Managing Managers: Words of Wisdom from Experienced Engineering Executives

I Asked Managers of Managers I Look Up To for Advice As I Transitioned From Team Lead to Director of Engineering

Daniel Korn
7 min readJan 5, 2022

I recently stepped into the role of Director of Engineering at Lemonade. Though I’ve been leading teams for quite a few years now, managing managers is a new challenge.

Left to right: Eti Noked, Shay Cohen, and Anton Drukh.

I turned to managers of managers, whom I value and don’t work with on a daily basis, to gain a wider perspective on what it takes to succeed in this role:

I asked them 4 questions:

  1. What worked for you and helped you succeed?
  2. Have you experienced failure? What would you have done differently?
  3. Were there any resources you found helpful as you grew into the role
  4. What piece of advice would you give your past self before entering the role?

Their answers were so insightful that I’ve decided to share them in this blog post, in the hope their wisdom will be useful for others.

Here goes.

Question #1: What worked for you and helped you succeed?

Anton: Just as two different people would code differently given the same challenge, two different managers would manage differently in the same situation. You need the fine balance between accepting other people’s strengths while at the same time drawing lines to prevent disasters.
Don’t expect your reports to manage the way you did. Distance yourself from how you’ve done the job that is now theirs but understand and communicate the ‘why’, and let them find their own way. Help them transcend your achievements, don’t limit them to your definition of success.

Eti: What helps me succeed, besides the obvious which is building a collaborative and efficient group, is establishing good relationships with peers, colleagues, and interfaces. Part of your job is to remove barriers and improve your unit’s KPIs. You’ll need your co-workers to work with you to make sure your unit can succeed. It takes a village. It can also help you expand your influence and make a significant impact within your company.

Shay: I started out replicating the “old” way of working from previous companies, roles, and I later pivoted. You can do a lot of testing to see what works and create your own style of management.

First, build relationships with your direct reports and constantly ask them for feedback. Secondly, set a clear vision for the group with well-defined goals/KPIs. Lastly, transform the team leads into a “first-team”. Work together as a team and collaborate with your peers as one team and less protecting their team’s agenda.

Question #2: Have you experienced failure? What would you have done differently to avoid it?

Eti: A manager should avoid making all the decisions themselves. You’ve hired/promoted managers, let them lead their units. It might be obvious for experienced managers, but it is even more important with “junior” managers. Guide them, ask questions and help them find their way. It might be different from the way you used to do things, but it’s important to let them rise. Be there to offer support, and back them up in case of failures. Either way, they will learn and evolve as a result of the process.

Anton: Two things come to mind. One, to under-do the delegation, and basically hand-hold the manager in their role. Their personality and independence should be seen and felt by their team, and if they see you not letting go, they won’t trust their manager either. The other is the exact opposite. Overdoing the delegation, basically not having a clear answer to how you help the manager reporting to you to succeed. Don’t leave them hanging, expecting them to only come to you when they don’t know what to do. I’ve experienced both of these failures myself, more than once :)

Shay: There are a few “don’ts” I make sure to avoid:

  • Don’t compare your way of managing your old team, to the new team leader. Don’t assume there is only one management style (your style) or try to enforce it on your leads. Let them find their path.
  • Don’t judge anyone’s performance based on their first few weeks of work.
  • Don’t work directly with team members without involving the team lead.
  • Don’t forget to talk with your employees to identify blind spots overlooked by your leads or you.

Question #3: Were there resources you found helpful as you grew into the role?

Eti: There are some great communities for managers in tech that I participate, learn and consult in, like “Engineering Manager IL” (Hebrew) and “Baot Managers”. Personally, I recommend finding someone you appreciate and asking for help or guidance. I’ve found that people mostly enjoy guiding and mentoring others. It’s very beneficial for both sides. I didn’t find a lot of reading materials for the higher-level management roles, but I do recommend “The Management Playbook” by Brendon Allen and “The Culture Code” by Daniel Coyle.

Shay: I continue learning and immersing myself with relevant books on management, leadership, and psychology. I constantly read or listen to something. I also take classes and workshops as much as I can. I try new things I learn with my directs and adjust my way of working.

There are many books I found helpful. Here are a few:

Anton: As a leader of a distributed team, seeking knowledge on diverse engineering cultures was very helpful to me. Reading material distributed through the amazing newsletter, as well as learning from the wonderful community was very helpful. My advice is not to dwell too much on reading — things become theoretical in a sense, and you may feel a false sense of confidence. Instead, make it a habit to gain an objective perspective on your daily experiences through these constant fountains of curated knowledge. Also, and I cannot stress this enough, seek some type of a support circle. The value of speaking to individuals going through the same challenges as you, but not being part to your daily work, was transformative for me.

#4: What piece of advice would you give your past self before entering the role?

Anton: We speak a lot about impact and influence, and how managerial roles require a switch in sources of dopamine. What worked even more for me is the realization that I need to learn more and more about myself as my role becomes more and more influential. As you get promoted, the stakes grow higher, and you may think that you need to trust your gut more and more. After all, what you’ve done so far has gotten you to where you are, and it’s a good place, so just do more of the same, right? Wrong. A bigger role requires you to gently doubt your strengths more than ever before, and use the daily interactions you have as an act of ‘polishing the mirror’ in which you see yourself more and more clearly with time. What kind of a leader are you? What are your true beliefs and strengths? You’ll find yourself shedding more and more expectations of yourself as part of your growth, rather than adding more and more expectations of what you should be doing. Had I heard this advice early on, I may have had an easier time seeing myself in that mirror :)

Eti: The tip I would share with my young self is that your impact now is not around writing code. As a team lead you occasionally have the time to do some hands-on, but it’s not your greatest impact as well. As a manager of managers you get to shape your organization, and you need to take the time and focus on managerial tasks, such as mentoring, planning ahead, and being thoughtful and aware of your employees needs and growth ambitions.

My Takeaways

While all the answers above are valuable, there are 3 takeaways I wish to focus on during the coming months:

  1. There are different styles of management and it’s likely that my reports won’t manage the same way I did. My job is to make sure they are aligned around the motivation and focus on the outcome.
  2. Hand-off/macro manage — give your leads the autonomy to run their teams and make decisions so that their team members develop trust and confidence in them.
  3. Find ways to proactively help your managers succeed and grow, do not wait for them to come to you.

Final Thought: Paving My Own Way

As I navigate my new role, I’ll figure out my way and adjust to managing, growing, and empowering leaders. I’ll give myself room to try out new things, and follow up with what works and doesn’t. Stay tuned!

I hope you’ve enjoyed my post and that you’ll find it useful. If you have tips from your experience or pitfalls to avoid, please share them in the comments section below or on Twitter.

Originally published at on January 5, 2022.