Some mess is ok
When you start writing code, every bug seems like a personal failure and every code review comment about missing a test twists the knife. But, over time you learn not every line of code needs test and all software has tons of bugs. Managing is similar, but failures hit harder as the 'missing test' is someone missing mentorship. However, your time and energy have real limits. If you devote energy to getting the individual mentorship, you may be dropping the ball on hiring an engineer who could mentor them.
This is hard, but at the end of the day, your primary job as a leader is to ensure the company is making money (or on the right track to). That focus may cause you to make tradeoffs that you as an individual are responsible for but cannot fix. The superheros are the people who can bend that arc over a long period of time, not who heroically put bandaids on everything and burn out quickly.
You have to sleep. The mess will be there tomorrow, but so will you.
Make your own moments of joy
As your role changes, you no longer get joy from shipping products.
You have to actively dig for things that make you happy. Those happy moments may be from re-engaging a teammate or coaching someone through a difficult conversation.
An important note about remote work is that I do believe making moments of joy as a manager is meaningfully more difficult over slack and video calls as you don't see people's attitude change over time - either positively or negatively.
Energy is everything
I thought that when people encounter a difficult problem they would read, research and discuss how best to solve the problem. However, most of the time, you have 3 min in a meeting and have to move on. In reality, small quick wins made day over day is how you make something great. Managing your energy so you can fully engage during those 3 min is critical.
When you encounter a difficult problem, you could you stay up late looking for different perspectives of people who have encountered the same thing - sure! However… after the 9am meeting you have 12 other active projects which need your attention and some urgent and important issue will probably come up at least once per day. You need to have the energy to both respond productively to the urgent issue and continue with the active threads.
Fundamentally, a strong ‘manager of managers’ are can have large impact out of a small bit of energy. This generally requires simply having seen lots of problems and being able to quickly map that experience on new problems. For me, part of writing this document is to ensure many of these lessons really stick, so that I can retrieve them in a 'low energy' way in the future.
A negative point costs 10 good points
Good days and bad days are normal.
However, in roles where you interact with the a large number of people on an irregular cadence, bad days become extra costly. A key stakeholder may think your bad day is your normal state or take the bad day personally.
Say you express frustration in a non-productive way, like 'ugh no one cares about our team' - lets call that a 'negative point'. This is different from being stern or insistent with your viewpoint or ‘hugging the elephant’ with a unifying statement like ‘I know many people are frustrated by x, I hear that, and the path forward to digging us out of this hole is y’.
That negative point is costly. It may take a meaningful number of positive collaborative experiences to correct simply one ‘negative’ meeting with these infrequent partners. People generally assume positivity, so but a negative experience can lead to people dismissing your feedback and not taking your concerns seriously or simply dismissing you to others.
In general — if you want to express negativity or express how a process made you frustrated, make sure it is worth it and ideally framed toward some solution or growth.
As a leader, your job is to quickly rally people behind issues you think are important. If you are seen as overly negative, the issue you bring up will be written off as you expressing lots of ‘concerns’ and not taken seriously.
NOTE: Asking people to put on a mask of positivity is asking people who experience frustrating working conditions to do more stuff. In addition to that being unfair, it has a low likelihood of working. Your responsibility to your team is to identify these issues, and then to coach and support individuals in digging out. However, sometimes the person experiencing those frustrating conditions is you in an unsupported environment — putting on that mask of positivity may be the only way to actually get to a more positive place.
Lean into vulnerability
Some people can lead with an iron fist. It…isn’t my style. I lead better through vulnerability, admitting where we are at and where we are trying to go.
Acknowledge things that are not being addressed and validate experiences to move forward. However do not mistake this transparency for a real story that brings people along.
Stay true to your definition of good
Trust yourself and know when to ignore corrective feedback and when to really dig in and listen. This is another area where having trusted peers can really help.
For example, I recently didn't receive feedback well that I thought was unfair - was like 'you failed in H2 because you didn't run a marathon in under an hour'. The failure there is significant but is really about failing to build a relationship with that person and having a conversation about reasonable expectations. It takes a certain confidence or a great network of peers to help you stand up to that feedback and then see the real problem.