Episode 155: Mastering the Art of Coaching in Product Leadership with Kate Leto, an Executive Coach for Product Leaders
In this episode of Product Thinking, Kate Leto, an Executive Coach for Product Leaders, joins Melissa Perri to unveil the value of coaching skills for product leaders and how to incorporate coaching into the workplace. They explore the difference between coaching and mentoring, how effective coaching nurtures successful product leaders, and how to master the art of coaching in product management.
You’ll hear them talk about:
[03:03] - Coaching represents a tool for self-development rather than divertice guidance. Real coaching empowers individuals to find solutions within themselves, differing sharply from traditional mentoring or leadership approaches that often prescribe solutions. Effective coaching involves asking good questions and listening rather than instructing or solving problems for others, fostering personal growth and problem-solving skills, and relieving the burden on leaders.
[10:50] - Effective product leadership goes beyond just instructing team members; it's about fostering a partnership built on trust and understanding. This means adopting a coaching style that is less about control and more about enabling team members to find their own solutions. Some key skills include being fully present in conversations, engaging in active listening that goes beyond simple nods and smiles, and understanding the subtleties of body language and pauses.
[26:39] - Despite lacking authority, product managers can stimulate change and foster problem-oriented thinking among peers, especially developers, and designers, by embracing a coaching mindset. However, you must discard a know-it-all attitude and engage team members through open-ended, reflective questioning. This will help you clarify all the challenges and opportunities, guide colleagues to self-discover limitations and solutions, as well as foster a collaborative and thoughtful work environment.
[32:26] - To manage tension and conflict through coaching techniques, Kate introduces the Karpman Drama Triangle, a concept where individuals oscillate between being a victim, a prosecutor, or a protector in different situations. Leaders often identify with the protector role, striving to be heroes. But the real growth lies in transcending these fixed roles. There's another coaching method called the Empowerment Dynamic, where individuals move from directive to coaching roles, encouraging empowerment and insight into others.
Episode Resources:
Other Resources:
Melissa - 00:00:01: Creating great products isn't just about product managers and their day-to-day interactions with developers. It's about how an organization supports products as a whole. The systems, the processes, and cultures in place that help companies deliver value to their customers. With the help of some boundary-pushing guests and inspiration from your most pressing product questions, we'll dive into this system from every angle and help you think like a great product leader. This is the Product Thinking Podcast. Here's your host, Melissa Perry.
Hello, and welcome to another episode of the Product Thinking Podcast. Today, we're talking about how product leaders can harness coaching skills to succeed in their jobs. I'm joined today by renowned executive coach for product leaders, Kate Leto. Kate has over 25 years of coaching and product experience, helping leaders navigate everything from cultural transformation of an entire organization to helping new product leaders through their first steps. She might sound familiar to you. Maybe you subscribe to her product leadership essentials newsletter, or maybe you've read her book, Hiring Product Managers. She has been a previous guest on this podcast talking about how to hire, and now we're going to talk about how to personally develop yourself. Before we bring Kate on, though...
It's time for Dear Melissa. This is that segment where I answer all of your burning product questions. If you have a question for me, please go to dearmelissa.com and drop me a line or a voice memo, which will get prioritized, and let me know what you have questions about. Now it's time to go to this week's caller.
All right, so this question I can see in two parts. It's how do you understand capability gaps in product managements in large enterprises? But there's two pieces to that. One is the people skill gaps and two is the organizational skill gaps. And that's what I consider when I come in and help with large transformations. So usually when I come into a transformation where we have a lot of people moving into the product role that do not have product backgrounds, I'm first looking at what the skills are of the team. In certain cases, there are people there who have done product management before, and they can be a great asset to help coach other people or to take on harder projects and show people what good looks like. So I try to go through that and identify who has previous experience and who does as well. Then I look at baselining the skills for the right people in that organization. So if we have a lot of junior product managers who have never done this before, that's where we might want to put them through some training, get them exposed to essentials of product management.
For me, I always put them through our Product, product foundations. And that gives them a really good baseline of this is what the role is of a product manager. And here's the entire gamut from talking to customers to setting goals to setting our vision and our strategy and breaking it down and working with developers and all the stuff that comes in between. Once they have exposure to that, then I work with them to help them get little wins and And the idea here is to get the reps. And people can only learn product management when they get the reps, right? So you want to make sure that they are talking to customers. Sometimes that's the best first step. So I work with them to get in front of customers, to interview them, to actually question if what they're building is the right thing to build, to get feedback on stuff they already built. That's usually a nice little aha moment of, hey, we could be doing something differently, or this is how I should be positioning my product for better customer value, right? It's things that allow them to really see the benefit of working this way. And that's what is really powerful when you're trying to take people who haven't done this before and show them and expose them to the benefits of product management. Now, with that said, in many organizations, you end up hitting a wall at this point where you've trained a lot of people and they go to put these practices in place, but the infrastructure of the organization prevents them from doing what they need to do.
So people will get frustrated and they'll say, oh, I can't actually be outcome oriented because the culture doesn't support that. Or I can't be outcome oriented because we have no access to data. And this is where those components of really understanding the capabilities of the organization come in. So when I come in, I really evaluate things across like four different categories that I made. And I have my own little capabilities matrix where I look at things like product strategy. Do you have a product strategy? How is it deployed? How is it created? Is it good? Does it ladder back up to the business goals? Does the company goal provide a focus for the product strategy? How does that actually look? Are they outcome oriented too? I then look at things like organizational design. So skills is part of that. Career ladders. But also, do we have the right people in the right places? Are they going to have ample coaching support once they get to junior people or placed in different parts of the organization? Is it structured well around products or services? And then I look at product operations. Do we have access to customers? Do we have access to data? And how are we running the product management organization? And then last, I look at culture. And that's really looking at the leaders embracing product management.
You know, how they support it. Are they supporting it? Are they just playing lip service to it? Are they doing what they need to do to really? Help product managers succeed? And are they embracing this way of working? So what I would encourage you to do is really look at both a skills gap for people and then a capabilities gap for the organization. But at the end of the day, you really do need to help people bridge that skill gap and help train great product management to help these organizations transform. Because you can set up all the rest of the pieces of that product management organization, but if you don't have people who can execute and do great product management, you're going to run into all those blockers, right? Like you're never going to get anything done. So that's really where I start is with the skill gap capabilities for product managers and looking at what defines a great product manager. What does that look like in our organization? And then how do we get the training that they need? But also how do I as a coach work with them to get some wins and to make that possible? So hopefully you can try to start there looking for that assessment. And from there, you might be able to do your plan of action and decide what needs to come first. So I hope that helps. All right, let's go talk to Kate.
Did you know I have a course for product managers that you could take? It's called Product Institute. Over the past seven years, I've been working with individuals, teams, and companies to upscale their product chops through my fully online school. We have an ever-growing list of courses to help you work through your current product dilemma. Visit productinstitute.com and learn to think like a great product manager. Use code THINKING to save $200 at checkout on our premier course, Product Management Foundations. Welcome, Kate. It's great to have you back on the show.
Kate - 00:06:53: Thanks, Melissa. It's so nice to be here.
Melissa - 00:06:55: So last time you were on the show, we were talking about hiring product managers and what kind of skill sets we needed for that. And lately, you've been doing something that's really interesting, which I wanted to dive into today, which is teaching product leaders about coaching skills. Can you tell us a little bit about how you got started teaching these skills and why they're important?
Kate - 00:07:17: Sure. Yeah, I'd love to. So it's been a gradual process. So I have been doing leadership coaching and executive coaching within the product space for about six, seven years ago from the time when I took my very first coaching accredited program. And as you know, there's been like this huge pull in coaching and product management, right? Like there's so many different types of coaches and it's become like this really kind of big trendy thing. And with that in mind, like I've noticed in my coaching conversations with leaders and executives that they often refer to, you know, different coaching moments that they've had with their own team members and they talk about how they coach their team members. So we often kind of dive into that. And what they might consider as a coaching moment is very far from what I consider as a coaching moment as somebody who's been trained and accredited. It's often something that is where they're providing like really, I would say, kind of harsh feedback to somebody without permission, without setting it up, without helping to kind of figure out what the outcome of that conversation is going to be.
There's absolutely nothing involved with it that I would consider coaching, like helping somebody understand what their own skills are, what their own challenges are, how they can solve this problem for themselves. It's more of massive like confusion between command and control and being really directive in being a manager and a leader and what I see as and what I've been trained to do with coaching. So that was a big part of it, just like this confusion over what coaching is and how people were thinking about it and bringing it into their own teams and their own workplaces. And then I started to get some requests from clients to actually, you know, how do they get trained as a coach? When quite a few, you know, well, they bring up the idea and want to know more about it. It was kind of the same mindset that I did back when I first started training to be a coach. And that was, I just wanted to learn the skills. I didn't want to go become a coach, but I want to figure out what the skills were so I could bring it into my own, like at the time, my consulting toolbox or their leadership toolbox. So I started to kind of play around with the idea of developing my own course to work with product leaders to do that, to learn how to bring coaching as a leadership style. Into their work. And it just went from there.
Melissa - 00:09:38: So it's really interesting that you said this. And I think there's some interesting misconceptions about coaching, like you said. Also like product coaches out there. There's a lot of people who are doing product coaching now who probably have never done product management in the past. I know Agile software development Coaches with that name gets a bad rap sometimes as well. But then we have the coaching in a leadership role too. This misconception about coaching, what is actually good coaching? Like what does a good coach actually do regardless of your product, if you're Agile software development, if you're a leader or whatever? And where are people getting that wrong?
Kate - 00:10:14: That's a great question. And I mean, we could talk for hours just on that because there's, it's such kind of a broad, vague term these days. So the way I think of coaching is a coach is there to help someone develop themselves and equip themselves to solve their own problems and their own challenges. A coach is not there to tell you what to do. A coach is not there to answer all your questions and all your problems. It's often really confused with mentoring, you know, what a mentor might do. You know, a mentor might actually probably would be somebody to say like, oh, I've had this happen to me before and this is how I handle it. This is what you should do. You know, a more traditional leadership style is going to be quite similar. So, but a coach is there to ask you questions. A coach is there to listen to your responses. A coach is there to help you figure out your own challenges and figure out how to handle that on your own. The big difference is if a coach becomes kind of more of that domineering, just do this, you. You should do that. Have you thought of this? Then they're really kind of pulling the rug out from underneath like their coach's feet, right? Because they're not giving the person the opportunity to really think for themselves. And so where I think coaching is super powerful as a leadership skill is that it really does help people realize they've got the answers to a lot of these challenges already within themselves. They just need a little space and perhaps some nudging and some questioning to help them figure it out for themselves. And by teaching people, helping people figure out how to do that, that takes a lot of pressure off the leader or manager because you don't have to answer all the questions.
You don't have to come up with all the solutions to all the problems because you've got a team of people who can do it for themselves. So that's where I think there's a big difference between what coaching is often considered within our product space, which can be, as you said, sometimes people have never done product before. Or a lot of times it's more teaching a functional skill. It could be an OKR coach who's not there to ask you questions and help you figure out for yourself nine times out of ten. They're there to help you do it. Could be a Design Sprint coach. And, you know, there's so many different ways that coaching is used and kind of tossed around. And how it got that way, I'm not quite sure. Coaching itself has become a very trendy thing within like our product community where product is already pretty trendy, right? And then if you add on like this trendy coaching aspect to it, then it's something a lot of people want to do. It's just something a lot of people are buying into as well, which is great. But unless you really understand the fundamentals of coaching, then I think we start to see this ongoing debate over what is a coach and what isn't a coach and how can coaching actually
Melissa - 00:13:02: help you and your organization. It also feels like there's probably a difference where people are getting this mixed up with like teaching first coaching, because I can hear that from what you were talking about of it's not just your response. It's not about you telling people how to do it or showing them how to do it. It's about them figuring it out for themselves. What is the balance, I guess, too, as a coach with how much domain knowledge and past experience you need in some of these things? And how do you incorporate that into coaching? So like if I'm a product leader and I've done, let's say, 8,000 MVPs before and my team's never done an MVP before, when do I know whether to tap into like teaching skills or coaching skills or how do I balance that and not use a teaching skill when I should be using a coaching skill? I feel like that could be really tricky to kind of unpack.
Kate - 00:13:47: Yeah I'd say a lot of times in that kind of situation, if you're teaching somebody or if you have some folks on your team who have never done something before, it's probably not a coaching time. That's probably more of a teaching time or a training time. Coaching time is when I think people are already aware of their strengths and weaknesses, you know, whatever that might be, and they want to do something about it. They want to create some change. So I think it doesn't sit at the very beginning of learning a skill a lot of times. But if you have a little bit of experience and maturity and you know enough to know that you don't know it all, then I think you're in a good place for coaching. It was really interesting because in setting up my course, I kind of stepped back into trainer teacher mode, which is something that I hadn't done in a while and found like really uncomfortable at first. But I kind of I had to because the people that I was working with knew nothing about coaching for the most part. So it's a hard line to walk. But I would say if people are really early in their maturity and understanding something, then the type of coaching I'm talking about is probably not the right time to introduce it.
Melissa - 00:14:54: So when you're a product leader, you have a whole team of people that you're overseeing. What are some moments where you would coach people? Like what are some typical situations in which you want to tap into that coach mode and not the teacher mode or not the command and control mode?
Kate - 00:15:10: I'd say a lot of times there's opportunities with personal development and even in your one-on-one conversations around, you know, how are things going with them and their role in their work and how are they feeling about their place in the organization? One-on-ones are like a ripe time for coaching conversations. But it's also full-on knowing that if we go back to thinking about command and control and more kind of that directive style, often our leaders and managers are using the one-on-ones to like get status updates. Like, just tell me what's going on with this project. Where are you hitting the wall? Let's figure that out. Let's move on. That's not the coaching time. So, but I would say in introducing coaching as like a new skill and a new habit, a new part of your conversations with teammates, what I've encouraged some people to do is just, you know, maybe one session a month, one of your one-on-ones a month is more of a coaching conversation than however you use them otherwise, be it a status update or something like that. So, but. You need to give everybody that time and space to have those personal development conversations to check in on their wellness, to see how they're doing with everything. And I think that's where coaching can really come into play. Once you get more equipped to it and once your team members get more comfortable with it as well, then I think there is a huge opportunity to bring it into even shorter conversations, more of your everyday water cooler moments. But it takes time to get to that point.
Melissa - 00:16:35: What are the types of coaching skills that a product leader needs? What are the types of coaching skills that a product leader needs?
Kate - 00:16:42: Good question. So they sound very, oh yeah, sure. But there's a lot involved with each of these. So one of the first ones is forming like a different kind of partnership or relationship with the person that you're coaching. Because again, you're stepping from that, I'm the leader, I'm going to tell you, or manager, I'm going to tell you what you need to do and how to get things done. So very command and control to non-directive and more coaching. So that means building up relationships in a different way, building trust with your coachee in a different way, making sure that people are aware that it's about them and not about you and the conversation that you're having, keeping your self-interest low. So there's actually skill building around trust and partnership that you start out with on a fundamental level. And then there's things like your presence in the conversation, making sure you're fully in, right? You're fully present. You're not being distracted by whatever is happening in your head, by your phone, by your computer, whatever physical things might be holding you back. You're fully present because the more you're present as the coach and in that moment, the more your team member is going to be as well. They're going to really lean into it. There's a whole mindset around coaching that needs to change along with that directive to non-directive and really believing that the person that you're working with and you're having this coaching conversation with, they trust them in a way that they are going to be able to figure things out for themselves. So there's just like this fundamental relationship shift that goes on. And then you let go of that and you're like, I'm going to be able to figure things out for myself.
On top of that, active listening is more than just the bobblehead, as I've described it before to people that I've worked with. It's not just smiling and nodding and making eye contact. It's actually going much further beyond that, paying attention to what, not just body language, but when people are talking and when they're not talking, what the pauses might mean. It's really being fully in on that type of listening at all levels. And then there's skills that kind of go along with that. One's called playback. We talk about that. It's kind of like a coaching course a bit where you're actually trying to play back as the coach, play back what you've heard from your coachee, what you think they've just said to one, help clarify it, to show you are listening, to show you are in, but also to give them some space to reflect on what they're hearing back. It's like, oh my God, I just said that. Yes, I said that and I didn't mean that, but that's where my brain is right now. So there's different skills like that. And then there's powerful questioning, asking open-ended questions that are really simple. And overall, the skills, like I always kind of think of coaching as like if you've got the iceberg, a picture of an iceberg, a lot of times in our one-on-one and our relationships with our team members, we're on that surface level, right? We might be talking about when we do have one-on-ones, it's status updates and then maybe there's some gossip and things like that. But all of these different coaching skills can help you get below the surface to help your team member figure out what's really going on. What are the patterns? What are their behaviors? What are their habits that might be holding them back in their work? Yeah.
Melissa - 00:19:44: So I feel like as a product leader, what I see people struggle with, right? Thinking they're coaching and they're not, which we kind of talked about, right? Like that command and control thing. And then also kind of balancing the need for direction versus coaching. And a typical thing I've seen a lot is newer leaders or people who are transitioning to newer ways of working, they'll come in and they'll say, I don't want to be a command and control leader. So I'm going to let everybody just make all the decisions. I'm coaching them, right? They should be doing some bottom up, bubbling up what we should be working on, right? And whenever somebody asks them to provide clarity or direction or something, they go, what do you think? And it frustrates everyone. When you're a product leader, what's the right balance between coaching, teaching, providing direction? Like what have you seen in the wild for pitfalls we might run into like that? And how do you get over them?
Kate - 00:20:39: I think the ideal thing is, well, I'm here to talk up coaching because it's hugely beneficial for organizations and teams and individuals. But there's also a time and place for that directive and command and control. So I think what ideally people should be working towards is figuring out that balance. And often a good way to start is by overcorrecting and by trying to go more towards the coaching side of things and seeing how that feels. And that's what the course that I'm teaching, we do a lot of practice. So people can really see what it's like to use some of these different tools and techniques and quote unquote real situation with another product leader. So the first thing you do, I think, is kind of understand, get really observant about how you're leading now. How many conversations are you having a day where you are just telling people what to do versus asking a question and start to observe that. And then as you do that, you're going to learn a lot about yourself, too. Because you're going to probably notice that you're trying to be the hero and trying to save the day and all of these great things, which we all kind of pride ourselves on. But through that shift and being really focused on the coaching skills and asking questions and helping people figure things out for themselves. And if you double down on that, then I think you can start to realize when's a good time to back off that. And when is it okay to actually have that directive conversation, teach somebody something, tell them more of, you know, what's the best way to do that, what's the best way to do that, what's the best way to do that. And then you can start to understand what you think they need to do. But, you know, it's hard to come up with, like, once you do this, you got this down. You've got, once you do x, you've got Y down. But really, it is kind of noticing what you're doing already. Then maybe overcorrecting. Like, I could tell you a story. When I first started coaching, I thought that after my first coaching training, probably seven or so years ago, I thought all I was supposed to do was ask questions.
So I went into a product coaching gig. And I was like, I'm going to do this. And I just sat there and I asked people questions. And it was the most uncomfortable thing in the entire world. Because they didn't know what I was doing, and I wasn't quite sure what I was doing either. But through practice and kind of trial and error and talking to some other folks who had been coaching longer than I had, I realized that it's like, it's not just about asking all the questions. There is definitely a time and place for teaching. There's definitely time and place for being directive. But what you've got to be careful of is if you overuse directive or command and control, then you're most likely going to bring yourself out and you're going to bring your organization out and you're not going to be moving anywhere closer to any kind of growth mindset or learning organization. So it takes time, but I would say a first step would be figure out what you're doing now and then see how you can overcorrect and let people know you're doing it. Because that's another thing I noticed came up in the coaching course was that everyone went back in between our sessions, because we had sessions once a week, and tried things out on their team members. And they're like, they didn't know what to do. I'm like, well, did you explain what you were trying? Did you explain why you were doing it? And there was just a big fat no look back on all the virtual faces that were staring at me. So it's not something to kind of jump into quickly, but to be very considerate about it. And realize that maybe once you do get really into coaching, you're going to notice more of where that balance might be between the different styles.
Melissa - 00:23:59: Can you give us like maybe an example of a product leader that you know or yourself when you kind of came into a situation and you approached it with coaching and when you knew to do a little bit of teaching? And what kind of that back and forth looks like? Like how does that evolve and what kind of situations would you use that around? Yeah.
Kate - 00:24:16: So I've had a product leader that I've been working with for a little while now, and he's going through a reorganization, a reorg. And he doesn't have lots of product experience and background. He's more of an SME that's been moved in. He has some, but probably not the kind of product that you and I would consider. And that mentality and that mindset. So while we started out with a broad coaching conversation, kind of focused on a certain area of change, because a lot of what coaching is all about is helping people through change in one way or another and helping them figure out where they want to go and how to get there. So we were going through that and I was asking some questions and it was more around what was the organization he wanted to build? What did he want it to look like? How would he know he's there? What would be some of the milestones along the way to look out for? And it became very clear the direction he was going in and that he was thinking would be pillars of success in this reorganization were not healthy, good ones. So we did have a moment where I was like, do you mind if I step? As more of a mentor or consultant and tell you a little bit more about product and why that might work and why that might not work. So that was an example of just last week where that happens. And when it does happen, I try to identify it and call it out. And make that shift. But it's a challenge to figure out when to do it and when not to. But again, I think it goes back to that thing I said a few minutes ago. Like, if you know somebody's at a very early maturity level, they're not going to be ready for coaching, you know, at all levels. And if somebody's at a very early maturity level in product and whatever functional area you're talking about, it's not going to be the right time to coach.
Melissa - 00:26:00: That's a really interesting distinction there about, like, junior maturity versus senior maturity on those things. And I've run into the same thing, you know, consulting and coaching as well. And I think when I first started consulting, I was like, I'm a coach. I'm supposed to just ask questions. Like you said, I can't tell people what to do. And then I quickly realized, like, people hired me because I knew what to do. And I have to step in and teach a lot of people who've never done it before. And then I go into teacher mode. And I think a lot of people go back and forth there. There was something you said before, too, though, about product leaders mistaking coaching for being... Being directive. And thinking that their coaching or that their leadership profile is more about telling people what to do and telling them what the solution should be. Can you tell us a little bit about, like, maybe a story or an outcome from when a leader switched their tactics from dictating down solutions to people and try to come back more into a coaching mindset and help their people that way? And what happened with their team? Like, how did it change?
Kate - 00:27:00: So another example, I often work with larger organizations and corporations, and I work with a number of leaders within a department or a group or a team or something like that. And then with the team, with the leadership team themselves. So another corporate client that I had recently, they were all kind of going through that transition. And sometimes they're more open to trying coaching for themselves and approaching in a like a less directive, less command control way than others. So when I've seen it work, it's really interesting because they do have, it's people entering like a coaching engagement with me when they want to make a change. They know they want to lead in a different way. Maybe they've been given some feedback in the past that they're not happy about and they want to make some positive changes there. Maybe they just know that they want to develop themselves personally, and then that's going to be reflected differently in how they work with their teams, whatever it might be. But so I had one person who did receive some negative feedback. From their, on their 360 about the way they were leading and that was more micromanaging than empowering as they wanted to be. So the conversations around that are never like, do this, don't do that. When you're talking to somebody, it kind of starts out with getting to know like where they're coming from.
You know, I mentioned that iceberg. So it's getting underneath that surface level to figure out like what are the patterns that and their behaviors and the actions that have gotten them to the place that they are with their leadership and how they're interacting with folks. And a lot of times out of those conversations, we can come up with an experiment, something they're going to try, try to do differently in a conversation that they might have with a team member going forward, how they might start a conversation, how they might like try to even end the conversation, whatever it might be, a different technique to bring into how they're working with folks. And yeah, they try it out for a week or two week in between our sessions. And then we come back and we check in on it. And we just like with product, you iterate and you go from there. So it does happen. The change does happen. The team members, when I've been, it takes a long time. It's not something behavior change doesn't happen quickly and definitely doesn't happen overnight. So over time, though, the team members, when they did their next kind of survey and checking in to see how engagement was to see what the feedback might be. The responses were much more positive quantitatively and qualitatively. So that was like good juju and like good energy for the leader to keep doing it and keep working at it. And, you know, it just by bringing in coaching and by helping people figure things out for themselves and feel more empowered, you know, it should have that response. People should feel more engaged and more ownerships and owners of their own work and their own world. And, you know, hopefully won't want to leave organizations. Retention numbers go up. All of that great stuff can happen. But your question is a good one because like it's got to be somebody who wants to make that change, is aware that they have some challenges, really wants to work at it, and is going to be committed to doing that. So it takes all of those different criteria to pull it together.
Melissa - 00:30:13: Are you eager to dive into the world of angel investing? I was too, but I wasn't sure how to get started. I knew I could evaluate the early stage companies from a product standpoint, but I didn't know much about the financial side. This is why I joined Hustle Fund's Angel Squad. They don't just bring you opportunities to invest in early stage companies, they provide an entire education on how professional investors think about which companies to fund. Product leaders make fantastic angel investors. And if you're interested in joining me at Angel Squad, you can learn more at hustlefund.vc/mp. Find the link in our show notes. So one question I keep getting at, and maybe this is even for not product leaders, but just regular product managers. There's a lot of people like wanting to transform their companies, obviously, from the inside. And they're not in a position of power. And that's extremely hard. And I have mixed feelings about like how successful you can be. And it all depends on the organization to do that, right? To make a big shift. But one thing I do think they can control, and I hear this a lot from product managers and teams, is I'm trying to focus on problems. But like my developers are not problem oriented, right? Or the people around me are not problem oriented, let alone the leaders. Like let's forget about leaders for a second. But like the people who are my peers that I do have some influence over and that I can talk to, they are stuck in their old ways of working. And I believe coaching can probably be a good tactic for helping them try to overcome that or question things. What kind of tactics or questions or coaching techniques do you think a product manager could use on, let's say, developers? To help them think differently or designers or anybody else around their teams to help move them a little bit more towards a problem oriented focus.
Kate - 00:31:54: So I think a lot of it, again, is making sure that whoever they're working with, be it somebody in engineering or design or whomever it is, wants to be quote unquote coach. They're probably not going to enter it as a coaching conversation. But just even asking questions, starting out like or asking things, what's the real challenge here? What have you tried so far? To not make assumptions. Because I remember those days when I was having those conversations with engineers or designers. And of course, in my magic mind, I knew everything that everybody should be doing already. So they just had to do x, Y, or Z and it would all work fine. Right? You know, sometimes I even went into the technology space that way, which was like completely ridiculous. But good ego and a product manager and that's what you get. So it's, again, shifting your mindset on what those conversations are, right? It's kind of entering with the mindset of you don't have all the answers, product manager. This person can solve this problem, you know, with just as much like grace and ease and confidence as you can if you give them the chance. And it's asking, you know, start asking some good open-ended questions. What have you tried so far? What are the other options? And what else? What's the real challenge for you here? What can I do to help? That's a great open-ended question to ask. When it comes to prioritization, asking people, you know, a basic question like, if you're going to say yes to this, what are we saying no to? You know, to help people understand that, you know, even if you're going through your backlog and you're reprioritizing, starting with that fundamental, you know, understanding that like you can't get it all done. So how can you have that conversation with somebody in design or engineering or UX or wherever it might be in the organization? Without coming across as the know-it-all. Instead, you want to engage somebody as like, I'm here to learn with you and figure it out together.
Melissa - 00:33:45: What I kind of like about that approach too is it flips it from, you know, you saying no and it helps them get to a no instead where they're like making them think through all the questions. And that's always been my approach for people are like, how do I tell them that we can't do everything? And I'm like, you ask them a bunch of questions until they realize that they can't do everything. And then they will figure it out for themselves and make that decision. But that to me has been the most effective way to get people to understand the level that you're at without coming off as a jerk and being like, we can't do that. That's insane. You're nuts.
Kate - 00:34:16: Exactly. No, I think it's an awesome approach. Ask a lot of open-ended questions and let them answer it and think about it and see what comes up. I've also done this with leaders as well.
Melissa - 00:34:25: Like another question I get all the time on the podcast is like, How do I help my leaders understand that, you know, they're dictating down solutions instead of problems, right? And to me, the biggest problem that I see a lot of people do is go back and be like, you gave me a solution, not a problem. Like, this is awful, right? And they start yelling about it or they get like upset about it and they tell the leader what they did wrong. And they do it in not a very taxable way. And instead, I tell them, like, if you take more of a coaching approach and you say, okay, like, cool solution. What's the outcome that you think we'll get when we build this, right? Like, how do you know? What kind of research have we done already? Because I'm not questioning your research. All I'm doing over here is just trying to understand what you know so that I know it and I can go build a great product. And I feel like sometimes taking that approach leads people to go, oh, yeah, we, like, didn't do any research and I don't actually know what we want to achieve at the end of the day. And you're like, okay, that's cool. Like, let's work on it together. Let's go that way. And to me, that's been extremely impactful for helping to point out to people things that I might be aware of, but in a way that's not going to burn bridges, right? And it's going to build relationships rather than tear them down.
Kate - 00:35:36: Yeah, no, that's a great use of questions. And especially kind of if you're in that role where you're trying to manage up, right? And build influence. Like you said, you don't want to burn those bridges, but, and you don't want to come across as kind of a smart ass either. It's just asking some really genuine, open questions and having a conversation around it.
Melissa - 00:35:56: I like that. So in your course, when you go through what you're going to learn and how coaching frameworks will help you change your relationships, you do mention this building influential stakeholder relationships like we're talking about. But another one that I think is interesting that I want to dive into a little bit is about managing tension and conflict and giving and receiving feedback. And I'm curious how you use coaching techniques for that.
Kate - 00:36:23: So tension and conflict, there's what we call modalities in coaching. They're kind of like our tools and techniques and our frameworks. Same, same product. We've got roadmaps and OKRs and KPIs and all this other stuff and different frameworks that we use in coaching. They're called modalities. So in times of tension and conflict, one of the modalities that I often go back to and that I taught in the course is called the Karpman Drama Triangle. Not sure if you've heard of that. So developed by Dr. Cartman, it's a triangle. And at one point, the triangle has three roles in it. And the theory is that at any point, it could be in a day, it could be in a conversation, it could be, you know, throughout a week or a project, we're going to flip between these three roles. One of them is the victim, where it's like, poor me, poor me, poor me.
I can't figure out what to do next. I'm helpless and hopeless. Another one is the prosecutor, who's just like kind of a bully and is not being helpful in figuring out a way out or a way forward, kind of being a bit manipulative. Sometimes that role is also called the villain. And then the third role is the protector, sometimes called the hero. So the protector is the person that's going to come in and save the victim from themselves, figure it all out, save the day. So often when I'm having a coaching conversation with somebody who's talking about a challenge that they're having, a challenging conversation they're going to have, whatever it is, you can see these three roles. So I often introduce that into the conversation to ask them what role they've done. And often with leaders, it's the protector because we want to be the hero. We always want to be the hero of the situation. And what we need to learn is to kind of flip it. And of course, there's another coaching modality. Called the empowerment dynamic, which is like the other side of the triangle, which encourages the leader to hold more of a coaching role. So instead of telling everybody what to do, coming in and saving the day, asking those powerful questions, helping people figure it out for themselves, and bringing up new insights that people can grab onto. The victim is also leaving that space and growing into more of an empowered role. And the prosecutor is as well. So everybody kind of flips So usually when in tension and conflict, it's interesting to kind of think of that triangle and to think, where are you now? And in coaching conversations and coaching engagements I've had with leaders and execs, a lot of times we can track through different conflicts that they're going through. Where were they before? What role were they before? Where are they now? And then have a conversation like, how can you get out of that? Where do you want to be? What would that be like? So that's tension and conflict. That's a coaching tool that I often use.
Melissa - 00:39:15: Wait, let's dig into that one for a second and then we'll go to the next one because I'm curious about this. I've run into a big situation as well with somebody on the team. Not getting along with somebody else. I've seen it with product leaders, but I had some salespeople or engineering or anything, like seen it myself in my work. But I've also seen it on teams where a director of product and just not getting along with somebody else. Let's say there's a bunch of tension and you're trying to help your direct report, who's the director of product, work through that. Let's just pretend I'm the director of product and I'm coming to UK and I'm like, this salesperson is driving me absolutely nuts. They keep trying to put all these things on the roadmap and I keep telling them, no, we can't do it. But they're being such a jerk to me. They're very, very rude when they're talking to me. First of all, it's just not nice, but I can't seem to get through to them. And they don't understand that when I say no, it's not okay. So they go to their leader and now their leader is yelling at me to do these things. What would you try to advise me to do? Because I've seen some product leaders be like, oh, I'll go talk to their leader. What's the right approach for handling that situation as a leader?
Kate - 00:40:21: Yeah, so as a leader in that situation, you're definitely trying to be the protector. You're trying to save the day. So I would challenge you, leader, to take a different approach and to take more of a coaching approach. So instead of going and solving the problem, what question could you ask your team member? How could you find out what's really going on below that iceberg?
Melissa - 00:40:41: What kind of questions would you ask me, right? Like if I'm the director of product coming to you, like and saying, this person just won't like listen to me when I say no, like what kind of questioning should we go down?
Kate - 00:40:51: So if you've got a situation where people are just not saying no and they won't respect you, I would ask, well, you could start out with some really basic things like, well, how are you feeling about that? What would you rather have happen? What's an ideal outcome for you with this? What are some different things that you've tried so far to solve this problem? What else could you try? Because a lot of times with coaching, you know, when you're in that mindset of like, nobody's listening to me, they don't respect me, nobody likes me, you know, then you're not thinking about other options that might be out there. You're not thinking about what might be driving this person to behave this way. You're just in your victim state. So we're trying to move you from being that victim to being more empowered. I'd really try to focus on what have you tried so far and get to the reality of the situation. One of the best coaching questions I ask, I think, in my humble opinion, is it true? You know, what evidence do you have? What evidence do you have? What evidence do you have? That that person really thinks of you this way or is behaving this way because of you? So it's challenging some of the beliefs that your direct report might be having. They might be limiting beliefs that are holding them back. Maybe they do have some like really thick, good evidence behind it. But I'd say nine times out of 10, when I ask that question, is it true? Is this true? Then people stop, think for a second, like, well, I don't really know, but they, you know. So those would be some of the questions I would ask.
Melissa - 00:42:20: Cool. That's helpful. And I think that kind of leads us into the feedback piece of this too. So if you're now, let's say we go back and find out that this person was not handling this the best way, right? And they were not conducting it well, how do you handle feedback to your direct reports or to anybody in a good way, in like a coaching way?
Kate - 00:42:40: I'd first try to understand what's really going on. It's the reality of the situation again, right? So one of the common coaching modality is T-GRO. So, and that spells out, well, it stands for topic, goal, reality, options, way forward. So this could be an interesting T-GRO conversation because T-GRO conversations are often about trying to create action or get people unstuck. So in this kind of trying to give somebody some feedback, I, you know, you first kind of go in and identify what's the topic of the conversation. What do they want to talk about? And what you're hoping to get out of the conversation as a goal, what they want to get out of it. So if it's, I'd like to talk to you about the tension and the conflict you're having with our colleague and get a better understanding of what's going on in your mind and how we can maybe move things forward. So you've got a goal reality. What's the reality of the situation? So if this is the feedback that, or this is what's happened, I would try to really dig into it a bit more. So instead of just jumping to conclusions and judging somebody and giving them kind of judgy feedback, I'd like to really understand their side of the story. So what's going on? Because there could be things going on that maybe you guys haven't talked about.
So get that all out on the table and then talk about some options. How could you handle it differently next time? Would you want to handle it differently next time? I mean, maybe this is something that they still think is like the best way forward, but open that kind of door for what are some different ways forward? What are the different options that you might have? How could you try it, you know, next time so-and-so, you know, says no to you or you feel like nobody's listening to you, how would you want to respond? So I would try to make it more of an open conversation where they can think through what the different ways, how they would want to change their behavior versus how I want you to change your behavior and go from there.
Melissa - 00:44:37: I can see that. I think a lot of new leaders struggle with the feedback mechanism. And I'm curious to hear what you've heard with it. But in my experience, it's been either too harsh, or they're afraid to give feedback, or when they do give feedback, it's not received really well. They're like, I am in the manager position. So how have you seen this kind of change that dynamic between like leaders and coaches? And how do you get them to realize where they need to course correct to?
Kate - 00:45:06: I think people at every level have a hard time with feedback. And I get it because we're all human. And the majority of us just want to help someone, but we're not quite sure how to do it. So it's one of those things where also as the director or, you know, the person giving the feedback, you need to understand what might be holding you back. So it's kind of a personal development thing on your end to figure out what are your own challenges with feedback. Maybe why don't you like giving it? You know, what's going on there? Maybe they've had, remember one coachee where they had a really tough manager before who gave them awful feedback. So they never wanted to give people feedback, negative feedback. So they had like course corrected massively on that and just wanted to be the good guy in the conversation and only give positive reinforcement. Right. So if as a manager on any level, if you're having a hard time, I'd first start to think about like, what about it really bothers you? Where's the challenge for you? How can you start to address that and realize that by giving this feedback in a way that is actually actionable and considerate, you're helping the other person out? 9 times out of 10. But, you know, I would say there's always that leader or manager that I've worked with that it's just going to take time to get through. That giving feedback doesn't mean just sharing your opinion and telling somebody how to do it differently next time. If you're going to make any change at all, you've got to understand where they're coming from, why they did what they did, and how they think they might want to do it differently next time.
Melissa - 00:46:40: I think that's an important lesson for a lot of managers out there to learn and will definitely help them steer product managers in a better direction too. So thanks so much, Kate, for being on the podcast. Where can people learn more about your course and more about coaching techniques?
Kate - 00:46:55: So come to my website, which is kateleto.com. You'll also be able to find me talking about it on LinkedIn. So if we're not connected, please find me and DM me with any questions that you might have. I'm also from time to time still on Twitter/X or whatever that might be by the time this podcast is released, whatever entity, that's it. But I'd say the most direct way is just come to my website and you'll find a bunch of information on it. You'll find ways to get in touch with me directly. And we'll go from there.
Melissa - 00:47:27: Great. Well, we will put all of those links in our show notes at productthinkingpodcast.com so that you can go find out how to connect with Kate. And we will be back next Wednesday with another episode of the Product Thinking Podcast. So make sure that you like and subscribe and that if you have any questions for me as well to answer on each episode, go to dearmelissa.com and let me know what your questions are. We'll see you next Wednesday.