Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva)

Melissa Perri: I’ve met a lot of organizations that think most of their issues are in the training of their people. And 99% of the time I see that it’s actually in the way that they’re setting their goals and deploying their strategy. Because once you train those people, they have no context on what to work towards. So it’s such a holistic approach when you actually go through these transformations, or try to set up a product organization, so you either need somebody in there to do it, or you’ve got to really be ready to move when somebody comes in to help you.

Recent Work and Teaching

Lenny: Through her speaking, consulting, interim CPO roles, and teaching at both Harvard Business School and online, Melissa Perri has seen more product orgs up close then possibly any human alive. In our chat, we cover the most common problems that product teams face, and how to overcome them, when to hire your first PM, how to hone your craft as a PM, signs you’re doing a bad job as a PM, also how to structure your product teams and product development process, signs your team doesn’t have a strategy and how to come up with one, also how to come up with a product vision, and so much more.

I loved chatting with Melissa, and I learned a ton. And I can’t wait for you to hear this episode.

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Melissa, welcome. Thank you so much for joining me.

Melissa Perri: Thanks for having me.

Common Product Team Challenges

Lenny: It’s absolutely my pleasure. I wanted to set a little context for folks that may not be familiar with you. How many PMs have you worked with and helped, would you say, over the course of your career?

When to Hire a CPO

Melissa Perri: Between teaching, consulting, and all of those different things, it’s probably north of 4,000 at this point. I think we’re approaching 5,000 now.

Signs You Need a CPO

Lenny: Oh my God. Okay. And then, how many companies would you say you’ve worked with?

VP of Product vs. CPO

Melissa Perri: If we’re talking deep consulting since I started Produx Labs, we’ve done over 30 companies where we’ve been in there, did something with them, either transformation-wise or setting up their PM work or setting their strategy, helping with roadmaps. If we’re talking training, we’re into the multiple hundreds.

When to Hire External Consultants

Lenny: Okay. Insane. Would you say that you’re maybe in the top three, maybe top five people in the world that have worked with the most product managers, or have even met the most product managers?

Is the Organization Ready?

Melissa Perri: I know a lot of people who do what I do, so I think probably among them. Probably among them. But I haven’t counted everybody else’s.

Lenny: Okay. For all these reasons, I’m really excited to dig into a lot of the stuff that you’ve learned along this journey, and things that people can take away from your experience. What do you spend your time doing these days? I know there’s a lot in your portfolio.

Holistic Organizational Change

Melissa Perri: Well, right now I would say my primary focus is on training in education in product management. So, I’m teaching at Harvard. I teach the second year MBAs in their elective program, product management, so they can choose whether or not they want to take that. But that’s been really great. And then, I have had an online school since 2016 called Product Institute. So it’s all a self-serve, online education place where we have multiple courses in product management.

We have trained almost all of the Fortune 100 companies at this point through that with product management, which is great. But a lot of different growth stage companies coming in there too, and smaller companies as well. Been doing that for quite some time.

And then, I more recently started CPO Accelerator, which is a program to help VPs and heads of product really make the leap into the C suite. So that’s been really great because I believe that the more we train people to be better product executives, the better products they’ll make, and the better product managers they’ll make by training them as well.

That’s been my primary focus. I am writing another book called Product Operations. After writing Escaping The Build Trap, I thought I would never write again, but it’s time.

Signs of Lacking Strategy

Lenny: I know the feeling.

Writing Strategy Documents

Melissa Perri: So I’m excited about that. I’m writing it with my former VP of product at Products Labs, Denise. Before I was doing what I’m doing right now, I was doing all of that, plus I was also consulting pretty deeply with companies through Produx Labs. But at the end of 2020, I took a step back from that to take a little break from it, focus more the teaching aspects of things, and try to figure out what else I’m going to do from here.

Testing If Strategy Is Set

Lenny: I love that you mentioned your book. You almost didn’t, and I was going to make sure to mention it. And we’re going to talk about it more in a little bit. And I have it right here. And hopefully I can get it signed someday in real life.

Before we get into that, you’ve worked with dozens of companies directly, hundreds, maybe, indirectly through the course, and then, like you said, thousands of PMs. When you come into a company, they basically bring you in to help them level up their product team, their product management function. What are two of the most common problems that you run into, or even unexpected problems you run into? Especially at modern tech companies, not Ford and things like that. No offense. What do you run into usually?

Strategy Alignment Reduces Internal Conflict

Melissa Perri: In 2014, I started consulting with companies through Produx Labs. And it’s funny because some people will be like, oh, well you’ve never worked with… I get two sides of it. I’ll get the, well, you don’t really work with the SaaS companies, but I had a whole partnership with Insight Venture Partners, where we’d go in and play the interim CPO role in their high-growth SaaS companies. We’d help them scale, we’d set their strategy and their roadmaps and all that stuff. So we did that for a long time.

And then, I have also come in and helped organizations that aren’t really SaaS, like banks, a lot of banks. A lot, a lot of banks. But your pharmaceutical companies, and all these other ones too, kind of set up product management for the first time. So I’ve seen the whole gamut, from super software-focused teams to companies that are still just figuring out software. And it’s been great because some of the companies I’ve worked with now, since 2014, I’ve been able to see eight years of their progressions and what they go through with that.

And I’d say it’s very different if you’re SaaS versus non-SaaS. But if we’re talking about the SaaS companies that get software, software is what they sell, software is a critical part of their strategy, they’re bought in, they know that it’s really important, one of the issues I see with them and product management is, at this pivotal scale up phase, where they go from, hey, I found product market fit, to I’m ready to scale, one, it’s hiring a great chief product officer that can help them figure out what the next phase is. So it’s basically there is this junction point where they go from single product to multiproduct, but then they have to manage a complex portfolio and then they have to scale rapidly. At that point, they have to rethink their entire strategy. And then they have to focus because they have all of these choices to keep building for their existing customers and just take everything off the backlog because everybody’s requesting things, they really have to focus and prioritize.

And that becomes absolutely critical, but it’s usually the first time that company has actually had to form a comprehensive strategy and a prioritized strategy, and deploy it to hundreds of employees, which will scale to thousands of employees. And that is hard. It’s not easy to do. And if you’ve never done it before, which a lot of people haven’t in that position, that becomes really complicated.

And then there’s some companies, too, that bypass that initial growth phase, because they already could clearly see what their second and third product should be, and they were scaling really fast, and it’s awesome, and they’re really, really successful. But then they start to plateau. And they have the same problem, where they have to rethink, reprioritize. And it just always comes back to how do I set strategy, how do I deploy strategy, and how do I make sure it’s well communicated and that everything that we’re doing on the tech teams, on the product teams, is laddered up into a company strategy that’s well prioritized.

But that has to be the biggest issue that I see with companies at all. They get the software piece, they know it’s a critical part of their business, it’s just, how do we prioritize it and double down?

Methods for Documenting Strategy

Lenny: And build the org and find the right people to build it all out. I’d love to double-click on that. What is a sign that it’s time for a CPO, and then what do you look for when you’re hiring a CPO? I know these are big questions, but I’d love to hear your thoughts.

Melissa Perri: Usually, whoever was the product leader, whether it was the founder or maybe somebody who was a little bit more junior. In those phases at the beginning, finding product market fit, trying to get into the growth stage, early growth stage, it’s really about execution at that point. It’s rapidly experimentation, trying to figure that out. And all hands on deck, you’re usually a little bit in the weeds as well, doing the work yourself, too.

And then, when you get into needing a CPO, it’s like, hey, we actually have to pull together a product strategy that’s all encompassing. We have to have great communication between product and the executive team. A big sign for me, when I’ve come in and worked with boards or executive teams as well, is they’re telling me, I don’t really know what’s going on in tech or product. I have no idea if we’re achieving our goals.

If your executives and your board are telling you that, the person who’s communicating those things to them are usually not chief product officer level. If your executives don’t know what you’re doing, that’s a big problem. So that’s usually the sign, to me, that we need that.

When I was going in and consulting pretty deeply, the first thing I would do is go to all the teams… if there was 5,000 teams, a smattering of teams. But I’d always ask them, what are you working on? What’s the most important thing you could be doing, and why? And I would try to ladder that up myself into a strategy and see if it was connected. And if it wasn’t connected, that’s telling me somebody’s not formulating the strategy and deploying it down. And then, that’s telling me there is a lack of strategy at the top. And that would be like, hey, is there a CPO here? And if there is, maybe this person isn’t right for the job. Or there’s no CPO, and we do need somebody around this to actually formulate the strategy.

On an org design perspective with the team, I’d look at the product managers. If the product managers aren’t… Sometimes you have great product managers, and they’re frustrated because they’re not getting the direction they need. And you can tell they’re great product managers. They know what they’re doing, they’re in there, showing me there’s a lack of leadership there. If there’s trouble hiring product managers, that’s a good sign that you need a CPO, you need somebody they can learn from and give them those opportunities. And if there’s a lot of junior product managers who’ve never done it before, it’s like, what’s their training path? Is there something in there? Is there a process implemented where everybody can follow it? Is there a way for them to learn? If those things are lacking, it’s telling me there’s a gap in leadership on the product level.

Developing PM Vision Skills

Lenny: Awesome. That is really helpful. Is there a number of PMs that it usually ends up being, of how many PMs you have when it’s time to maybe hire a CPO?

Melissa Perri: It really differs. I’d say the critical junction points I’ve found deal more with company strategy. We used to talk about this a lot at Insight, but it’s like if you’re going above $10 million in ARR, it’s usually when you hit around 20 to 30, you start to bring on a CPO in a high-growth company. What the product starts to look like is you have multi-products, so you have more than two or more. Sometimes you can have a VP of product over two, that’s totally fine, but as soon as you start to think about expanding into a more complex portfolio after that, I’d look for probably a CPO. If you’re expanding geographically, if you’re going into new markets, drastically new markets… The more complex your portfolio, the bigger the sign is that you need a CPO. If you’re doing a major transformation or pivot, if you’re doing a huge merger of two companies, you’re probably going to need a CPO of those two things. So those types of events usually lead to, if you don’t have a CPO, it’s time to get one.

The number of product managers, I’d probably say it starts to hit around maybe eight, seven to eight is usually what I’d look for. But it depends on what the rest of the team looks like, too. A lot of times, chief product officers, especially in a high-growth company, are not going to be over just product. We’d have product reporting into them, design, some kind of product operations, sometimes analytics, depending on what company it is. And then, even in certain cases, I’ve put engineering underneath a CPO when there hasn’t been really strong engineering leadership, and you need to have product leading tech. And maybe there’s a disconnect there, and you don’t have time. You need one leader. You need to simplify it and go.

So depending on the scope that somebody is covering as well, if they’re only seeing product, and there’s no opportunity for them to be over design or something else, we would probably stick with a VP of product. But if you need a singular leader to bring all those things together, that’s where I would start looking for a chief product officer, too.

How to Write Product Visions

Lenny: What do you suggest companies do up until that point? I know titles are not necessarily consistent. I imagine usually there’s a head of product before that point. Is that what you’d recommend? What should you do up until you get to a point where it’s time for a CPO?

Melissa Perri: Head of product or VP of product, I think, are very interchangeable, in my head. What a VP of product or a head of product is, is a functional leader around product management. Sometimes you have design reporting into them, sometimes not. But they’re very good at implementing processes so that product works smoothly. They can pull together the roadmap across all other product managers. They can usually train lower level people.

Where the gaps come between that and becoming an executive is interfacing with the board, understanding the financials super deeply so that you can create revenue projections off of what your roadmaps and your product’s strategy is going to be. So chief product officers have to deeply understand how to get from roadmap to revenue and how to analyze those things and put it into perspective. So they’re usually joined at the hip with the chief revenue officer, or the head of sales, the CFO. They can confidently project to the board. They’re a fantastic executive navigator when it comes to dealing with other executives and bringing those things together. And they can oversee a lot more functions than just product, usually. Everything can kind of… They’re a senior enough person where you can have a couple different functional lines report into them with a head of design, head of product reporting up.

So VPs of product are usually fantastic at growing one or two products. But then, when you get into multiproduct strategies, or very complex platform strategies, and the scope starts to really creep, that’s where I would start to bring in a CPO.

How to Improve Strategic Thinking

Lenny: I was going to ask you about what to look for in a CPO, and you answered it. So, amazing. Real quick, before you move on to the scale of product management and some thoughts there, when would it make sense for a company to consider bringing in someone like you to do either interim CPO role or just to help out?

Product Ops and Data Foundations

Melissa Perri: Yeah. I hope you never need me. That’s my goal with everything I do. I’m always like, I would love to put myself out of business one day because I just want this to work really well. But where I am needed is usually when a CEO isn’t sure who is the right person to hire. They’re usually on the fence. I’ve come into organizations to help CEOs where they’re like, do we need a product person to oversee this? I don’t know what a product person does. And I usually talk them through like, hey, what are the challenges you’re having? And they tell me everything, and I’m like, okay, these ones are actually caused by you not having that partner to work with. If you had that partner, this is what they could take off your plate and free you up to focus on your vision, and fundraising, and all the other stuff that you have to do as a CEO.

So typically, that’s where I’d come in to advise. And when I came in in consulting in the past, my motto was always… Well, first I will say I spent a long time doing transformational work, where I would deeply embed and try to push org design, and deploying strategy, and really taking these organizations that didn’t understand product management and helping them design how to do it. So I did that for quite a while. And then, when I started working with growth stage companies, my objective was, how do I get in and get out as fast as possible, and bring them in the right leaders?

So what I learned, being deeply embedded with these organizations doing this transformation work, was somebody needs to be at the helm of all of this work consistently. And they also have to be able to make the decisions, as well. So you can hire a consultant, but if you don’t listen to the consultant, nothing’s going to change. And that does happen more often than you think, where everybody just hires and they’re like, no, not that way, and you’re like, okay, well, it’s up to you at the end of the day. I can’t change it for you.

I’ve also had people hire me as a consultant and be like, well, no, you change it. And I’m like, I can’t. You can’t just tell me to do your job. You have to go out there and do it yourself. But I will give you all the informed choices and try to design it to meet your needs. And sometimes it’s not coming out super ideal and perfect, but it’s all a transition. We make roadmaps for transformations.

But, being deeply embedded like this, I was starting to think, how do I make sure that this lasts? And that’s where I believe strong product leadership comes in. Whether you train somebody up in the organization to take that role over and keep driving it forward, or you hire in somebody who knows what they’re doing.

So when I started working with Insight, our premise was, we will never touch a company, or be in a company hands-on, for more than three months. The idea was, within that three months, we hire in a chief product Officer to take the helm, and we do just enough to keep it on track, playing an interim CPO role, to make sure that they can keep delivering, they can keep growing. We’d have just enough of a roadmap to keep the teams moving. We train them a little bit, we’d help implement some processes. We’d help get all the information a CPO would need so that when they walked into that organization, they could read the background on their customers, understand what the strategy is so far, look at the current roadmap, watch some customer interviews, know who to talk to, get the lay of the land and have some people working on stuff. And then they could take the time they need to actually build a strategy that’s going to help grow the company.

So really, at the end of the day, when you need some help, you realize something is not working but you’re not sure how to make it right. And then, you can either hire in a leader… Sometimes the question is what kind of leader. That’s when you try to hire consulting, get some outside expertise on that. Or, if you want to hire an interim CPO type person, you have to understand that’s very temporary, unless you’re trying to convert that person into a full-time, which is totally fine if you want to do that and have those expectations going in. But consultants can only help as well when you’re willing to take action.

So I tell some companies as well at the beginning, you’re not ready for this unless you are ready to take action. And sometimes that’s drastic change. Sometimes that’s changing up people. Sometimes you look at your organization and say, this isn’t the organization that’s going to get me to the next level, so we’re going to have to make some changes, we’re going to have to hire in some more senior people as well who can help train the masses of other people that need training. We’re going to have to make some hard decisions, and you have to reevaluate your strategy a lot of the times, and figure out how to set course with that too.

I’ve met a lot of organizations that think most of their issues are in the training of their people. And 99% of the time, I see that it’s actually in the way that they’re setting their goals and deploying their strategy. Because once you train those people, they have no context on what to work towards.

So it’s such a holistic approach when you actually go through these transformations, or try to set up a product organization. So you either need somebody in there to do it, or you’ve got to really be ready to move when somebody comes in to help you.

Lenny: I was going to save these questions for later, but it’s as good a time as any to get into them around strategy, which your book is about, I would say, is the fact that people just build features, features, features, and don’t really have a strategy or aren’t using a strategy. And so, just spending a little time there, what are signs that your team or your company either doesn’t have a strategy or aren’t using their strategy?

Strategy is Making Choices

Melissa Perri: Yeah, that’s a fair question. Signs that there are no strategy, teams are all working like dogs. They’re working 80 hours a week. I see this all the time. People are heads down, crunching, crunching, crunching, releasing, releasing, releasing. Or sometimes not releasing, but they’re working like crazy and none of the metrics are moving. So the executive team is going, what is happening? Product is a black box. Tech is a black box. We’ve got all these people. What do they do all day? A great example of when there is no strategy.

And what usually is happening is there’s this missing middle. It’s like, we all know exactly what each team… We don’t all know, actually, what each team is working on. The teams all know exactly what they’re working on, which is usually some kind of feature enhancement, new features, whatever you’ve got. Bug fixes, all that wonderful stuff. The people they report to usually know what the teams are doing, but the executives are like, cool, how does that matter to our business? How does that actually ladder up into our vision, where we want to go, our objectives for the year, our goals? Great sign that there is actually no strategy deployed correctly.

Now, when I say, too, there’s no strategy, there’s usually some kind of strategy, but it lives in people’s heads, and they’re really bad about writing it down and getting it out. So I always tell people, too, if you think that there’s no strategy, go interrogate people for awhile. Go talk to the leaders. Is this good if we hit these numbers? Is this bad? Why? If I release this thing, what do you think will happen? What numbers will change? What behaviors will change? How will this make us better? I usually can pull out what people believe the goals to be, and sometimes they’re just not explicitly written down.

So that’s an exercise that I typically do, too, when I don’t see strategy well-manifested in these organizations. I just go in and I say, okay, what does good look like for you? Where is the vision and where are we going? And I ask all of these questions, too, to a lot of people. And you find that there’s different answers across the organization, and that shows a lack of alignment on a complete strategy, as well.

I once asked all the executive team at a healthcare company, what’s the vision for this company? And they said, to be the backbone of healthcare. And I said, what does that mean? And they couldn’t elaborate. Nobody could elaborate on that. And I said, cool, that’s a tagline, but it’s not a vision. What are we manifesting into? What are we doing? What are we not doing? Who do we want to be when we grow up? Five to ten years from now, how are we different than we are today? Those things, more often than not, are not written down, and they’re not clearly communicated.

So one of the exercises we do is we write. If I see that there’s no strategy, I have CEOs write two-pagers on where did the company come from? How is it different today? What are our external treats to our market? What’s our competition? How do you view our competition? What should we care about? What should we not care about? What are we going to do? What are we not going to do? And then prioritize their strategic intents, or what I call them, which are really big business movers, for the next two, three years. So it’s like, are we going to go up market? Are we going to go down market? Are we going to expand geographically? Are we going to innovate into a completely new market or a new opportunity?

Those types of things need to be clearly prioritized at the top, and then we can start to make the product portfolio at the bottom. And when there’s a missing strategy piece… I call it the missing middle is usually gone, which connects those strategic intents and those business outcomes back into what the teams are actually doing. So it’s like, great, that team is building a widget for sales people to do cold emails. Why? How is that going to move us into what we want to do for our vision? Is it retaining people because we have a problem with our current market? Is it allowing us to enter a new market if we put it together?

But if we think about all the things that teams do in isolation, it’s not enough, usually, to move those business metrics. So what people do in a lack of strategy is they spread the team too thin across tons of initiatives. One team usually isn’t enough to get some really hard hitting metrics out there. And then, you don’t see the progress that you’re actually looking to see as an executive.

The Rise of Product Operations

Lenny: If a feature ships but no one knows about it, did it really ship? Keeping customers and internal teams like sales support and marketing in the loop on what’s changing across your product is surprisingly hard. First, you have to dig through tickets and poll requests just to see what’s been done. Then, you have to figure out what’s relevant to each person, craft updates, and then share them across all of your channels. Multiply this by the number of things that ship every week, and that’s basically a full-time job just to keep everyone updated on what’s changing.

That’s why high velocity product teams like Monte Carlo, Armory, and Popsicle use Makelog. Makelog makes it easy to see what’s happening across tools like [inaudible 00:26:54], Linear, Assan, and GitHub, and then to write bite-sized updates, which you can immediately share with your audience, wherever they are, including within your app, on Slack, over email, and even on Twitter. No more long, boring, blog-style change log posts that slow you down. Just quick and easy updates that keep your users informed and happy.

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So you’re a PM on a team, or even just a leader of a company, and you’re like, hmm, I think we might have a strategy, maybe we don’t. I’m hearing things that are true at our company, and I’m worried. What does it look like for me to have a strategy? You named a few things that you should probably have, a vision, intents and actions, and things like that. What’s the checklist of, oh, if I have this, this, this, that, we probably have a strategy in place, at least?

Melissa Perri: A good test is you go to all of your teams, and you ask them what they’re doing and why, exactly what I was talking about before. And they all tell a similar story. We’re working on X, Y, and Z because it goes into this initiative, and it causes this type of value for these customers, which, in return, is going to get us this business value and help us enter these new markets. They can connect everything they’re doing, from the tactical stuff on the team, all the way back up to the business metrics.

And if you deploy your strategy well, your product teams will deeply understand how their stuff actually impacts the business. And if you don’t deploy it well, they’re going to be like, I don’t know why I’m building this stuff. If you have a bunch of people asking you, why are we building this, then you didn’t do a good job as a leader explaining what it is that you’re after. So everybody should be telling the same story.

Another amazing sign when this is all done really well, too, that I love, is there’s usually way less infighting across stakeholders and executives. One of the biggest issues I see in organizations is when executives all have different goals, and they’re not aligned on the same goals for the company. So it’s like, sales teams over here are like, no, our goal is new logos. And you’re like, cool, but in what markets, and how is that prioritized against what we’re building from our product roadmap, and why is this not in sync?

And I’ve seen really bad CEOs pit their executives against each other with different goals, so they don’t see each other as one team. And the executive team should be one team. And the best teams I’ve ever seen, the most successful companies I’ve ever seen, everybody works together, and they’re like, these are our goals, and these are our business goals.

So when strategy is deployed correctly and you have that type of culture, too, with your executives, they’re all on the same page. So you can have very calm trade-off talks about, are we going to do strategic intent one or two? If we do this, then we don’t get that. Are we okay with that? And it’s not emotional, it’s more objective, because we’re all there together to further the business.

And a lot of times, we complain, as product managers, about stakeholders all asking for different things, and that’s always going to be the case. There’s always going to be a little bit of that. But you typically will get less of that on the team two, because the priorities within each part of the business should be aligned to the overall priorities. And it will be easier to manage, and it’s easier to push back on why we’re not doing one thing over the other thing, because we all know what our goals are, we all know what the company priorities are, and we can see why one thing versus the other won’t work.

How PMs Learn Without Information Overload

Lenny: So you have these conversations, which make so much sense. Just talk it out, see if everyone’s on the same page about your goals, how you think you’re going to get to that goal. What do you do with that? Do you usually recommend people throw it into a Google doc that everybody sits there and just confirms as happy, and is there a template that you share with people, like, here’s what we’re going to fill out by the end of this, say, three month process?

Melissa Perri: Yeah, I think it varies from company to company. Some companies already have their own template, and I’ll just use that. I don’t try to reinvent the wheel when it doesn’t need to be reinvented. But I’ll say the memos that we would write are probably… They’re very easy to explain, two pages for me on what’s the vision, where are we going after, how are we positioned in the market and against competition to reach that vision, where are we today, what’s the current state of our product, what does it actually look like, what are we going to do to get there, what’s our priorities. And then I make people prioritize them, so I’m like, if we’re going this way, are we solving this problem? What does that mean, context-wise? And then, what are the outcomes that we’re actually trying to achieve when we get there?

And I do that at different levels. So we typically have executive teams writing the strategic intents for the business level. We’ve got product management leadership, directors, VPs, CPOs writing the product initiatives. Usually the CPOs aren’t writing them, it’s more like director-level VP for their scope. Product initiatives are usually very problem-oriented around big problems we can solve for our customers. They’re meaty. They’re usually made up of multiple epics. And then you’ve got your product teams on the ground floor working with the developers. I use [inaudible 00:32:07] everybody doesn’t agree on what they are. I call them options, sometimes, too, but it’s the solutions. What’s the solutions you’re going to build to actually get into those product initiatives? Solve those problems for the users, and then hit those strategic intents.

So you have to pretty much write a one-pager or two-pager like that for every one of those levels, and I think that’s great. I think the more we write about these things, the more we talk about it, the more we put it into pros, the better. And it’s not like a product requirements document that’s 20 pages, it’s like a two-pager, just explaining what we’re doing and why. And that context, we usually throw into Google docs or Wiki or something like that, link them all together so that you can go from one to the next, and then read all the way up the strategy tree.

Conclusion and Final Thoughts

Lenny: I love that. It’s so simple and not so formulaic that it feels like any company could do it, and it’s not this rigid, one way to do it process.

Melissa Perri: Yeah. And I don’t think there should be for certain things. I think every company, with a lot of these processes and tools and frameworks that we get into, you’ve got to massage it all and make it your own. And you’re going to find certain things are going to work for one company that don’t work for the other company, based on their culture and what they do. But I think the more that we can write and talk about things, the easier it is for all these different companies to find their way of working. And then you codify that, and you deploy that throughout your organization.

Lenny: On the vision piece specifically, it reminds me, when I was managing PMs, one of the most common areas of development for them was get better vision. Because it always is like, mm, here’s an opportunity to get better, vision. And it’s always hard to explain exactly what that means and how it looks when they’re doing better at vision, other than just coming up with an incredible idea that we execute on. So maybe very tactically, what’s a form factor you suggest for folks to even lay out a vision? It sounds like you really encourage writing. Is that how you like to think about it? Or do you find storyboards are often great, or sketches, or anything else?

Melissa Perri: Yeah. When I write out visions, I like writing. I think that, to me, is probably the easiest way I’ve seen people lay it out. I’ve also seen people put together a great [inaudible 00:34:14] was in there consulting. We had one team with a fantastic head of UX and a VP of product who would sit there together, and they made a great presentation of the vision. But they mocked up prototypes of what it could be. And it wasn’t tested or set, but the visual pieces of that got people really aligned over, oh, okay. And the diagrams, I find, when you can show how certain things relate to each other, sometimes it does come off in words.

So I like a combination. I like a combination of some kind of presentation plus writing. And I think if you do those two things together, it becomes really powerful. But for me and for a lot of people, especially executives I’ve seen too, sometimes they’re more visually oriented. So if you can grab your UX designer and sit there and sketch out ideas… And it doesn’t even have to be wire frames. It doesn’t have to be the end state of the product. It could just be how customers interact with things, or diagrams about the ecosystem and stuff like that. That just helps to draw a little bit more color on it. But I think those two things go hand-in-hand.

Lenny: I love that. I find that anytime I have a designer helping me with anything like that, I always look so much smarter…

Melissa Perri: Oh, so much better.

Lenny: … because they made it look so much better. Yeah, exactly.

Melissa Perri: Oh, I love it.

Lenny: Such a superpower.

Melissa Perri: It is. And it’s amazing. But I’ve seen that in every type of presentation. You bring in a designer to help you with board slides, and you’re like, oh my God, it all makes sense now. I could talk over these types of things…

Lenny: Right, you look like a genius.

Melissa Perri: Yeah, you look like a genius. You’re like, damn, these look real good. So I think there’s just such a joint relationship with any type of presentation where you’re trying to explain where you’re going or what you want to do. If you can explain it through visuals and with design, it’s just going to be so much better for everybody.

Lenny: Yeah. On the vision piece, do you have any general advice for getting better at vision?

Melissa Perri: I try to think about a lot of… There’s a couple tips, here. One, a vision should be concrete enough where people can picture what it will be in their head. It can’t be a fluffy… be the backbone of healthcare. What does that mean? I don’t get it. So people need to be able to look at a vision and say, I can understand that we’re going to get there one day. I don’t know how we’re going to get there today, but we will find out along the way. That’s a good vision. It’s lofty, far enough away where you can’t just be like, oh, we build that one thing, we hit it. That’s not a lofty enough vision. It should be something that you really want to iterate through, and test, and try to figure out how to get there.

It should not be what you are at today. That’s a sign of, you hit the vision already and maybe you’re just tweaking and exploiting it, which is totally fine. But that’s not really a good vision for the future.

I’d say, too, the way that I think through it is, how are we different? And it’s crazy how many visions I’ve read where nobody actually talks about how they’re different. It’s like, we’re going to be the best. Be the best, all right. How are you going to do that? And I think it’s fine, while you’re formulating a vision.

And this is why I personally like writing. I just literally brain dump in there, and be like, well, our competitor A does X, Y, and Z, and we definitely don’t want to be like that. So what could we do to be different? We could do this, this, and this. And if you just brain dump all those ideas about what type of value it will bring for your customers, who you want your customers to be. Sometimes I don’t read about future customers or who you want those customers to be in the future. How is the value different than the value you provide today? Is it going to be different, or just doubling down on what you do? The ways that you provide those values, how is it different than your competitors? Why is it better? Not just being better, but why is it better? What’s the ways that you’re going to win?

And then also, I think good visions also say what you don’t want to do. I love reading a vision that’s like, we’re not going to be like that. And that, to me, is so powerful because you’re like, oh, okay, we’re not going to copy that. We’re not going to go after that. Because you can easily have a whole team be like, oh, let’s just copy what they did over there.

Lenny: I’m learning a ton. Thank you for sharing all this. This is, for me, really helpful, too.

On that topic a little bit, say a PM wants to get better at strategy, which we talked a little bit about. Do you have any advice, someone trying to get better at being more strategic in thinking about strategy?

Melissa Perri: Yeah. It was interesting. I was just talking to one of the chief product officers who graduated from my program last year, and now she’s the CPO of a company. And I said, what was your advice for especially people who are not chief product officers yet, or ICs? Because I hear from a lot of people, I’m not getting the opportunity to work on strategy. And I loved her advice because she said, even when I didn’t have that role or responsibility or that scope, I sat there and I still imagined what I would do if I was in their position. And I think that’s powerful. Pretend you’re the CPO. Would you do something different? What would you do? Can you dig into the data? Can you ask questions? Can you get into there?

And I’m not saying, go reinvent the wheel for the company. But it’s going to give you reps. It’s going to give you the experience asking those questions. So I think that’s powerful, picturing what you would do in their scenario.

If you want to get better at strategy, talk to people who really understand the market, really understand the financials. I’d go talk to your chief product officer if you have one and just ask them, what’s your process? How do you set this? We got to these three priorities, or something, how’d you get there? What’d you look at? I think that’s important, just having conversations with people about what their thought process is, how they analyzed it, what that means. I think that’s really important.

When you get into setting strategy at higher levels for product, a lot of it has to do with the market, and the customers, and the financials, and things that we don’t get exposed to as much as a team-level product manager. So the more you can talk to people in other disciplines… Go have a conversation with sales and see why people were buying competitors? What was your win-loss analysis? Why are we losing? What do you think is the issue? A lot of times, we just don’t go and talk to other departments. And they have a wealth of knowledge. And we’ve got subject matter experts sitting in certain places that can fill you in on how the market’s moving, and what things are happening there, and how people are innovating. And it is fascinating to talk to those people.

So I would do that. I would talk to other departments. I would talk to your leadership, try to understand their thought process.

If you are a leader and trying to figure out how to do a lot of this, one of the biggest issues I see for leaders, and why I got very excited about product operations over the last couple years, is the lack of data. One issue I see is that leaders have never really set strategy before, so they get into these positions and they don’t know where to start.

And the place that you need to start is data from everywhere. You need to start with internal data, and you need to have an analyst on your team. I also tell them, hire a data analyst. Hire somebody, some ex-McKinsey consultants. They’re great at crunching data. I had them on my team. It’s amazing. But they’ll pull the numbers out. They’ll find interesting patterns for you. And you say, I want to answer these questions, and they will go get the data for you, put it into ways that you can actually look at it, and then you can actually start making informed decisions.

So you want to take that data. You want to take customer research, so whoever is talking to customers, you want to bubble that up and make sure that you can see that as well. You want to take the company goals and put that into context.

And then, really, strategy always comes down to asking the questions about how can we win, how can we get further to the goal, which is the vision. But it’s also keeping into context of where we are now and what we’re able to execute on now. And I think it’s interesting because we don’t always make the right choice when it comes to strategy, but you’ve got to make a choice. And I think that’s the hardest part for some people. They’re like, I want to be 100% certain this is going to work. And you can’t. And I think a good aspect of being a leader, whether you’re a product manager on a team or even an executive, is making the best informed decision that you possibly can at the time, but then also being willing to correct yourself if you find out it’s the wrong one by looking at all the information, and then saying, okay, let’s try something different.

And that, to me, is how we do great strategy. We take all the information we can, we make the best possible guess to go in one direction, and then we just keep reevaluating it to make sure it’s the right direction. And if it’s not, we pivot.

Lenny: I love that your answer is talking to people, getting information, gathering data, thinking, and it’s not, go read books on strategy, go get an MBA, or anything like that. You get better by doing it and learning from other people, right?

Melissa Perri: Yeah, and seeing it, too. For me, when I’m learning about strategy, because it’s not like I just started project management and started doing strategy immediately, I analyzed how other companies did it. So I was like, how did Netflix do their strategy? How did this company do their strategy? And reading how a company goes from point A to point B is fascinating. There’s tons of articles on there about how companies have done it. But it just helps you see that everybody does it differently. Everybody’s got a different framework. Doesn’t matter what framework you use, as long as it works for your company. But they all got to that framework by asking those questions, and looking at the data, and deeply understanding their market, and deeply understanding their customers, and just trying to piece it all together.

Lenny: Awesome. You touched on product operations, which I know is the book that you’re working on now. I know that there’s a role, an emerging role, product operations. Can you give us a preview of that this book’s going to be about and what people should be thinking about there?

Melissa Perri: Yeah. Having worked with all these companies, especially the ones that are scaling pretty rapidly, I started realizing, hey, we trained all the teams. We deployed the strategy. We’ve got a bunch of people, now, in this product management role. And then you look at certain things, and you realize it just didn’t scale to the rest of the team. And things broke down. One standardization of processes, everybody had a different roadmap. Cool, I can’t do anything with that when I’m trying to set a strategy. If I can’t compare your roadmap to that roadmap, all your time horizons are off, all your data is off, nothing’s set in the right format, I can’t roll that up into my strategy as product leader.

Two, maybe there’s no career ladders for the product mangers. Three, we’re having 18 different types of meetings and all the wrong people are in the room.

Product mangers can get the data that they need to make the informed decisions on the product strategy. We’re interviewing customers one off, and then I find out the same team is hitting up all these customers over here again. They’re getting really upset. These customers don’t want to talk to the same team over and over and over again.

Product management at scale is really hard, and that’s where product operations comes in. So what it does is it helps you get the right insights to the team, and then help standardize those outputs and those check-ins to make sure that you’re on track for the right strategy.

There’s usually three parts to it that I say, and not all companies have all three. And it depends where you’re at for where you want to start with this. But typically, we have internal data and insights, and that’s a team that’s going in and taking all the data that we have that lives in our financial systems, our user analytics, all of these different things that live inside our company, and they’re helping to surface this up in ways that people can look at them, see the progress of our strategy, and track those OKRs, and say, okay, we’re going to go this way or that way. So that helps give us the inputs we need for strategy, helps monitor the strategy, and it helps us make decisions.

Then, there’s also customer research and user insight, so that’s really the external data. And market research. Customer insights and market research. So that’s the external data that doesn’t live in our company that we need to get from our customers or our market to help inform strategy.

So from a market research perspective, that might mean having subscriptions to publications, or making sure that we have subject matter experts who are giving this great advice where the market’s moving. But then also, for customer research, it’s standardizing the approach so that product managers can go talk to customers so we’re not hitting up the same person all the time. We’re recording all the user interviews we do in a way where we can actually search through it and gain that information later, when we go and revisit those things. It’s really helping to streamline it. It’s not centralizing user research as a practice, it’s helping to scale user research so that we can enable more people to do user research, especially when you get into some of these companies.

When I first started doing this, it was at Athena Health, and we had 350 product managers. And we had to make sure they weren’t bothering the people at the same hospital over and over and over again because they were when we came in. And we said, wow, okay, cool. We’ve asked these people, now, the same question 10 times from 10 different teams. How do we make sure that those things don’t happen, but how do we also empower those product managers to go still talk to them when they need to? So we’re not taking user research away, we’re just helping make it more scalable, more efficient, give them more tools for it.

And then the last one is standardizing your processes, your cadences for strategy check-in. So it’s like, hey, we do roadmap check-ins every month. These are the people that need to be in the room. We do quarterly planning sessions with executives, and this is the inputs to it, this is the outputs to it, here’s the decisions we make in this meeting. This is what we review. And those people can help do that part, and then help standardize the product management processes that touch other divisions. For instance, if I need to update roadmaps to sales, they will help own that cadence of what that looks like and how those formats go out.

But what I say is it doesn’t standardize stuff that only belongs to a team. I don’t care how a team does their stand-ups. You choose how to do that. I’m not going to standardize that. But I do care what format your roadmap comes in. I do care how we make sure that we have a good working relationship with sales. I do care that we have a good working relationship with product marketing, those types of functions. That’s the interactions we want to standardize.

Lenny: I can’t wait to read this book. When do you think it’ll be coming out?

Melissa Perri: We’re aiming to get it out before the end of the year.

Lenny: Oh, wow. Okay. That’s pretty soon.

Melissa Perri: I know. It’s coming up.

Lenny: On that topic, as a PM trying to learn, trying to get better, there’s so much information out there. There’s books, newsletters (guilty of that), tweets, advice, podcast, all these things that are always coming at you as a PM. And I hear a lot from PMs that are burnt out from all the information always coming at them. It’s just never ending advice. Do you have any advice for either new PMs or just any PM of how to take in knowledge that’s all out there, and not just burn out?

Melissa Perri: I’m going to burn them out with more advice. [inaudible 00:49:17] the advice.

Lenny: This is the only advice they’ll need.

Melissa Perri: So I’d say, one, the best thing that you could possibly do as a product manager, even if you’ve been in this role for a while, is to make sure that you’re always learning. But the way that you’re going to learn the most, usually, is from execution. So what I’d say is first, focus on that. Focus on doing your job every day.

Then, I would analyze your job and say, what’s working? What’s not working? And then, take out certain pieces of it that you want to get better at, and then do a deep dive into that.

So for me, when I was thinking about my career and my stuff, I did a similar approach where I’d just run into problems, and I’m like, I need to learn more about why that problem is causing this. One of them was Agile. I found out that a bunch of people who never did product management before became product owners. They were writing 8,000 user stories for very small, little features. I’m like, why are you writing so many user stories? So I went down a rabbit hole, interviewing everybody who wrote the Agile manifesto and [inaudible 00:50:19] and taught all those things to find out where this came from, so then I could figure out how to fix it.

And I think you need to carve stuff out like that, where you go, what’s this topic I want to get better at? What’s this going to do to help me get to the next level? Where do I need to learn and help fill in my skill gaps? For instance, if you’re not great at user research, or you haven’t had a lot of experience talking to customers, I might deep dive on that. If you’re not great at data analytics, I could deep dive on that.

But I think there’s a certain point where we get to, okay, I understand the basic product framework, and everybody’s going to have different opinions about what that framework should look like. But we all generally agree at the end of the day, you should be talking to your users, you should be working with your teams to develop what a test should be, run some tests, figure out what your users want, build it with your team in an iterative fashion, measure success, and keep going from there. That all generally stays the same. But how you do each part of that, you’re going to find some people have one opinion, some people don’t. And you have to find something that works for you, and then stick with it, and then find out that if it doesn’t work for you, change it.

And this is where I get really passionate and frustrated with Agile processes, which I used to rant about a lot. But I feel like some places, we’ve solved this problem, some places we haven’t. But I try to tell teams that started with scrum or started with some of these more dogmatic processes, if it doesn’t serve you, move on. Change it. Everything is meant to be iterated on. Everything is meant to be adapted. If it does not work for you, you do not have to keep doing it.

And I think that’s the biggest message I can tell to anybody learning, is really, sit down, do a retrospective with yourself, and say, is this helping me get better at being a product manager? And if it’s not, change it. Change your approach. Do something different. If it is, keep it. Keep it in your toolbox. Create your own toolbox and go from there.

Lenny: What a perfect way to end our conversation. Where can folks find you online, and how can listeners be helpful to you?

Melissa Perri: Yeah. I am on Twitter all the time @lissijean, so feel free to tweet with me. I love hearing what you guys are up to. You can also submit questions, if you have questions, to me at the Product Thinking podcast. So if you go to productthinkingpodcast.com, or dearmelissa.com, I take questions there all the time.

I’m always curious what everybody’s thinking about. What are your questions? What are your burning questions? That’s how you can help me. I am very passionate about figuring out what are the problems that we’re facing as product managers, and that’s what makes me happy, trying to figure out where they’re coming from, how do we solve it, what’s on people’s mind. So definitely hit me up with questions. I always answer them on the podcast.

And then my website, melissaperri.com, has all my other information, if anybody needs to get in touch.

Lenny: Amazing. If anyone has any problems in their PM job, just tweet you, and they will get an answer, is what you’re saying.

Melissa Perri: Yes. Do that.

Lenny: Amazing. Thank you so much, Melissa.

Melissa Perri: Thank you.

Lenny: That was awesome. Thank you for listening. If you enjoyed the chat, don’t forget to subscribe to the podcast, and even better, leave a review, which helps a lot. You can also learn more at lennyspodcast.com. I’ll see you in the next episode.

Glossary

English	中文
Agile manifesto	Agile 宣言（敏捷软件开发宣言）
ARR	ARR（Annual Recurring Revenue，年度经常性收入，保留原文缩写）
Athena Health	Athena Health（公司名，保留原文）
Canva	Canva（公司名，保留原文）
Chief Revenue Officer	Chief Revenue Officer（职务头衔，保留原文）
CPO	CPO（Chief Product Officer 缩写，保留原文）
CPO Accelerator	CPO Accelerator（培训项目名，保留原文）
dearmelissa.com	dearmelissa.com（网站，保留原文）
Denise	Denise（人名，保留原文）
Dropbox	Dropbox（公司名，保留原文）
epic	epic（敏捷开发中的工作单元，保留原文）
Escaping The Build Trap	Escaping The Build Trap（书名，保留原文）
Head of Design	Head of Design（职务头衔，保留原文）
Head of Product	Head of Product（职务头衔，保留原文）
Head of UX	Head of UX（职务头衔，保留原文）
IC	IC（Individual Contributor，独立贡献者，保留原文缩写）
Insight Venture Partners	Insight Venture Partners（投资机构名，保留原文）
Lenny	Lenny（主持人/昵称，保留原文）
lennyspodcast.com	lennyspodcast.com（网站，保留原文）
McKinsey	麦肯锡（知名咨询公司，使用公认中文译名）
Melissa Perri	Melissa Perri（人名，保留原文）
Melissa Tan	Melissa Tan（人名，保留原文）
melissaperri.com	melissaperri.com（网站，保留原文）
OKR	OKR（Objectives and Key Results，目标与关键结果，保留原文缩写）
Product Institute	Product Institute（在线学校名，保留原文）
product marketing	产品营销（产品管理领域的职能）
Product Operations	Product Operations（书名，保留原文）
product operations	产品运营（产品管理领域的运营职能）
product owner	product owner（敏捷开发中的角色，保留原文）
Product Thinking podcast	Product Thinking podcast（播客名，保留原文）
productthinkingpodcast.com	productthinkingpodcast.com（网站，保留原文）
Produx Labs	Produx Labs（公司名，保留原文）
retrospective	回顾（敏捷实践中的反思会议/活动）
scrum	scrum（敏捷开发框架，保留原文）
toolbox	工具箱（比喻个人积累的方法和技能集合）
user research	用户研究（保留原文术语含义）
user story	user story（敏捷开发中的用户需求描述单元，保留原文）
VP of Product	VP of Product（职务头衔，保留原文）
Webflow	Webflow（公司名，保留原文）

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