"I really messed up in coaching this leader."

I shared this with a coach I was mentoring the other day (I don't like the term "coaching supervision"). I told him that years ago, a client told me he was swamped and needed help managing his time and productivity. I immediately jumped into solution mode; my mind flooded with apps, a new calendar system, workflows, and truisms.

I had this.

But I didn't.

I hadn't asked enough questions to uncover what was really happening. I missed the fact that he was having trouble saying "NO" to anyone, so he was overwhelmed. That was the issue.

Whether you're leading an organization, having a planning conversation with your spouse over dinner, or just navigating life, we often compound our suffering if we get too rigid in what we think is true or right or the direction to go in.

This reminds me of the ancient Taoist parable, often retold by philosopher Alan Watts, about a farmer:

I want to be clear: having a direction you want to go in is important. There are times when you do have an answer. Of course, there are times when your hunches are accurate.

The problem is when we forget or confuse our hunch or hypothesis for truth. Our choices narrow, and additional information is invisible to us. Our field of vision becomes too narrow, and we can miss critical information.

So, it's important to hold what you think as a hypothesis.

I often visualize holding a small bird in my hands very gently. Hold your theories, hypotheses, and beliefs like a little bird. A way to practice this is to borrow from the story above.

Use the word "maybe."

Maybe

Stick that on the back end of your assertion; it'll help loosen your grip, soften your hold:

• "I know what he needs... maybe."

• "Oh, she is not seeing the whole picture!... maybe."

• "This won't work. I know it won't... maybe." And a follow-on: "Maybe I haven't figured it out yet." (this last part opens things up a bit, yes?)

What about a concern that too much "maybe" thinking could lead to decision paralysis? How do we balance remaining open while still taking necessary action?

Find a Balance Point

The 'maybe' approach isn't about permanent uncertainty – it's about productive uncertainty.

Think of it like driving at night. Your headlights only show you 200 feet ahead, but you can still make a cross-country trip. You hold both the clear direction (your destination) and uncertainty about specific conditions ahead.

For example, when leading a team through a major change,

• Hold a clear direction: 'We need to adapt our business model for sustainability.'

• Hold the 'maybes' about the specific path: 'Maybe our first approach needs adjustment based on what we learn.'

• Take action: 'We'll start with this pilot project while remaining open to course correction'

The key is to act decisively while maintaining the humility to adjust based on new information. It's not 'maybe we should do something,' but rather 'we'll take this step... and maybe we'll learn something that helps us take an even better next step.'

What about in more complex situations?

This can help navigate complex, multi-stakeholder situations. For example:

Consider a tech company facing declining employee engagement. The CEO's initial reaction was, 'We need better perks and higher salaries to boost morale.' But by using the 'maybe' approach, the leadership team discovered something deeper:

'Maybe it's not just about compensation' 'Maybe we should talk directly with teams before launching solutions' 'Maybe there are systemic issues we're not seeing.'

Holding these 'maybes' and conducting deeper conversations revealed that the real issues were about decision-making transparency and career growth. Teams felt disconnected from the company's direction and couldn't see their path forward. Middle managers were overwhelmed and defaulting to top-down decisions.

Instead of just increasing salaries, they:

• Redesigned their planning process to include more voices

• Created clearer career frameworks. Invested in management training

• Established regular town halls for strategic discussions

The result wasn't just improved engagement scores - they saw better innovation, reduced turnover, and more effective cross-team collaboration. Had they stuck rigidly to their initial hypothesis about perks and pay, they would have spent more money while missing the real opportunity for transformation.

This multifaceted solution emerged not from certainty but from their willingness to hold their initial assumptions lightly and remain curious about what they might be missing.

The 'maybe' mindset can help leaders uncover and address root causes rather than just symptoms, particularly valuable when dealing with complex organizational challenges.

Remember: Maybe 

So it's good not to be sure.

Don't be.