Paradox and Leadership: A Client Story

I live for the 'ah ha' moments and new connections made in the intimacy of a one-on-one coaching conversation. I want to share a story from a session this week because I think it has broad value. Let's see if I can articulate it well, because when I'm in the moment with a client it feels so real and so important, but later it's often hard to put words to.

This client had recently experienced a public setback at work for an oversight on a project where certain quality standards hadn't been met. Luckily, the oversight was inconsequential, but its nature was such that had it happened in a different part of the project could have had severe implications. We were using our time to debrief the experience in order to extract some learning.

We talked about visualization as a leadership tool. (There's plentiful research demonstrating the power of visualization, especially with athletes). What if this leader replayed their actions from the project in their mind, was there an opportunity at any point where they could have and would have taken different action?

Nothing immediately came to mind for specific actions, but what did emerge somehow through the magic of the coaching conversation, was the client's mindset. They revealed how they were so focused on success and meeting the timeline, "tunnel vision" took over. So I did what coaches do and asked a risky question: was the force at play here, that appeared to be optimism, actually denialism? They said “yes!” and threw their head back and laughed, which told me we’d hit on truth.

But wait, how can what appears to be optimism actually be denialism?!

This client was denying the possibility that something could have been missed. They were busy convincing themselves they were ready. For them, to ask the question, "What might I have missed?" would be to invite delays, invite problems, invite diversions on the path to success. Who would do that!?

In reality, though, asking the question, "What might I have missed?", as pessimistic as it felt to this leader, was what was needed to get them out of "the tunnel" and ensure success. By going to that uncomfortable place of facing the possibility of a mistake, this leader was actually investing in success.

This would be new territory. It felt like a delicate balance between a focus on forward motion and a willingness to pause and scoop up any missing pieces. It was a balance between feeling confident and dedicated to bringing the project over the finish line yet accepting the possibility that they were human and could have missed something.

So what we were really talking about is an essential leadership skill: the ability to simultaneously hold two seemingly opposing viewpoints. Zen master Shunryu Suzuki once said, "where there is paradox there is truth if you have the eyes to see."

The opposing perspectives need to live together in order to keep a leader in balance. Here are some examples:

  • "This project is on track. And yet, there could be problems with this project."

  • "I am focused on success. And yet, let me check if there's anything that might impede my success."

  • "I'm optimistic we are doing well. And yet, is there anything we're not doing well?"

  • "Everything looks good from where I sit. And yet, let me look outside my box."

Playing devil's advocate, when done harmoniously with optimism, is a healthy, helpful leadership skill that brings success.

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