Managing Managers - A Challenging Transition

Every career, like life, has a few constants – one of them is change.  We all face transitions sometimes big, sometimes small, but each time with new challenges we may be ill prepared to handle even when we know they are coming.  Much has been written about transitions and career changes, especially the big ones such as becoming a first-time manager or experiencing a major organizational change.   Michael Watkins has created some of the most comprehensive works on career transition covered in The First 90 Days and Your Next Move – two books every leader should have in their library.   

One challenging transition that I have found less has been written about is the shift from managing a group of individual contributors to managing managers who each have their own team of individual contributors. 

For me personally this was arguably the most challenging transition of my career.  I wasn’t blindsided by it.  A thoughtful and insightful leader who I was privileged to work with told me it was coming, and that it would be the biggest challenge I had faced yet. Despite the heads up, I still struggled.  

I had already managed multiple teams successfully. Each team had 5-6 direct reports who were all individual contributors. I fancied myself as a reasonably good manager as team engagement was high and the teams produced good work. I had strong relationships with my team, we had many solid proof points of our success, and the team culture was extremely strong. That was of course why I was being given the opportunity to take on the next challenge – managing managers.   

Specifically, I was promoted to Senior Director of Product Management and given the task of building up a fully functioning and high performing product team starting with a small core group. As a lifetime learner I read as much as I could, engaged with peers who could provide insight on the transition, and developed what I thought were clean and clear plans to help me.  

• Cultivate trust across the team. 

• Set a clear vision and align on the strategy to get there. 

• Create transparency and effective communication both up and down. 

• Ensure clarity on how each person can grow and help them on the journey.  

Understanding the tactics, while certainly a crucial step, was just that – the first step.  Unfortunately, there were key shifts in how you go about executing the bullets above that differ from how you might execute similar principles when managing a small team.  My learnings took time and along the way I made mistakes that negatively impacted people I managed and genuinely cared about. Here are a few lessons I learned the hard way, and what I did once I figured it out in hopes they may help others avoid the same missteps.  

Your Product Is Your People  

This may be the most important lesson I have learned as a product leader. I picked it up in Marty Cagan and Chris Jones’ product management leadership must read – Empowered. It was a lightbulb moment for me. As a product leader it's 100% true that you are accountable for the results of your product portfolio – but as you grow in your career what you do changes. When you are a product manager or even a group product manager, oftentimes you are directly enabling product success through your actions. When you become a product leader managing managers this all shifts.  

If you’ve properly empowered your teams, essentially very few if any of the key product decisions are made by you directly. The bulk of your time shifts and now must be spent on creating the environment for success for your team, clearing away obstacles, coaching your managers to become excellent product leaders, and helping them elevate the skills of their product managers. When done well the outcomes take care of themselves. The product and the portfolio are successful because your teams are doing the right things on a day-to-day basis that drive good decisions, great customer outcomes, and positive business results.  

Unfortunately, early in my career as a young manager I focused on accountability of the product outcomes directly. I felt that my personal and professional success was directly tied to it, and while I recognized I needed the team to be able to do their work, when push came to shove, I didn’t always let them. There were a few times when things got very tough where I not only stepped in, but I also took over and it destroyed the trust I had worked hard to develop. They needed my support, they needed me to manage external factors like challenging stakeholders, a demanding CEO – they needed me to create the environment where they could do kick ass work. Instead, I stepped in and tried to do the work.  

When I read the statement ‘your product is your people’ it all suddenly clicked. I realized I was spending too much time in the products and in the detail, and not enough time recruiting, coaching, developing, cultivating an engaging positive team environment, and elevating the talent and performance of the individuals of the team. Once I made this shift, I saw team engagement go up dramatically, the team delivered amazing results for our customers, and my own personal mental health improved dramatically. One of the hardest parts of this shift was getting the trust right, and then actually letting go so the team could fully do their thing.  

Cultivating Trust Is More Complex and Takes a Lot More Time  

When you are a manager with a team of five cultivating trust is hard. However, with five people you can be aware of what each member of the team is doing at a pretty detailed level. Developing personal relationships is straightforward if you are putting in the time and effort, holding regular 1:1s, making sure you take the time to ask about their lives and their families and genuinely caring about who they are as a person. Lastly, coaching and helping to the team develop are just the two of you – you are the one dedicated and supporting everyone’s professional development. This work is hard, but the tactics seem straightforward if you are willing to dedicate yourself to following them.  

When you shift to managing managers, the scale goes up, and a layer of abstraction is inserted in your team. It’s no longer just you and the people you directly manage, which was hard enough. You now manage 4-5 Directors who are each managing 4-5 members of their own team. Whereas before you were staying in the loop on the work, personal lives and professional development of a handful of people – now it's 20–30 people and there are layers involved that you must navigate thoughtfully. To develop trust with all members of the team, to make sure each of them genuinely believes you believe in them and are dedicated to helping them achieve their full potential - it’s a different level of hard. You need to create personal relationship with your direct team and cultivate skip level relationships without undermining your managers.  

This is another area early in my management career I struggled to get it right. It’s a super hard balance to be close and connected with the team, but not too close. When I first became a manager of managers I decided to focus heavily on my managers, the people that directly reported to me. I saw them as my core team and that I needed to really focus on our relationship, developing their careers, and supporting their work. Now an elevated level of focus there was right, but my mistake was being too distant with the rest of the team. I was concerned about overstepping my managers and undermining their ability to lead their teams. The result was we simply weren’t a cohesive unit. We worked more like three different teams, and the individual contributors didn’t really trust me, because they didn’t really know me. I also couldn’t openly trust them because I didn’t know them either.  

As I grew in my career and saw the negative repercussions of my initial approach, I made key changes. It took a bit of refinement as I didn’t have anyone side by side to coach me through it. There is a whole suite of activities and systems I put in place to help manage a team of 30, but when it comes to getting trust right there were three key things, I believe created the most leverage in improving results and the team dynamic:  

1. Build personal relationships with everyone – take the time to meet with everyone on the team regularly. When I joined my last organization in the first 3 weeks, I met with every member of the 35-person team 1:1. We talked about our backgrounds, our passions, our personal lives and our professional goals. I followed that up with regular 1:1s at a minimum 3x per year with every person on the team in addition to ad hoc conversations via chat or email. These conversations were deeply insightful about the people I had on the team, gave me insight into the core challenges they were facing, and helped me develop a real relationship that set and supported a foundation of trust for us that was critical when things popped up throughout the year. The result was engagement scores on the team exceeded Great Places to Work’s benchmarks for the top companies.  

1. Celebrate the small wins – most teams are fairly good at celebrating major launches and big wins.  Where I have seen tremendous value for the team is taking time to celebrate the small wins that happen every day. Product and technology jobs are hard and can oftentimes be a bit thankless. But every day someone on the team is doing kick ass work and crushing it. You just have to listen and look for it. I have a few strategies to gather these small wins both from my team and our partners in Engineering, Design, Data or Operations. Each Friday I would send ‘Thank you’ notes to each person thanking them for their work and for being on the team. That note was always extremely specific about what they did, that was great, and included all the leaders I thought were relevant. I encouraged those leaders to pile on their gratitude. The result was at the end of the week someone who did great work that might otherwise never have been noticed got to end the week feeling appreciated and others got to see and even take part in expressing gratitude. I found that this simple act of gratitude went a huge way to showing that I was aware of their work, that I cared about and valued their work, and that I was grateful they were on the team.  

1. Clearly Set Expectations and Over Communicate with Your Leader – leadership tactics have evolved dramatically over the last 30 years. There are a lot of ideas floating around and there are leaders out there who still work under foundations and principles they learned in the 1990s.  It’s important that you understand your leader’s perspective on your management approach, that you both be aligned on that approach, and that you regularly communicate what you are doing to manage your team.  I did not do this effectively and my leader and I were misaligned.  I didn’t communicate about the professional development plans of my leaders.  When one of my leaders showed up to present to key senior management leaders he was thrown off.  He expected me to be doing the presentation because of the audience.  I was giving a leader on my team exposure with senior leaders, to show what she was capable of, and continue her growth.  What my leader saw instead was that I had delegated an important meeting because I didn’t recognize its importance.  I had assumed he’d understand what I was doing.  This was when I learned how important it was to overcommunicate professional development plans and where my team was on their plans with my own manager.  To make sure I was truly clear with my manager about what I was doing and why. I have since followed that approach, I have found great support for what I am trying to do, and we go in together and aligned which is key not only to my success but to the success of the person I am trying to elevate.  
   

The transition from manager of a small team to managing a team with multiple layers is a big one, especially in product management.  While these are not the only changes you’ll need to make if you are in this transitional stage, to me, they were big ones. Getting those right helped set the foundation for some of the other key changes that were also necessary such as clear strategies for:  

• Communication up and down the team to ensure alignment.  

• Expressing your product vision and strategy in a way often enough so that everyone understands it and can also help others outside the team understand it.    

• Putting in the product operations and management systems in place that will ensure the team is working effectively and efficiently.  

For those of you who have also made this transition successfully where did you struggle? What helped you overcome those challenges?