Have you thought about working with a professional coach?
Well, your next career milestone might be closer than you think. Learn how career coaching can provide the clarity, confidence, and strategy you need to get there, no matter where you are at any stage of your professional journey.
On October 8, 2025, we held an online event for the VentureFizz Product Management Community – and we recorded it, for you!
Speakers:
Matthew Mamet – Fractional Product Leader & Leadership Coach; Former product leader at EnergySage, EverQuote, TripAdvisor
Ravi Mehta – Product Strategy Advisor; Former product leader at Reforge, Tinder, Facebook, TripAdvisor
Topics:
- What a coach does
- When coaching is best for Product Managers
- How to choose the right coach (and get the company to pay for it)
- How to optimize value from coaching sessions
- Measuring success and ROI
Video Transcript
If we haven’t met yet, I’m Keith, the founder of VentureFizz. As you probably know, we’re a website that’s focused on the tech industry, largely Boston and New York. We have a product management community and we help people find jobs, so we do a lot of things.
One of the things that I’ve been very curious about is career coaching. Think about it: some of the best professional athletes have their own coach outside of what the team provides. Tom Brady always had people helping him—his separate quarterback coach, trainers, and nutritionists (which became TB12). He was always hyper-obsessed about being the best he could be, all outside of what the Patriots provided him. There are lots of other athlete examples that do the same. So, why, as professionals trying to be the best in our industry, aren’t we working with professional coaches?
I have two insanely amazing speakers today: Matthew Mamet and Ravi Mehta. I’ve had the luxury of knowing both of these individuals for many, many years. Matthew and I go back to the Permission TV days, and from there, he had great product leadership roles at TripAdvisor, Everquote, and Energy Sage. Ravi, I got to know you at TripAdvisor, too, and you’ve gone on to do amazing things at Facebook, Tinder, and Reforge. I’m going to let the two of you just give a quick little background beyond what I just shared. Matthew, I’ll let you start.
Sure. Thanks, Keith. I’m really excited to be here talking to you and Ravi as well. I’ve been doing product and growth work for a number of years, a number of decades. From that experience at TripAdvisor, building and launching their e-commerce for hotels platform, as well as at Everquote building and launching an online insurance marketplace, I’ve seen a lot. As a result, there comes pattern recognition. I’ve benefited from having a coach and I’ve benefited from being a coach, so I’m really excited here to talk a little bit more about that.
All right, Ravi, when we met you were in Boston, but now you’re on the West Coast. Share the details of what you’ve been up to.
Yeah, sounds good. So now I’m based in LA, but spent most of my life in Boston. Matthew and I actually worked together for about five years at TripAdvisor. I’ve been a product leader throughout my career. I got my start at Microsoft, where I was a product manager, one of the early folks on the Xbox team. Since then, I’ve been focused primarily on consumer product management and product leadership.
I helped build the consumer product team at TripAdvisor. That was my first opportunity to work with a coach, and I found it so incredibly valuable. It really opened my eyes to how powerful that relationship can be. A few years ago in 2021, I actually started a company called Outpace, focused on making it easier for people to find a coach. We ran that for about two years, worked with hundreds of folks to help them find the right coach and work with the coach in a way that they were going to get the most value from it.
Since then, I’ve both been a coach and had coaching; it’s been a key part of my life. Today, I’m a full-time product adviser. I work with companies on a fractional basis to help them with product strategy, build out their product team, think about growth, think about AI, and how to work in an AI-native way. I also do a lot from an education standpoint: I work with Reforge, helping them launch their Product Strategy, Product Leadership, and AI Strategy classes. I’ve been very focused on growth, both for myself and for helping other people grow.
I just got to give a plug. Ravi, he’s got a brand, too. He was part of Lenny’s spin-off podcast, hosted by Claire Vu, How I AI. Check out that episode. It’s amazing.
All right. So Matthew, a coach sounds amazing, but what do they actually do? Like, I could kind of picture what maybe an athletic coach does, but what’s a professional coach do?
Yeah, that’s a great question. There are different types of coaches as well:
- Executive Coaching to help leaders operate at a larger scale or a wider remit.
- Career Coaches who are laser-focused on helping you navigate the arc of your career from company to company and role to role.
- Functional Coaches (e.g., a Product Manager coach or a Sales coach) who help you build your craft.
- Life Coaches who take a whole look at your life (professional and personal) and help you work on the whole person.
It’s really important to understand what it is that you’re seeking and what you want to work on as you think about trying to find some help to get there.
Well, Ravi, how is it different than, like, “Oh, I have mentors” from me in VentureFizz? How is this different in that regard?
I think it’s different in a key way, which is it’s the only professional relationship that you have that is not pressurized in some way. Every single other person you’re working with has some backdrop that adds a little bit of pressure:
- Your Boss: They’re also evaluating your performance.
- Your Peers: You don’t want to feel like it’s not a co-equal relationship.
- Mentors: You’re depending on them to volunteer their time; you might worry about taking too much.
A coach is completely devoid of that pressure. It’s a relationship that exists solely for you, where you can be as candid as you need to be to get unfettered advice and guidance and to understand the questions that you should be asking of yourself. It’s really unique and special. I encourage people to think about their coaching relationship like that. This is a service that you’re paying for. It is for you. Don’t worry at all about judgment or hold anything back. The best coaching relationships are when you can communicate as freely as possible.
Yeah. And when I think of the mentors that I am grateful to be working with, there’s not always the consistency. It’s not like we have an ongoing, recurring, in-the-weeds conversation. The conversation is usually like, let me share the weeds at a high level because we only have so much time. It’s not that consistency.
So, Matthew, how is coaching different than, you know, is it like an opportunity at a venting and like a therapy session?
Yeah, no, no, it’s not. Sometimes people come to coaching for different needs, and there’s a mismatch in expectations. Ravi really nailed what’s the difference between coaching and mentoring. I might just throw in one little extra thing: a mentor will probably mostly focus on what they’ve done (“Here’s what’s worked for me or what didn’t work for me”). Whereas a coach will try to elevate the conversation a little bit more and help you build a muscle so that you can solve those challenges or overcome those challenges.
Working with a coach is work. Continuing the athletic analogy: sometimes you don’t want to get up on the treadmill, and an athletic coach is going to say, “Well, we’re running today, so let’s get up there and build that muscle.” And that’s another key difference from something like therapy. People think they’re interested in coaching because they have a lot on their mind they want to unpack in the professional setting, but that’s really not what a coach is going to do. We’re not going to focus too much on the past. We’re going to be focused on understanding how we got here, sure, but then we want to build a plan to act and move forward.
If coaching becomes a venting session and a desire to get the answer from the coach (“Just tell me what the answer is”), then those are relationships that don’t succeed as well as folks who are coming into it with an open mind to build some new muscles and to get outside their comfort zone in a safe way. Trust and safety is pretty important.
So what about time frame of when someone should engage with this potential path of working with a professional coach? I mean, I guess not to harp on the athletic analogy, but I think it is a perfect analogy. When is the right time to start thinking about working with a professional coach?
I think it could be as early in your career as you want it to be. As soon as you feel like you could use a little bit of help or there are some things that you don’t quite understand how to approach, and you need some help reflecting on that and putting together a plan, that’s a great time. From an athletic standpoint, people start working with coaches in little league. It shouldn’t be any different in the professional arena.
The reason it has been is coaching has this reputation as being really expensive. And because it’s expensive, you need your company to pay for it, and your company’s only going to pay for it when you’re senior enough. But to some extent, you could argue that the folks that are super senior in the organization don’t actually need coaching; they’ve been able to figure things out on their own.
I’m a big advocate for working with a coach as soon as you feel like you’re ready. You have to be willing to put in the work. You have to want it. And now there are great coaches who will work directly with folks who are, you know, it is an investment. But for folks that have been through it, there’s something like a 95% satisfaction rate with coaching. People reflect on, “This is the best money I’ve ever spent.” It’s given me a sense of mastery, and it’s also helped me get the promotions or the raises that I wanted. It really does have an ROI. I’m a big advocate of get coaching as early as you can, as early as you’re ready for.
I would 100% agree with that and add in that there are also moments in time throughout your career that lend itself to finding a coach:
- When you’ve stepped up to a role at a level in the organization that you’ve never seen before. (Organizations sometimes promote first and figure things out later, and you are now in the hot seat.)
- When your scope shifts (e.g., individual contributor to manager, or managing multiple levels of the organization).
- Starting a new job is a great time to ask for a coach. When negotiating an offer, you can say, “I’m stepping into a new role at a new company, maybe at a higher level, and I’d like to continue to work with a coach.”
I would say there are probably some times where they’re not a good time to look for a coach. If you feel like you have low job security or you’re not getting along with your team or manager and are thinking about moving on, that’s probably not a great time to throw a Hail Mary to a coach and see if you can fix all the things. Mostly because coaching takes time. We don’t start running a marathon on day one, and you may not have the time to really work on anything before those scenarios kind of play through their course.
There’s a professional coach on the West Coast that’s like this luminary that was a coach to Steve Jobs and all the big Silicon Valley names. Those individuals leveraged this resource, and you would think they didn’t need it, but they saw the potential. When you expect people to take on more responsibility, some people might just naturally be able to handle it, but a lot of people got to figure it out. And you’re either going to learn that on the job, or you can work with somebody to help you stretch yourself and get better at it instead of just being thrown into the fire and expecting to survive.
I do recall that luminary on the West Coast. There’s a great book about him called The Trillion Dollar Coach. Encourage everyone to read it. The individual is Bill Campbell. And I think democratizing coaching, which is something that I know Ravi’s very passionate about, is absolutely worthwhile.
So, when I think of coaching, it should be like, “Hey, I’m looking to continue to get better.” It’s not like a fix if I’m frustrated at work. This is talk about the expectation over the long term.
I don’t think it’s a quick fix. The initial thing that I think is a breakthrough for a lot of people is stepping outside the situation. That can be good whether the situation is challenging or really positive. If you’re in a really challenging situation and your Spidey sense is going off that you don’t feel like you’re getting the credit you deserve or you don’t understand the mechanics of how decisions are made, coaching is great for that. The coach can come in through questions they’re asking, through alternative perspectives they’re providing, and help you step out of the situation.
One of the reasons that athletes use coaches is like Tiger Woods can’t see his own swing at the end of the day. He needs an outside perspective to understand where he can do better. And it’s the same thing professionally, even more so because a lot of times the political dynamics, the interpersonal stuff, can feel invisible until you start to probe and ask the right questions.
If you’ve just been promoted to a new role, you might come into that with the perspective that you’ve always had, which might not be the right level of scope for the new role. Often, what happens is people get promoted, and there’s an unsaid change in expectations. The thing that made you an all-star performer last year, your manager and other leaders have now invisibly changed the goalpost and have these much higher expectations of you.
When you’re working with a coach, they can paint the picture of, “Okay, you’re now at a different level in the organization. You’re engaging with different people. Let’s start to think about what the expectations might be and how you can suss those out to make sure that you are playing by the rule book that applies to you right now versus the rule book that got you to where you are.”
I think in both the cases, whether you’re in an opportunity-rich situation or a challenging situation, that ability to see outside yourself to come in with a different perspective is incredibly valuable. And coaching does take time, but there can often be very quick wins that you can get where you can start to see the value and then build on it in a compounding way.
I think something, Ravi, that you said that really resonated with me was how the rules change on you, and they’re somewhat hidden or opaque. It creates a feeling of psychological unsafety for whatever reason. The ground is kind of shaky underneath your feet, and you’re not sure why.
Thinking about it from the other perspective of the executives or the leaders who have already arrived at that state: it’s sometimes difficult to get 12 executives to agree on a plan. When you’re working at that much higher level of combining strategy and tactics and different points of view and different functional areas, it is important to have folks in the room who can play that game well. There are certain rules of operating at that level, and that group can be insular and keep you out if you’re not playing by those rules, even if you have great ideas or deserve to be there. It’s just this unwritten set of rules of how we play this game that need to be exposed.
Ravi, the question that you brought up that I was thinking about all along was the financial piece. I think a lot of the reasons why coaching hasn’t become more accessible is the fact that it is expensive. What about having a company support this and have a budget to pay for it? How do you approach that?
I think the first step is to ask. If there are official programs at your company, great, take advantage of them. The next step is to ask your boss or ask your HR rep and say, “Hey, I want to have the biggest impact here possible. This is something I’ve been thinking about. Is it possible to get expenses covered?” The worst you’re going to hear is no, and that’s not a bad no; you just said, “Hey, I want to have an even bigger impact here.” That’s never a bad thing.
Sometimes you’ll hear surprisingly that they’re willing to cover it. Sometimes you can meet somewhere in the middle and say, “Okay, I’ll pay half, you pay half.” Corporations like that because then they know it’s not always about the dollars; it’s really about, is the person committed to this? Is this money we’re going to spend going to have a high ROI? I always recommend talking internally first. The question actually reflects positively on you.
And then if you feel like you really do need the support, it’s okay to pay out of pocket around this. It’s helpful to figure out how much you’re comfortable with and just know that that’s something you’re investing in yourself. When people are paying out of pocket and it’s on the edge of what they feel comfortable with, it pressurizes coaching: “How do I get my money’s worth out of it?” And that’s counterproductive.
So, find something that’s comfortable, and then find a coach who you really resonate with and feel great about. It used to be that the only people doing executive coaching were people that were also themselves pretty senior, and rates were really high. Now there’s a lot more people across very different levels of seniority that have come into coaching. It’s not the case that the best coaches have always had the most senior roles. There are people earlier in their career that just have a gift for this. So, there are great coaches available no matter what your budget is.
The most important thing is to:
- Try to get your company to cover it.
- Figure out what cost you’re really comfortable with.
- Find someone that you resonate with where the cost kind of becomes secondary because the relationship is so valuable for you.
And if it’s not valuable, that’s okay. You can always stop and pick a different person. It’s up to that coach to prove their value to you.
I would have no idea what the expectation around the cost is. It does vary. I think it’s anywhere from like $100 an hour on the low end to a lot of the executive coaches will charge $1,000 an hour or do some monthly retainer. I think if you can spend $1,000 a month and know that you can do that for 3 months or 6 months, that’s a really good starting point where it opens you up to a lot of great coaches. In the grand scheme of things, that’s typically single digits of what a person is making annually. If you can improve your productivity, improve your happiness, get the raise, it’ll pay for itself really quickly.
Matthew, so we were talking about how do you ask for it? What advice would you have there because that’s kind of like the big piece of this is who’s paying for this?
It is a big piece. Folks are uncertain and often don’t allow themselves the ability to even ask for such a thing. A lot of that is related to impostor syndrome, which can also be driven by this feeling of the ground being uncertain because the goalposts have changed.
What I always tell folks is quite simply, link it to the business. Our shared goals and the business’s shared goals are happy, healthy teams that are operating on all cylinders and driving value for the organization. That’s what I’m all about, and I think I could use some help. So, linking it to business goals is important.
We talked a little bit already about asking at the right time. If you’re doing this on the heels of a promotion, that’s a great time. Sometimes timing is everything.
And then I think it’s important to make it easy for folks to say yes. Some of those arrangements that can work include the shared cost, or making it about a pilot. A great coach should be able to show some inflection point or positive signs within two to three months. Frame it as a pilot.
Another tip I’ll always throw out there is to involve other folks. Sometimes it can feel like this is a conversation between you and your manager, which has a power dynamic. But there are tons of programs and opportunities that generally come out of HR that you may not already be aware of, like professional development and coaching. I can speak from personal experience; I weasled my way into the TripAdvisor coaching pool because I learned that it existed.
What I always tell folks is there’s nothing bad that can come of it. The worst thing that can possibly come of a conversation like this with your manager or HR is they can say, “Sorry, we’re not going to share the cost at all.” And everyone in the organization who you talk to about this now knows you’re someone who wants to succeed to drive business success and is thinking of putting in extra effort and work in order to be great at your job. So, I would encourage folks to have a plan, be intentional about the ask, and make it.
How do you go about finding and determining who is the right coach? Is it important to have the person specialized in your line of work? What are the types of ways of vetting out a coach?
I think the first step is to ask people that you know. It’s best to find someone that you’re connected to. You’ll find as you ask people that they’ll either use coaching themselves or they might know people who know people. That connection is really important.
Second, once you have a set of folks, look at their online presence. Look at what they’ve written. There are very few great coaches that I’ve met that don’t have some online presence, aren’t trying to share their knowledge and their approaches with the world. If that thought leadership resonates with you, that’s a great sign.
Third, meet with a handful of coaches. I’d suggest meeting with three, doing half-hour, 45-minute sessions. Coaches should be willing to do that to get to know you because it’s a fit thing. They want to make sure they gel with you and you gel with them. They should be willing to do a 30 to 60-minute session before you commit to anything. If they’re not, that’s a red flag.
You should come out of that session feeling like, “Wow, I really found this person’s advice and their perspective valuable. I enjoyed speaking with them. I felt like I could be honest and authentic with them.” I try to get at least one unlock during the session—something that was a pattern of behavior or a way of thinking that they’re now starting to think differently about. If you spend 45 minutes with someone and you leave with a slightly different perspective or a new way of thinking, that’s amazing.
Try to get introductions. There’s also good curated lists, especially for product folks. Lenny has a list. Marty Kagan has a list. Look at their online presence, see if you resonate with that, and talk to at least three of them.
I want to underscore the first thing Ravi said: referrals are everything. Bill Campbell, we don’t even really know his name, and he liked it that way. The preface of the book involves a story of how he wouldn’t even allow that book to be published while he was alive.
And then the last thing is trust your judgment. A quick question to ask yourself: when you see that person’s face come over the Zoom for the next call, are you going to say, “Ugh, I got to do this meeting now,” or are you going to say, “Oh my god, it’s Ravi! Yes, I’m so looking forward to this.” That emotional response is the sum of all of those factors.
Matthew, once you identify a coach and you’re like, “Okay, let’s get started here,” how do you even get started? How do you optimize that value from these sessions, and what can someone expect kicking things off?
It can be hard to find the groove. Often times, a coaching engagement involves an hour on the Zoom for a week or every two weeks. That time needs to be treated as pure gold. Moving the time, skipping the time, letting the pressures of the day-to-day overwhelm that time is not a great way to get started.
Moving right from your previous meeting into a coaching meeting can also put your mind space in the wrong spot. So, give some time for prep. I would prefer for folks to prep 24 hours in advance. Take some time at least the day before to work through what’s on your mind, write up your thoughts around what’s working and what’s not working, and send that over. This is not only helping ground the conversation but really helping accelerate the work. A pitfall to avoid is spending 30 minutes updating your coach on what happened over the past 2 weeks when that could just be written down.
Be prepared to do some homework. That homework over time should be given to you by the coach: “Here are some things I want you to focus on or do differently.” Prepare for your session, go into that session with no distractions in a great mind space, and then be ready to do some post-call work (reflection and post-call work).
Anything you’d add there, Ravi?
I would add that if you feel like you don’t have time for this, it’s probably not the right setup. If, on the other hand, you feel like I don’t have time not to do this, then it’s a really good relationship and the right setup. I’ve had both. The coaching relationship is 100% for you. So if it’s not working for you, make sure you’re working with someone who you feel like you’re getting a huge ROI from.
Ravi, as an extension of that, how do you know if it’s working? How do you know if it’s working?
I think there’s three pieces, all equally valid:
- It feels like it’s working. If you subjectively feel more masterful, more prepared, and more able to get things done, it’s working.
- Feedback. If you’re getting good feedback from your boss or from other peers, that feedback loop is really important.
- Objective Measures. This could be hitting your OKRs, getting the promotion that you’ve been aiming for, or a really successful product launch.
You should be hearing feedback that confirms that it’s working, and then eventually that should show up in objective results that you can measure.
Matthew, how am I going to measure the ROI? And in addition, what do companies expect if they are partly or fully paying for it?
I think Ravi kind of outlined the measures of success really well. I might say that some of the forms of feedback that you can ask for are things like 360 reviews. That helps you solicit feedback up, down, and side to side in a way that is detailed and helpful. It gives you things like, “Your communication style is resonating with these pockets of the people that you interact with but not with these other folks. So consider a different communication style for those types of stakeholders.” I find 360 feedback to be an effective way of putting some measurement around some of the things that often are subjective.
From the company perspective, as you move up the organization, results matter more and more, and happy, healthy teams are less and less of what is discussed because it is assumed and understood that you’re a positive force for leading and creating happy, healthy teams. When a person is struggling to hit their objectives, which involve multiple people or influence up, down, and side to side, or worse, is doing things in a destructive or ignorant way, that keeps the whole organization from meeting those business objectives. So sometimes what the manager wants is all of these problems that are getting in the way of doing the job, “I want them to go away.”
A manager is not often going to get a thumbs up because you’re doing a great job, but what does happen is someone will go to the manager and say, “Matthew’s really not performing the way that’s right for me and my team.” A zero indication of anything off on the team and morale side, and then yes, an ability to get more things done.
At the end of the day, many people are looking for their next step. If you are a director reporting to a VP, they may be eyeing a C-level position. They want lieutenants or trusted resources on their team that they can hand big parts of their job to. So, long story made short, a pipeline of succession planning and leadership development is another thing that folks are looking for. If you can become a great leader, awesome. If you can create great leaders further down the line, that’s really what they’re looking for, and sometimes a coach can help you get there.
Kristen, thanks so much for your comment here. She goes, “I found an executive coach to be amazing, critical at a time when I was stuck/plateaued in my career. I was fortunate enough to have an amazing boss who somehow identified what was holding me back and suggested an executive coach. The company was willing to invest, and I got a clear return on investment. I essentially created OKRs with my boss to assess the value of the coaching.” That’s awesome. Great testimonial there.
Can you talk about the push/pull dynamic of working with a coach? What’s the balance like between asking a coach for help with a specific issue versus expecting the coach to set a longer-term goal and helping you achieve it?
From my perspective, I think it somewhat depends on where you’re at. If you have a very clear perspective on what you need to accomplish, then maybe the right thing is to get someone to help you with that specific issue. If, on the other hand, you’ve got this Spidey sense that something’s not right, but you’re not quite sure what it is, then it’s good to spend time with your coach doing a diagnostic, and then your coach, through the conversations with you, will be able to help you figure out a goal to focus on.
I prefer doing it like that where it is somewhat dependent on where you’re at with respect to the problems that you feel like need to be solved. Other coaches might have a particular specialization, or some are more Socratic, focused on reflection and asking the right questions. Others are more experiential.
I think answering this push/pull question is partly taking stock of where you’re at and then looking for the right coach. It may change over your coaching engagement. You might say, “I want to make progress on this one specific thing.” And then, through getting to know your coach, they may say, “Okay, here’s some other things to work on.” I think about the push/pull dynamic as somewhat organic and should be driven by you in terms of your understanding of what needs to get solved or your understanding that you need to do some discovery around that.
Yeah, I tend to agree, and I think there’s three broad stages that you can think of:
- Up to the Waterline: You’re in the role, and you’re feeling like the water line is right up to here. You’re needing a little bit of help in a more time-sensitive way to address an issue in front of you. Your coach should help you reduce that water line while also helping you understand what your longer-term objectives might be.
- Operating Right: We’re operating right where I think we should be for the level I’m in. Now, a coach that is more Socratic starts to become more valuable because you are now shining your headlights a little bit further down the road.
- Everything’s Running Great: You have a team that’s just crushing it, and you don’t really have much to do. You’re now thinking about either switching to a different department or graduating to the next level. At that point, your coach should really be helping you think about where you want to be in 5 years so that you can go from that stage to minimizing the amount of time in Stage 1.
The most professions have a credential that the person may gain because no one graduates with a degree in coaching. So, what should you expect your coach to be certified?
There’s there’s many certifications. In my experience, there’s no one single one that really stands out as the one to get. I don’t have the certification, and I’ve been able to do a great job. I’ve not looked for that as a prerequisite in the coaches that I’ve worked with.
One of the traps to look out for is someone who has a lot of these accreditations, and when you get on the line with them, they’re not really giving you that one unlock really fast, and they’re more talking about their process and their accreditations. Those can be a mask for something that you probably want to avoid, but I don’t think they hurt. Not a requirement.
I feel the same way. I think one of my ways of thinking about the accreditations is these accreditation companies are businesses, and so they have to offer a credential where they can credential anyone. A lot of them focus on more of a Socratic method where they say the coach’s responsibility is not to draw from their own experience and advice but to ask the right questions. For me, that’s not the type of coaching that I think is the most valuable for a lot of folks. I think you do want someone who has been there, done that to some extent.
If there is a credential that you feel like you do want to look for, my advice is to go to that credentialing company and get an understanding of what their philosophy is around coaching. Do I like this style? If so, great. There’s a particular accreditation called Co-Active, and that’s an approach to coaching that I’ve seen a lot of people really like.
At the end of the day, the biggest thing is getting referrals, which is the best credential to look for.
