Leading with Doubt: A Tool for the Insecure Overachiever

How many of us set an exceptionally high bar for ourselves, and even when we reach it, we feel like it’s not enough? We’ve climbed the corporate ladder and are now leading others, but the rungs we haven’t yet reached are the ones that really have our attention. We focus on relationships. Still, we work too much, we compare ourselves to too many others, and when we’re not receiving feedback, we worry. Are we not leading our people in the best ways? Is there something more we could be doing for them? Is there something important our people are afraid to tell us?

This is the life of the insecure overachiever. Can you relate? I know I can. And when we’re in leadership roles, we crave information. Tools like Leadership Circle are phenomenal, but they’re also expensive. So I’d like to offer you another tool. One that I created out of a necessity for this kind of information. It’s free and takes less than a day to complete, and here’s how it works.

1. Find someone neutral and not in your chain of management.  The typical candidates are project managers, agile coaches, or someone else who supports your team. If you’re working with a coach, this is also another excellent candidate. Whoever it is, find someone curious and known for asking good questions.  We’ll name this person Luca.
2. Luca interviews each of your team members individually. When they meet, he draws this triangle in Miro or on a white board with the following script.

“I’d like you to put a single point somewhere in this triangle for how you view your manager Jennifer.

• If you put it in the People corner, this means Jennifer is focused solely on her people.  Her entire concern is ensuring her people are well cared for, they’re doing work they enjoy, and their growth is paramount.
• If you put it in the Policy corner, this means Jennifer is focused solely on the environment in which we all operate and its organizational policies. She ensures the team remains solid organizational citizens.  She appreciates, tweaks, and speaks the language of the system fluently, especially in the context of how it impacts her team.
• If you put it in the Product corner, this means Jennifer is focused solely on what the team is building.  She recognizes that to stay in business and remain secure at this organization, we must continue to build things that solve our customers’ problems.

Why these three? All leaders are a blend of these with a focus on you the individual, the system in which we all operate, and the mission we’ve been tasked with. However, no leader is ever perfectly balanced so Jennifer won’t land in the center. She also isn’t one dimensional so she’ll never land in any one corner. Otherwise, there are no wrong answers so put your dot anywhere inside the triangle based on where you think it belongs.”

3. The team member places the dot, and Luca takes a pic or screenshot of how the team member answered. He does this for all appropriate team members.
4. Luca sets up time with Jennifer and draws the same triangle and explains the same exercise but his actions vary:
   1. Ask Jennifer to put a dot for where she thinks she is in this triangle.
   2. Ask Jennifer to put a dot for where she would like to be in this triangle. It may be the same answer as above. It may not.
   3. Ask Jennifer to guess how she thinks her team will generally place her in this triangle.
5. Share with Jennifer the triangles each team member drew.  If anonymity is important, remove all names. 
6. Get curious about how Jennifer views the data, how it varies from her self-view, how it varies from her hypothesized other-view, and whatever else shows up.

We’ve armed the insecure overachiever Jennifer with a view of herself, her team’s view of her, and some thoughts for what she wants to work on.  And perhaps Luca and Jennifer decide to do this exercise again in a few months.  If so and to avoid anchoring, don’t share the previous triangle from a few month’s prior until the very end.

Give it a try and tell me what you think. If you’d like a hand, I’m willing to do this exercise with your team and offer you my time to help you overcome the insecure overachiever inside you. Set up a complimentary discovery session by clicking this link. See you all again soon.

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