Leader Spotlight: Guiding PMs up the career ladder, with Karen Letendre

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Karen Letendre is Director of Product Management at Brightcove, a video streaming provider. She began her career in proposal management and product ownership at Cigna, where she spent over a decade before transitioning to product management at Upland Qvidian, an RFP response and proposal management software. Karen then joined Brightcove as a senior product manager before assuming her current role as director.

In our conversation, Karen talks about how she helps her team advance in their careers via mentorship, upskilling programs, and more. She shares the basic qualities necessary in product management, as well as any career, to move up, such as leadership skills, communication skills, prioritization, and time management. Karen also discusses her team’s mantra that “clear is kind” regarding communication.

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Helping the team progress in their career

As a leader, how do you ensure that there’s a clear career path for product managers?

As a leader, it is very important to me that our team has a trajectory and growth path for product management, starting at associate level all the way up to chief product officer. To provide this, a clear definition of these paths needs to be easily accessible and understood by each individual. This enables each member of the team to plan their career path and empower themselves to take on new responsibilities and learn new skills.

When developing this, I worked with our HR team to understand the hiring levels at both an individual contributor and management level, as well as how we describe each of those roles. I learned that we had a very solid definition for the individual contributor path, but we didn’t have much definition for the management track.

I did some research on the different types of requirements and responsibilities when you get into each of these different roles, as well as how they differ. In working with HR and product leadership, we revised the product career path, which we now call the career ladder. It covers every level that we hire for in our product team and also provides a short description of what that role is and the responsibilities for that path.

We’re currently in the process of revising it to make sure that it shows a clear delineation of how someone can grow from one level to the next. Along with the roles and responsibilities, we also include the necessary skill sets, because as you progress throughout your career, you start to lean into some skills more than others, so this will help people prioritize which skills are more important to focus on.

How do the core responsibilities and skill sets differ by level within the career ladder?

When you’re starting as an early product manager, there’s a lot more emphasis on information gathering, analysis, and the business analyst role. You’re starting to collect information, put it together into stories, and form a hypothesis of where you want to move forward. As you start to progress, it becomes less about information gathering and more about how you can take all the information you’re getting from different sources and turn it into a meaningful story. This means working with ambiguity and starting to distill what the true problem is and whether there’s a business case for it.

Further, you’re leaning more into communication and relationship-building as you progress because you want to validate all of that information with your stakeholders, both internal and external. Are you caring about the right things? Is this shaping up correctly? As you move up in the career ladder, storytelling and communication become even more powerful, but at a higher level. You start to go from the weeds of the information to the bigger picture and strategy and how they all connect.

Depending on where you are in that path, the skills you have around communication and storytelling as a foundation start to formulate how well you can communicate at a higher level.

How do you help product managers navigate any challenges that they might encounter as they grow into these more strategic, relationship-building roles?

One of the things that the team, as well as myself, have struggled with at times is understanding how to transition from tactical to strategic.

There’s a lot of information available online and in books, but what I like to do with each one of the members of my team is start to understand where they sit on the career ladder and what the right next step on the ladder is for them. It’s important to understand what they are struggling with, what they are focusing on and enjoying, and, most importantly, where they are succeeding right now. If we understand their strengths and weaknesses, this will give us a clearer path to overcome their challenges and give us something to work toward. Strategy might not be the only area to focus on, but can be something to build an understanding of while they improve other areas.

Self-managing and looking at the bigger picture

What do you find to be the ‘basics’ as people grow into the higher levels of product management?

It comes down to leadership skills, communication skills, prioritization, and time management. These are the basics that you need in any career — they’re not exclusive to product management. Honing in on each one of those areas can help anyone on the team make sure that they’re focused on the right things.

It also gives them time to take a step back from being in the weeds. A lot of times we get buried in the day-to-day, and we don’t give ourselves the breathing room to look at the bigger picture. It’s important to ask yourself, “How is what I’m doing contributing to the team? How does it contribute to cross-functional teams, and how do all of these work together to impact the business?”

When it comes to strategy, it’s important to look at the bigger picture. Where do we want to be? Where do we need to be, and why do we need to be there? Understand your competition and your market, and how any of these things can change at any point. Also, make sure you’re staying flexible in adapting to those changes.

Beyond those skill sets, what do high-performing product managers need to demonstrate to move up?

One thing that is going to help anyone shine is being able to self-manage. Can you take a step back and evaluate how you’re contributing to their team, the company, etc.? For some folks, that means time-boxing throughout the week. For other folks, it means putting little 30-minute blocks in your calendar periodically to get certain things done so that communication with leadership is done before they even ask.

Anticipate the needs, communicate them, and be clear in your communication. If someone can do those things consistently, then that means they are good at anticipating and understanding what it takes to contribute to the business and the team. As you start to get into different levels, the only thing that changes is the level of information and the responsibilities necessary. If you can start learning these fundamentals early and grow it into a habit, that will carry you very far in your career.

The importance of leaning on your team

PMs wear so many hats. Where do delegation and effective workload optimization come in?

Just because you own something doesn’t mean you have to be responsible for doing it all. Delegation is a core aspect. A lot of PMs, at various levels, can be intimidated by delegation because they think they’re putting their work on somebody else’s plate. It’s not really about that. We’re all helping each other. We’re all one team. We all can take different pieces of the puzzle and work on it together, and asking someone for help is not a sign of weakness, it’s a sign of strength.

When I see folks trying to take everything on themselves, I view that as a red flag. It’s a sign of someone who hasn’t quite figured out how to leverage others to get their work done. When you get into those higher levels, you receive a much higher amount of information with shorter turnarounds. You absolutely can’t get all of that done in the timeframe that you need to get it done. You have to lean on your team. The earlier you can figure that out in your career and build relationships with others to help you, the better off you’ll be.

Once you recognize high-potential product managers on your team, how do you, as a leader, ensure that they have exposure to the right projects or leadership opportunities?

Many folks will want to raise their hand for everything that seems interesting or high-profile. This may sound counter-intuitive but this is where the art of saying no becomes really powerful. Of course, everybody wants their hands on high-profile projects, but if you take on too many things, you run the risk of performing them at a lower quality. Yes, you will get recognized, but you may not get recognized in the way that you want to be.

When ensuring that product managers get the right recognition, it’s important to find opportunities that will allow them to stretch without falling over. With that said, it’s OK to not take everything. It’s OK to not be on the coolest project — there’s always going to be another one. Prioritization and time management are key here. Because even on projects that may not seem high-profile or high-visibility, if you can execute them really well, that’s going to shine brighter than if you were to do a very fancy project at half capacity.

Creating an upskilling program

At Brightcove, what strategies do you use to help your team members take ownership of their own growth and professional development?

Something I started on the team earlier in the summer was what we call an upskilling program. I did a lot of research and put together a document of all the different areas that product management touches throughout one’s career. Then, I reached out to members of my team to share it with them, because as we were working through the career ladder and where everyone’s strengths and weaknesses were, there was an ask for specific training and programs.

Yes, you can pay consultants to come in and teach you, but that gets very costly. And a lot of this information is readily available — It just comes down to providing yourself with the structure to self-manage. So that’s what I focused on. I provided the structure and tools, got input from the team on how to run the program, and everyone on the team was excited about it. They wanted to learn more. They wanted to grow themselves, but they didn’t always know how and didn’t have the bandwidth to do it themselves.

From there, we decided that every week, we’d pick a topic. I gave them a maximum amount of time, like two hours maximum, to spend on it. If they spend less, great, but my expectation wasn’t more than two hours. At the end of the week, everyone comes together to share what they learned. I also asked them to implement a start, stop, and continue framework. Essentially what are you going to start doing, stop doing, and continue doing based on what you learned?

The goal was not to get them to start making immediate changes but to build a toolbox for themselves on every topic. That toolbox would allow them, at any point in their career, to come back to, “What did I learn and what were the things that I wanted to start doing? What were the habits that I had that I wanted to break, and what were the things that I was doing that were good that I needed to continue?”

What were the results of the upskilling program? Was it well received?

It started about six months ago, and since then, we’ve grown the group. They want to keep going. We’re at the end of the lesson plan, but we’re going to continue it. They have taken that start, stop, continue framework and start applying it in their work life. I’ve gotten tremendous feedback from executives and from other members of my team on the improvements that they’ve seen. That helps my team really embrace what they’re doing. It’s at the point now where they want to take over it themselves and self-manage the initiative.

I’m super proud of them and the program. All I had to do was just give them structure, show them how to find the information, and demonstrate how they can incorporate it into their role every week. That’s ultimately helped them figure out how to grow themselves going forward.

‘Clear is kind’

Are there specific tools or frameworks that you encourage your team to use to identify areas of improvement, set goals, and reflect on their performance?

I love OKRs because they provide a clear set of goals for you to march toward. I also am a huge fan of force multipliers. That was the catalyst for our up-skilling program. If you can take what you’ve learned, help instill that in others, and then give them the framework to carry that forward, that’s amazing.

Another tool, which sounds really basic, is clear communication. Clear is kind. I say that constantly to the team. A lot of the time, when you’re stuck in a tough situation or have to have a tough conversation, being ambiguous about your needs and what you want to accomplish is frustrating. We try to make sure that as a team, we adopt a “clear is kind” mantra in everything we approach, whether that’s how we respond to feedback, how we address our career growth, etc.

Lastly, how do you give your product managers the freedom to experiment with new methods or approaches while ensuring they have the necessary guidance and accountability to stay on track?

I am a huge fan of failing fast. I want my team to experiment with different methodologies and approaches. I first ask my team to talk me through how they want to approach the situation so I can understand their thought processes. I’ll make sure they check their biases and assumptions before moving on, and provide them with guidance on different ways to approach it or things to consider. In general, I don’t want to tell people what they can and cannot do because they’re not going to learn from that. They have to experience it themselves to grow.

I also am a firm believer that if you’re the smartest person in the room, you’re in the wrong room. I want to learn from my team. They’re all very smart. Some ideas or learnings will come up from them that are way better than mine. And that’s fantastic.