is something I work with leaders a lot on where you have to have the conviction to lead the team to say, “This is where we’re going”, and they have to believe in you. On the flip side, you also have to be open to feedback in order for them to believe in you. So how do you be open to feedback and also have that conviction to really grab the reins and run with it?
My general heuristic for this to think about is that you want to have conviction in the process and the hypotheses. This is the process that we’re running and this is how we’re managing it. The SPADE framework is a nice mental model to use for that. And then here are the hypotheses that we have and how they line up together. And by the way, if any data in there changes where you break one of my assumptions because new information comes to light, then we will change the approach. But the logic is really, really strong.
And then humility on the outcomes where anybody that tries to predict the future, especially today when everything is changing, look, that’s going to break your credibility right away. But if you have humility in the exact outcomes, but a really, really strong sense of how to operate and the process you’re going to go through and the hypotheses that you’re making, then you can adjust based on hypotheses changing over time. If you really think about this as you approach things, then as a leader, you can not only make the right decision, but you can get the support that you need.
Making and Executing on Critical Decisions – Key Takeaways
Keith Cowing: So wrapping it up real quick, and then we’ll open to Q&A, some key takeaways here. Number one is tell the story where humans, yeah, we like bullet points, we like data, but we love stories. And stories resonate with people. If you illustrate to people what’s happening in the market, “Hey, small practices are getting bought by big practices. So there’s actually a trend towards big practices. Big practices represent 80% of the patients in the market, and especially the ones with rare diseases that are having really hard time finding the right therapy. And therefore going after these large practices enables us to accomplish our mission and do the things that we came here to do. And therefore it’s inevitable. And the question is, what’s the path to get there?” When you tell that story, then people can start to see it.
And visualize it as much as you can. You work in a complex system, so break that complex system down in a way that you can show to somebody else. Dragonboat is a great example of a tool that you can use to say, “Hey, I need all the puzzle pieces on the table at once in order to show somebody why we’re starting in this corner”. Because if you can’t see the puzzle, there’s no way you’re going to buy in on the decision. And a lot of people can’t see the puzzle because they don’t have the context that you have, and you see so many things as a product leader. It’s your job to help them see the story.
The second one is telegraph your moves. Just be clear about what you’re doing. Hey, we’re going to time box the next two weeks. We’re getting inputs. If you want to provide input, it’s now. And then we’ve clarified the alternatives. We’re going to make a call. We made a call. Now we’re going to roll it out. And those pieces of communication are extremely important.
The third part here is navigating from curiosity to conviction to commander’s intent. These are three different modes of operating. I stole this from Sarah Liebel, who’s the COO at Nayya and recently interviewed her for a podcast. And I really like how she framed that because it’s a mental model both internally, but then also that you can share. When you’re in curiosity mode, you’re just collecting inputs and you’re asking questions. Once you have conviction, you’re going to switch and say, now I’m in conviction mode and we’re just tightening up our alternatives because we’re going to make a call, and I think I have what I need in order to make that call, but we’re dotting I’s and crossing T’s and making it tight. Then eventually at the very end, there’s always going to be the last mile where somebody is providing some friction,and you’ve run the process really well – at that point, it’s commander’s intent. It’s just time to push through and make it happen.
I will wrap it up there. I’ve found that if you have the right process and the right mindset around decision-making, it can make an incredible difference for you, for your product, for your organization, for your company, and ultimately for your career.
Audience Q&A
Becky Flint: Wow, this is amazing, Keith. I can’t believe how much, how dense the wisdom is and so much to unpack. I’m just barely keeping up with you on all the great stories here. I think we have some audience questions, but before that, if I could ask some of the questions, I want to double-click some of the topic you actually had to cover.
I think let’s just start with the last one you actually talked about, which is the last one you discussed is around curiosity to conviction, to commander’s intent. I think that’s incredibly important. Regardless that you’re a product executive or you’re a product manager or product operations, you always go in shifting between different modes when you interact with others. I want to use the example when I worked for an executive at PayPal earlier days, he was also earlier in his career as a new executive and he realized that when he was talking to people, people didn’t really realize that is, is that a question? Is he trying to gather information or is his decision? So there was a lot of confusion around it. I think this is a framework very similar to that. So what are some of the techniques or some of the things you’ve seen that either your product managers or product leader interact with the others? How they go about doing that? Do they start a conversation with that? What are some of the examples, advices and breaking this down further?
Keith Cowing: Yeah, I think that’s an incredibly important point. If we zoom out a little bit, this is an example of labeling your behavior, where sometimes you have to be in different modes, but that hurts the mental model of consistency for the people you work with, where in some meetings, if you come in as a leader and you’re maniacally in the details and you’re pushing and you’re making all these things and sometimes you show up and you’re like, “This is yours, I’m just here to sip coffee and ask a few questions”, then they don’t know what they’re going to get. And an incredible amount of their energy actually goes towards predicting your behavior and trying to figure out in this meeting, what does this leader want? And so you can cut off a ton of that by just telling them and sharing it.
I’ll give you an example from LinkedIn, Jeff Weiner, who was not the founder, but had been given the reins by Reid Hoffman and operated like a founder. A lot of people talk about this founders mode content these days. When Jeff Weiner was in meetings while I was there, he had this, he sounds compelling, he has a lot of contacts who’d throw opinions in. And then after the meeting, people would run around and they would change all their priorities because the CEO kind of gave them input. And then sometimes you realize, hey, that’s not what I intended at all. I was just brainstorming with you and you went and changed all the priorities. That should not happen. So he wrote a blog post and came back and told the whole company, he said, “Okay, look, from now on, I have three modes in a meeting. One is I’m just another opinion in the room, and I will tell you that and you’re bringing up these things. I’m a product person. I love talking about it. I have opinions, take them, but treat them the same as anybody else’s and then make your call and go. And I mean that. The second one is a nudge where you are providing input and you think you have some context and you think you’re right, but he still was giving permission to that person to make their own decision and he meant it. Go live by this, learn, et cetera. And then the third one is what he called the executive mandate of, I want you to do it this way and I expect you to.” And he has that card as a CEO. If you’re really clear about where you’re pulling it out and where you’re not, then you can label your behavior ahead of time as you’re going through what it is and people know what to expect and how to behave. And he said, and if I’m not clear, by the way, it’s your responsibility to ask me and make me clarify so that then we both know what we’re working with.
Scott Belsky at Adobe had a recent conversation with him. He does similar things where there’s some, as a designer that runs the whole design team and product team at Adobe, he’ll actually dive into the details and say, “hey, on this one, I’m holding myself personally accountable. So I’m going to be in the details. Extremely so. On this one, I’m going to delegate so that you can understand that.” So labeling your behavior in advance is really helpful both for you and your team because then you can change modes, but they still know what to expect from you. It’s predictable.
Becky Flint: This is super helpful. Labeling your behavior. I think there’s another question, really similar style, which is you shared a lot of great stories and examples. If you have details on where to find the information, please share with us so then we can share with the audience who attended or not. We can put it on our website as well so you can find them. I think there’s a similar question around the SPADE decision-making framework where you find more information around it. Would love to have that information from you as well.
Now, related to that, you mentioned about telling the story. Going back to earlier on, you talked about how when you, you know, the company running to sort of critical decisions whether go to a larger practice or a smaller one, there are a number of things coming through. Can you share a little bit of how you, I think sometimes product managers or product leaders will be able to find data to make that kind of suggestions and sometimes they struggle a little bit on that. How would you go about it if you would, like this happened a lot in many company I went to, it’s like, should we go this way, should we go that way? And then where we go and then the data may change.
So if you could help a little bit of how you think about what data to get, what are other supporting information you’re going to get? And then obviously we have opinion at Dragonboat because we built a system, but I would love to hear from you how you go about approach this sort of the critical decision and how things coming together.
Keith Cowing: Yeah, there’s a couple of things I’d recommend. The data is going to vary radically depending on the situation. It’s so situation dependent, but there’s some principles that are consistent. One is understanding the marketplace and ecosystem that you’re working in. As a product manager, as a product leader, part of your job is to zoom out and then zoom in on demand and talk about a pixel in the top right, and then in your next meeting, talk about all the competitors and how AI is changing the landscape and who’s going to play where. Being able to understand both of those at the same time is super important.
I would say, there’s a framework by Todd Jackson on product market fit. He’s a partner at First Round Capital that I think colors this in a lot, which is on your product, you’re always thinking about the persona the problem, the promise and the product. So like, who are you serving and what markets are you in? And then what problem are you focused on? What’s your value prop and your pitch? And then how do you actually bring your product to life? You’re going to have different conviction at different points of that at different times. And you’re constantly looking at, okay, we were confident in our problem, but now at Flatiron, we have a new persona to focus on. If you’re thinking about personas and whether or not you go into that new persona, you probably need a lot of market data to understand like, is that persona big enough to be focused on? In our case, it was, and it was the most important one, so, okay, we have to go there, how do we get there? And if it’s really about the problem that you’re solving, then that might be a user research heavy thing of like really getting into the mindset of your customer and that empathy and drawing customer journeys and stuff like that, maybe less about data and more about time in the field. And then if you’re talking about value prop, maybe that’s similar, you get into product and you get into some of the details of it could be A-B testing or design techniques, et cetera.
I think there’s different tools for each of those. Persona tends to be very market focused, and then when you get into problem and value prop, it tends to be very user research focused. And product, there’s a lot about usage data and things like that.
Becky Flint: That is very, very cool. I don’t want to use this opportunity also just to bring up a diagram, which sort of connect the pieces together. I’m not sure you get a chance to see that before.
We call it the product operating model where you can see sort of the strategy and outcomes to your product roadmap. Now, these are not one direction, they’re actually two directions. Meaning, like you said, when you look at your, the example you use sort of the larger practice versus the smaller ones, you actually look at the number of patients, not just by the accounts, where accounts is different. But if you look at the number of patients, you realize that the 80-20 rule actually had a flip. So if that aligns with your mission, then it would have more drive for the larger number, the most patients you can affect their health, then it really helps you make decisions. Now, that’s definitely the conviction based on the data.
There’s another part of that I want to highlight a little bit as well, because you did mention there’s a conviction that’s based on process and hypothesis. There’s also, you have to be open to change based on the outcome. And that’s something that we definitely at Dragonboat focus on a lot as well, to say you have a strategy, which is always a hypothesis, right? If it’s based on some data, you have a hypothesis, and then you go ahead to start building your roadmap. As you come through, you may realize that it may go the direction you want it to be, may not be going through the direction you want to be. Like in your example, actually did go through. So in some other cases actually didn’t. So when you can tie your product to the outcome you’re going to drive and realize that may or may not be the things you move, you make changes.
So would love to hear an example if you have anything handy to say when and how you make changes on the direction and you want to move because your strategy is no longer. How do you make that change? You know, I know you talked a lot about the change of the team, change of the roadmap, marketing, but talk a little bit about the decision process. How do you look at the data?
Keith Cowing: Yeah, and this has changed for me actually recently where I think the world is moving at a faster pace than it has in the past in terms of rate of change, which means that I think you have to revisit your assumptions more frequently than in the past. In the past, we had a three to five year timeline where the technology paradigm would shift completely and you had to reinvent yourself. And now that’s shrinking and shrinking and shrinking. Assumptions that used to last three years, maybe only last six months now. I like how you frame this because then you can take all the pieces and pull it together.
OKRs are one framework a lot of people use. I think that’s a really nice way to try to do this where your mission should probably never change. This is why we are here, tthis is what we’re fundamentally focused on. You may tune how you articulate it, but the fundamental thing is not going to change. Then you have your strategy. How do we delight our customers and differentiate from people in the market to build a motto and generate margin for our business and your pillars of investment that bring that to life? And then you have your tactics, the individual things that you’re doing. Tactics, I think, should change constantly, but should change under the light of a strategy.
Maybe 70% of your energy is going into products that drive value today, and 20% are going into products that are going to come out next year, and 10% are venture bets if you’re a bigger company. If you’re a startup, maybe you only have two bets to place and you’re all in. It really depends on your situation. But I’d say tactics, you should be constantly open to changing. Strategy, hopefully you get them right, and hopefully you’re not changing it very frequently. But you probably need to zoom all the way out and revisit quarterly, every six months, every year, depending on the maturity of the business. And then mission and vision, you’re maybe just seeing if it’s properly resonating, but hopefully not changing it much.
Becky Flint: Right, right. That makes a lot of sense. And I really want to call out something that you mentioned, right? Before, it’s probably OK. You don’t have a system, especially you can do three-year planning. Now, with the rate of a change, you just don’t have the luxury, you really need to be able to continuously evaluating at least your tactics, see if it’s moving the direction you want or not.
So it is so rich content, barely can keep up an audience agrees as well. For some of you who want to have more resources, want to learn more from Keith, you know, obviously, it’s like a free course today from Cornell, right? And, you know, obviously, Keith on LinkedIn. I know you also have a really good podcast. Would you like to take a minute to share what it is?
Keith Cowing: Sure, you can find it at Executives Unplugged, and you can also see my website on the podcast. I’m very interested in leadership, as you can tell, and particularly in helping people get outside of the bubble of just finance and tech. And so on the slate of interviews coming up, it’s people that run restaurants that run Broadway show productions that run sports teams that are all over the place. But it’s all about how do you perform as an individual, and how do you get the most out of your team from a teamwork perspective. I’m having a lot of fun over there. And if you’re interested in this type of content, I like sharing things for free. And that’s one of my outlets for getting free content out there.
Becky Flint: This is awesome. And pay it forward, Keith. I really appreciate you sharing. For some of you who want to learn a little bit more about Dragonboat, here is the link. Go check it out. Also, you can go to dragonboat.io/cpo.
With that, we conclude today’s CPO Series. Thank you so much, Keith. And thank you all for tuning in today. We’ll make it available online as well, so you can get additional resources from today’s session. Thanks, everyone. Until next time. Bye-bye.
