In this Dear Melissa segment, Melissa answers subscribers’ questions about hiring CPOs, career management, and how to research a company you’re considering joining.
Show Notes
Q: I have been offered a senior leadership role, but part of me feels I still haven’t proven myself with any actual company outcomes as an individual contributor. Should I take the role, where I’d be fairly hands-off, or spend more time honing my craft?
Q: Is there a way to evaluate an organization before applying?
Q: Do you have any tips for finding a good VP of product for a growth-stage startup?
Resources Melissa Perri on LinkedIn | Twitter MelissaPerri.com
Episode Transcript
Hello, and welcome to an episode of Dear Melissa, from the Product Thinking Podcast. The lines are now open, and we're ready to answer your most pressing product questions. Which prioritization framework would you recommend and why? Hi, Melissa. Do you have any suggestions on developing a product strategy?
Whoa, whoa, whoa, whoa, whoa. That's a lot of questions. All right, let's dive in. Hello, and welcome to another episode of Dear Melissa. Today, we're going to talk a lot about hiring CPOs, figuring out what's a good product company to work for, and a little bit of career management. So we've got three great questions that I'm excited to dive into.
Here's our first question. I've been a big fan of all your work ever since I became an accidental product manager. My company didn't have a formal product structure and adopted waterfall approach.
After reading your book, I convinced my senior management to become more product-led, which led us to hiring a CPO. Excellent. She's implementing a formal product management function, and it's super exciting to see all the positive changes so far. My question is around my career path. The new CPO knows that I led the push to become product-led, so wants me to step into a senior leadership role.
This is a great opportunity and one I'd love to take, but part of me feels that I still haven't proven myself with any actual good outcomes as an individual contributor. Do you think I'd be better off taking the senior leadership role where I'd be fairly hands-off or spend more time honing my craft as an individual PM? That is a fantastic question.
I think there's a lot of things to think through when you're considering moving into this role, and we're going to talk about that right after this. And we're back, and we're talking about whether or not you should take the senior leadership role.
So first off, I want to talk about the success you're talking about. You say that you haven't really proven yourself with any actual good outcomes as an individual contributor. One, I think that's really hard for product managers. I hear this a lot from individual contributors and from a lot of people who are on teams, and they say, I feel like I haven't been able to reach all the goals that I set out to do at this company, so I'm not sure if I should be taking the next step.
It's so hard to tie your success as an individual to the company outcomes when you don't have full control over them. Some companies move very slowly, others move quickly. Sometimes there's so much baggage in the vision and the strategy and the leadership levels that you as a team member or individual contributor couldn't possibly be able to make those differences.
So ask yourself, were my sights set really high on these outcomes that I was trying to do, or did I make marginal improvements?
Did I actually contribute to moving the ball along, even in a maybe dysfunctional place? And in that case, you have to give yourself some slack, right? You've done the best that you can, but you just don't have the control, and you won't until you're a senior leader. That's so hard for us to come to terms with as product managers because we always hear we are responsible for the outcomes.
We're the place where it lives or dies. But that's really not true when you're just a team member in a giant cog of a machine that's a company. So ask yourself this question when you're thinking about, do I want to stay here and feel like I can make more work, more work as an individual contributor, try to get some of these outcomes, or do I want to be a senior leader?
I'd ask myself, do you feel like you know what you're doing at the individual contributor level? Have you made good progress? And not hitting those outcomes, was it from you not being able to do your job because you didn't know how, or is it from the other circumstances in your company?
Was it because marketing didn't get on board, sales didn't get on board, you didn't move fast enough, there was a lot of political angst at the leadership level? Sometimes it's due to that. Then ask yourself, can I make a bigger impact as an individual contributor or as a senior leader? I think you've got a little bit of probably imposter syndrome going on here because honestly, an experienced CPO would not ask you to step up and take you under their wing and be able to coach you through this if they didn't think you could do it, right?
Experienced leaders, and I don't know how much experience you have with your CPO, but I'm hoping you got an awesome one, and I'm pretty sure you do. They would not ask you to take this opportunity or take this leap if they didn't think you could do it. So one, I would think about that and say, is this imposter syndrome?
Do I really know what I'm doing? Have I helped steer this company in the right direction? Do I want to take this leap in my career? I'll also say it's hard to transition a lot of times from an individual contributor to a senior leader.
So if you feel that you're competent at your job, you still got a little bit to learn, this person's going to teach you, that's totally fine, but you're competent at your job, you know what you're doing, you can coach individuals who will be underneath you in good product management, then I would say go for it, right? But if you feel like, actually, I'm not really sure what I'm doing, I don't feel competent coaching a team around this, I don't know if I could steer it in the right direction, and I'm not sure how much support I would get from my CPO, then I would start to worry. But if you feel like you got the support, you got the competence, you'd feel comfortable coaching people, take the leap, take the leap, right?
Try it. Don't hold yourself back because of imposter syndrome, right? Really consider what this could do for your career, because it could be a great leap. And I'll also say this, a lot of people want to move into management roles, because that's how we progress in product, right? There's not a lot of really senior individual contributor paths, and I wish there was.
I talked about that in another episode as well.
But if you want to keep going in product, you know, sometimes you do have to manage people. And you might get into this role and find out, like, I actually hate this. And a lot of people do. A lot of people start managing others, and they're like, nope, not what I want to do. And then they can go back to the individual contributor role very confidently and feel like, okay, I could just kill it here.
So that's something to think about. Like, you might not love this role, or you might find out you're awesome at it. And as you get more senior in product management, your skill set changes a little bit as well, right? As long as you can competently coach the people underneath you into good processes and practices, you're also going to be taking on more of a strategic role too.
So think about that. It's like you might not know exactly how to put all the strategy together, but that's why you have a CPO who's going to coach you through this, right? But can you think strategically? Are you thinking strategically? Are you excited about strategic problems? Because that's now going to be your new role.
And if the answer is yes, then I think you should take it.
If you're like, no, I'd rather just work with developers and, you know, just spit out the features and do the hands-on work, that's when you can start to say, maybe I don't want to do that yet. Maybe I'm not ready for it yet. But don't hold yourself back on this outcome thing because so much goes on in these companies, right?
It's not all up to you to lead success. So how are you measuring your success? And are you giving yourself enough credit for what you have done would be my questions there. I hope you take the leap. We need some more good product leaders out there. And I hope your CPO coaches you through this. All right, next question.
Dear Melissa, the episode you did answering questions about product transformation was so helpful. A number of light bulbs went off for me. Thank you for that. My question is, how do we find a company that is a good product management company when we're looking for a job? You've talked about finding a good CPO to work for, but how do we know the CPO is good?
You have great interview questions to evaluate a company when you're interviewing, but is there a way to evaluate an organization before applying? Any guidance is appreciated. This is a fantastic question.
It's really hard to understand if the company is a good product management company from the outside, but there are some things that I look for, especially when companies ask me to come in. My biggest thing that I look at is what are the customers saying about the company and the products? And you can kind of see how much work needs to get done.
So one of the things I do, whenever I'm consulting with a company, joining the board, whatever I do, I first go to things like G2 Crowdsource or anything that reviews products. And I look at what their customers are saying about the products. And if the customers are completely saying like, this product doesn't do anything for us, I left and I went over here, like, okay, wow, we have a lot of product issues, right?
Or sometimes they say, fantastic product solves all my needs, but it's so hard to use. And I'm like, okay, it's got a UX problem, but that doesn't necessarily mean it's super dysfunctional. But you can learn a lot from customer reviews. You can learn about their sales processes. You can learn about the product, whether people really like it.
You can learn about whether the industry is moving on. You can look at the features. So I start to really study that. I really dive into those customer reviews and I start to think about what is this telling me, right? Like, is this a, you know, is the company creating great products for its customers?
And the ones that like have glowing reviews about their products probably are a good product company, right? Because it's hard to create great products if you don't have a great product management team. So think about that. Think about what the clients are saying, what the customers are saying. How does that relate back to the products?
So I'd look at that first. Two, I will look and see how long people have worked for the company and the product management positions as well. And that will kind of tell you like, has the CPO been there for a long time? Are they new, right? And then also based on that, like, are the product managers new?
Are they there for a long time? You're going to see a couple patterns.
If you've had a CPO there for a couple of years, have the product managers changed? Have they turned over? Usually if there's a good CPO, people will stick around. I'd also look at the CPO's background. Have they done this before? A lot of CPOs are new to the role, not necessarily new to the company.
That's fine if they're new to the company, whatever. That means that they probably recognize they had a problem and needed a change. So what is that CPO's background? Have they been an extensive product manager for a long time? Do they have that experience? If they don't, then you have to start to question, like, is this just a subject matter expert that people think could handle a product?
Or is this person really a product person? You can tell that by the backgrounds by looking at it. I always look at people's backgrounds on LinkedIn. Then you can start to see, like, where have they worked before? Do you recognize those companies? Were those good product companies? Or maybe you go and read the reviews about those companies as well and start to see if the customers had good things to say about it, see if it improved.
I would go do some research there. What else could you do? I think you can also just reach out to people who work there in the product organization. Be like, hey, I am thinking about interviewing for your company. I just wanted to know, like, do you enjoy working there? I've seen people do that a lot, and that's totally fine, right?
It's not gonna ruin your chances or anything to say, hey, I'm really excited about your company. Would you mind just answering a couple questions about this? That might be a good way to see if people enjoy working there. I'd also, when you go into the interviews, start talking to the product managers about the changes that they're going through.
What's changed? What's new? What do you think you still need to improve about the product company part of this? They're gonna tell you. They'll be like, oh, we need to work on a process or we're resetting our strategy right now. And you can start to sense, how much do they know that they need to change or how much are they actually committed to change or is it just humming very smoothly?
Those are good things to look at. And I'd look at the rest of the product team too, especially new hires. Are they coming from good companies or good product companies? People who are good are gonna go to good companies. So that's something to look at as well. So lots of LinkedIn searching is what I'm getting into.
Lots of background. Customer reviews tell a huge story about a company. We talk to customers a lot as product managers and a lot of customers will write exactly what they think about the company online. So a lot of Googling there just to see what they're saying. And that's the whole point of being a good product management company, right?
Building things your customers love. So if the customers love the product, if they have some constructive criticism, but you're like, that's fair, that's constructive, it doesn't feel dysfunctional. I say you're probably in a good place. And I'd also just make sure you follow product leaders who know what they're doing, who have some experience in that and who are there to really coach you and improve you.
So I would look all over LinkedIn, look at the people who work there, look at their backgrounds, look at the customer reviews and that should give you a little bit of an inkling before you actually do the applying. All right.
And now we're on to our last question. Dear Melissa, any tips on finding a good VP of product for a growth stage startup? We've got 6 PMs and 60 engineers. I'm on the interview panel and today's candidate included SAFE in their presentation of how to run a product org. Signed, humbly hiring my boss.
Well, first of all, I think it's awesome that you're hiring your boss and I'm glad that the company gave you the opportunity to do that. So that's really cool. SAFE would be a red flag for me at a growth stage company of 6 PMs. That is way too much overhead for a company of your size. So I think your intuition there is good.
But this is how I used to hire VPs of product and CPOs for growth stage companies. I did a lot of this when I was working with Insight. And what we would do is we'd sit there and we'd put together a scorecard of what we needed in the product person. And we'd look at all of the challenges that the company was actually going through.
So we'd go, you know, do we need somebody to own the strategy of the product portfolio?
Or is the CEO doing that?
Hopefully it's a VP of product. Do we need somebody who's like super strategic? Or do we have a pretty well thought out roadmap? Do we need somebody who can teach us better processes because we don't have process? Or is that being owned by the engineering team? Sometimes they'll implement agile processes, but we still need product processes.
Do we need somebody who spikes as a subject matter expert or leans more towards like a specific type of product leader, like a platform leader or something like that? So we think through all of those criterias and we put together the scorecards, got usually five or six key skills that we're looking for. And then I would start with the screener on the phone of all of our candidates before, you know, putting them through the whole gamut.
And I'd ask them very specifically related to those criteria that we found to tell me about the time where they'd done those things before. So for instance, if you're in a growth stage company, you've got 6 PM, 60 engineers, I can imagine that you're going to be scaling very quickly as a lot of growth stage companies do. Do you need somebody who's great at building a team and hiring people?
In that case, I'd ask them on the phone, tell me about a time, you know, where you hired your team. Tell me about like your past companies too. Did you just walk into a team and take it over? And in case like, how did you win the hearts and minds of people? Like what'd you do when you took it over? Was there churn?
You know, those types of questions. Or were you coming into a blank slate and you needed to hire people or grow people or scale that team very quickly? And how did you hire people? If we interviewed one of the people who've been reporting to you, what would they say about you? And then also, can you like demonstrate or tell us about a time when you coached somebody on your team and they went on to like bigger and greater things?
One of the best answers I got from a CPO candidate was like, yes, I had this director of product reporting into me when I was chief product officer of this company and I coached them and they went on to be a chief product officer now with their company and that company's killing it. Right? That's telling me you were really good at molding and shaping and growing teams and you're really good at coaching people.
If they don't have any stories like that, I'd be worried. I'd be like, I don't know if they could take this on. I also think my favorite questions when I'm screening and interviewing people is about, tell me about a time. So I always ask every VP of product, every CPO, tell me about a time when you set a product strategy.
Who did you oversee? What did your team look like? What was the outcome of that product strategy? How did you put that roadmap together? What did it look like? I want them to walk me through the process, but then I also ask them like, what was your responsibility in setting that strategy? Right? Like, what were you accountable for?
What did you literally do?
And then how did you work with the rest of the executive team to do it? And this is a great question as well for people who may not have had that CPO role but are trying to make that leap and they've been a VP of product before they've been a director of product. If they have demonstrated competence and ownership over a big enough piece of the pie in their company, I'd be like, okay, they know how to set strategy.
They just got to do this on a wider scale. And maybe this is the right opportunity for them to make a leap, right? This also helps you not just look at people's titles but you really get into what did they do before and what were the outcomes of it? And I've met some amazing director of products at larger companies who've overseen big portfolios and made big, big change and made a lot of money for that company.
And I'd hire them as a VP of product or as a CPO at first stage companies. So that's something to look for. Like tell me about a time when you set the product strategy, ask them about what their responsibilities were, what they directly were responsible for, how they did it, what's the process, what was the outcomes?
Like make them get detailed. And you can start to see if people are ever thinking strategically or are they more tactical? And this is going to tell you who's going to be a great leader versus who's not. So the people I found that actually weren't thinking strategically who were not going to be great VPs of product or CPOs, they would tell me super specifically about taking in customer requests and executing on those ideas.
They'd be like, well, we worked with this big client to like build X, Y, and Z. And what I'd want them to say was like, that was a proof point to lead to scaling to other clients. Or we then went from there and built a roadmap around that because we found this out and then it made all this money, something like that.
But the people who aren't really thinking strategically, they get tactical. They talk about customer requests, they talk about executing ideas, they talk about coaching the team a lot through that, but they don't really talk about interfacing with the executives and driving a strong agenda through. So you want to make sure you understand how they work with the rest of the executive team.
You can ask them about difficult executive teams. Have you ever worked on a difficult one? What happened? Who didn't you get along with? How did you remedy that? Those types of things are really going to set apart a great product leader from just an average product leader. The politics, the working together, the driving the agenda.
The product leaders who succeed are the ones who are able to do that. The product leaders who fail are the ones who don't want to work with the executive team, have a problem communicating with them and don't want to help drive those agendas forward. So try to dig into that. Again, look at their backgrounds, look at who they've worked with before.
I always do references as well for, you know, CPOs when we're hiring them, like what do they need to work on? What were they good at? And you can usually tell with those references, like how they operated with the rest of the people. And you also tell by the references that they actually submit, who they worked with, right?
If you've got a chief product officer that has like five years experience as a chief product officer and all their references were like direct reports and not the other executives, I'd be very worried because I'm like, okay, that person's not working with their executives. What's going on? It's one thing if they're leaving a company and don't want to rock the boat before they leave or whatever.
But if they don't have people in their past either who were like higher up that they didn't work with, that's a question. I have questions about that. I want to see like peers. I want to see people reporting into them. I want to see old bosses. Like those types of things will tell me that this person was really a leader and somebody who collaborated with the executives and who pushed for agendas and getting things done.
So that's another thing that I'd look at. But yeah, it's all, tell me about a time when. Same things that we use for user research. Make them pinpoint what they did. Make them talk about it. You'll start to see trends. You'll start to see people who've really led things and pushed agendas forward and got stuff done.
And you'll see people who just pay at lip service but nothing ever actually amounted to it. I like this presentation too that you kind of had where it sounds like you asked them about how you would run the product org. I used to do that as a final stage of a lot of my interviews. I put together a really small case study scenario that directly related to the company's problems.
I just like fudge some numbers or whatever. And I'd ask people how they would approach setting a roadmap for it or setting a strategy. So you don't have to get to a roadmap. Talk to other people in the organization as you're going through these interviews. And I would tell them this before they got into interviewing with the rest of the organization.
I'd say, you're gonna meet with the sales people. You're gonna meet with product people. You're gonna meet with everybody else. While you're doing that, ask them about what you would need to know to be able to recommend what you would do and present back the biggest challenges this company has. So that way I'm really understanding if the person that I'm hiring understands the challenges, understands how to solve those challenges, and I'm not asking them for a big solution.
Like I'm not asking people to do work here that we're gonna take and be able to execute on. It never comes out to that level. It never gets there. But I wanna know how they would approach it. I wanna know what they would do in their first 90 days. I wanna know what their plan would be. And I wanna understand if they understand our challenges and they feel confident in actually solving them.
So I always like to take that little case study, start them off with it, have them talk to a bunch of people in the organization and then just present back really quickly, 30 minutes. Here's what I think is your problem. And this is how I would approach solving it. I only know what I know, but like, this is what I know.
And this is what I've gleaned so far. And yeah, I think I could kill this. And this is what I think I would be doing. That is gonna give you a lot of insight into how people approach problems, how they solve problems and what they've done in their past. And the people who are tactical are gonna spend all of their time on org design.
I've seen that a lot in process. And they're gonna be like, I need safe, I need agile, I need that. And if it's a strategy problem and they glance out over that, like you know you don't have a strategic leader there.
You have somebody who's a lot more tactical, a lot more focused on process and that might not be what you need. So always good to do those types of things. Always good to have a scenario and have people talk you through it. Then you're gonna start to see how they think rather than them telling you what they think that you're gonna hear.
So I hope that helps. So thanks for tuning in to today's Dear Melissa. If you have questions for me, I would love to answer them. So go to dearmelissa.com, submit your questions. We do this every other week and it could be about anything. It could be about a scenario going on in your company. It could be about career paths.
It could be about anything. Give me some good stuff to think about. I love answering these questions. And also, if you're enjoying this podcast, please leave us a review. Anywhere that you're listening to it, that helps tremendously for people finding it. We love it. We love hearing your stories. I love hearing that you like this.
So you keep me going. All that feedback is great. So I'd really appreciate it if you could leave us a review and we'll see you next time.
