Episode 117: Answering Questions About Successful Career Changes and Managing People Efficiently

In this Dear Melissa segment, Melissa Perri answers subscribers’ questions about how to choose the best product career path, escape your career trap, and why a product manager can become a senior faster in a startup.

Have a product question for Melissa? Submit one here and Melissa may answer it in a future episode.

Q&A:

  • Q: As a product manager at a company that prioritizes product discovery, experimentation, and collaboration, I’m faced with a dilemma. Which product career path will have the greatest long-term impact? I come from a previous company that was more of a feature factory, where, despite having a higher role and greater control over processes, I could not change the mindset of valuing customers over outputs. However, my ex-employer has asked if I want to come back and drive a big product management change. While the opportunity to drive change and take on a leadership role is tempting, I worry about returning to the same problems. Although I have learned and grown in my current role, the potential for personal growth and business impact in the long term is uncertain, as there are many people in the company over 500, and the previous employer was relatively small, 20+ in a business unit, but had limited mentors. Can you help me weigh the pros and cons of each option?

  • A: I give individual contributors this advice, and it’s a little bit different for leaders. But I feel like it’s worth saying if you’re an individual contributor and you’re stuck at a place where it’s not really doing great product management, and you’re like, should I stick around and try to change the culture, or should I go somewhere that’s doing it well, my advice for them is, do you want to be a change agent and do you have the authority to actually enact change? Or do you want to be a great product manager? As leaders, we do have to enact a lot of change. So you need to be a change agent, but sometimes those paths are rockier in certain companies than others. So that’s really where this comes down to.

  • Q: Despite years of writing and speaking by product management thinkers like yourself and Marty, there are still many feature factories in my city. I would say that the majority of companies are feature factories. There are many product managers who follow PM thought leaders and understand what good product management looks like. But I haven’t been lucky enough to work in that environment. What would your advice be to one of those product managers who is trying to escape the feature factory hell and ascend to empowered team nirvana? How do you think an applicant can overcome that disadvantage when applying for jobs at good product management companies? How do you escape the career trap?

  • A: I’m just going to say that I would love it if all companies were not feature factories anymore. But the majority of them still are. What I think you could do is concentrate on what you can control in your current job and make it a good story. So look at what you have control over and if you’re applying as an individual contributor, it’s like working with your teams. How do you prioritize your work? How do you set goals? How do you do those things? Talk about what you can execute and how you do them well. Talk about how you did experiments in challenging environments, right? Talk about how you worked with your developers well. Talk about how you worked with the leadership team to pull OKRs out of them even if they didn’t want to do it right. Turn that into a story.

  • Q: One of my product managers is asking me what he needs to do to become a senior product manager and get this new title as a result of his next performance review. Our structure is small. Only three product teams. So there really won’t be a change of responsibilities from moving from Product Manager to Senior Product Manager unless we grow. It would just be a change of title. I tend to think that no matter how well this person is doing, to be considered a senior PM, you need at least four to five years of experience. It is weird to call someone senior with less than three years of experience on the job. Is it the same for a startup as for a bigger company? Can a PM become a senior faster in a startup? Any tips on measuring the seniority of a Product Manager?

  • A: In startup environments, people can get to the senior title faster than in a big company. Why? Because you ship faster, you do things faster, and you actually produce. So I would not go on complete time here. I wouldn’t look at that. If the person is performing at the level of a Senior Product Manager, they deserve that title. And you do see people level up in startups way faster than big companies because they can produce ten times as much as a big company does because you can ship faster. Besides that, why does this person want to be a Senior Product Manager? Do they feel like they’re actually doing the role of a Senior Product Manager? When I look at Senior Product Managers, they’re doing the same things as a product manager, but they need really little oversight. They need a little coaching on individual contributor product manager roles. So they know how to do these things cold and they can oversee a really large, complicated scope of product feature set.


Resources:

Melissa Perri on LinkedIn | Twitter

MelissaPerri.com | CPO Accelerator


Transcript:

Host - 00:00:00:

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 Perri.

 

Melissa Perri - 00:00:36:

Hello and welcome to another episode of Dear Melissa. Today I’ve got three questions for you all about careers and managing people. So I’m excited to dive into those with you. But I just want to remind you that if you have a question for me, you can submit it at dearmelissa.com. I’m thinking questions and answering them every other week on this segment and ask me about anything. Give me context, tell me what’s going on. I want to know. I want to know what’s up. So let’s dive into this week’s questions.

First one: Dear Melissa, as a product manager at a company that prioritizes product discovery, experimentation and collaboration, technically PM Heaven, I’m faced with a dilemma. Which product career path will have the greatest long term impact? I come from a previous company that was more of a feature factory, where, despite having a higher role and greater control over processes, I could not change the mindset of valuing customers over outputs. However, my ex-employer has asked if I want to come back and drive a big product management change. While the opportunity to drive change and take on a leadership role is tempting, I worry about returning to the same problems. Although I have learned and grown in my current role, the potential for personal growth and business impact in the long term is uncertain, as there are many people in the company over 500, and the previous employer was relatively small, 20+ in a business unit, but had limited mentors. Can you help me weigh the pros and cons of each option? So this is a really good question, I think one that a lot of leaders actually face in their careers. I know some people who have been leaders at great companies. They go to another one, they have to be a change agent now, and it’s not for them. 

So let’s talk through what you should take into account here. First, I give individual contributors this advice, and it’s a little bit different for leaders, but I feel like it’s worth saying right now, if you’re an individual contributor and you’re stuck at a place where it’s not really doing great product management, and you’re like, should I stick around and try to change the culture, or should I go somewhere that’s doing it well, my advice for them is, do you want to be a change agent and do you have the authority to actually enact change? Or do you want to just be a great product manager. Part of that you do have to weigh as a leader as well. But I will say as leaders we do have to enact a lot of change. So you need to be a change agent as a leader a lot of times, but sometimes those paths are rockier in certain companies than others. 

So that’s really where this comes down to. If you are like, my full goal as a product person is to just be the best product person, be the best product leader. You might not want to go the change agent route because what you’re going to do is spend the majority of your time trying to change hearts and minds and culture rather than just executing on great product management with no boundaries. So you need to think about that. Now there will be some level of cultural change and influence and politics and talking to other people and getting people on board at any company. So this might be a great chance for you to actually go and flex that muscle if you’re not really sure about it. If you feel like it’s a welcoming environment, if you feel like you have really good leadership support and the CEO is like, yeah, we want this, I want you to lead this, you have my full support. If you need something to happen, I will do it for you. I will pave the way. You just tell me what needs to go on. That’s a great place to actually be a change agent because you have the support, you’ve got the buy-in from the top dog. That’s really what you’re looking for to be a successful change agent. 

Now you might have to educate the CEO a little bit, but if they’re amenable to it, if they’re very much like, yes, I’m on board, I want this, do this for me, that’s key. If the CEO is not on board at this company, you’re going to have a really hard time because you’re going to face resistance in the C-suite, most likely. People are not going to understand what’s going on. You may be really, really good or flexing the muscle and getting better. Let’s say that influence and bringing people on board and changing hearts and minds and getting the C-suite to trust you and understand that. But if you have somebody on that leadership team who’s just totally against this and you’re never going to change their mind, it’s going to be really hard for you to do what you need to do. So I’ve seen some leaders come into these organizations that have never done product management before. Totally win them over, right? It was that they felt the pain, the leaders felt the pain. They said, hey, even as a salesperson, I don’t know what’s going on. I don’t have a roadmap, I can’t make my numbers. I’m really angry. People used to fight with me about what product management was. I know I need to sell these certain things. I’m not okay with this. So what are you going to do about it? And if you come into that situation, that means that that person has felt that pain. So they’re willing to change, right? They’re willing to change what they have to do to work with you. And that’s good in. So you play into that. I’m here to help you. I’m here to make this easier for you. I want you to hit your numbers. I want us to be a really great organization where you sell so much stuff that you can’t keep up with it. And you got to grow your team, right? You’re there for them. So that’s key. And if you feel like you can bring them over with that type of influence, that’s a good place to be set up. 

Now in other places, I’ve done big large scale transformations where we actually had to restructure a lot of things. And the leadership team was not on board with that because one, the leadership team besides the CEO, the CEO was super on board. But the leadership team was like, hey, I’ve had developers reporting into me. I can dictate exactly what they need to do. I don’t need to go ask somebody else for permission as a head of product anywhere. I like that. I want my control, I want to hit my numbers. I care about my business unit. We had to take those people out and make a centralized product organization in that case. And that really made people upset, angry, and they were not on board. So the CEO in this case stepped in and said, if you don’t get on board, you’re out. Which was really, really helpful. But I’ll say if you don’t have that CEO support, I would never have been successful there, right? They had to tell people, get on board. Even though we laid out all of the ways that they can request their things, they can make sure that they’re hitting their numbers, how we prioritize all that stuff. But it had been ingrained in them for 40 years and they did not want to change as the leaders. So this is really important. So you need to understand what leadership team you’re walking into and who are the detractors, can you possibly win them over and how much change actually has to happen. Sometimes it’s like you are set up and it’s just about kind of bringing people onto your side, making partnerships. But you don’t have to do a wildly big structural change. Things don’t have to change that much. It’s more of a mindset change. In which case I think that’s sometimes a little bit easier now if you’re doing a large scale transformation where it’s like, hey, we’ve never really done product or software before and we have to build this team from scratch. We have to educate like 5000 people in this organization. It sounds like yours is smaller, so that’s good, but that’s harder. It’s going to take longer. So you have to really think about, am I up for it? How long is this change going to actually take? Who are my detractors, who are my leaders? And do I have full and total support and buy-in from the CEO? That’s really, really important there. 

Now, if you want to be a leader, like I said, flexing those muscles, understanding the dynamics of bringing people onto your side who might be against you or against your ideas at first, that’s a really important skill. So if you feel up for it, I feel like you can learn a lot, but if you’re like, I don’t really want to fight that battle, I just want to make great product. You will probably get burnt out and exhausted in that situation. So in the current situation, it sounds like there’s a lot of people there. So you don’t have upward momentum. Maybe you do, but maybe that’s just you blocking out the opportunities in your head or thinking that you don’t. But there’s a lot more people, let’s say, gunning for the next job. You can always leave and go to another place and move up a level by leaving right to another place that does good product management as well. So in this case, you’re still going to have to change jobs. It will be an unknown quantity, you won’t know that company. But if you do suss out that they’re doing really great product management, it could be an easier transition where you don’t have to do all that politics. I think it really comes down to what type of energy do you have to enact change and how long do you want to stick it out? Right? Because if you’re like, I want to lead this change and do it, you have to know that it’s at least a three year commitment, let’s say, to see meaningful progress in a larger organization. This sounds a little bit smaller, so if all those prerequisites are lined up, you might see actual meaningful impact in a year. But it really depends on how much people want to push back and how much control you have and how much authority you have. Are you on the C-suite? If you’re not on the C-suite, this is going to be really hard because other divisions might not want to listen or might not want to work with you. So I see people be successful if they’re great operators at the C-suite. But if you don’t have that type of control, this might be a really big challenge for you. So think about that. If you feel like you’ve got total control, you’ve got all the support in the world, and you have all those other things I lined up, it could be a really interesting challenge if you’re up for it. But if not, it might be better to stay where you are and just hone your craft as a great product manager and then look for the opportunities where you can move up. So you really need think about how fast do I want to move up and how do I want to move up? What do I want to do on a day to day basis? Think about what your job needs to be on a day to day basis. Are you going to play politics and influence, or do you want to do great product management? 

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Next question. Dear Melissa, despite years of writing and speaking by product management thinkers like yourself and Marty, there are still many feature factories out there. In my city, I would say that the majority of companies are feature factories. There are many product managers who follow PM thought leaders and understand what good product management looks like, but I haven’t been lucky enough to work in that environment. What would your advice be to one of those product managers who is trying to escape the feature factory hell and ascend to empowered team nirvana? How do you think an applicant can overcome that disadvantage when applying for jobs at good product management companies? How do you escape the career trap? 

Like that? Nice little play on words there. This is true. I’m just going to say that I would love it if all companies were not feature factories anymore. But the majority of them still are. There are plenty of great, high powered, SaaS companies that are not feature factories. But there’s so many companies out there in the world. Not everyone is going to be great at product management yet. I’ve seen a huge shift, though. I’ve seen a huge shift in people getting better at product management. So I’m extremely hopeful that in another ten years we’re not going to be having these conversations. So here we go. What I think you could do is really concentrate on what you can control in your current job and make it a good story. So look at what you have control over and if you’re applying as an individual contributor, right. It’s like working with your teams. How do you prioritize your work? How do you set goals? How do you do those things? Talk about what you can execute on and how you do them well. Talk about how you did experiments in challenging environments, right? Talk about how you worked with your developers well. Talk about how you worked with the leadership team to pull OKRs out of them even if they didn’t want to do it right. Turn that into a story. 

Now, the resume when you’re applying for these jobs is huge. That’s absolutely huge. So I screen resumes all the time for people in the companies that I help for hiring. What I’m looking for is keywords. Like, I set goals based on X, Y, and Z. Here’s the outcomes that I got. Even if it’s not a great outcome, if you can just say that you were striving towards an outcome or you were oriented towards it, that helps. Use the language that you know is good in your resume and describe to the best of your ability what you tried to do. Now, when you go into the interviews, let’s say you get past that screen, you go into these interviews, tell them why you’re leaving. Be like, my company doesn’t operate super well with product management, and I know there’s a better way. So I’ve been pushing. I’ve been trying to help them realize that they could do these things better, that it would be easier for them if we actually operated in these ways, that we could be more impactful and we could do outcomes. Here’s what I did to try to get them on my side, but I’m just facing resistance at these leadership levels. I want to come to a company that really does great product management. I’ve been honing my craft, even in an environment where it’s been hard to do that. And this is how I’ve taken initiative. People love it when you say, I’ve taken initiative. I tried these things. I didn’t just wait for permission, right? I actually tried to do these things, and I went out there, and even if it was small and feels like it wasn’t super meaningful, that’s a big deal. So tell that story, right? Have a really good, compelling story, and I don’t think that’s going to block you from getting into a good product management company. Just think about what it is that you bring to the table as well. Think about the skills and talk about the skills that you’ve developed there and really hit on those core product management skills. I think if you could tell a story about how you’ve done product management well, even in a challenging environment, that shows that you’re taking an initiative. You recognize what good looks like, and you want to be where good looks like. And I’ll say first of all, too, having product manager on your resume is already a huge step ahead, right? A lot of people are trying to break into this. You’re already there. Now you just got to find a company where you can actually execute. So just tell your story really, really well. All right, last question. 

Dear Melissa, one of my product managers is asking me what he needs to do to become a senior product manager and get this new title as a result of his next performance review. Our structure is small. Only three product teams. So there really won’t be a change of responsibilities from moving from Product Manager to Senior Product Manager unless we grow. It would just be a change of title. I tend to think that no matter how well this person is doing, to be considered a senior PM, you need at least four to five years of experience. It is kind of weird to call someone senior with less than three years of experience on the job. Is it the same for a startup than for a bigger company? Can a PM become senior faster in a startup? Any tips on measuring the seniority as a Product manager? 

So I do think in startup environments people can get to the senior title faster than a big company. Why? Because you ship faster, you do things faster, you actually produce. So I would not go on complete time here. Like I wouldn’t look at that. If the person is performing at the level of a Senior Product Manager, they deserve that title. I’ll put that out there. And you do see people level-up in startups way faster than big companies because they can produce like ten times as much that a big company does, because you can just ship faster. So think about that. Besides that, though, why does this person want to be a Senior Product Manager? Do they feel like they’re actually doing the role of a Senior Product Manager? When I look at a Senior Product Manager, they’re doing the same things as a product manager, but they need really little oversight. They need really little coaching on individual contributor product manager roles. So they know how to do these things cold and they can oversee a really large, complicated scope of product feature set, let’s say. I’m not talking about a whole product. They probably can’t oversee a whole product, but they can oversee a lot more work. And you don’t have to worry about them. They’re just able to run, right? They’re able to do things. That’s how I measure seniority, right? Are they actually showing that they’re growing? As a product manager, you don’t have to worry about them day and night. You don’t have to give them a ton of direction. You just have to point them in the right direction, explain the vision, explain the goals, and they can run. If they can do that, they’re pretty much a Senior Product Manager. If they can’t do that, they’re not at that level yet. I’ve had people who have been really young and early in their career and they’re just gunning for that Senior Product Management title. And a lot of those people are actually coming from places like banks or consulting. And they had a thing where after two years you become a senior something after four years. Some of them are VPs in banks. So the titles in these types of environments are very different than the titles in startups and software. 

Now, your person might be expecting that and you might have to have a reconciliation there about what a senior PM actually looks like, but they should be extremely competent in those things. Also great at engaging with stakeholders, great at presenting, great at storytelling, great at connecting the dots of what they’re doing, back up to leadership, and explaining how it all comes together. If the person can’t do that, they’re not really at a senior product management level yet, and that’s okay. You can tell them what they need to do to get there. So I’d really try to figure out why this person is gunning for the role. Do they feel like they’re actually doing all those things right now? And do you feel like they’re doing all those things right now? They might have different expectations than reality, or are they just expecting it because they come from a different line of work and they should have senior title already in a different place, like a bank or something like that? I’d really kind of dig into that and kind of suss out what’s going on. You can always incentivize, too, people with, like, a little bit of a pay raise instead of bumping them up to a senior title. Even if you have three teams, if that person’s really performing like three teams, you might be overseeing a ton of scope. That person might be overseeing actually a lot. Your product might be a little big, and you could use a couple more people, and this person is just like, breaking their butt, really performing, then they kind of deserve that senior title. Even if you feel like the scope hasn’t been dramatically changed from what they’re doing right now, you have to take into account where your product is right now and how much this person is overseeing.

So I dive into those factors, really have a good conversation with them about how you value them and you really want them to be here, and there’s going to be growth opportunities, but you’re not just quite at senior level yet. Or if they are, bump them up, give them that title change if you believe that there’s somebody to retain and they’re actually doing that job. 

All right, that’s it for Dear Melissa this week. Thank you so much for joining us. And again, if you’ve got a question for me, go to dearmelissa.com. Submit those questions, leave me a voicemail. I love to hear your voices. We’ll see you next week with another Product Thinking guest. Until then.


Stephanie Rogers