[On Demand] Product Management Webinar: The Role of a CPO

Janna Bastow: [00:00:00] Hello everybody and big welcome to this ProdPad series of webinars that we run here. This is one of our expert fireside webinars that we’re running. As we run these on a regular basis. We’ve been running these for years now, so we’ve got this history of them where all the past talks have been recorded.

And we’ve run them in the past where sometimes they’re a presentation, sometimes they’re a fireside. Today’s going to be a fireside and they’ve all been recorded. And so they’re all up at ProdPad.com/webinars. This one is also going to be recorded. That’s one of our main questions we always get, but this is being recorded.

You will have a chance to get a copy of this and share it with your team. Watch it again later, whatever you need to do with it. And the focus of these is always with bringing in amazing experts from the product sphere, our circle of experts out there. And so we’re going to be hearing from Giff Constable today, who is, of course, a product expert [00:01:00] in the field.

We’re going to be hearing from him in a short while. But to give you a little bit more information about what we’re doing here as I said, it’s a whole focus on the learning, the sharing, the experience, real stories I guess going to be talking about what it takes to be a chief product officer, what that journey looks like.

You will have a chance to ask questions, so make use of the Q and A area. You can add your questions. You can see other people’s questions and vote them up. So make use of that. So we can see which questions are the most burning ones and make use of the chat today as we’re talking, get involved.

Have conversations. We want to hear from you. So we’re going to hear from Giff in just a second, but let me just tell you a little bit about what we’re up to here at ProdPad. So ProdPad is a tool that was built by myself and my co-founder Simon Cast. If you know either of us you might know us from the Mind the Product community that we founded years ago.

But basically we were product managers ourselves and we needed tools [00:02:00] to do our jobs and this didn’t exist. So we started building something and we needed something to help. And so we needed something to help us keep track of all of the ideas and experiments and all the stuff we could do. And we needed something to show off what was going on to our roadmap and get our stakeholders on board with it and give transparency into the product management process.

And so building ProdPad. Gave that control, that organization, that transparency, it brought people along on that product journey and helped create the single source of truth for the product decisions that we’re making. And so now it’s being used by thousands of teams around the world. It’s a tool that is free to try.

You can jump in and start a free trial. We even have a sandbox area. So the sandbox is a version of ProdPad that is free to use. Pre loaded with example data including how lean Now-Next-Later roadmaps work. You can see an example. Okay. Ours. You can see [00:03:00] how it fits with customer feedback and you can move stuff around.

See how it all fits. Add your own data. Mess it all up. And then reset it and then put stuff in your own account when you’re ready. And our team is made up of product people. So, we’d love to get your feedback. We love to hear how it’s working for you. And keep in mind that this is something that we are constantly iterating on and building on.

And on that note, I want to tell you about a couple of things that are underway as well. So, a lot of you, hands up, who here uses Slack already? I’m guessing a lot of people are Slack users. Cool. So we have a Slack integration. And if you don’t know, we’ve had this Slack integration for years.

So this isn’t the new part, but the Slack integration basically allows you to capture ideas and feedback where the conversations are already happening. It allows you to jump in on conversations. That is what is happening in ProdPad. So stuff gets posted from ProdPad into your Slack. You have the conversations in Slack and it syncs back to, to, to ProdPad.

You can give your thumbs up, thumbs down, give your [00:04:00] thoughts. And also it allows you to search your ProdPad without actually leaving Slack. But one of the new things that we’ve added to it is the ability to interact with Copilot. A lot, no one here has probably heard about Copilot because it’s brand new.

This is actually something that’s kind of a secret. Beta mode right now. Copilot is going to be coming out in due time, but it is an AI version of ProdPad that allows you to interact with it and ask it questions. And this has been activated secretly as part of the Slack integration.

So if anybody’s using the Slack integration or is using ProdPad and Slack, connect the two and you get advanced access to Copilot. And the other thing, anybody here using teams, Microsoft teams?

Yeah. Some more hands. All right. So team teams, good news. We have a similar integration coming along your way as well. So, good to know if anybody’s actually interested in getting a [00:05:00] demo of. The slack integration, the team’s integration, or this copilot thing drop your details through and we’ll get you a demo.

We’ll get you set up. One of our team will probably drop a link to book a demo in the chat in a second. And that way you can get a sense of how it works. And speaking of copilot, just to give you an idea of what we’re talking about, this is going to be coming out in the app as well, because there’s no point building something that cool and then hiding it away in a little hidden thing in your Slack integration.

But what it’s going to allow you to do is talk to your prod pad. Right. And in your prod pad, you have information like, well, what’s your big picture strategy? What’s on your roadmap? What are your goals? What have you delivered? And what are you hoping to deliver? What are your customers asking for?

And this co-pilot is going to help you do so much, so you can feed it ideas and it can help you log it and prioritize it. We’re teaching it to take a look at images so you can say, here’s my roadmap [00:06:00] today. Can you help me turn it into a Now-Next-Later? You can ask it to help you build a product vision.

It works as a product coach. If ProdPad, we already have a one click product coach within ProdPad. Well, this will act as a bot that you can use and chat to, and it’ll follow up and have a conversation with. You can ask it things like, Hey, can you summarize all the feedback from that customer and remind me if it’s, in line with this goal that we’re building?

Can you remind me what we’ve done in line with this goal or this objective that we’ve got? Some really cool use cases there, and I’d love to hear what sort of use cases you might be using it for as well. This is an open field that you’ll be able to play with. So, I suspect there’s going to be some really interesting testing on this when it comes live.

If anybody wants to get access to that, or get a demo of it again, get your. And we’ll show it off to you. We’ll talk you through how to make the most out of it. And we’d love to hear how you’re planning on using it too. So [00:07:00] enough about us, because I could talk about ProdPad forever, but we’re not here to talk about ProdPad.

We’re talking about here to talk about what it takes to be a chief product officer. And specifically we’re here to talk with GiffConstable. So GIF, thank you so much for joining us. Of course Giff has a really impressive track record. He has served as the chief product officer at meetup. I bet everybody here knows about meetups.

com and has gone to meetups in the past. He’s the CEO of Neo, which is an innovation consulting company and he’s held product leadership roles in both startups and growth stage companies. He’s the author of. A couple of books talking to humans and testing with humans. Giff, what order did they come in?

Giff Constable: Talking to humans was the first, they’re two sides of the same coin, one’s on discovery and one’s on experiments. 

Janna Bastow: Excellent. Yeah. And you’re also teaching several courses. Multiple courses, just telling me about another [00:08:00] course on Maven, so always getting out there teaching and sharing and getting the word out there about product management practices.

So huge. Thank you for that. And thank you for joining us here today. 

Giff Constable: Thanks. 

Janna Bastow: Awesome. So, Giffto get started, I would love to hear about your journey through your career and how you ended up as a CPO at Meetup, for example. 

Giff Constable: Like many people. I got into product in a slightly securitous way.

The early days of my career, because I’ve been in tech for 30 years now to date myself, there really wasn’t this thing called product management. You had people in marketing working with engineers. And maybe if you were lucky, a designer and then the field started to emerge, but I spent a lot of the beginning of my career really on the business side of things, but I always ended up in the seat where I was the bridge between engineering.

I was always in software really between the engineering side of the business and the business side of the business. So I always played that role, even though it wasn’t formal. Title [00:09:00] and in the process of working through a number of startups and starting and selling some of my own and some scale ups and things like that.

I ended up realizing that my, and I had to sit in the CEO seat a couple of times. Neo innovation. I’m not CEO of that anymore. That business was sold to pivotal. So that business doesn’t exist anymore. But that was having sat in the CEO seat a few times. I realized that my, my happy place.

It’s probably more living in product and engineering and design than all the crap you have to deal with as CEO. And where a chief product officer gets frustrated is where sometimes you, you wish you were CEO because you don’t get to make the final say, you also don’t have to deal with all the stuff that the CEO does have to deal with.

So I came to that realization at a point in my career. And it so happened that right after I sold Neo, where I was CEO, a friend of mine was a venture capitalist and said, boy, I have a [00:10:00] portfolio company that could really use you and like, would you go run a product for them? And I said, yes, and I just loved it.

I loved it. And then I went from there and over to meet up as well. And frankly, I’d still be doing it, except I had some sort of Family obligations difficulties that made me take a step back. And so that’s why I actually, I teach these days cause that can fit into the needs of my life right now.

Otherwise I’d still be working with teams as a CPO. 

Janna Bastow: Yeah, I hear that. I hear that. So it sounds like you don’t believe the whole thing about, as a product person, you are CEO of the product. 

Giff Constable: It’s a loaded expression, isn’t it? You are, and you aren’t, but it’s certainly sent out. You don’t want to say that about any role, right?

What does it even mean? Does it mean that you feel accountability and ownership over what you’re doing? And you hope that every role has that feeling. You certainly have, there’s a lot of things about being a CEO that resonate with being a product manager, right? A good CEO is not just telling [00:11:00] people what to do, but is actually leading through influence and through coaching and by delegating and empowering others.

And that’s a lot of what product management is. Product managers need the same amount of charisma and ability to pull teams forward and unify them and align them, so, and you’ve got to be really multidisciplinary. Like the, I’ve often said that, like, there’s 2 roles where you have to really be a jack of all trades.

And 1 is being a founder and 1 is being a CEO. And then everyone else has to be a specialist, but. Product management actually is a bit like that too. It’s one of the closer roles to that. 

Janna Bastow: Yeah. 

Giff Constable: So I get why the expression emerged. It just has led to some bad behavior. 

Janna Bastow: I, yeah, absolutely. It’s a contentious point for sure.

You mentioned that you came in from the business angle. Did you find it difficult not having the technical background? A lot of roles, particularly back then, required more senior product people to have those tech jobs to move up. 

Giff Constable: Yeah, [00:12:00] it’s, I’ve joked with like mutual friends of ours, like Melissa Perry and stuff that product management was originally created by business people to babysit engineers who probably really didn’t need babysitting but the business people really didn’t get what was going on.

And so they felt like they needed someone to, Keep them all in line, which is a ridiculous statement, but, and I think there is a hint of truth in some of that, but really, I’m a bad coder. I can code, but I’m a bad coder, but I’ve spent a lot of time trying to really understand deeply how we.

The craft of how we make products and really appreciate the disciplines of engineering, software engineering, and of design. And so that I’ve got some chops in that. I’ve got a lot of empathy for it. I know where things hurt if they go wrong. And, so that. So basically I got technical enough that I could be loosely fluent in it and really understand how to work really well.

And I’ve managed, I’ve had to manage multiple [00:13:00] times. I’ve joined a company and all of a sudden the head of engineering is gone for one reason or another, and I’ve had to be a CPTO. And. And I’m not, I’m not going to be your technical architect in that role, but I do know how to manage people and I know how to ask questions and I know how to pull people forward.

And so, I was able to slot into that role pretty well, because I had invested in having a lot of empathy and understanding of the engineering practice, even if I am not the best engineer by a long shot. 

Janna Bastow: Yeah, absolutely. I think that’s so much more important than having deep technical knowledge.

I call it having a sense of humor in line with how the development process works. Right. You can go. Yeah, I will. I can understand why you’d say that’s complex or, how that might be straightforward, but, how to actually do it. No, I’ll make an absolute mess of that, but you can work with the people to get to that point of understanding and making it happen.

Giff Constable: And the funny thing is actually, I think that Both product and product engineering and design, the more senior you get, once you get to the top, the jobs really converge, 

Janna Bastow: right? [00:14:00] Yeah. You’re 

Giff Constable: doing kind of the same things because you’re not hands on anymore. It’s your team that is hands on. 

Janna Bastow: Yeah, that’s absolutely fair.

And so, that’s actually a really good point. You said that you’ve, you found that you’ve ended up as a CPTO. So the technical. Chief Technical Officer as well. Have you found the same thing being transferable to the design type role, CDO or, running design teams and that sort of thing?

Giff Constable: Well, I have more of a natural predilection towards design, a passion for it, or I really value it deeply. From a UX perspective I’ve, Tried to be hands-on with that sort of stuff. I’ve had the benefit of getting to learn, some of my colleagues at Neo, for example, were Josh Seiden and Jeff Gotheld, who are really great minds in the UX field.

And I learned a ton from them. So I value that practice very deeply and I’m good enough at it to be dangerous. But I also know my limitations. I think [00:15:00] would be a good manager. You need to be aware of your own limitations and not overstep. But yeah I care deeply about that field. 

Janna Bastow: Yeah, that’s a really good point is making sure that you are creating space for other people to step in and manage it or, to do the role so that you can manage those people.

I think it was Julie Zhu. The making of a manager author who pointed out something really apt, which was she hadn’t realized how much she was thinking that it was her job to do everything. And it was only when she realized that actually, it’s not her job to do everything that really freed her up.

Did you have any sort of. Moments of epiphany or was there a slow learning or how did you evolve into a manager? I’ve 

Giff Constable: made every mistake there is to make, as I think a lot of people do, with humans, we tend to learn things the hard way with maturity has definitely come some wisdom, some patience, some empathy, some understanding.

It’s funny. I was, so I mentor a chief product [00:16:00] officer. Really talented and I’ll use they were having a challenge where 1 of the areas, you know, multiple parts of a product, multiple. Products and a portfolio underneath this person. And one area was struggling and they were asking me like, I can dive in.

Should I dive in? And of course, beyond doing the coach thing of like, well, what do you think what, where my brain was going is, once you get to that really senior position where you’re managing a portfolio and things like that you have to, Like everything that pops you, you do have to diagnose and say, okay the, this is also a conversations, but this recurring thing with me and Tommy Forsstrom, who you might know also in the chief product officer world, there’s this question of doing things the right way and then doing the right things.

And like, I firmly believe that doing the right things always trumps doing things the right way. Ideally, they align, but so when something like this [00:17:00] emerges, you have to ask yourself, like, the right way is to build a system underneath me as a leader and so either coach this person up or replace this person, but it’s not doing it myself, but to actually have.

Build the correct system, build the right leverage and have the right person in the seat. Who’s actually overseeing this and making this area successful rather than going and doing it yourself. However, you learn that there are times when you look at something and go, you know what?

This is really urgent. It’s a really critical. I don’t have that. That’s a 3 month process. I do not have that time. I actually have to. Either steal someone from somewhere else or I have to lean into this myself. And so there are times when, like, you just have to roll up your sleeves, but you, that’s a, you want that to be like last resort, but you’re just, Oh, everything is always like, there’s the right way.

And then there’s the right thing and which one. 

Janna Bastow: And how do you recommend that teams are the CPO sort of balances out things between different goals in the [00:18:00] business. Like you’ve got the strategic goals for the business, the strategic work that the vision as well as the day to day work that they need to Make sure that they’re doing as well as the team is doing.

There’s a lot of tension there that ends up pulling the CPO in different directions. 

Giff Constable: For sure, you’re managing and designing an entire system and there’s someone, I think when you posted on LinkedIn the other day and one of the responses I really agreed with, which is like the CPO job is, was really close to the CEO job, except as I said before, there’s some unfun stuff.

You don’t have to make your problem. Which is great. Yeah. And, you don’t have to go out and raise capital and deal with all these headaches. And like every problem in the business doesn’t have to become your problem and the like. But what has happened, I think, as every business of any scale has become a technology business And of course, technology is a living organic thing, as opposed to like a bottle of [00:19:00] Gatorade that you just, it’s just repeat.

And now it’s also about how you sell and market it. What that’s done is that’s put product at the center of all of our businesses. And. What that has done then is made the person in charge of the product, the chief strategy officer, as well as the chief product officer. Right. And to a certain extent, if the way you need to think about it, from my point of view, is that you’re not the CEO, but you still own the entire system because you need to.

You need the product to be successful. Well, the product isn’t just successful because of the way you’ve done some UX inputs on a screen or how quickly the load time is right. The product is successful on how it’s going to market, how people are onboarded, how they’re converted, how they’re supported, like the entire.

System of the business is your product now. Yeah. And within that, you also have the product part of the product, but the whole thing is your product. And you’ve got to think that way. And so your brain has to switch to this portfolio thinking approach. And. [00:20:00] And you were trying to, the only way to solve that, you can’t solve it all by yourself.

The only way to solve that is through colleagues, through great relationships, through aligning people, through empowering others, through getting a lot of people to help you do this sheer volume of work that needs to be done. But I have found that there are certain things that you just can’t fully delegate like sometimes ultimately, like seeing your way through the strategy and building the decision making principles that are going to help all your teams, not just in product and engineering, but elsewhere, make better decisions.

As you go along, because they get what you are and where you’re trying to go. Like, some of that work really, it requires someone very senior experienced who’s thinking about that. And so, like, you can’t really delegate, you can get help, but you can’t fully delegate that stuff. And there’s other pieces as well that you just, you can’t delegate as much as you’re thinking about the system of people underneath you.

Janna Bastow: Yeah, absolutely. And as you talk, it [00:21:00] dawns on me how different CPO roles appear in different companies. 

Giff Constable: Yeah. 

Janna Bastow: Sometimes the CPO is well supported. You’ve got a chief strategy officer and you’ve got a CMO and you’ve got a CTO and other times you’ve come in and you are clawing the product strategy away from a founder and you’ve been left with.

Basically the company strategy and you’ve got to figure it out. Come hell or high water. And there’s a lot on your plate. 

Giff Constable: That’s right. We all know this, like it’s all context specific, how you do products, the, forget the theory. The pragmatic reality of how you do product is different in so many different places.

And yeah, where is the business strong? Where is it weak? What support do you have? What stages of that, all this stuff. I remember I interviewed one time with a CEO when I was thinking about moving and they said, well, how do you approach things? Like what’s your system? And I thought back to like the last few roles and they, I had, I done things so differently in.[00:22:00] 

In each company based on where what, what was working and where was the mess of what needed to be fixed? Like, I’m very much a first principles. I always, I try to be a first principles thinker of like, okay, like, let’s where are we? What, and what does that mean for what needs to be done?

And so I couldn’t really answer their question. I could tell them I had these values. I had these values that sort of sit on top of the tactical things I do, but the tactical things I’ve done, it’s like roadmaps, roadmaps 20 different ways, because like, okay what needs to be done here? How does the CEO or the C suite, how do they absorb information?

Like what’s the best delivery method? What do I need to emphasize? All that kind of stuff. And so it’s, yeah. 

Janna Bastow: Yeah. And you end up just summarizing it down to, I love how it was Josh Seedon and Jeff Godolph who wrote the book Sense and Respond. Like, well, you just sense what’s there and then you respond accordingly.

Hate to sum it up in just a couple of words, but it depends. Can you tell me about your bag of mess? And then we’ll [00:23:00] talk about how we fix it. 

Giff Constable: Yeah. Back to Doing the right thing. Trump’s doing it the right way. Yeah. 

Janna Bastow: Yeah. That’s a really good point. And actually, it’s not that much different than other product roles.

Every product manager role is different. Every junior product manager role is different. When you’re applying for a role at that level, you’ve got to really think about what and what it involves and who else is going to be in those roles and how big of the company it is and that sort of thing.

Giff Constable: But, Chrissy Jackson, just in chat, I actually did turn that up, even though I said I wasn’t going to, but just said values, principles, guidelines, guardrails, because the foundation I love. No, Chrissy, don’t apologize. Thank you. Because that word guardrails is really important. It’s really important.

I think because you can’t do it all because you can’t be everywhere. Once your organization gets beyond, once the product and your organization gets beyond 20 people, meet up, I had 150 people like. What, how do you get the [00:24:00] ideas that you want of how to work well to scale?

Well, it’s the behaviors you model as the leader yourself, not what you say, but what you do, and that’s what you choose to do in order to model. These things is really important. That like says more volumes about your values and how you want people to think and act than anything else. Creating these strategic.

Well, I call decision making principles, these guidelines so that if people are thinking, how do I choose between customer a or customer B or, new features versus supporting old or tech debt versus, everyone gets pulled in multiple directions, like, creating guardrails that help people know at any point in time, I’m going to choose a over B.

It’s the values that you actually discuss with your team, build with your team and have everyone buy into these all become as well as like The mission and values of the company itself, these all become these critical guardrails that just make, it reduces drag. It reduces the friction in the [00:25:00] organization.

People are still going to mess up. They’re still going to make great calls, make some bad calls, all that stuff. But the more you can reduce, not just like getting great people on the bus, but like we’re just reducing the friction of doing work and making decisions all the time, it could really turn an organization from struggling to flying.

So that’s, well, 

Janna Bastow: that’s 

Giff Constable: worth, that’s as a leader, that’s worth really spending time on. 

Janna Bastow: Yeah, absolutely. And I remember seeing maybe I can find the link to this. There’s a great talk from I think it was the CPO or somebody of a similar ilk at Slack about their principles and how they used them to guide the team on what it is that they needed.

From the company as they were scaling, because ultimately at a scale that big, how do you have the entire design team, the entire product team making decisions that align with each other? And they’re talking about how principles underpin, underpin that. And yeah, having guardrails, making sure that everyone’s pointing in the same direction.

And I always think about guardrails in terms of saying, let’s talk if [00:26:00] goes beyond this, in this direction or beyond this, in this direction. Otherwise you’ve got free remit within there. 

Giff Constable: That’s right. And repetition, the thing I learned when I actually was in the CEO seat is how much you have to repeat things to the point that you’re almost nauseous about it.

You’re like, do I really have to say this again? And you just realize that, Look, everyone, I think the thing that I realized is, and the same thing as a product person or a product leader, when you’re in the exec meeting and the VP of marketing, again, says, what are we working on?

And you’re like, Oh my God, I just told you this three days ago. Why are we doing this? No, I’ve explained this to you ad nauseum. Everyone’s got their own crap. Everyone’s got their own fire drills. Everyone’s got their own goals. They’ve got their own issues. Like they’re in their own world.

Of course, they’re going to forget about your world. Yeah. And the same thing goes for things like values and decision making principles is like, that’s all fine and good. But when the crap hits the fan, [00:27:00] then like ever everyone’s in a mess and everything gets cloudy in people’s heads.

So figuring out ways to repeat You know, when you’re getting up and talking or when you’re getting your people to get up and talk encouraging, like, remember to repeat these stories, remember to raise this up, remember to bring up why we’re doing this share the context, share the values again, and like trying to build that repetition.

And because, in the day to day of our work, all that stuff is. Everyone knows that it’s there, but it’s so easy to forget. 

Janna Bastow: Absolutely. Ben asked a question and the Q and area Q and a area when working with founders of CPO, they were often the head of product prior any tips for managing the relationship with a founder from the CPO role?

Any things to look out for when interviewing? 

Giff Constable: Yeah. Due diligencing, the thing that I’ve been spending a lot of time thinking about over the last few years as I reflect back due diligencing the [00:28:00] company, but really the CEO is so critical and like, how do you do it and how do you do it well, as everyone knows, right.

The interview process is a sales process. Both sides are vetting each other, but everyone’s selling as well. And like. The company is selling you. They want you to until they decide they don’t want you to come. They want you to come. Right? And so they’re going to put their best foot forward. Everyone’s going to be on their best behavior.

You’re not going to really see the messy stuff until you get inside. And then you go. Oh, right. So how do you work your way around that? And I’ve been trying to think through methods for doing it. What is an astoundingly difficult method to do, but oh, my God, if you can do it is to do diligence outside of the organization.

And so if you can get to someone that has worked for the CEO before and say, can I get just 5 minutes of your time? Ideally, you network to them through someone they know which will make it easier for them to say [00:29:00] yes to that. And you’re not actually asking them to. To divulge too much about the CEO because everyone’s going to be really tight when no one wants to throw someone else under the bus and everyone’s gonna be really tight.

What you are basically saying is, if I describe me, if I describe how I like to work, am I a fit? Like, are we going to get on? Super well and I’m going to be exactly what the CEO needs or is it not going to be the case, and would you advise that I should, maybe think about working differently if I am going to go there and work for this person, I think that’s a slightly different question to ask that could get people to open up to you a little bit more if you can get to that person and if you can’t get to that person, then it’s really about, yes.

You’re going to talk to the CEO multiple times in the lead up to accepting an offer and you’re going to spend time or you really should spend time talking about how you like to work? Why did it not work out with the last product manager? What are you paranoid about when it [00:30:00] comes to hiring a product leader?

Oh, they’re not. Business savvy enough, or is it, technical, like, what is it where they don’t communicate something. And, but then you also in your interviews with the other executives figuring out how do you ask questions that get stories to unfold?

You can’t ask the question directly, and get a straight answer. But if you ask for stories about things that happen, it’s just like doing product customer discovery. Yeah. Right. It’s like the way you ask the question matters so much about the insights you’re going to get back. And so if you get them to tell some stories about things that actually happened, you can start to piece together the puzzle as to how the CEO works.

And it’s so worth it, like, putting a lot of time and thought into the questions you ask, are you getting enough information? Because it will make or break you. Yeah, your relationship with the CTO is really important with the chief marketing officer. If they have a head of sales or revenue there, that’s all really key, but it’s a CEO, Anyway, so back to the original question about like a [00:31:00] founder, one is you have to have a lot of empathy for what they’re going through.

That’s really critical. And so you cannot cut them out. You got to figure out how to engage them? How do I engage them? What I’ve been thinking a lot about recently, probably also due to some Discussions I’ve been having with Tommy Forsstrom, is it’s so easy sometimes to, or at least let me talk about myself.

I have fallen prey at times to getting frustrated with flaws in my CEO or a peer. And it’s not that I’m not flawed as well. I totally am. I know that I’m working on my flaws and sometimes from the outside, it doesn’t look like they are and things like that. And, and like, you’re, everyONE is just a human being.

We could fall prey to putting them on a pedestal and like, okay, you need to be the full package. And it’s really helpful when they are the full package, but they’re often not, when I was CEO, I was just a human being too. And I had my blind spots and I made my mistakes and everyone does. So one of the things to think about with a founder who’s now [00:32:00] letting go is how do you keep them involved?

Because. If they get totally disconnected, even if they’re disconnecting themselves, if they get totally disconnected, it’s like a rubber band. It’s going to stretch and stretch. And it probably at some point in time, it’s going to break and that’s going to turn into a real mess for you and for them.

So you want to keep them involved. And then we’ve got to think through where their strengths are. Like, I need to think strategically about how I use this person. And there may be some things about them that frustrate me. Like they’re diving into my teams too much.

And then my teams are in chaos for an entire week until I discover what’s happened and things like that. But the answer to that isn’t always to stop it from happening. But actually, how do I evolve that? How do I use the CEO in a way that is inspiring and helpful to everybody without just trying to block it and like to get the most out of the strengths that they’re bringing to bear.

And that sometimes you have to gently coach [00:33:00] the CEO and say, here’s what I really could use for you. And usually something like that goes over pretty well because they want it. They’re just trying to help, right? They’re trying to make things successful. And And you could send a lot of times the best delivery of that is this is happening with my teams.

I’m noticing that this is happening with my teams. Like, they’re meeting with you and I want them to meet with you. But then these ripple effects happen. So I’m going to go coach my teams on how to work with you better. But here’s my question for you as well. And you tell me whether. You like to ask, or if you want to do something differently, and that can turn into a really productive conversation.

But yes, you often have to go coach your teams as well as to how to interact with that CEO, like being explicit about when is something a brainstorm versus when is it an order. And when do you need to escalate and pull it, pull me the CPO in versus when do you just, run you, you want to set up a structure where everyone feels trusted and empowered but have safety nets essentially.

Janna Bastow: Yeah, those are really good [00:34:00] tips. And I also like the thinking of doing that due diligence or that outside due diligence. One of my other takes is to ask you mentioned questions in the interview process. One of the other things you can do is ask to see their roadmap because the roadmap is really telling, right?

And then ask questions like, well, okay, so where did this roadmap come from? Talk to me about who has control over this roadmap or who made this roadmap or does it get updated or who has expectations. Hanging on this what happened the last time something on the roadmap didn’t get delivered what happened the last time something failed that was put on the roadmap.

And it takes the focus off. The person who was delivering on the roadmap, you might be replacing or whatever, but it starts them talking about what’s on there and how they deal with the work that’s coming up. And then as to help to understand as to whether you’re going to have control or whether they’re going to have control.

Really telling. And of course, if they won’t show you the roadmap, that’s a red [00:35:00] flag in itself. 

Giff Constable: Yes. Although sometimes there is no, well, I got there was no roadmap 

Janna Bastow: and you can take that as an opportunity or a challenge in itself too. 

Giff Constable: Yeah. To be honest with you I’ve been pulled into a lot of fixer upper situations.

And what happens when. You get senior people hire people they think have seen the movie they’re going through or think they’re about to go through. Like that’s what they’re looking for. And it’s really important as you’re thinking about marketing yourself or positioning yourself as a leader as well as, what kind of CPO are you, what movies have you seen?

And of course you’ve probably seen them all, but which ones do you actually put forward so, because everyone’s looking for that safe pair of hands. And so a company that is their business model is struggling all of a sudden where it was working before, or, product management and [00:36:00] engineering are at each other’s throats, or maybe the business side and product engineer at each other’s throats.

It’s like, I have so many stories about healing those things, fixing them, redesigning them, but people are like, ah, okay, Giffcan help me with that. And so I started. building up an experience base of fixing things. And so, yeah, I get hired to fix things because that’s what I’ve, that’s what I’ve done.

And yeah, so I do know about coming. And so you 

Janna Bastow: get all the jobs around having to fix things. Yeah. And you just want one, one thing that works. Yeah. 

Giff Constable: Yeah. You have to decide if I want to go through that movie again? I happen to enjoy the intensity of that. I remember when I was interviewing at Meetup, the VP of design was like, you just came off of this.

Are you sure you want to do it again? And I was like, that’s a very fair question. Yeah. 

Janna Bastow: Yeah, no, that’s a really good point. What you’re really trying to do is understand, and you can sometimes get these clues from the job spec or from doing your due diligence from the outside, looking at press [00:37:00] releases lots of little clues that you might pick up about the company, about what.

Problem they’re trying to solve by opening up this job. And this applies for the CPO role or anything, even less senior than that. They put out this role. They’re obviously trying to solve a problem. It’s not just to put somebody in the seat because they’ve got some spare salary kicking around, some spare money kicking around.

So what are they trying to do? And therefore, based on that, how can you solve that problem? What skills are you bringing that you can uniquely solve that problem for that, for them and get that information into your cover letter, into your email approach, so that they can see that right up front as to, basically, as you say, what movie you’ve seen and how you think that’s going to apply to their case because it’s really competitive out there, and it can make a big difference when you can say, Hey, I see that you’re trying to grow from here to here, or that you’re a company that’s doing, this type of thing.

Here’s what I’ve done in the past and how I’m going to help you do the same thing. That can make a really big difference. 

Giff Constable: It does. It can be painful sometimes to restrict that [00:38:00] optionality because most of us have done many things. We have seen different things. Movies and you got to narrow it down to one or two, is it a stage, like some people position themselves as I’m a scale up growth stage CPO.

That’s me. That’s where I play. I know that I’m now outgrowing being a startup, but I’m not yet an enterprise. Like now. And so what you’ve just done is you’ve just closed off a whole bunch of options, but by saying, narrowing down what you are to one or two things that makes it a lot easier for someone to pick you as opposed to being everything.

Yeah, even if you can do everything, you probably can do everything. But And of 

Janna Bastow: Of course you can spin a different story to different companies, right? So if you’re saying, Hey, you know what, I’m out there looking and I know that I want a CPO role or a senior product manager role or a senior leader role, here’s what I’m good at.

And I’ve got, FinTech experience and also this sort of [00:39:00] stage management, Experience you can sell your fintech experience to one type of company and your, your stage experience to another and, either one works, but you’ve got to make sure that you’re putting something forward as to how you’re going to solve those particular problems.

Giff Constable: That’s right. It’s you and it’s okay. I’m not saying you can’t change and go do new things, but you have to do it in a pivot. Fashion. Yeah. So, if you want to change your role from designer to product manager, we’ll stay in the same industry, right? Right. Let’s see, you just need some aspect of your story that is de-risked for them, where they’re like, okay I know you at least know this part of healthcare, so then I can take a risk on you moving from designer to product manager.

But if everything’s a jump, everything then it gets really hard to get chosen. Yeah. 

Janna Bastow: Yeah. Yep. Good point. All right. And speaking of the jump so I’m sure there’s a bunch of people here who are in VP or head of product. So what do you think the biggest difference is in the problems you’re solving as a CPO versus for example, a VP product in [00:40:00] a midsize company?

Assuming a mature enough product is the question posed by Anonymous here. 

Giff Constable: Right, right. Well, 1 glass ceiling that is clear to me that exists out there for a lot of folks in product is finance, really understanding the business. We’re exceptional in our field, understanding metrics at doing data analysis, but that’s not quite the same thing as finance and really connecting the dots to finance and understanding The books and understanding company valuation and all the things that the CFO, the CEO and the board are worried about very much.

And so understanding that language, understanding how it connects to product priorities and to product metrics is critical. And if you don’t have that, it you just won’t appear as. Impressive at the C suite because that really is your common language to the other parts of the organization as well as to the board.

Everything the board is doing is about protecting you’re growing the [00:41:00] value of the business and you need to understand what those levers are. It’s not just about, I got to make revenue higher or profitability higher. Those are part of it, but it’s not just that. So that’s something to invest in, spend time with the finance organization, build up, like, every project you do, like, make sure you understand where it could go, the financial upsides and downsides, how, even if it’s indirect, how it connects to it and be talking to finance, they’ll be so happy for you to do it because, they’re always, Moaning about how there isn’t financial literacy 

Janna Bastow: across 

Giff Constable: the organization and in product.

Janna Bastow: And that’s a good point. As product people, we can talk about our user needs until the cows come home, right? We do customer discovery, like no one’s business. And this is actually no different than customer discovery or stakeholder discovery. You’re just discovering the needs from a different direction.

The stakeholder needs from the business and ultimately what you’re building isn’t. For the users. It is for the users, but why is it for the users? It’s for the [00:42:00] business. Oh, 

Giff Constable: yeah, exactly. Right. It’s, as an executive, you’re there to enhance the business, to grow, protect the value of the business too, right?

Now you do that by delivering value to your customers. You do that by having exceptional employees doing exceptional things underneath you, like et cetera, et cetera. But. At the day, like you, you are there to lift the business. That’s who pays you. That’s what hires you. And companies and people can go astray when they all of a sudden start like getting too short term thinking or they’re putting, they lose sight.

They get so focused on the impact to the business that they lose sight of the customer. And then of course, they fail to deliver the impact of the business as exactly it’s a circular. So that’s definitely one. The other. Change I think that people can struggle with although I think there’s more awareness of this now.

I see a lot more people talking about this now. Is the radical the [00:43:00] change is from. Yeah, I have 3, so finances 1, this will be 2 and I have 1 more if you want to go there. The change goes from being in this happy place with designers, engineers, and other product people, and just customers and product metrics and your Northstar and all that kind of stuff to all of a sudden, like your first team is the other parts of the organization.

And this comes back to what I said before about how you are designing a system. Yes, you are in charge of the product organization, but for that, for the product to be successful means the business has to be successful means the entire system has to work. So how well you work with the CMO with the head of customer success or customer support with the head of ops, like, with the CFO, how well you keep them aligned?

How well you keep politics from destroying value creation and things like that becomes really critical. Those relationships, how you navigate those relationships. Disagreements all that it becomes really important. Now, the good news is that product managers practice alignment as you come up, [00:44:00] but that becomes so critical and it’s outside of the little happy zone that we often get to play.

It’s these others. Realms and other roles and parts of the business where we might have less fluency, but that’s okay, actually, because if you just take it again, it’s the same thing. If you take a learning mindset and open mindset, if you make sure you’re, everyone’s feeling respected and heard, and you’re really listening, even if they don’t get their way, if you’re really listening to that VP of customer success, then.

And that can carry you a long way. So that, product leaders that stay too siloed inside looking downward and thinking just about product metrics and product people will bump. That’s number two. 

Janna Bastow: That’s a really good point. And you said there was a third one as well that you wanted to tackle as well.

Giff Constable: There was a third. Can I get it back? Let’s see. There was a third. 

Janna Bastow: Finance. The other people. 

Giff Constable: Yeah. I feel I’ve lost it. If it’s important, it’ll come back. That’s all right. It might 

Janna Bastow: come back to you. [00:45:00] That’s right. Maybe. Okay. So somebody said, related to the question above, what are the skills you think are necessary to go from VP to CPO?

How do you think people should evaluate whether being a CPO is even a good path for them? 

Giff Constable: Right. Well, to a certain extent, I think that question is: Is it around, do you love working through other people? Does that become your joy or do you want to do the work yourself? And that’s your happy place.

That whole IC versus manager track decision. It used to be that it only existed in engineering and it was a terrible thing that it didn’t exist in product. Because it was such a waste that the only way to move up was to manage people. 

Janna Bastow: And just to clarify for anybody, anybody doesn’t know, I see being 

Giff Constable: individual contributor, right?

But essentially like, are you being a product manager? Versus are you now doing your work through other people? And the [00:46:00] crazy thing here is that, in technology based businesses, the amount of economic leverage you can get from an exceptional product manager is staggering, right? It’s not like a consulting business where someone gets paid per hour.

Right. And like, the leverage that they give is just the amount of hours they can give. No, the economic leverage a great product manager can give is massively scaled and exponential depending on the success of the product. And so that means for you. Biggest impact, biggest outcome, and potentially biggest risk product areas.

The more senior, the safer pair of hands you have as a product leader on that, the better off you’re going to be. You will, your ROI on that is like huge, it’s huge. So there’s this great economic justification now that there wasn’t before for having someone in that seat. And I think that realization is why this like principal product manager role is whatever you call it is starting to emerge as opposed to just being pushed to manager.[00:47:00] 

And it is always unfortunate to watch someone who wants the promotion. They want the extra pay that they want to feel good about themselves moving ahead in their career. And they’re not cut out to be a manager of others. And they go down that path and they become a bad manager.

You want to. You want to learn to love, like, I love getting my hands dirty. I love being in the mud and playing with the pigs and doing that work, but you have to learn to love doing work through other people to be at the C suite. I believe and you also have to be willing to have the grit.

To make unpopular decisions you need to have the resilience to get through doing really awful things like firing people and layoffs doing the tough things that businesses sometimes need. You have to learn how to take care of yourself and pace yourself when you’re going through those things, and you have to learn to deal with the fact that it’s actually the loneliest job as CEO for sure.

Being CPO is [00:48:00] not quite as lonely because you still have peers. The CEO doesn’t have any peers. It’s sometimes a little easier for a founder if they have a co founder, but at least as a CPO, you’ve got your CTO or your CMO or your CFO, or one of these people that you’ve got a good relationship with, and you can just, go out for a coffee or a beer or whatever it is.

And instead of. Vent to each other about how you’re all worried about the organization and stuff like that. And then the CEO doesn’t have that, but it is still lonely because the more information, the higher you get, the less information comes to you where all of a sudden you’re a product manager and everyone’s telling you everything.

And here’s the bad news. And oh my God, this is going on. Like no one wants to rat out the bad stuff that’s going on. So like. And it’s the worst as CEO, but as CPO, it’s the case as well. Like things that you really need to hear about do not bubble up to you. 

Janna Bastow: Yeah. And this is why I always recommend products to get people together, right?

As your product person, you’re often outnumbered. So get together with your fellow product people. This is what I told people. Go connect with the other people here, drop your LinkedIn, get to know each other [00:49:00] here and find people at the same level going through the same sort of things that you are, because they’re the people that you might go out for a real or virtual coffee with.

And you can complain to them about what’s going on because there might not be somebody at your level in your business that you can do that with. On that note. In 

Giff Constable: LinkedIn, one of the things I loved was how often people said get help in, in various ways. And what you just said is so true. Find a peer set.

Find a coach if you want to work. I’ve had some fabulous coaches find that people don’t reach out and ask for mentors. And it’s crazy to me cause there are lots of people out there who would happily mentor someone, but no one ever asked them to find a mentor. If you don’t like working with them, stop working with them, but find your peer set.

It will help you think through stuff, get through hard times. Yeah. 

Janna Bastow: Absolutely. All right. Good stuff. Well, Giff what’s the best way that people can reach you or learn more about these courses that you’re doing? 

Giff Constable: Yeah. So I’m teaching some courses on Maven. I’m on LinkedIn. I’m not [00:50:00] on, on X anymore.

I’ve given that up, but I’m on LinkedIn. I’ve been having some fun posting to YouTube as well. And I, but I, so these links are actually on my blog. I haven’t been actually blogging a lot because I’ve been doing more on LinkedIn and YouTube, but I need to start updating that. But if you go to giffconstable.com, you’ll see some links to Maven. You’ll see links to the YouTube posts and I’ve been having fun trying to do some short form, like, like wisdom dropping on YouTube and may continue that. 

Janna Bastow: Fantastic. All right. Good stuff. Thanks so much for coming along.

Just a couple of final things here for everybody who knows that we do these things on a regular basis we’ll be back here in a couple of weeks time. This time it’s going to be me, myself and I, and probably one of the other prod patterns doing the Q and a part of it, but we’re going to be talking about how to analyze and make use of your customer feedback.

So come join us for that session. And then the one after that. Book your calendars for [00:51:00] October 15th, same time, same place. Same hour as this one, whatever your time zone is. We’re going to be talking to Melissa Appel about how to say no to the CEO, which if anybody has moved their way up to the CPO place this might be very relevant to you.

And actually, frankly, regardless of which role you’re in, if you’re a product person saying no, particularly to the CEO is going to be a common occurrence. And on that note, if anybody’s interested in getting a demo of ProdPad, then hit up ProdPad.com/demo. We’re always happy to talk to you and take you through one of our product experts standing by.

And on that note, everybody says huge. Thank you for the Giff. Thank you so much for coming along. If it’s been wonderful chatting with you, thank you for sharing your insights and talking through all these questions and sharing your experiences today. This has been wonderful. 

Giff Constable: It’s been a lot of fun talking to you and hopefully people have enjoyed it and thanks so much.

Janna Bastow: All right. Awesome. And best of luck with your new courses. Thanks for putting all that stuff out there and sharing all this knowledge. This has been brilliant. 

Giff Constable: Excellent. [00:52:00] Thank 

Janna Bastow: you. All right. Take care. Bye for now.