Leaders: I hate to burst your bubble ... (actually the bubble should go)

This is a cautionary tale of a senior executive. Consider this a case study—a composite of stories from colleagues and me—told in the first person for expediency. Meet “Sebastian.” He was the head of his department. I’d known him for a couple of years. We came up the ranks together, though he was senior to me, but still we managed to bond over the years. He moved from being a big thinker / get his hands dirty kind of manager, to a manager who needed an advance team to prep him for even a coffee. His team wanted to protect him, but the down-side was he became insulated.

The meeting. I was asked by him to get on his calendar to preview a program he had chartered—a 30 minute meeting to talk about what’s happening and what’s to come. The meeting, which he described as “top priority” and urgent was scheduled for 7 weeks out. And then the advance meetings and check ins begin from his team. What am I going to talk about? Is anyone else coming to the meeting? Can I provide bios for each person? (It’s just me and a team member he knows). And of course make sure my materials (I’m providing a deck, right?) are delivered at least 3 weeks in advance, appropriate for black and white printing (Sebastian is concerned with cost cutting so no color ink!) and finally the presentation must be printed double sided since Sebastian really cares about reducing waste! The list goes on.

The handlers. In all I receive 8 emails with instructions from his team on what I need to do to prepare for this 30 minute meeting, not counting the number of times the meeting gets moved. None of the instructions actually cover any questions or content related feedback. It’s all what I would call “handling”. By the time I make it to the meeting I am pretty amused/exhausted. After all, I know this dude. He’s my partner in crime. The meeting starts with him reviewing the deck which I don’t really intend on using since this is more of a discussion and he’s thumbing through it and complains that it’s hard to follow since it’s printed double sided. And then he quips everyone insists on printing double sided and it’s seriously annoying. Then he had to take a call and stepped out of his office.

The Whiteboard. Sometimes I’m diplomatic and affable, and other times I’m loaded with truth bombs. In this moment, I decide on the magic of the whiteboard, and began to draw out —infographic-style the “journey” I took to get to this meeting. I wrote the numbers in large letters.

30 minutes

18 pages

7 weeks

3 people

Then I explained....

30 minutes

  • informal meeting between 3 colleagues for an update on a project we all know and care about. Simple?

18 pages

  • of instructions/requirements for things like biographies and whatnot which has nothing to do with the project

7 weeks

  • to get this scheduled not to mention the 7 times the meeting got rescheduled

3 people

  • not involved in the content above but who took up a ton of my and my teams’ time. Those 3 people focused on insulating and creating extra process which it turned out Sebastian didn’t even want.

Sebastian walked back in and apologized for the delay. He looked at the whiteboard curiously as I narrated my observations. I ended with: What if you removed yourself from your bubble, even a little? How much more could you get done? What is hidden from you that you could become aware of? How much more productive would you and your team be?

So that happened. Time was up and we ended on that (awkward) note. Sigh. I left seriously nervous and worried as he was very quiet. (Surprised? Offended? I didn’t know). I went home and had a giant glass of wine. Or Tequila. You get the point. I sat at my computer and wrote and email saying thanks for the feedback and I looked forward to next steps. I gave him a link to the HBR podcast episode with Tasha Eurich on Self-Awareness. Then I said something like “hope I’m not banned from using your whiteboard.” I didn’t sleep that night. I was anxious that I had burned a bridge. And then the next morning he responded to my project comments and not a word on my whiteboard tangent.

Epilogue. We kept working on projects together. His team backed off quite a bit, from me and others I came to learn. I think about this conversation a lot, because while I meant well, I worry I could have been less flashy in my delivery—having a more open and empathetic conversation.

My takeaway. Executives and leaders are busy, often under high pressure and literally running back to back. But what I’ve learned is it’s important to not build walls so you are removed from the teams, context and challenges around you. Let things be messy sometimes. And let people share uncomfortable truths.

What do you think? What would you have done? Would love to hear your own take!

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Leaders & Teams: The trap of “handling” someone versus giving candid feedback