Coaching Skills 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.
Episode Transcript
Melissa: 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: Thanks, Melissa. It's so nice to be here.
Melissa: 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: 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: 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: 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: 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: Yeah, it is. And I think that's where the art of coaching comes in. And that's where the experience of the coach comes in. So for me, I've got a lot of product experience, but I don't use it in my coaching. I'm not there to coach people on how to do product. I'm there to coach people on how to be a better leader, how to be a better person, how to be a better manager.
And that's where I draw the line. And that's where I think the distinction is. But when you're a product leader and you're coaching your team, you're going to have to figure out where that line is. And I think the best way to do it is to be very transparent about it. So if you're going to go into a coaching conversation, you say, I'm going to coach you on this.
And if you're going to go into a teaching moment, you say, I'm going to teach you this. And you make that distinction very clear. And you also ask permission. So if you're in a coaching conversation and you feel like you need to teach, you say, do you mind if I step in as a mentor or a teacher for a moment and give you some advice?
And then you go back to coaching. And that's where I think the balance is. It's about being very intentional about what you're doing and why you're doing it.
Melissa: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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.
And then you start to ask questions about what they want to change and how they want to change it. And then you start to introduce some of these coaching skills. And I've seen people who have been very directive and very micromanaging, and they've been able to shift to a more coaching style. And what happens is their team members start to feel more empowered.
They start to take more ownership of their work. They start to come up with their own solutions. And the leader is able to step back and focus on more strategic things, which is what they should be doing anyway. So it's a win-win for everybody. It's a win for the leader because they're not micromanaging anymore.
It's a win for the team members because they're more empowered. And it's a win for the organization because they're getting better results.
Melissa: That's a great story. I think that's a really good way to put it. And I think that's what we're all striving for, right? To have those empowered teams that can make decisions on their own. So thank you so much for coming on the show and sharing your insights on coaching. I really appreciate it.
Kate: Thanks, Melissa. It was great to be here.
Melissa: That's it for the Product Thinking Podcast. I'll be back next week with another episode.
Kate: Thanks for listening to the Product Thinking Podcast. If you enjoyed this episode, be sure to subscribe and leave a review. And if you have a question for Melissa, please go to dearmelissa.com and drop her a line. We'll see you next time.
