Navigating the transition to a leadership role

Three years ago, I accidentally found myself in the position of product leadership.

My manager was going on maternity leave and would be away for six months, and she was delegating everything to me. From one day to another, I became the product leader of a tribe of three product teams and a manager to four product managers. I knew it would not be easy, but it didn’t feel like an impossible stretch.

Then the universe decided to increase the difficulty level of my first product leadership experience by a millionfold. Within six months, four major things happened:

1. Our company had a reorg
2. My manager decided to not come back
3. My tribe went from three product teams to eight
4. And I went from managing four product managers to 12

What was supposed to be a healthy stretch suddenly became a complex situation that highlighted how completely unprepared I was for this role. And the impact of this unpreparedness was two-fold:

1. On myself — I felt like a headless chicken. I didn’t really understand what the role was all about and didn’t feel like I had the right skills for it. I was constantly stressed, frustrated, and insecure
2. On the people I was supposed to be leading — I got feedback from my team that I was unable to give them any clarity. They didn’t feel that they had the right environment and support to succeed

The thing is, my story of unintentionally finding myself in a leadership role is a pretty common one. There’s a good chunk of us product leaders out there who became leaders because there was a gap that needed to be filled, and we just happened to be there. We got asked to step up and it didn’t occur to us to say no. This, unfortunately, makes my story of ineffective and bad product leadership also a pretty common story.

That’s why I’m writing this article for all you potential product leaders and managers of potential product leaders. I hope to share the scope and challenges of a product leader, tips for aspiring product leaders to prepare for a leadership move, and tips for managers of aspiring product leaders to help your team prepare for the role.

That way, when you find yourself face-to-face with opportunities for leadership roles, you can confidently say yes because you know you already have the tools to execute on your new scope.

The scope and challenges of being a product leader

To prepare to be a product leader, we need to understand what exactly we’re preparing for.

What does being a product leader mean? What are the accountabilities of one? And what makes a good leader? Let’s jump in.

Providing a strategic direction for the organization

When we become product leaders, we’re no longer just defining objectives, strategies, and results for our product team. Instead, we’ll have to do it for the multiple product teams that make up the organization we’re leading.

We have to define an inspiring vision and mission for our organization, and design a strategy that will enable the organization to contribute to the company’s overall goals. The strategy should not only inspire and motivate our organization to action, but also empower them to make decisions moving forward.

Personally speaking, this is probably one of the most fun things a product manager can look forward to doing as a product leader.

On the flipside, there are a few things that a new product leader might find challenging with this scope:

1. Understanding the broader industry, business, or company context — As PMs, it’s very common to have a narrow focus on our own scope, our expected product outcomes, and our immediate stakeholders. However, as product leaders, we will be expected to:
   1. Have a deeper understanding of our industry, emerging trends, regulations/policies, and corresponding market behavior
   2. Constantly be able to connect our organization’s operational context and product outcomes to the company’s revenues and costs
   3. Have an intimate understanding of what different product teams are building, outside of what we used to build ourselves
2. Defining a strong product/portfolio strategy and communicating them clearly — Defining a strong vision and an accompanying strategy that is well-aligned with the company’s business goals can be a complex exercise, especially at a domain or an organization level. And a lack of buy-in from senior leadership and stakeholders can lead to misalignment and difficulty in executing
3. Handling uncertainty and change — Life and people are unpredictable, and so is the industry, the market, and even our own organization. We might be in a stable environment today, but tomorrow might bring an acquisition bid, a strong competitor, or a new disruptive technology. When we’re not used to handling these kinds of uncertainties, it’s very easy to find ourselves in stress that we can transmit back to our teams

Setting up the organization for success

When we become product leaders, it’s also our job to make sure that our organization is empowered to execute on the strategy by providing them with the correct environment to operate in. And how we do that is by:

• Making sure that their organization has the right budget to operate properly
• Hiring the right talent so the organization will always have resources and capacity
• Defining processes to help the team be productive and be aligned with company policies

So what are the challenges that a new product leader can run into when faced with this responsibility?

1. Securing and managing a budget for their team — For new leaders, being able to translate strategies into a necessary headcount can be hard. And the challenge does not end here; we often need to defend the headcount we want to hire to if we want to secure the budget in the first place
2. Hiring talent — When our budget gets approved, product leaders need to hire new team members. This means needing to understand what the requirements are for the incoming product manager. What skills and expertise does the successful candidate need to have? And more importantly, how can we evaluate candidates correctly to make sure we’re hiring the best fit for the role?
3. Recognizing and rewarding the team — In short, this means salary increases and promotions. We need to be able to evaluate our team’s performance fairly. How do we decide if somebody performed well and if that merits a salary increase or, better yet, a promotion? And how do we decide how much? How do we ensure that the people who didn’t get any reward will maintain their engagement?

Helping our team grow in their roles

As product leaders, it’s also part of our responsibility to grow the next generation. We must use our experience and expertise to:

• Help our team improve their skills and their performance
• Help people gain perspective about their situations
• Help people understand their strengths to come up with the right solutions

This means that we shape the culture of our organization — seeking accountability and raising the bar for everybody.

But this is not easy, especially for new product leaders. And we might find ourselves faced with the following challenges:

1. Balancing leadership and empowerment — As the more experienced product person in the room, it may be very difficult to find the balance between giving very specific guidance (aka telling them exactly what to do) versus giving teams the space to exercise their decision-making skills, take ownership of their work, and learn from their mistakes. We may fall into either extreme of being too much of a micromanager or too hands off
2. Providing constructive and continuous feedback — Giving constructive feedback is a very important skill for product leaders. Being able to give helpful, actionable, and kind feedback is even better. When not done well, this can lead to demotivation or even unhealthy conflict with our teams
3. Tailoring coaching and mentoring style to the individual needs of the team members — There’s so much diversity that we can face in our teams, like level of experience, personalities, and cultural background, to name a few. And one style that works for one that may not be a fit for everybody else. Unless we learn to understand the individual needs of our team members, the way we coach and mentor them may not be effective at all

Staying well and happy ourselves

Some of the challenges we may face can impact us in a more personal way:

1. Feeling stressed and overwhelmed — The role of a product leader can be very demanding. As we have seen, it requires having to wear many hats that have their own scope and responsibilities. This may lead to stress, burn out, and demotivation
2. Managing impostor syndrome — Suddenly being put in a position to make high-stakes decisions quickly, train and empower people, and also stay on top of the business and industry can be daunting. This may trigger low self-confidence and a feeling of not being ready or capable to do the job well. And this feeling can have a lot of impact on our performance and motivation
3. Handling criticism and failure — New product leaders are prone to mistakes. And that’s ok, it’s part of learning. But it can be hard, especially when these mistakes are paired with very strong feedback from the people we work with

Tips to help prepare for the transition to leadership

Now that we have a better understanding of what’s expected from the product leader, it’ll be easier to prepare for it! When the opportunity comes by, we no longer will be be caught by surprise.

Here are some things I can recommend you to start doing as soon as possible to start preparing for a product leadership role.

Prepare to give strategic direction

First and foremost, read your company’s financial reports! Know where your company stands in terms of revenue and expenses.

Next, stay on top of current news and trends. Immerse yourself in industry and technology news and white papers. Go to conferences! Read the publications! Zoom out!

Lastly, have a genuine curiosity for what other teams are building. Get to know what they do, what their challenges are, and how they’re contributing to the company goals.

Prepare to set up teams for success

Engage your engineering manager counterparts to understand their decision-making process on when they need to hire more people and why. This will help see their needs holistically and staff them correctly. Also, volunteer to be part of hiring committees or interview processes. This will help you really understand the personality and skills the teams are looking for.

Be curious and pay attention. Understand why new people are getting hired, why you got a salary increase (or didn’t), why new organizations are designed the way they are, and the criterias your leaders used to make those decisions. This will all help you be an effective leader when it’s your turn to be a part of these conversations.

Prepare to help teams grow in their roles

This seems self-explanatory, but constantly ask for feedback from other people. Give feedback to them too. This is helpful not only to know what your improvement areas are, but to build a practice of sharing feedback openly and continuously with your peers and leaders. Read Radical Candor!

Further, volunteer to mentor more junior PMs within the team or within the company. You can also find mentoring and teaching opportunities outside of your company to connect with new faces and perspectives.

Finally, read relevant materials that teach you how to relate with other people, understand their motivations, and manage them. A few great examples are The Culture Map, Strong Product People, and Becoming a Manager.

Prepare for the personal challenges leadership can bring

Aspiring leaders can prepare themselves by getting a coach for themselves. A coach (or mentor that you look up to) can help you really focus on what’s most important, set clear boundaries, and detach yourself from difficult situations that might have a negative impact on your mental health.

Tips for managers of aspiring product leaders

If you’re reading this and you’re already in a leadership role and are managing aspiring product leaders, then it’s also your responsibility to make sure they’re ready. After all, not only is it part of our responsibility to grow the next generation product leaders, but we’re also expected to have a succession plan in the event that we have to vacate our roles for other opportunities.

Here are five things that I recommend you to start doing to prepare your current product managers to take up the product leadership mantle at any time.

1. When hiring new PMs, involve aspiring product leaders throughout the hiring process. Work with them to define the job descriptions, include them in the interview process, and share with them your criteria for deciding who to hire from the candidates
2. When possible, volunteer aspiring leaders to be part of projects or initiatives to take your place. Support them throughout it as well
3. Expose aspiring product leaders to presentations or other communication with senior leadership and stakeholders. They’ll have to do a lot of this if they want to move into leadership, after all
4. Practice giving and receiving feedback with aspiring leaders. Constantly ask them for feedback and work with them on their structure. Share feedback regularly with them too so they get used to the practice of sharing feedback openly and continuously
5. Lead by example. Provide clear guidance to the aspiring leader and set expectations on what you want them to be autonomous on

Conclusion

The shift from individual contributor to leadership is not an easy one to make. It requires a change in mindset, new sets of tools, and a stretch in one’s ability to cope with different scenarios all happening at the same time.

When unprepared, this can be overwhelming and stressful. Lacking preparation can heavily impact an aspiring leader’s performance and motivation. And worst-case scenario, health as a constant barrage of stressors can lead to burnout.

But an aspiring leader doesn’t have to start their leadership journey like a headless chicken! There are a lot of things that can be done to help them understand the scope, build their toolkit, and stretch their mental and emotional muscles, such as exposure, delegation, and training. And to get them ready is a shared responsibility between the aspiring leader themselves, and us, as their leaders.

Featured image source: IconScout