How to Step into Leadership and Grow a Winning Product Team

Welcome, Hosts, and Webinar Overview

Jake Yingling | 00:00:00–00:02:40
There we go. Let’s go ahead and get started with today’s webinar titled “How to Step Into Leadership and Grow a Winning Product Team.” I’ll be your MC today. My name is Jake Yingling. I lead our client services team here at Productside.

Prior to joining Productside a little over a year ago, I spent 15 years as a PM and leader of PM teams. Most of my time has been spent in the financial services space, but I also had tours in consumer goods, e-com, and the interactive agency domains as well.

I’m joined today by a very special guest, Brooke Huling. Brooke is currently a Vice President of Product for Dell Technologies. Brooke describes herself as a true product strategist with the heart of an entrepreneur. She has over 18 years of product and technical strategy experience and is well versed in SaaS business models, delivering exceptional customer experiences, and innovation at every level.

Brooke will do a far better job introducing herself in just a bit.

We really don’t want the conversation — and I use that word very intentionally, the conversation — to stop after today’s webinar, so join us over at the LinkedIn Product Leadership Group and leverage that leadership group to help you continue to hone your craft, brainstorm with your peers, and follow trends in the PM community. We’ll drop a link to that in the chat momentarily.

Engagement, Logistics, and Productside Overview

Jake Yingling | 00:02:40–00:06:05
During the webinar, we really like interacting with the audiences during these sessions, so throughout we encourage you to ask questions. This is not intended to be a lecture of any sort, so the more interactive you can make it, the better the overall experience.

You should be able to use the Q&A box at the bottom of your screen to type in questions at any time, and we’ll do our best to answer as many as we can. We’ll also reserve time at the end for general Q&A, so load us up.

Let’s talk a bit about Productside. We’ve been around for more than 20 years now. We’re based in Silicon Valley. A fun bit of trivia — our name is derived from the highway that connects San Francisco down to San Jose.

Our mission is to really empower product professionals with the knowledge and tools to build products that matter. We strive to make product people and product organizations strategic. We believe an optimal product organization delivers better customer experiences, increases revenue, and reduces operating costs.

Before we get started, let’s take a quick poll to understand a bit more about our audience. So Michelle, if you’re ready to start this poll, we just want to find out who’s in our audience and what layer or what level they’re at in their career. Let’s take 25–30 seconds now and tell us where you are.

Audience Poll and Transition to the Topic

Jake Yingling | 00:06:05–00:08:05
We’ll give about five more seconds.

All right, thank you, Michelle. So we’ve got a healthy mix — a good amount of folks in the senior management or executive tier, a fair amount of seasoned ICs, and then some who are new to management as well. So a great, a great healthy mix in the audience today.

So Brooke, I’ve done enough talking. Talk to us about everything we need to know about stepping into a leadership role with the product team and ultimately growing that team. And then you can give me the cues of when I should advance the slides.

Meet Brooke: Background, Family, and Influences

Brooke Huling | 00:08:05–00:11:10
Sounds good. Thank you for the lovely intro, Jake. Good afternoon, good morning to everyone who’s joining us from all over the place. I am coming to you live from Austin, Texas, where I am hanging out with my sons who are home from football camp today if you hear any lovely background noises.

Today we are going to talk about one of my favorite topics and something I personally feel is overlooked more often than not, so this is near and dear to my heart. We are going to talk about the transition from rockstar product manager to rockstar leader of product managers — and what that really looks like.

How do you make that decision? What skills do you need to make the transition? How do you grow a happy and healthy, effective team — which sounds easy and amazing but requires a whole different level of thought. And then really, how do you empower your teams to be successful? Our goal as leaders, as we grow, is to grow more new leaders. So how do we do that?

I’m going to reference a number of books and tools and things that I have been fortunate enough to collect over the years, and I will actually share a lot of those with you. We have a list of sources at the end of the presentation that we can talk about as well if anybody needs some extra info.

I would love to have some group participation. I wish I could see all of your beautiful faces, but in the absence of that hopefully we can at least get some good Q&A going. I’m happy to pause and answer questions. We will save plenty of time at the end as well. If you want to save up those questions, we can come back to them later too.

So let me dive just a little bit more into who I am. I mentioned where I’m at. We can move to the next slide, Jake.

I will share just a little inside peek at my life. I am a boy mom — I mentioned two of them, I have three in total. We lead a busy life. So you know, product management isn’t crazy enough, I tacked on three tiny humans to take on the journey with me, and a very, very supportive spouse thankfully who helps me do all of the juggling.

I’m a big fan of Corporate Women Unleashed. You will hear me mention many things today that I was fortunate enough to get from them through a coaching program with Kate Byers many years ago. Amazing group of women in the industry if that’s something that interests you.

I am a Longhorn. I did marry an Aggie. We are in a very, very house divided, so there’s a lot of good fun around here in football season and other sports as well. I was born and raised in Baltimore, moved to Texas, came to UT, decided never to leave Austin from the 90s — and boy has this city changed since the 90s. So it’s been a great ride.

For the fun side — what do I do when I’m not running product teams and all of this other crazy stuff? We have a little place out in the country in Texas. Anybody that has land somewhere, it’s called a ranch. Doesn’t matter how many acres it is, they’re all called ranches. So we have one of those.

I spend a lot of time working on really, really crazy complicated puzzles, which as I’m sure many of you can relate, a lot of what we do in this industry is like a crazy puzzle. So funny enough, that carries over into my personal life as well.

And I would be remiss if I did not mention the Productside. I actually am a certified product owner. I did that course with them many, many years ago when Agile was new — not new anymore — but I got a lot of great value out of that. So I am an alumni.

I’m very philanthropic, so my son and I are part of Young Men Service League. We spend a lot of time volunteering. You will hear me mention that today even in terms of how you are growing and coaching your team. Philanthropy can be a big part of that. It’s great for team building and bonding and other stuff. So you’ll hear me mention some of those things, as well as Landmark.

If you are ever looking for something to help you clear your head, if you are making a big decision and you can’t sort through the cobwebs of your past, Landmark is a great tool. I’m very grateful to them. I’ve done several of their courses as well.

We’ll talk about lots of other fun tools today, but these are just a few that help make up who I have become over the years. I’ve had many wonderful mentors and bosses and amazing leaders throughout the years, teams that I am fortunate and blessed enough to work with, and I am very, very thankful for all of them and for all of the lovely programs that I have been through at various companies.

That all really helps add to our tool belt. So we’re going to talk a lot today about the tools in your tool belt specifically as you make this shift to leadership.

The Nonlinear Product Career Journey

Brooke Huling | 00:11:10–00:17:55
I am going to be really vulnerable for a minute, which by the way — hint — is another key to leadership. I’m going to share a little bit about my story and how I got into this crazy profession and what that career growth plan can look like.

Spoiler alert: it’s probably not linear. There will be some bumps and bruises and a roller coaster, so fasten your seatbelt.

Here’s how all of this got started. I thought I was going to be an accountant. I came out of UT, had that amazing accounting job, was going great, living the dream, bought the sports car, all the things. And then I realized I did not want to be an accountant.

That was shocking to me. I thought I knew for sure, but that just was not the case. So sometimes bad things happen. I was let go from that company.

I took the summer. I worked the hard jobs that I had never really done in the service industry. I did some accounting on the side, and I really dug deep and thought about what I wanted to do.

Ultimately I ended up as a customer database engineer for a software company fixing accounting databases, and I loved it. I loved the challenge. I loved the technology. I loved helping customers.

I found very quickly that that customer interaction was really rewarding. When you could fix their problem — when the accounting clerk calls you in tears because their database is broken and you can fix that — it just felt special to me.

So I was very lucky to do that, be recruited into QA. Now I’m testing the databases. I’m climbing, I’m riding the high.

After a short window of time, I was recruited again. This amazing lady came to me — I just loved her. She was a magnetic person. She dressed the part. She was phenomenal with customers, and she was running our product management team.

She knows who she is. She’s still in the Austin area, now retired. And she tapped me and said, “You have to come to product management.”

That was the high. That was the holy grail. That was the high — I got into product management and I just fell in love.

From there I became a manager. I built a small team. And then things changed. I was there for nine years and it was time to do something different, and I felt like I was in a bit of a rut.

I went to a different company. I was at a startup. I ended up pregnant with my second son. There are these ups and downs.

I was then recruited to Dell, ended up getting that Senior Director title, went to another software company. Same thing — you find yourself going through these ups and downs. You have another child and that just shakes up your whole life.

You choose to go to a company that you find out doesn’t match your culture or is just not what you thought it would be.

You get a 360 review that is a smack in the face because you feel like you’re doing all the right things, but that’s not what the 360 review says. For anybody who’s done a 360 review, I would say most of the time you should read the review with a glass of wine in your hand because it is a lot.

It’s a lot to take. And Jake, I’m sure you know as well, feedback is a gift, but sometimes reading that feedback can be very, very hard to do.

That’s what makes us, right? That’s what makes us human and that’s what makes us leaders. That’s what teaches us how to deal with these ups and downs.

Now, as I’m actually talking to all of you — as I make my next big transition over the next few weeks — I will be moving to a different organization in a different role, still running product, but a slightly different role.

It has always been this: the highs are high and the lows are low, but we have to pick ourselves up. We have to make or find new tools as we go, and we carry those forward to the next thing.

Our job as leaders is to help all of the other people who are going through this. Some of you on this call are at the beginning of this journey and you may be in a high right now. Some of you are on this call because you’re in a low right now and you don’t know why.

You don’t know what happened. You don’t understand why it’s not quite working. You’re just looking for answers or someone that can tell you something magical.

Hopefully this resonates with all of you now that I’ve shared my story. I’m not quite to that CEO goal yet, but I am working my way there. It has been 20 years and I’m not there yet, but I hope to be there someday.

I hope all of you have that goal and you’ve got it written down in your notebook somewhere, so that every time the highs are high or the lows are low you can go reflect on that next step to get you closer to your goal.

You are in good company. We all have the lows and we all have the highs. So with that, I would love to move into some of our polls. I’ll let Jake and team take it away and let’s see where you guys are at.

Jake Yingling | 00:17:55–00:19:05
Michelle’s got that launched already. And Brooke, just really sage advice. I think the next time performance management season rolls around, I’m going to be reading those and digesting those with a glass of wine and bourbon in hand. That’s really good advice.

All right, we’ve got some answers coming in already. Brooke, I think you’re pretty spot on. A lot of folks are on that roller coaster, so I think we’re going to see a lot of good pieces of information from you today. Really looking forward to it.

Deciding Whether Leadership Is Right for You

Brooke Huling | 00:19:05–00:25:55
Fantastic. And for those of you that are linear, that is awesome as well — all good. If you haven’t thought about it, hopefully after today you will start to reflect.

My lovely scribbled rolling line on that slide came from a coaching session I had a few months ago. The coach started the call by asking us to take out a blank sheet of paper and draw our career path. That’s all it took, and very quickly you realize the scribbly line starts to show up with each inflection point.

So how do we make the leap? I am very fortunate — I was in product management, I was in the mine, I was writing the user stories. I think I’ve written tens of thousands of user stories in my career, and the acceptance criteria and all the things. I’ve groomed all the backlogs, I’ve done all those things.

So how do you go from that, where the product is your baby — that is your life, you’re living and breathing your products and it’s every move, every roadmap item, the launches, the highs and lows of the product — you may be sunsetting something, you may be building a new product from scratch; I’ve seen it all.

How do you go from that to leading a team of people doing that?

As much as I would love — and I did, when I was back in my early phase of my career and I had just become a new manager and then a new director — I thought a great product manager made a great manager. Of course, right? You’ve done the job, you know how to do it.

The reality is: doing the job, knowing how to do the job, is a very small piece of being a great leader.

I saw somebody make a comment about women in this profession. This profession is starved for women. There are not enough of us. But it is equally starved for leaders who have that deeper connection with their team.

I would actually say that if we can grow more of those leaders — more product managers who have a deeper connection to their customers, more product management leaders who have a deeper connection to their team — we would start to see more diversity. We would start to see more career growth and different things transpire from that way of operating.

So I will ask all of you some rhetorical questions for a few minutes.

Where are you at in your life right now?

If you’re about to make this leap — if you’re one of those people from the poll who said you’re an IC and you’re considering management, or you’re new to management, or even those of you who are senior leaders or executives, maybe you’re considering your next step — where are you at in life right now and what does that look like for you?

Are you at a place where you can really embrace this kind of shift? That matters tremendously, because we bring to work every day where we are in life. If we’re having a rough time in life, we bring that to work whether we want to or not. Everybody does. It’s normal.

But is it the right time to make that shift?

The thing I learned that was, I would say, the most shocking was where I was getting my joy and purpose from. Because when you’re a product manager, when you’re writing stories every day, when you’re working with engineering and you’re shipping and launching and doing demo days — that’s your joy, most likely.

When you become a leader, that goes away. And you go into the purpose and joy desert for a while.

Jake, I’m not sure if you’ve ever experienced that, but it’s a tough thing to get through, isn’t it? And it’s lonely.

That joy will have to shift. Your joy and your purpose will now come from growing your team and seeing them thrive and watching them on stage.

I will never forget: big conference, it was our conference of the year. I had shifted into a director role. I had this amazing team and they were up on stage. They were presenting. I just did their intro — I did the MC intro, Vanna White off the stage — and watched them present and watched the customers go crazy. Standing ovation every 60 seconds for new features.

That was the switch. I realized my joy was now coming from watching them be successful, watching them get the applause. It wasn’t about me anymore. It was about me getting them to that point.

That shift can’t be underestimated. It can take years for some of you. It could take weeks or months for others. Just talking about that — I feel like the more people I tell that story to, the faster they’re able to make the shift, which is why I share.

I would also say to think about your needs. We’re all humans. Last time I checked, hopefully there’s no bots on this call. We’re all humans. We all have needs.

We all need our health — without our health we have nothing. We can’t do this job without health. And this is a tough, tough profession, so health is critical.

We need our leisure, we need our downtime. We need our connection and our purpose.

Esteem is another one. Is your leader giving you the esteem that you need, or do you need to find that in a different way?

Where are you at with your needs, and how does that map to what you want to get out of your career?

Does that next career step actually meet your needs? If it doesn’t, how are you going to meet the needs of your team?

These are some really important deep questions. I can’t give you the answers unfortunately. I can just inspire you to think about them a little bit.

Where are you at on that journey? Where are you at with your needs? And is the next step — is moving into management — going to meet your needs?

I’ve actually had several people who thought it would. Thankfully I left some space for the communication. After I moved them into a management role, they came back about a year later — and this has happened multiple times — and they said, “You know what? I’m miserable. This is not meeting my needs. I can’t make the transition. I don’t feel purpose. I’m missing my joy.”

Because we use those words and we talk about it openly, they were able to articulate that back to me so that I could actually move them back into an IC role.

There’s nothing wrong with that. They were ninjas, they were rockstars, they were amazing product owners, senior product owners, technical product owners — and management just wasn’t giving them what they needed. It wasn’t meeting their needs.

So really think about those things and realize that when you’re in a leadership position, you are now responsible for other humans and their joy and their purpose and helping them figure out what that may look like.

If you’re not clear on what yours are, how are you going to help them with theirs?

Making the Leap from IC to Leader

Brooke Huling | 00:25:55–00:31:40
So I would say it starts there. The leadership journey starts there. It starts with you knowing where you’re at.

Seek feedback. Talk to other people who have done this. Talk to people who have done this and then transitioned back, and ask them why. Why did they go into management and then come back out? It’s really, really important that this is not just to climb the ladder.

It’s not just because you think it’s the next step — “Oh, well, if I don’t get into management then I’m not doing what my friends are doing, I’m not doing what my cohort group has done, I’m falling behind.”

That is not the right reason to get into leadership in this profession.

It’s really about you and your purpose and what brings you joy. It can’t be just to check a box on the career ladder. And that ladder is not going to be a linear ladder — it will be the roller coaster.

I think by design life is supposed to be that way. It teaches us lots of lessons, and when we’re in those lows I think we all learn to appreciate the highs a lot more.

So with that, let’s move into the next sort of deeper version of this.

You’ve gotten clear on your needs, you know this is what you want, you’ve made the transition, you’ve got the job. They had a role, you applied, you got it. You’re now a manager, a director — whatever it is — of other product managers or product owners, technical folks. It could be a combination.

It could even be product management and product marketing. There are — I don’t know, Jake — how many different versions of hybrid models out there? Thousands. Plenty.

You have to make now this conscious effort because now it’s not just about this great product manager who’s now a leader.

You have to seek out the tools. Nobody, trust me — nobody, doesn’t matter big, little company, something in between — nobody’s going to come to you and hand you the holy grail of management handbooks.

Much like when you have children, there’s no handbook. This is no different. For those of you that have kids, you know they don’t come with a handbook. It’s the opposite. Every day is a new day.

You have to find the tools. You have to ask. You go to HR. You go to your boss. You go outside of your company.

I have found more often than not, the best tools are the ones that I pay for myself — as painful as that is sometimes.

And I will ask for the company to sponsor me. There are different ways to go about doing this, but sometimes you have to invest in yourself.

When we get out of college and MBA grad school, when’s the last time you paid for yourself to develop further?

Do you have a coach? Does your company — will your company — sponsor you for a coach? A lot of them will, but you have to ask. They don’t necessarily love paying for a coach, but they will if you ask.

If you get a coach, the first thing you should consider is getting a 360 review — not right away. Give yourself six to nine months. Forming, storming, norming — get to know your team, get in that leadership role. But don’t wait years.

You should be getting a 360 review. If you’re unfamiliar with that term, it’s basically 15 to 20 people: bosses, superiors, people who work for you, peers, counterparts across your company or business. It’s a good healthy group of people at all levels who have to answer some very in-depth questions about you and your style.

That review, albeit painful and might require a glass of wine, will give you and your coach a year’s worth of topics to start plucking away at.

I can assure you, the best leaders do this often. They do this every year or two. They take the feedback, they work on it, they go pick up new tools. No one is a perfect leader. It’s not supposed to be that way, just like no one is a perfect human.

It’s impossible to be a perfect leader. The best leaders are constantly growing. They’re looking for tools, they’re seeking feedback — as painful as that feedback may be sometimes, it is always a gift whether or not we like it.

Then you take that. You might get feedback that you’re not doing enough for the team — that you’re good at managing up, but you’re not good at managing down. Very common feedback.

In fact, you could get feedback the opposite — you’re good at managing the team, but you’re not good at managing up. So what do you do?

You talk to your coach. Your coach is never going to tell you what to do, by the way. A good coach will just ask you lots of questions. They do these Jedi mind tricks and they make you figure things out on your own in their own special way.

You go online. You find groups like the Productside. You find other professionals like yourself. You find cohort groups. You find other people that are getting similar feedback and you talk about it.

The one thing I will tell you that I’ve learned time and time again throughout my entire career is: if we don’t talk about it, nothing changes.

It’s impossible to fix something — you can’t just think your way through this. As much as all of us ethereal people on this call would love to just think our way out of things, it’s not possible.

We have to talk about it. We have to figure out what’s holding us back. Most of the time it’s something from our past, it’s something that was done to us, it’s something that we learned in our childhood even. Yes, by the way, your childhood impacts you as an adult.

We have to figure out and process those things, and talking about it is what lets us do that.

I mentioned this earlier. I will mention it again: the assumption at all levels is to be really taking those best product managers and making sure that they move into leadership — “the best product managers make great leaders.”

That is categorically false.

In fact, I’ve seen the best product managers fail as leaders. In some cases, they’re the ones who have come back to me and said, “I hate this. I want to go back. Please, how do I go back to being a product manager or product owner?”

Don’t make that assumption.

If you are a leader, be very careful making that assumption. If you are thinking because you’re a great product manager you would be a great leader, I would be careful there too.

Really dig deep and go back to what I said earlier about purpose and joy and making sure that you’re really clear on what makes you tick. You really have to know yourself before you can lead other people.

And my final sentiment on this: now that you’ve made this leap and you’re really thinking about management, give yourself the space to fail.

The highs are high and the lows are low. I will say that several more times.

One of my favorite HR leaders used to tell us all the time “space and grace.” I stole that from her years ago, I use it all the time, give her credit. It is true though.

Give your team space and grace. If you’re a new leader, if you’re taking over this team and you’re walking in the door, give them some grace. They’re terrified of you, even though you may not be a scary person. I assure you, you’re a new leader — they’re scared of you.

Let them get to know you. Be authentic. Give yourself that grace. Give yourself some time. Learn to fail. Go get the tools. Seek the feedback.

Don’t just assume that you can make this transition with no help. That is the most important thing that you take away today. The transition from product manager to manager will require tools.

It requires a support system, and it requires mentorship.

If you don’t know where to go to find mentorship, there are any number of online resources — Productside, myself. You can reach out to anyone in this profession and we can help figure out what the right mentorship model looks like for people who are trying to make this decision, who need a sounding board, etc.

So lots of good opportunities there.

Jake Yingling | 00:31:40–00:33:35
Yeah, this relates to the coach and mentor. As you were mentioning just a few seconds ago, there’s going to be different types of mentors for all different facets of our own career.

But the lesson I had to learn just a few years ago was: don’t be afraid to fire your coach.

We, as individuals, are responsible for our own careers, and we have to determine what we need out of that coaching relationship. If it’s not working, we have to be empowered to call the ball and say, “Hey, this isn’t working.”

Don’t be afraid to go find a new one. So that’s a hard lesson that I had to learn.

Don’t be afraid to cut ties with coach A and go find coach B. It just depends what you need out of your career at that point in time.

Brooke Huling | 00:33:35–00:35:10
Very well said, and I couldn’t agree more. Your coach has to either grow with you or you graduate, you move up — just like school.

The Hard Parts of Leading Product Teams

Brooke Huling | 00:35:10–00:41:15
I would be remiss if I didn’t say it’s not all roses. I think for those of you who have made this leap — there’s lots of you on this call who are already in leadership or an executive of some sort in this profession — you know it’s not all roses.

Every example on here has happened to me and other people I know in this profession.

I hadn’t even started yet. I accepted the role, I was all excited, I had this team. Somebody quit. They didn’t even meet me, they just quit.

What does that do to your psyche? “Wow, they didn’t even meet me and they’re already leaving.” What’s wrong with me? What’s wrong with the team? What’s wrong with the company?

It’s going to happen. It’s not about you, trust me. Although some of us like to get in our own head — it’s not about you.

The team will assume you are coming to shake things up. No matter how many times you say in that first meeting, “I’m not here to make any changes,” that is the exact opposite of what’s going through their head.

You just have to recognize it. You can’t necessarily change their hearts and minds out of the gate.

You have to be authentic. You have to build the trust. Trust is earned, it is not given on day zero.

So know that going in. Know that you really have to work your way up the trust ladder with every person on the team — getting to know them, their families, what makes them tick, their career plans.

Ask a lot of questions. Don’t go in on day one to talk about the product portfolio and all of your ideas that you had about what you want to change. That’s not day one. That comes much, much later.

My other favorite is forming, storming, and norming. I had another fantastic HR leader in my lifetime tell me, forming and storming — along with the norming — take a good six to nine months, even in the best of circumstances.

You really have to think about what that looks like in the product management profession. You’ve got any one new person — so maybe you’re the new person, maybe it’s an entirely new team, maybe you are hiring one, two, three new people for this team. Every time you add a new goldfish to the aquarium, it starts all over again.

You have to get everybody reacclimated. This one new person, whether it’s you or somebody else, can really change the dynamic of a team meeting, of a Zoom call — fill in the blanks.

So really take that to heart and know that it is going to take time. Back to the space and grace for a second: six to nine months is not exactly fast.

If you’re 30, 60, 90 days into a new leadership role and you can’t figure out why the team’s not gelling yet — it’s too soon. Six to nine months in the best of circumstances.

Bull in a china shop — my favorite. Most of us in this profession, admittedly, are A-type, and we like to come in guns blazing. We’re coming in and we’re trying to figure out how we’re going to make these changes, and we want the team to love us.

Chill. That’s all I can say. Take a deep breath. Chill.

Let them get to know you. Go to a dinner with the team. Spend time getting to know them.

If your boss is asking you for results in the first week or even month that you’re there, something is amiss. And I would actually get that sorted out before you even accept the role. Get clear on what your success measures are and the period of time.

Don’t be a bull in a china shop. Go in and really spend time getting to know the people first. People over product.

If you do it that way, they will now trust you. Now it’s a lot easier to have a product conversation because they trust you.

You’ve started to build that relationship with them, and when you start asking them about the portfolio — “Why is that product that way? Why are those stats that way? Why is this not doing well?” — now it’s coming from a place of genuine understanding and not a place of, “I’m the new boss, I’m here to shake things up, and I’m a bull in a china shop.”

So that’s how you shift that dynamic. It’s about the people first, products later.

Communicate. I have always been shocked at how much communication it takes.

Great example: I have an organization of 95 people right now. I have 12 plus or minus direct reports, 95 in total.

To get down to that 95th person, even if you don’t have a lot of layers — doesn’t matter — it takes an amazing amount of communication.

Because — newsflash — people don’t read emails. If they do, it’s like the first sentence at best.

They may not read Teams messages. They’re overloaded on Slack channels, and the list goes on.

So communicate early and often — and five more times. That’s what it takes so that everybody’s on the same page.

It’s that way with strategy, with the changes you do want to make.

By the way, product managers always want to know why. So if you’re a new leader, you can’t come into this and say, “Oh, and we’re going to go do these five new things,” because everybody sitting there is thinking, “Why? Why would we do that? Why do they think that’s a good idea?”

I would say most of us are like five-year-olds — our favorite question is “why.” So know that going in.

And then finally, I would say: check with your team. To build that trust and that relationship, they have to feel like they can tell you what’s working and what’s not.

Your assumption should be that things are working. Not everything will work all the time. And if you change up the dynamic of the team, some things will stop working.

You may have something that’s working great for two years and all of a sudden it just stops working. You have to ask those questions.

I do that — I’ll give you guys a couple of examples a few slides from now. But I do a stop-start-continue frequently.

Sometimes I do it, I have HR do it, I’ll have my team leaders do it. That information is so valuable, because whether or not you agree with it, it doesn’t matter. Now they’ve been heard.

And if they’ve been heard, they trust you. Now you can continue to figure out what it is you need to change.

But I keep coming back to this trust word. It’s the foundation, and we’ll talk a little bit more about that in a minute when we get to tools.

Tools and Frameworks for Growing Product Teams

Brooke Huling | 00:41:15–00:49:10
All right, before I go through my favorite tools, Jake, are there any that you’d like to share?

Jake Yingling | 00:49:10–00:51:15
I just want to add to what you said in a previous slide, Brooke. It’s trust — that’s hugely important.

But I think when I hire PMs, one of the attributes I look for probably more than anything else is this sense of natural curiosity.

I think if we as leaders can pull that forward such that, when we take the reins of a new team and be curious, that’s how we win.

Asking why — be curious about everything and frankly assume nothing.

I think that’s how I found success leading teams: make no assumptions, go in and have those one-on-one conversations with the team members and ask them, “Why are we doing things a certain way? Why is this product still alive? What are we doing and why?”

I think that has lent itself to be super helpful in my career. But yeah, let me digest this one — I may be able to chime in in a minute then too.

Brooke Huling | 00:51:15–00:58:40
Thanks, Jake. I appreciate you sharing.

This is a very short list. There are many, many, many others. I can’t do them all justice — it would be four-point font. These are some of my favorites. These are the ones that I have all of my teams take a look at.

I suggest them to my friends, even some of my family. And so I’m doing the same for you all today.

My favorite, starting with trust, is The Five Dysfunctions of a Team. It is by far one of the best books to really figure out what trust looks like. I believe they call it a leadership fable. It is fantastic.

The next one I would recommend is StrengthsFinder. That is one of my favorite ways to really make sure that everybody is on a level playing field. They understand each other.

I like leading people by their strengths. I want to know what their top five strengths are, and I’m going to focus on those. Because if those are their strengths, then they can become even stronger in those things.

So we focus a lot more on those than we do other things.

And then I also really like Discovery Insights. It’s a great vocabulary. It’s a little bit like a new version of Myers-Briggs. It’s a great way for people to understand each other, have a new vocabulary. Lots of really powerful things come out of a Discovery Insights working session.

I mentioned the Productside earlier. This job is hard. So let’s say you’re getting into product management leadership and you’ve never been a product manager — that happens. Maybe you were an engineer, maybe you were doing something different at one point.

Go get a certification. Go do a product management course. Go learn a product framework. There are tons of resources out there, all sorts of different opportunities for your team to really trust you.

They’re going to want to know that you know what it’s like, that you’ve been there, that you’ve done that, that you’ve written a user story. And if you haven’t, that’s okay — but show them you want to understand what that looks like. I think that’s critical.

And then if you are in that leadership role — let’s say you’ve come up through product management — don’t underestimate refreshing those skills.

I have not been a product owner now for a long time, so I put myself back through the training with my team.

I will go get budget to train all of my new people. I usually pick one or two different options for my marketing and product teams. We have them get certifications. I make sure we keep budget for that every year.

Some of it goes through our corporate training program, some of it we do through outside stuff — but don’t underestimate you having those skills, and them seeing you go through those classes.

Do it with them. It’s a team-building experience, by the way, when you do it with your team.

Then figure out what framework you want to use. It’s good for us, no matter how big or small your company is. Having that language, having something that — when you say, “Okay, this needs to go through concept, this needs to go through a launch plan, this needs an engineering plan” — having a common vocabulary is a big, big part of that day-to-day communication.

It helps eliminate misunderstandings. It helps keep your team on track. So really focus on a framework, a common vocabulary. Productside has one. There are many, many others out there. Pick one and focus on using that so that you can bring everybody together with it.

One of my favorites — and I say this with a smile — is The Five Love Languages. It works for work and it works for home. It works for kids, it works for spouse, it works for everybody.

I will say the one — there’s one love language which is personal touch. I’m not talking about that one, just to be clear.

But everybody has a love language. So when you’re a new leader of a team, one of the first questions I ask people in a kind of roundabout way is what makes them feel valued.

Is it time with me? Is it money? Is it title? Is it some combination? Sometimes it’s gifts.

Notoriously I send people stuff for their birthdays and their anniversaries, even at a giant company, even with 12 direct reports. It’s worth it to me, even if I pay personally, to send them something for their birthday or their anniversary. It means something.

Sometimes it’s Tiff’s Treats. Sometimes it’s a bottle of wine. Once it’s a bottle of bourbon, because I have some folks who like that too.

Sometimes it’s, “I’ll take them to lunch,” just because they want to spend some time.

Really know what their love language is. If you’ve never read that book, it is a life-altering book. It’s very easy to read.

One of the others that I don’t have listed here — it’s on my sources list — there’s a new book. Actually, Marty Cagan just came out with his Inspired second edition. It’s like reading a diary if you’re in product management and marketing. It’s phenomenal.

I highly recommend sources like that, and then have your team read it. Buy them that book for a holiday or for their birthday, or expense it if you can. Not everybody can do that, I understand.

But get everybody reading the same thing, and then after 30 days, get everybody together on the Zoom call usually and have them talk about it.

Do a little book report. Have everybody share what they learned. Use those things as ways to bring your team together, give everybody common vocabulary.

And then I have some team rules, and these are pretty straightforward.

Almost everything is a team sport. We do comp planning — team sport. We do talent reviews — it’s a team sport.

Because it’s a team sport, there’s another rule on this list you’ll see: nobody can lobby me. There is a no-lobbying policy.

If you are now a manager or leader of other leaders, you will very quickly find that lobbying starts to sneak its way in. They will — “Well, I just need to promote this one person,” right? They come to you directly.

No. You’re going to talk about that with me and the whole rest of the leadership team, and you’re going to get feedback from them about promoting that person.

Then we’re going to talk about promoting that person versus another person versus another person.

And at the end of that conversation, the beautiful thing that happens is: even if we’re not promoting the person that that one asked you about, they are now bought in on who we are promoting.

Because you can’t promote everybody at one time — at least we can’t. I don’t know about you all, but that generally doesn’t happen.

Now you’ve got this new layer of trust. They trust in the process. They trust you’re going to bring everybody to the table, and they know you’re not going to let any one person lobby you.

So everybody’s getting a fair shot at pitching their case, and then there’s this weigh-in to buy-in.

When people get to weigh in, even if they don’t get their way, they’re usually bought in — which is the beauty of communicating and doing things in that way.

I also have a general rule: I lift everyone up when I’m communicating outside.

If you hear me in meetings, in other places, I have a team of rockstars. I’m blessed. These are all true things. I’m not being untruthful.

But that is a critical part of being a leader if you’re making this transition — how you talk about your team externally really matters.

The way that you know it’s working is in six months, maybe a year depending on your company, you will have people banging down your door to join your organization if you have an opening.

If you have somebody who has left or you’ve got a new req that you can open, you will have people banging down your door to join because you have a reputation as an organization of being somewhere everybody wants to be.

You are now the popular nightclub downtown with a line around the block. And it is a great, great place to be — especially when you’re looking for more talent.

You want that reputation. It takes a while to get there, but it is possible.

And my final sentiment is to celebrate the wins. Life is hard. Life is short. Work is hard.

We don’t know how long we have, unfortunately, and COVID has taught all of us that in a very, very real way.

Celebrate the wins, no matter how small they are. New person came on board, they ramped up really quickly — celebrate. At the beginning of every staff meeting, celebrate the wins.

It feels cheesy sometimes, but it means something. It’s positive. It’s something to reflect on.

In a big town hall, call people out. Celebrate the wins. Rotate through. Make sure you’re not leaving people out.

There’s always one person who’s like, “Hey, you didn’t mention my program.” That happens. But try to really recognize people and support them and get to know them.

We celebrate births, we celebrate weddings, we celebrate all sorts of stuff. We make a big deal about life events — even with 95 people, 400 people. It doesn’t matter.

The bigger the team, it just means you have to spend a little more effort in making sure you capture all of those things. But I cannot underscore enough how important that is.

Measure, Iterate, and Evolve as a Leader

Brooke Huling | 00:58:40–01:03:10
Last but not least, I wouldn’t be a product manager if I didn’t talk about tracking, measuring, and iterating — in the spirit of Agile.

So much like our Agile development process, you growing in this leadership role — whether you’re deciding to move into one or you’re already in and you’re trying to grow — you really have to iterate.

Everyone should have an individual development plan. If you don’t know what that looks like, there are lots of resources online.

Everyone should have some kind of career plan — you included. The more you know what yours is, the easier it is to help other people.

You should be doing career check-ins. You should be iterating, making sure people update their career plans and you update your career plan on some kind of regular cadence.

That may be six months, twelve months. There’s no right or wrong.

Really get to know people. Get to know what makes them tick. Make sure you get people exposure outside of your organization.

In this industry, especially if you’re in tech, people are going to move around. I have a rule, much like plant the seed and let it grow — I love it when I have amazing people move into other parts of the company.

Now you have a phenomenal relationship with another part of the company. So really get to know them, make sure other people know them.

Then, when they’re ready for a change, they already know these other organizations. You’ve been talking highly about them. It’s very easy to help them move.

And now you have this amazing new resource in another part of your company, which ultimately will help your team be more successful long-term as well.

I mentioned stop-start-continue. Really try to do that a couple of times a year.

Do not run them yourself. Let your leaders run them. Have HR run them. You run one, but don’t do all of them.

People want to talk to other people. Sometimes they feel more comfortable if it’s different people.

At the end of the day, it’s all about searching out, seeking feedback, tools, and refining your leadership skills.

I will leave you with this: leadership is a journey. It is a roller coaster. The highs are high and the lows are low — just like product management, just like our career.

It is never, ever going to be perfect. But you can make it the best possible if you’re always looking at iterating and if you always recognize there is more to be done.

There are more tools, more ways, more tips, more tricks that you can pick up throughout your years.

And with that, I will hand it back to Jake. Thank you all for your time and attention. I hope this was helpful.

Jake Yingling | 01:03:10–01:06:00
Brooke, thank you so much.

I did have a chance to think about some additional tools here real quick. On the left-hand side, to build up the tools for the tool belt — listen, we as PMs in our day-to-day have to be persuasive. We have to influence.

There’s a great book called The Charisma Myth, and I think it’s by Olivia Fox Cabane. There may or may not be a really great 40-minute version of it on YouTube — I think she’s lecturing at Stanford’s d-school about it. It’s fantastic, and I think it really parlays well into managing PM teams.

On the team rules side, if you had asked me this 10 years ago if I’d be saying this — when I was first taught this value — the value is called “assume positive intent.”

At first I was like, “Well, of course. That’s a given.”

I think in my journey, we all don’t assume positive intent — but we need to. And I think it just reinforces that trust is the foundation for success.

We have got to trust one another and assume that we are all out for the same goal, either in the team itself or the larger organization.

So “assume positive intent” is one that I’ve been saying more and more lately too. But I love the examples and the norms that you cite here. I think they’re really great.

Training, Development, and Closing Thoughts

Jake Yingling | 01:06:00–01:10:10
Listen, Brooke, thank you so much again. Really, really great tips and techniques in there, and I just want to say thank you.

As it relates to honing your core PM skills, as Brooke mentioned, I would be remiss if we didn’t plug our own products here at Productside.

Our mission is to make PMs more strategic, help them conceive and deliver products that matter, and our OPM — our Optimal Product Management course — can help you learn and hone those skills and help you build and manage products that matter for you and your team.

So take a look at that.

I also want to plug that we are returning to in-person training. We’ve got Mr. Tom Evans. This is three days of expert instruction and team-based exercises for PMs really of all levels.

So I highly recommend our OPM product, but it’s even more special when it’s done in person.

Let’s take a quick poll. Again, we love data — we are PMs, we love data. So help us understand: how helpful was this webinar in providing you just even one or two actionable nuggets of information on the topic of leadership?

Let’s take about 15 seconds, and we’ll move on from there.

There are lots of great questions in the chat that we can get to. We’re going to get to them, absolutely.

Okay, good. I’m seeing some really high marks in here. So number one, thank you for all the audience participation.

Again, Brooke, thank you for you and your expertise and for sharing your story with us. Let’s get to some of those questions real quick.

Q&A: Start–Stop–Continue, Remote Teams, and Human Connection

Jake Yingling | 01:10:10–01:11:30
Let’s see. Brooke, you mentioned this — so I’m going to throw this one at you right away.

Can you expand on how to conduct a start-stop-continue exercise?

Brooke Huling | 01:11:30–01:13:50
Absolutely. The reason I like it is because it’s simple.

Whether it’s you or HR, whoever it is, you get a team together. I recommend small numbers. The more people there are, the less people will talk.

So the rule of three, five, and seven applies — just like Agile. Very small group.

I would strategically go through by topic. So think of topics that matter to you. It could be communication. It could be team culture. It could be — I see a different question about product strategy versus product tactical activities.

You go through and pick out a couple of key topics, and then you ask specifically of the team. Tell them in advance what the topics are, by the way.

Ask what they want to start, stop, or continue with respect to those topics.

So with communication: “What do you want to start?” Somebody will say, “I think we should do newsletters.” That’s pretty common.

Then say, “What do you want to stop?” They may say, “Well, I think we should stop doing those email blasts every week. It’s not working.”

Okay, fine. These are just data points. You’re collecting data points. You’re not making decisions on the fly. You’re collecting data points.

You may run a few of these with small groups and then aggregate the data.

The most important thing is to share it back out. Share out what you heard. And then I usually get my leadership team together and we start choosing which of those things we’re going to tackle.

You cannot tackle them all. You should not tackle them all. Pick the top two and go after those.

So that’s, in a nutshell, how I would run a stop-start-continue.

Moderator (Jake, paraphrased question) | 01:13:50–01:14:15
Next one real quick, Brooke: any suggestions for leading entirely remote teams?

Brooke Huling | 01:14:15–01:17:05
My favorite. I have had a remote team now for way more than just COVID.

Over these last few years, though, technology has improved. So I’ll list some of my favorites.

Get a — I am a little biased, I work for Dell — but a two-in-one device with the pen so that you can whiteboard and annotate on slides so that it’s not so static.

Fun stuff: Zoom happy hours every month. I have an amazing leader who loves running these happy hours. She finds all sorts of things. There’s games online, there’s Pictionary and bingo and all sorts of stuff.

We include people’s kids. We do Halloween costume contests on Zoom. We include people’s families and pets.

We’ve done music for the holidays. We did a huge holiday celebration. We did a U.S.-based one and then we had an international time-zone friendly one.

You can do these things for free. You can do these things for a lot of money. I’ve done virtual wine tasting where my whole leadership team got a wine case and we had a sommelier on Zoom who walked — I mean, it’s all out there.

You just have to be creative. Like I said, some free, some expensive, everything in between.

That part of the culture, though, when you’re running teams that are entirely remote, that is a huge part of your role as a leader of that team — to keep that culture.

Just remember, they’re all human. They’re craving connection and they’re not going to get that from PowerPoint or back-to-back-to-back Zoom calls.

You have to do more to get people really talking and engaging, even if it is over a camera.

Jake Yingling | 01:17:05–01:19:30
Two things to consider there too — something that, a practice that we’ve started here.

We all suffer from Zoom fatigue these days, and it’s real.

We have started doing walking one-on-ones where we simply hop on the phone and talk to one another.

It’s amazing how much more connected you are over the phone than just looking at someone through a screen. Something about the dynamic just changes, and we’ve seen some really great interactions through just a simple phone call and having that walking one-on-one.

But related to one-on-ones, it’s also creating a space to have 30 minutes once a month where you get together and you don’t talk about work.

Talk to them as if they’re humans, and have that one-on-one connection too — especially with your direct reports, but especially with your skips too.

It’s on us as leaders to really carve out and make that time. It’s hard, but we owe it to our teams to do it. I think that’s super important too.

Brooke, we are at time. Again, I want to say thank you, thank you, thank you. Great session — learned a lot. The audience was clearly, clearly engaged, and I think they found a lot of value in it too. So thank you.

If you have any further questions about this, feel free to reach out to me at Productside. I think, Brooke, your information might be shared as well.

Find us on our website. We’ll do our best to answer any questions that you have. But again, thanks for attending and we’ll see you in the next one. Bye now.

Brooke Huling | 01:19:30–01:20:00
Thank you so much. Goodbye, everybody.