Questions for a panel about managing managers

A moderated a panel about managing managers during digital transformation stuff (organizations getting better at software, doing the DevOps, etc.). Here’s my vision for the panel and the questions we churned over. We didn’t directly answer all of them, of course. The panel was great! The recording should be up soon (it says September 10th 2020).

The idea/point/premise of the panel

In larger organizations, there are layers of managers, in a good way: teams aggregate to a manager, that layer of manager aggregates to another, then somewhere there’s executives, and, I don’t know, the mythical shareholder. Everyone has a boss. I want to discuss what it’s like to be the boss of all those managers and help them transform into all the existing, new fangled agile and digital transformation stuff. Most of the discussion I encounter is about individual staff and the product teams (those working on software or running it), but I don’t hear much about the management structures above those teams. Also, it’d be interesting to talk a little about what exactly things like “servant leadership” mean and how one manages their career (gets promotions, more compensation, etc.) when they’ve moved from being The Boss to a servant (to be tongue in cheek about it).


  1. We’ve heard the notion of servant leadership, which sounds, you know, helpful. Can you give me an example of what that looks like though, like an actual one that happened?
  2. I was watching a webinar that Jana did recently on her white paper. In the Q&A, they asked attendees something along the lines of “do you ever think of your organization’s vision and strategy, does it ever determine what you work on and how?” As I recall, almost zero percent of people responded yes. This seems like a critical tool for managers to use if they’re setting up autonomous teams that need to make decisions on their own – they need to know the principals, the goals. How should managers be moving beyond facile vision and strategy?
  3. For years, I’ve heard about “the frozen middle,” managers who don’t want to change despite the urging and permission of executives (“above” them) and enthusem of staff (“below”). Is this cliche real? If so, what causes that frozen-ness?
  4. (Following on from that), when you’re managing managers, what are you doing in this new, agile, world? Are you a servant to the servants?
  5. There are occasionally “accidental managers” who sort of ended up there. But most of them have been pursing a career of going “up” the meatware stack. They want to grow their career, which usually means responsibilities, the glory and power that goes with it, and the rewards. So, if you’re a servant to people below you, how do you end up managing your career?
  6. As you push responsibility down to teams, what are safety nets you put in place as they figure it out?
  7. What are some the first things you delegate?