🤯 Being Too Helpful

Many of you have asked me to share notes from real coaching sessions and here is a recent session I hosted.

• The coaching client:
  An experienced operator who had worked in fast moving consumer internet.

• The problem:
  He was acting like part of the executive team instead of a board member. It was frustrating the founders who were expecting a different type of working relationship.

• The result:
  The founders felt they were being managed by him in times of crisis. They needed someone to help on HOW rather than WHAT.

When he started speaking, he was fast and breathing shallow. His hands were dancing away. He listed a bunch of his challenges.

Board meetings felt slow. The conversations were too broad. People spent too much time discussing problems he thought could be solved in ten minutes.

In his operating career running a ridesharing and quick commerce business, speed and decisiveness had been a strength. He had made a name for himself as someone who gets things done, but he had burnt himself out in the process.

• When numbers were down, he acted.

• When marketplace supply was tight, he acted.

• When a competitor launched a new discount or promotion, he acted.

He made small decisions quickly and got his team moving.

But it was also how he now showed up in board meetings.

He was telling me about a recent board meeting. A problem came up. He had given the team his answer almost immediately.

I stopped him.

• 🔵 “What happened after you gave them the answer?”

• 🟣 “They had a path forward.”

• 🔵 “Did they come up with it?”

• 🟣 He paused. “No.”

• 🔵 “What might be the issue with that over the long term?”

He thought he was helping the team move faster but he was taking the problem away from them. Eventually:

• The founder stopped thinking out loud.

• The team stopped exploring and brainstorming together

• Everyone started waiting for his view.

He was solving the short-term problem but he was creating a long-term problem.

We looked at what happened inside him when a problem came up.

• He felt a rush.

• His mind got busy.

• He saw patterns and had ideas.

He felt useful again.

This was the kind of work he knew.

High stakes. Fast decisions. Clear action.

We spoke about the discomfort that comes with the kind of value that is harder to feel in the moment. The kind that relies on delayed gratification.

• There is no immediate result.

• No team running off to execute your plan.

• No quick dopamine hit of satisfaction.

We gave the two versions of him their own names and identities.

• The Fixer:
  He sees a problem and jumps in. He brings speed and certainty. He likes being needed.

• The Steward:
  He still has a point of view. But does not need to take over every problem.

We started to discuss how the Steward might show up in the most important moments:

• He asks questions first.

• He gives the founder room to lead.

• He helps the team see what they might be missing.

• He leaves the decision with them but is available if needed to input.

I asked him what The Fixer would do when the next problem came up.

“Jump in. Diagnose it. Tell them what I would do.”

I asked what The Steward would do.

“Ask what they see. Ask what they’ve tried. Ask what decision they need to make.”

We agreed on one small experiment so he could start to shift his interactions.

At the next three board meetings he would pause before giving his views.

He would notice the urge to jump in. The leaning forward. The faster breathing.

Then he would ask one honest question before offering any opinions.

• “What do you think is really going on?”

• “What have you tried so far?”

• “What decision do you need to make and by when?”

The question could not be a question masquerading as a direction. It had to be a real question.

The goal was to stay in the room and increase the depth of the room - without taking over the room.

The things that make us successful in one role can get in the way in the next one.

• Speed can become impatience.

• Experience can become overconfidence.

• A strong point of view can become control.

He needed to stop proving his value by fixing everything.

His job was to help the room work better rather than proving he was the best operator sitting in it.

When we met again he shared how he had made the shift. It had come with teething problems but he felt he was being valuable in a different way.

The team he worked with also noted the shift in presence that he made which in turn helped them make smarter and more thoughtful decisions.