Coaching Pilot Teams

Welcome back to Product Therapy. Today, I'm joined by product coach and transformation leader, Gabby Buffram, for a conversation at the heart of meaningful change inside organizations, pilot teams. When a company commits to the product model, the question often becomes, where do we start? The answer, when done well, is often start with a pilot team. But these aren't just test groups or isolated experiments. When set up intentionally, pilot teams are a powerful proof point that actually accelerate organizational and operational change. In this episode, we dive into what makes pilot teams succeed, what mistakes to avoid, and how leaders can coach, maybe protect and scale what's working. If your company is transforming or thinking about it, this is an episode you want to hear. Gabby, good to see you. Welcome to Product Therapy. So nice to see you, Christian. Thank you for having me. Always a delight to work with you or spend time with you. And Gabby, you have worked with several companies around the globe, helping them move to the product model. And kind of like I always say, you know, the reason we treat the transformation, when people say, I want to transform in a project model, where it's kind of this top-down, cascading, hand-off, sequential way of working, to the product model, which is kind of an empowered model focused on delivering outcomes, when companies commit to doing that, more likely than not, they often say, yes, we want to move to product. We want to move to outcome. And so they start by saying, let's do a transformation project because that's kind of what they've always done. They've solved their problems through projects. And what you're trying to coach people into is the way we transform to the product model is like a product where we iterate and experiment. And that's often why we recommend pilot teams. So maybe start with how you define them. What is a pilot team? And how is that different from, say, a normal team? Yeah, and I love that you called out, Christian, how they create a project for this, right? Which is so against what we're trying to do. We're like, how would that solve the thing we wouldn't go away from? And I really talk about it being like a spiral instead of like a project. It's something you're always evolving. And to your point, the pilot team is key. It really is an important aspect. And I tell people that the pilot team is more like a poster trial team. We're calling it a pilot team, but we want the team that is going to be in this different island, this different place where they are being taught a different way of working. And honestly, they're being expected to succeed. So that's why we call it the poster trial team. They are the team that's going to show what is possible when we do work in the empowered way. It's a proof point. I actually do differentiate for companies right now. It is actually not a prototype. It's a proof point. It's to demonstrate what's possible with the right structure, the right context, the right coaching to get outcomes. And when we tell companies, the second you commit to move into the product model, it's a race. It's a race to outcomes. You don't have the trust. You don't have the credibility. We don't have any proof points that we can work this way. So really what the pilot team is doing is creating a proof point to earn you enough trust for the next proof point or earn you enough credibility to participate in thinking differently. So I love that you've kind of framed it that way. And this is a small empowered product team, taxed with working in the model before it's rolled out broadly. And that's the whole idea around a pilot team. Now, let's go tactically. All right. So you are telling me, I want to transform to the product model. I need a proof point. I need to demonstrate in the company what it means to work this way. So how do I pick? How do I decide which pilot team to start with? And maybe use that to narrate what makes a good pilot team. Yeah. I normally ask people and I tell them very clearly, like, this thing fails. We are in hell. like we are in a really bad place i also tell them like people are going to be looking at this team and to your point christian like we're not starting from actually like not having a lot of trust we're starting from trust debt like by the time they bring us in they probably have tried some other stuff they did other things so the organization's already like what the hell is going on with these people so we really have the pressure of delivering something great so i tell them like for that to happen you need to give me your best people like i want your best designer best engineer best pm and sometimes they don't have pms a lot of the times they're moving from a different model where they didn't have a traditional product manager and i tell them what i look for in a pm so a really empathetic person business-minded great collaborator very proactive and i'm like send me five of those i'll talk to them like let me help you find your next pm or sometimes you were like, I think I have the guy. And I'm like, and then when I meet them, I'm like, yeah, you have the guy or the girl. And that is like coachable, right? They need to be open to this. They need to be open to learning. They also need a clear scope. So I've seen pilot teams that it was like, oh, they kind of own this, but they kind of own whatever. And I was like, OK, well, our first job is to understand what this team really owns, because they need to know that. I need to know that. You need to know that. They need to be customer centric. So I think that means like something clearly aligned with the customer that's delivering value to the customer. That's normally the ones that I like to start with because then we can see tangible results, which means they need to have access to customers. If they don't have access to customers, I'm like, how can we build something that is for them if we can't talk to them? That's a big one. And then having a clear problem to solve. So I normally work with the leadership team on that. and we decide what is the problem that this team is really solving this quarter. And together with the access to customers, having access to data, because I tell them if we can't measure, if we can't know, it just becomes kind of a feelings game of like, oh, I feel this is going better. And I tell them like, we're not gonna win on that. We need to win with some hard data and execs love numbers. I joke that like an exec love language is like Excel. So you give them like a well-populated Excel that shows progress. Like we have a happy conversation moving forward. So you're calling out what makes a good pilot team a real problem to solve. You talked about a cross-functional team with strong products design and engineering leads. You talked about access to customers, access to data, access to business or stakeholders. You talked about maybe some guidance and a coach. But I think you're also calling out the environment has to be context-led because that's what is not just about the talent and the people. It's also around the environment. And maybe to some extent, that environment is created by leadership. I often get the question, where do I start? Do I start with the worst type of team that everybody believes cannot change and coach them up to prove that they can change? Do I start with the easiest one or the one that is already rocking and rolling and the rockstar team that's already doing well just so that it is easy for me? How do you respond to that? Yeah, I tell them, like, you definitely don't start with the worst one. I have a lot of companies that tell me that and they're like, these are the most problematic people. Let's start there. And I'm like, why? Why would we start there? Like, this thing is hard enough as it is. Like we changing behaviors We changing how people work We changing what great looks like And people can tell you they like change They don like it Most people don like to change and they'll feel afraid. They'll feel worried. So like, why would we go there? And then there are some cases that people are like, well, this team, everyone already believes that they're working this way. And if we go there, they're just going to be like, well, that was a win already. And I'm like, well, we also don't want that. So we want kind of something in the middle. We want like a media enough problem that is not going to break the business. Otherwise, we won't get the access that we need. And we want people that are open to it. Like I'll tell them, like, I'll take a PM with zero experience as long as they have the right mindset, because that I think it's something that you can coach. But it's just going to take a lot longer. And again, to your point around time, like we don't have a lot of time. We have about like three to six months to show some sort of results. And by results, you mean an outcome because you're trying to tell a story that we had a problem to solve and we worked collaboratively as a team by giving the problem to a group of people. They solved the problem and got an outcome. And pretty much what you're saying with the pilot is it can happen here and we can do it more places with more teams. And maybe that's the message. One of the things maybe we haven't talked enough about in this pilot is the role of sponsorship around it. like the executive sponsor who signs off on this, who approves this idea of fine, we will do a pilot? I talk about this all the time with my clients. Like we need leadership buy-in and it's not leadership buy-in of like, we like these outcomes. We want them. Like everyone likes that, you know, everyone wants them. But I'm asking people like, okay, you want to do that? Would you want to go to the gym with me for like two hours every day? Are you committing to that? Are you committing to going swimming? Are you committing to waking up early? Like these are the changes that we're looking for. So you really, I believe, need the leadership team to be fully bought in. And there's a client that I love and he tells me all the time, like I asked him, like, oh, what's plan B? Like, what if this doesn't work out? And he's like, there's no plan B. He's like, this needs to work. And that's what I look for. I'm like, I want to know that you're fully invested in this. And if you are not, then it becomes a way harder convincing job for me and for the people that are trying to bring us in. So, okay. So Gabby, let's say, fine, I'm going to sponsor this team. I'm the leader I'm brought in. What do you expect of me? What is my role now in supporting this pilot? I think that there needs to be really clear communication with this team of like, hey, we are doing something different. That doesn't come only from you. That comes from leadership. And success for you now looks different. What it means to deliver something looks different. And we now are almost like, yeah, playing a whole different sport, a whole different game here. And I like to talk about like how normally with the project model, it kind of feels like you're on a swim team. You're still like on a team, but like each team player is like swimming their own thing. And then you get to the end and it like tallies the points. Right. So that's the project model. And there's like handoffs and all the problems that come with that. And I like to think about empowered teams as a soccer team. And really what that means is like you can't play soccer without the goalie. You can't play soccer without like the offense. And you only win if you play together. There's no playing alone. And unfortunately, like my own country is a good example for this. But like Brazil has incredible players, like incredible soccer players that somehow can't play together. Like when we play in the World Cup, like I get so sad. I'm like, look at what you do for Barcelona, Real Madrid. And then you come here and you can't play together. So like stars are not enough. You know, you need like a constellation for people to really be able to shine. And I think leaders need to talk about this. and really explain that like we're doing something different. And in order to get different results, we need different actions. I mean, you talk about evangelism, they have to be maybe the champion of why they are doing it. Someone asked me the other day, you know, oh, my CEO was having doubts. Like, I don't know if this whole product model thing is going to work. Like, what do you respond? As I said, the same thing to any CEO that asked me, like, is this going to work? I say, I don't know, but do it best. I mean, it's kind of asking me, I cannot predict what that is. There's no guarantees around this. And I tell the CEO, do a test. They kind of take a step back. He's like, what do you mean? Like, I'm like, well, we are positioning that you all can win better as a company, to your example, playing soccer than playing as a swim team. You can win better with an empowered model, moving to outcomes than delivering projects. And I said, let's do a test. And a pilot team is a test. And they say, well, what is my job? I said, well, on one end, you need to be the chief evangelism of outcomes. You're telling your whole company over and over again, the best way to serve our customers, serve our business is for everybody to be focused on outcomes, to empower people better. And I say, well, tactically, yeah, the things I want you to do. One, when we pick a pilot, you've got to protect them from all of your old habits. All of those random stakeholder requests. I'm like, look, this is why we're not changing your whole organization. We're picking a small group. So it's not crazy to say we're going to protect just this one squad or these two squads. And I say, look, we want them to be staffed with competent people with a necessary range of skills to solve a problem. You know, now you're choosing to play soccer. I need a goalkeeper. Maybe you didn't have one before, but we're going to staff them. You see, it's a small area to do that. You want to make sure you give them a problem to solve. You want to make sure you know what good looks like and an outcome. Most importantly, they have never played this game before and they've never played together. And I said, look, we've got to coach them. We've got to coach the leaders and we've got to coach the team. And I said, there are two muscles that they haven't really practiced well. The team has not practiced the muscle of solving a problem. They are very good at the muscle of delivering something. And the leaders haven't practiced the muscle of deciding which problems to solve with context. They've practiced the muscle of control and let me tell you what to do. And I say, you see, this is all we're trying to do in a pilot. We'll pick a small group, Your job is just to protect the group from old habits, from politics, from external pressure. And then we're going to coach them to deliver outcomes. And if it happens, now you have proof that it can happen here. I tell them, like, they're creating an island. It's really a separation between the mainland and the island. And I normally get asked, like, oh, is there a bridge? I'm like, no, no bridge. There is a boat that goes very infrequently. And you need to be in charge of this boat. but yeah we're communicating we're telling these stories but like this is an island and they're holding kind of like the shit umbrella you know it's like let's not let it rain in this island let's have this island be a happy place so that people can learn a new skill i have just been learning a whole lot from you gabby this idea of like no it's an island and you know there's not the bridge there are some boats that can take things back and forth how do you deal with someone's counter argument of like, oh, but Gabby, I mean, this is not the real world. You did everything to set them up for success. You put an umbrella over all of their problems. This is not what happens in a real world. You know, you protected them from noise and chaos. How do you respond to that? Yeah. I tell them like when someone is just learning to run, you don't sign them up for the marathon. You're not like, let's go. Like now real world Ironman, let's do this. Like you teach them in a controlled environment and then they get better and then they start being better at communicating with stakeholders and the boats can start running more frequently And maybe you like yeah maybe we do eventually have a bridge But to begin with you start by giving them the chance to succeed because that what they need They really need to change their mindset. They need to change their behaviors. And they're learning all these new skills while also being expected to deliver results. That's pretty hard already. I do get many variants of that question. You know, it's like, oh, but Christian, you put Gabby on it. That's why it was successful. I say, what do you mean by Gabby? She's very good as a product manager. That's why it works. And so I say, well, are you saying to me that if you put a competent product manager on a something, we will get good results? Or they'll be like, oh, but Christian, the reason it works is because they protected the team and they didn't let any chaos or noise bother them. I say, are you saying to me that if you have more leaders that protect their teams from distractions and chaos and noise, that good things can happen here? You know, everybody tries to find the excuse for why their things are not working on people. And I'm like, but you're recognizing these are the things we're trying to demonstrate. What does it take to deliver a good outcome in the company? And in some ways, you're just showing those principles. There's focus. Leaders are protecting the team. There's a good line of communication. What does it take? So I love that. And I love, Christian, how you turn their questions into coaching opportunities for them. That's... Of course. Yeah. Because you're just like, wouldn't it be great if you had more people that protected the teams? That's amazing. That's right. That's right. You know, it's unfortunate because one of the things I explain to companies all the time in transformation, I try to explain that this is not an argument that good work doesn't happen in your company. And I tell leaders all the time, I want you to reflect on the last time you did something amazing as a company. The last time you delivered an outcome. The last time you did something great. And it's always a story. Every company has a story. Sometimes it was in COVID. I remember when things were going down, how we rallied together. And often, unfortunately, what many companies do is they go into the hero mindset of things. They find some rationale that is impossible to replicate. And I say, okay, let's play back the last time we were very successful. I say, explain it to me. And when they are going through, I say, hold up here. So you mean everybody was in the room when it happened? They're like, yes, leaders rolled up their sleeves. So I said, so there was clarity about what the problem was. They're like, yes. And you know, and then we all walked in. I said, so you mean we didn't care about titles and roles and kingdoms and chiefdoms. Everybody just jumped in. They're like, yeah. But they always end with like, it was so stressful and exhausting, but we won. It was so cool what we did. And so right after that, they go back to how they've always done things. And companies have these spikes of great work. And all I try to say to people is, I want to identify what makes great work in your company. And I don't want it to be pointed to a hero because we cannot replicate them everywhere. I want it to be pointed to the environment, to the context, to the principles, because that is what I'm saying to you we want to accomplish in the product model. I want that to be who you are in most places at most times, not in some places at some times. And that's the whole essence of your transformation. And it's a great way to say the pilot, all he does is for you to get those proof points. Look at what happens when we focus. Look at what happens when we lead with contacts, not control. Look at what happens when we give teams problems to solve. And then everybody's saying to themselves, we could do that in more places, can't we? That's the essence of a pilot. I love that so much, Christian. It's so good. And I often say that success goes beyond the pilot with the leadership team, because they start being like, I had a recent client, And the pilot team was telling me about this design approval process. And I was like, well, that goes very against everything that we're doing. So like, why do we have that? And then I talked to the leadership team and I was like, hey, what's up with this design approval process? And they were like, oh, no, we haven't had that in months. And I was like, well, your teams definitely think that you do. So how do we change that? And you start being able to change some pretty systematic big things because you get access to how the teams actually work and how they see the world and you become a part of their journey. Gabby, how do you know a pilot team is working? Maybe how do you define the success of a pilot team and what are some of the signs that it's working or not working well? I think there's like a twofold sign of success and one will seem really obvious to people, which is they are achieving outcomes, right? They are actually being able to make the world a better place while also helping the business. Like that is what we want. We want to serve customers in a way that also helps the business. So they are doing that. And that is the obvious one. That's the one that looks good. That's the one that people see in like the spreadsheet and the numbers go up into the ride and it's exciting. And then the other part that for me is really exciting is that you start getting people wanting to work on that team. Like I start getting emails. The CEO starts getting emails. They're like, that team seems awesome. Like, how do we join that? And in my mind, I'm like, well, you can't join that because like we already have a designer. We have a thing. But I'm like, that is what we want. We want people to start wanting to work this way. That for me is a huge proof of success. Many people will argue outcomes are so lagging. You know, if I'm trying to grow revenue, it might take me three months, six months, one year before I see the outcome. But you're kind of talking about what we'll call signals of transformation. Like people want to work that way. There's this riling cry internally around this. I think other signals for me are around the muscles we're trying to develop, which is like discovery. Are there signs that we're actually experimenting, testing, spending time with customers, validating our answer before making decisions? Maybe the muscle of strategy, there are more insights in our decision making. There's more focus in the culture. There's also behavioral change with people. Like we're working more together and we're working in handoffs. You're building confidence in a new way of working. There's like more proof in the company today that collaborative problem solving yields better outcomes, that context is better than control, that trust is better than control, that those things I think are super important. It's about outcomes. You're right. It's also around the signals. Yeah, absolutely. I love seeing teams that like catch themselves. So they say something to me and then they're like, no, that's how we used to do things. Now we do something else. And then they normally feel bad. And I'm like, no, no, no, this is progress. You're making progress. You didn't used to catch yourself. before. And now you're course correcting. Or I think a big one is that they want to get value to customers faster. And I remember one of the PMs on a pilot team that I'm coaching now, he was just like, oh, yeah, this team said that they want to deliver by the end of the quarter, but not if Gabby has anything to say about that. And I'm like, yes, that's right. Like I want them to deliver ASAP. So what can they get in the hands of customers today? Obviously, the whole intent of a pilot is as a catalyst for your meaningful transformation or a proof point for it. But how do I know it's ready? And maybe what am I doing next? All right, we did a pilot. Everything is going well. We deliver an outcome. The CEO is happy. Then what? Do I roll out another pilot? Do I jump to the whole thing? What do I do next? I think that to the first one on how do you know that it's ready is I really like to think about kind of going through at least one or two like really clear discovery loops with people so that they have a chance to practice and they have a chance to learn because when they go out kind of in the real world alone without me, they know they've been exposed to this before. And to leave them with a real toolkit that they can use, not a process, very clear, but a toolkit. Things that are like, oh, yeah, that's broken. Cool. How do I fix this? I have this tool I learned and they have that understanding. I also have something that I do with teams when I think it's getting to that point And I ask them like what have you learned so far And where were we at when we started and where are we at now And normally they describe this kind of epic journey to me by the point that they in the end I'm like, okay, like, how do you feel about continuing that? That's so good. One of the things that I see as even when you see some pilot teams working is companies that do what we call pilot theater, you know, where the pilot works, but it doesn't lead to any broader change or they are stuck in pilot cycle forever. How do you avoid that where you're just like, OK, infinite pilots. So we're just pilots and pilots and pilots and nothing really changes broadly in the company. An important combination is that you're coaching the leadership team as you're coaching the pilot team. And I tell the leadership team, like, I must coach your pilot team. There's not an option. Like, I need to be involved there because I need to see the stuff that you guys can't see because you're at a different vantage point. And sometimes they're like, oh, I want to be in the room. And I'm like, I don't want you to be in the room. I want you to be as far away from the room as possible because like they're not going to be the same with you in the room. They'll be the same with me. And they feel like they have this avenue, which is great. But I tell them like for this to work, we need to coach at these different layers. And they start influencing each other. And I talk about companies as being like ecosystems and you add one different species. Everything changes to the ecosystem. And it might be like a really small thing. It might be teams now ask themselves, like, what new did we learn from a customer every week? That's amazing. That's meaningful change. So that would be my core answer. Gabby, on the other end of this is the pilot team actively doing the work. I can imagine if a pilot team does the work and they are successfully yielding outcomes, many people quickly see them as the golden child or some special outlier. They have all these names, Tiger Team, Awesome Squad, Seal Team, Six Team, that they do amazingly in the company. How do you avoid a company maybe using that team in that manner or seeing them like the golden child where great work you did that. We're going to keep throwing all of our hard problems to you because now we have a team that does that and not change the whole company to work like that team. Yeah, great question. I actually call all the pilot teams that I work with a dream team. I'm like, you're joining the dream team. Like, welcome to the dream team. And even like in our team communication, that's what it is. And I tell them like there's some responsibility in being part of the dream team. And a core responsibility is that what you learn, you're going to teach other people. So you are getting this awesome experience and you're part of this team. And I normally ask leaders, I'm like, who do you want to promote in product? Who do you want to become a manager? And like I have this amazing story of this company and he wasn't even a product manager when we started. And now he is a director of product and he grew so much. And it's because the leader saw potential in him. I saw potential in him and now he gets to coach other people. So the work doesn't stop by like, now we are awesome. It's like we need to enable awesomeness all around. You actually go into the heart and soul of why we did the pilot team. And the key measure beyond the outcomes is that they can get other people in the company to walk this way. And you called out coaching the leader. I often tell people if a leader has seen good work and what it takes to do good work, the fastest way to scale is you can literally move that leader to another part of your company and magic happens there because they know what the environment looks like. They've seen the elements of positive work in your environment. This was fantastic. All right. Quick wrap up questions here. Maybe what is one mistake you've made coaching a pilot team or one big red flag you've seen in companies setting up pilots? I think a core one is like when we talk about the layers, like the leadership and then the pilot team, there is a lot of layers in between normally at a bigger company. So it's forgetting about these people, forgetting about like actually the managers of these people, because very rarely like they're reporting to the CTO or the CPO or the head of design. They're normally reporting to a whole other layer of people that are scared. They're like, my job's changing, but I'm not in the pilot team. Like, how do I actually get looped into this too? I think that understanding that that transformation needs to happen at all layers and that actually the managers of product managers are really key to making that succeed. Have you seen a pilot team fail and maybe what did you learn from it or what did you do about it when it failed? Yeah, I'm very grateful that like I haven't had a pilot team fail really with me. I've had situations that we were able to handle, but I think like head of Agile wants like all these scrum masters to join the team, stuff like that. And I'm like, well, we can have one of these people here as long as like we give them a row. And but there are, I think, like many things that I was like, oh, red flag, red flag. But I think one thing that I see often and companies try this maybe like even before they bring us in is they try to do like the pilot team factory. It's the like, we've decided this is the way, let's have like hundreds of pilot teams. And I'm like, that's the opposite of a pilot team. That's just a bunch of teams. So I think when they try to just kind of like cookie cutter or like this process worked here, so we're just going to repeat the same thing over here. Those are when I see it really not work. But remember, it is part of the coaching mindset of it because you're coaching people out of a project, big bang, learn everything at the end mindset to a iterative, experimentative, discovery-centric mindset of like, let us learn about all the antibodies. Let us learn about all of the issues. I think one of the undertone we haven't called out directly is that there's politics involved. There's ego involved. There's kingdoms and chiefdoms and ownership. Everybody wants to be a part of the success. Everybody wants to get away from the failure in some ways. And there's that risk involved in it. So, you know, it's an important thing to navigate and coach through. But I think if you are coaching the leaders and also coaching the teams, then you can kind of walk through those two dynamics. Leave me with one maybe piece of advice. If I am thinking about doing a transformation, how would I sell the idea of this is how we start to my executives? Yeah, I think you sell it as like, hey, I know this is a lot of change and I know this is going to feel different. So let's start with a controlled experiment. And if it works, amazing. We can do more and we can learn from there. We know our business is important, so we don't want to rock the boat on everything. So let's pick an area that makes sense and let's make sure that we set it up for success. And if that happens, we can do more. Gabi, what a gift. What a fantastic, fantastic conversation. I have loved that chance. I think we can talk about any topic for a long time, but this was truly insightful. I really enjoyed it. Thank you so much for being on Product Therapy and for the energy and candor and grace in which you've run this session. I hope to see you or have you back again soon. Thank you so much, Christian. This was awesome. Thank you for having me and thank you for the great conversation. It's a near and dear topic to my heart because it really is very, very powerful. It's a small thing with insanely powerful results. I love it. Thank you, Gabby. Amazing. Thank you. Want to learn more until next time? Please check out svpg.com, sign off for our newsletter that Maddie Kagan puts out, join us for one of our workshops near you, and get access to all of the articles and content we put out. And thank you to everyone for joining us. Until next time, have a good day. A quick disclaimer, while this podcast is named Product Therapy, it is not hosted by licensed therapists or mental health professionals, and it is in no way a substitute for professional mental health services. We recognize the importance of mental well-being and encourage anyone facing personal difficulties to seek support from qualified professionals. See www.findahelpline.com.