We’re often focused on doing the “right” things “right.”

For some, like me, you fight a tendency to do things perfectly. I’ve been working on that since I was a kid and probably always will. “Perfect” is subjective to each of us, but it usually shows up when we believe there’s only one right way to do or be something, that we need to follow a rule, or comply with a certain requirement of “right”.

Three years ago, I was reviewing a coaching case with Michael Hudson (CEO, Hudson Institute of Coaching) which is something that we do fairly often as coaches – usually a coach will work with another supervising coach on a specific case, not revealing names or divulging any confidential or identifying information. Anywho, I was reviewing a case with Michael, and I was worried that I wasn’t handling this client case “perfectly.” Of course I wasn’t saying that out loud, but the way I was describing the situation (my analysis of what I thought was going on; the mental battle I was having with what-to-do and how-to-do-it) most likely sent him a signal that I was focused on only one “right way” of handling the situation. I was trying to formulate a script in my head of how I thought things were supposed to play out with this client and my coaching work with them. I was fixated and locking myself up.

After he patiently listened to me (for a while ), he simply said “what would messy look like?” I’ll never forget that.

Just asking that question to me in that moment freed me up to think about new possibilities, and to help me move past what I thought should happen. We talked for a few minutes more and I walked away from our conversation with new perspective, more agency, and a sense of relief. My “right” was a prison, and “messy” was the coaching prompt I needed to let go of “right” and get back to being curious about my client and what they might be experiencing.

There are many forms of “right”, but the beautifully surprising thing is that there are even more forms of “messy” that work out better in the long run. Messy doesn’t mean careless. It means that we can trust ourselves to be resourceful in exploring other options of what to do when we’re faced with a difficult situation. We’ll need to be a bit vulnerable to allow that “messy” to happen, but it might be one of the most liberating things you can do for yourself.

As a leader, allowing “messy” to happen usually means less micromanagement, greater psychological safety within your team, and more innovation. As a coach, it will help you stay present, partnered, and curious. We’re all better off with having a little more messy in our lives.

Here are a few resources that I’ve been sharing recently…

// “Reconsider Work that is Good Enough” – I love this quote from a recent HBR article on what it costs in being a perfectionist manager. Lots of practical examples and suggestions to help manage perfectionist tendencies. (8 min read)

// The Humble Check-In – kicking off a project or program with a simple check-in helps us all center and focus on the reason we’re together, and to unload what might be on our mind. It also shows everyone that it’s OK to share things with each other, starting on Day 1. (8 min read)

// “How Can I Help?” – I love the simplicity of this question. And if we’re truly interested in the answer, we’ll hold ourselves back from offering what we think would help. (2 min read)

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