How do senior leaders make hard decisions they keep putting off?

Why does a decision stay almost made for months?

A postponed decision is often waiting on a different question. Take a founder weighing whether to replace a head of sales. The open question may be what that role needs to do at the next stage of the business. Until that is answered, the first question cannot close, and the decision keeps coming back onto the calendar.

Naming the real question is usually the first piece of work. The real question tends to sound smaller and more specific than the decision that was being carried around.

What does a private space to think change?

Most senior leaders have few places to say a half-formed option out loud. A team reads reactions into it. A board hears it as a position. A coaching session is consequence-free: the leader can say the option, hear it, and drop it without anyone acting on it.

Dave's working view is that a leader's one job is to decide and adapt. Reflection comes first so that the choice, once made, can be acted on and adjusted as new information arrives.

How does Dave work through a held decision?

Sessions are 60 minutes, virtual or in person. Dave asks questions, and the leader does the deciding. A session moves through reflection and choice, and each one ends with what the leader is doing next and why. Action and information-gathering happen outside the session, and what the leader learns from them comes back into the next one. Dave calls this the Readiness Flywheel: each turn leaves the leader more ready to act on the next decision.

What kinds of decisions does Dave work on?

Personnel, product, partner and positioning decisions that a leader wants to make and has not yet made. The leader has the authority to act and the decision sits with them.

What if the leader already knows the answer?

Many leaders already know the direction and say so in some form: I know what I should do, I just haven't. The work sits in the step between knowing and doing, and that step usually has a specific obstacle that can be named in one conversation.

What is the next step?

A 30-minute intro call with Dave is a fit check. Dave listens to what is on the leader's plate and says honestly whether coaching suits it.