Ep. 4: What Most Surprises New Product Leaders?

Ep. 4: “What Most Surprises New Product Leaders?”

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Hope Gurion: Do you dream of moving from being a product manager to a product leader? In this episode of Fearless Product. We're going to learn from five experienced product leaders what they found to be the most surprising when they first started leading product teams. Being a product leader is a great role, but the clearer you are on what it is and when it isn't, the more successful you will be at positioning yourself for these opportunities.

In this episode of Fearless Product Leadership, we will hear from experienced product leaders who have led product at multiple companies answer the question: What most surprised you as a new product leader?


Let’s get right into it.  In this episode we hear from:

·      Amanda Richardson, CEO of Rabbit, who previously led product at Hotel Tonight, Prezi and Snagajob

·      Troy Anderson, Chief Product & Technology officer at SPINS

·      Margaret Jastrebski, Product & Strategy Advisor and former SVP Product at Shop Runner

·      Prasad Gune, SVP of Product at Signifyed, formerly SVP of Product at Open Table

·      Al Ming, VP of Product & Design at CNBC formerly head of product management at Scripps Networks and the NY Times

First up we’ll hear the 3 things Amanda Richardson found most surprising as a first time product leader.

Amanda Richardson: I remember the first time I was a product leader, and there were a ton of surprises. I think, I took the role because I wanted to really work on product strategy, I was super excited to think about the direction of the company, and how we were going to evolve our business. I of course, like everyone else had a ton of feature ideas I wanted to implement and thought now that I'm in charge; we get to implement them. And then, grim reality set in.

So, I think the biggest challenge and surprise factor for heads a product is how much time you spend on people management. No matter how big your team is, no matter how many direct reports you have; there will always be an issue around, an employee who's unhappy, someone you're recruiting, someone who's getting a competitive offer from another company, someone who can't get along with engineering was really talented, design, there are so many different things, people management is just a huge amount of your time. So, you have to be passionate about leading and working through those issues. Otherwise, you should find another job. The other thing is that I was surprised by, I wasn't the only one with a list of features that I wanted to get developed; all the sudden the CEO was at my desk with his list of features to get developed. And then, there were board members who had ideas, and then they were other people who had ideas.

And so, what quickly was my product roadmap, really was the company's product roadmap still, so don't get confused that it's not your chance to drive everything. Everybody's driving strategy, everybody's trying to push forward. So, now you just are the one voice who gets to decide, and so all those voices are coming to you get ready. And then, the third thing that also really surprised me, at one company I worked at, we called it the Star Chamber; and so this is the executive meeting, everybody, knows when the executive meetings happening and they always wonder what's happening behind those doors.

So, now is the head of product, you get to go into that meeting. It's not nearly as Star Chamber-y as it may look like from outside. Priorities are changing, they're trying to figure it out, it's a working team and things are probably a lot less organized than they are presented to the company, and I think that's a function of life. Every company creates a plan, but that plan has to react to how users change, how competitors change, how the technology changes, how the industry is changing. And so even a plan is only as good as the number of days ago it was written. So, it's constantly evolving, and I think that was always a surprise to me, as I thought, “Oh, we'll come in, we'll just execute our plan; it's super clear” but every week is a new thing and a new idea, and sometimes, that roadmap you just made, is a complete waste, because we're going left instead of right. And I think it's a surprise to see how frequently companies are working through those things, and always trying to figure it out. 

Hope Gurion: Next we’ll hear from Troy Anderson, who recognized early in his product leadership career that as product leader, it’s not about your will and vision, it’s about your people.

Troy Anderson: People are crazy, and people all have their own desires. And people have their own missions, they have their own things that propel them. And, it's like being a psychologist. So, a lot of people come into play, and it’s like “Oh cool, I'm going to come up with this new product and it’s going to do this” you are essentially, completely at your people's mercy. Your job, as head of product, is to make your people shine. The key is not to your great vision. The key is not, whatever it is, you think is cool or otherwise; that's like being an R&D person.

If you want to be a better person, you are enabling your staff to be exactly what you would probably want to be, if you could. I want to do these cool products and do these cool features, and I think this would be really cool. That's what your product owners will do, that's what your job is. Your job as head of product is not to remove your ability to scale, your ability to scale is to empower these people. They don't work for you, you're for them. And to the extent that you think that people are going to work for, you're a superior product; you've got it all wrong. So anytime you're leading your product team, you're not! You're actually supporting your product team.

Hope Gurion: I love that Troy hones in on the necessary servant leadership mindset product leaders need to embody to be effective in their role.  Next we’ll hear from Margaret Jastrebski, who shares how new product leaders may be surprised how to navigate being decisive and owning those decisions.

Margaret Jastrebski: I think what's most surprising to people, when they start to grow in their product career, is the concept that you now are responsible for setting the pace and the tone. Maybe a fine line, maybe it's a fine switch, I'm not sure, but I think about when I was a Junior Product Manager, I had leadership ahead of me, above me, that really was the one saying, “We're going to go for this. We're going to go do this” and I never really thought about why, other than kind of broad fly like, “Oh, there's an opportunity and market opportunity, blah, blah, blah” but I never really thought about the process, as to how that person actually got to that decision, to set that as the direction. So, I would get direction and be like, “Okay, a worth it order to build APIs, okay, let me go build these APIs”. This is roughly what we need to do.

As I started growing, as I started growing in my career, and as I started taking on more and more challenges, that's been the biggest switch that I've really had to learn;  I really had to internalize and really had to own in practice. Where you get into an environment, where now all of a sudden, you're not being told, “This is the direction” you're being asked or expected to set that direction. You're being expected to have a very strong opinion, and to have an opinion in front of people that might be market experts, when you're not. That might be experts on the data, when you're not. That might be experts on the financials, when you're not; and you have to turn around, and you have to speak with conviction, and you have to speak with, and not just speak but really internalize the problem and articulate the problem with authenticity. You have to be able to speak from your heart, and your gut and say, “This is what we're doing, and this is what we're doing and why” and sometimes, I'm not going to have all the information. But, here's the market forces, here's what I'm seeing. And here's what I'm laying out. You're putting yourself on the line, you're putting yourself out there, you're putting your neck out there. You're basing your decisions on like, this is me, this is my decision making, and I'm owning this. I just find that which to be a really big switch. I find that switch to be a really big switch with more junior people or more people potentially earlier in their careers, as they get later in their careers; when you have to call the shots.

Again, it's one of those things where you have to call the shots, not just for your area, but for lots of different areas that might impact a lot of different organizations. So, now all the sudden, it's not just me building my cute little API over here, but it's me building a whole suite of API's, me building front end tools, me building an accounting solution, me building all of these things that now come together to create a business or to create a product. And, and once you start to have to be responsible for all of those things, I think that it's a very strong and valuable responsibility. But it's also something I think that comes with practice. I think it's one of those things where I see product managers that really truly own their product and are willing to make those calls, and willing to go out on a ledge and say, “No, this is what we're doing” are the ones that tend to be the most successful. Again, it's making bet to one of those things, as long as you're right 51% of the time, you're like me right all the time, but as long as you're right, a good bit of the time, I think really putting yourself out there and owning your product, speaking authentically, and then really kind of owning that decision making, that's the makings of being a really good product.

Hope Gurion: Next we’ll hear from Prasad Gune, who was surprised at how non-product tasks can quickly eat up his time.  Prasad shares how he found the right way to protect his time for all the necessary parts of the product leader role.

Prasad Gune: To address the question of what I found most surprising, as I started up my product management, leadership career as against being an individual contributor. Many things I think, but the one to definitely call out, is how much time is spent in doing non-product stuff. I think I've always  - and it's not unimportant stuff to be very clear, they're all important things; they are things like, building cross-functional relationships, getting to know, folks in the executive team, career development for your team, performance management, compensation management, you know, managing a budget. There are all sorts of things which are so crucial to being an effective product leader. But if you notice each of those things, you might say, career developers a little different, but many of those things are not exactly directly working on a specific product, and if you're not careful, I think the thing you have actually watch out for is that those other things, while important, can end up spending all your time; and you sort of lose connection with the product. And I think that's the one thing that I found, and it shouldn’t have been as surprising as I probably found it to be, so that's probably learning for me. Don't be surprised by things like that. But it was initially, and what I discovered very soon was that not that, you don't do those things, but you do absolutely have to do is to structure and carve out time for the product. If you don't do that, then those other things will take up all your time.

I mentioned a few of the things, but there are other things too, you're opening a new office, you're doing the hiring, you're doing succession planning. All these things matter, and they will pick up 100% -120% of your time, if you allow them to. I think the key is to be focused on those things, but time-box them. It’s not just a question of time boxing them, it's also, I think, you do have to be very thoughtful in structuring product time. In my own case, the way I've tried to structure product time is, I'll set up product reviews I try to do -wherever I've gone, I try to introduce a product review process, where I sit down with the product and design teams. We talk product and product features, and the things that they're building, we tend to do that at least once a week, and that keeps me very close to what is it that people are working on, and also gives a chance for product people and designers to shine. It's not just me, by the way, I get to invite other product executives, or invite other folks from across the company for those sessions. It gives them a chance to sort of show off their skills and abilities to a broader audience. It gives me a chance and the broader exec team a chance to also provide input early into the process. So, you're very close to the product, which you otherwise wouldn't be, but in addition to that, trying to hold regular all-hands meetings. Try to do your one on ones religiously with your direct reports.

I think by I'll spend a minute on that; one-on-ones tend to be, you look at your calendar, your calendar starts filling up and the one-on-ones become the most obvious things of short risk. Without a doubt the thing I've learned through, deep and sometimes bigger experiences, is don't shy from into one-on-ones. Make sure you carve out time for them. I've come to an acceptance that I do a my one-on-ones, once every two weeks, but I spend an hour for them. I found that doing the shorter ones, you end up in a 30-minute session, you end up with just 20 minutes worth of real content with an hour and get at least 50 minutes, you can go really deep. Anyway, those are examples of something that we were there multiple things like that, doing design reviews, doing product reviews, during your one on ones regularly doing skip level meetings with your team members.

And also, you know, doing things like, you know, in my last role I would invite people had worked with before to come and talk product management, with my product team. And it was a great opportunity, many people are looking for ways to expand their repertoires; so they're happy to come. It's interesting for your team to see somebody doing product management in a very different way than that you are. The most interesting takeaway for me from those meetings was not that people, some people come to say great, you hosted most you love the session, but it was the next day with you will come back and say, “You know what? So and so came to speak. I really enjoyed the conversation, but I didn't agree with them on these topics.” I'm like, that's awesome! I love that. In fact, I would imagine SEO is great, I enjoyed everything. And nothing, my life was changed because of it. Well, not that we're worthy. But if you came back and said, "I passionately disagree with this element, or agree with that element", that to me is you’re internalizing it. And so, I find that those kinds of special really useful. But nonetheless, I think, you know, long story short, keeping close to the product. While in managing a bigger team, I think is a balancing act; but one that we have to do so that that can be was the biggest letting.

Hope Gurion: Finally, we hear from Al Ming, who was surprised at how he needed to shift his mindset from just doing it to a more sustainable model of coaching and developing his team.

AL MING: First off, in terms of something I don't think most people realize when they go from being an individual contributor, Product Manager, to being a product leader, is similar to what happens to most folks when they go into management or leadership roles, that they don't realize that the skills that they developed as an individual contributor, do not necessarily equate to the skills they have to learn as a leader. They're always connected, of course, and you can't manage product managers if you don't know what a product manager does; but I think there's a tendency for new leaders to try to brute force success for their teams, by kind of just doing it themselves. Like you almost can't stop yourself, you want to reach out and just show them what to do manually yourself. In some cases, especially with high performing product managers, that works for a little while. You can brute force a couple of teams, you can force them to learn their strategy to set a strategy, you can fix their stories, but it's not sustainable. I think that's one of the things that was the hardest to learn for myself as someone who was a strong product manager, and before that a strong developer, a strong designer, actually, I was a mediocre designer, but a strong product manager.

Stepping into that leadership role, you just want to just do it yourself, and you can't you have to delegate, you to have to coach, you have to jump over that gap between being the strongest IC and being a strong leader and manager. There's a lot of nuances to learn very quickly as you step into that space, and the quicker you can kind of say and admit to yourself, “I don't know how to do this.” Ask for help, ask for help from your cohorts, ask for help from experts, and learn that quickly that these are these new skills you have to develop the better in terms of your ability to deliver great product to teams.

Hope Gurion: The new product leaders that I coach, are often surprised to find out how much of their time is pulled inward towards the leadership team at the expense of spending time with customers and on product development. Fearless Product leaders know that they must rigorously prioritize their time because it is their most valuable resource. They enable their product teams to achieve meaningful goals and create value for their customers and their companies by aligning the leadership team and  removing blockers for their team.

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You can find me, Hope Gurion, on Linkedin and Twitter or subscribe to “Fearless Product Leadership” on your favorite podcast platform to be notified of new episodes.  You will find transcripts, videos versions of each episode as well as more information on my Fearless Product coaching and consulting services by visiting my website, Fearless-Product.com.