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By Randall Kaplan
An hour with a coach can disappear into a detailed account of everything that happened since the last meeting. We may leave feeling understood but still uncertain about the decision that brought us there.
The session becomes more valuable when we arrive with a clear question and enough evidence to examine it. We don’t need to solve the problem beforehand. We need to make the problem visible.
For 25 years, I’ve coached hundreds of entrepreneurs, business owners, and executives. The work becomes concrete when we can move from a broad frustration to the situation, decision, or behavior we actually want to change. Preparation helps us reach that point sooner.
“My team needs to take more ownership” may be a useful starting thought. A specific example makes it possible to work on the issue.
Perhaps a manager returns every pricing exception to us even though we believe we’ve delegated that authority. We need to decide whether to clarify the boundaries, develop the manager’s judgment, or change the approval process.
That decision gives the session a focus. It also reveals questions we may have skipped. Did we actually explain the authority? Does the manager have the necessary information? Have we reversed previous decisions without discussing why?
The more clearly we describe the situation, the easier it becomes to examine our own role in it. That can be uncomfortable, which is one reason the preparation matters.
Before the session, we can separate observations from interpretations. “The manager asked me to approve three exceptions” is an observation. “The manager refuses to take responsibility” is an interpretation.
Both belong in the conversation, but they should not be treated as interchangeable. The coach may help us see another explanation that changes our response.
Relevant material might include a role description, a short exchange, or the wording of an agreement. We should respect confidentiality and share only what is appropriate for the engagement. A concise summary is often sufficient.
We can also note what we’ve already tried. If a previous conversation produced no change, the details of that conversation may matter more than our conclusion that it failed.
One useful preparation question is what we secretly want the coach to confirm. We may want reassurance that a colleague is unreasonable, that our plan is sound, or that a difficult decision can wait.
Recognizing that preference helps us remain open when the conversation challenges it. Otherwise, we may spend the session presenting only the evidence that supports our preferred conclusion.
Extreme Preparation® includes examining our assumptions before they become the foundation of a decision. In coaching, that may mean bringing the fact that complicates our story rather than leaving it out.
We can tell the coach where we feel conflicted. “Part of me wants to give this person another chance, and part of me is avoiding a hard conversation” is something we can work with.
If the issue involves communication, we can rehearse the actual conversation. Saying the opening aloud may reveal that our intended message sounds accusatory, vague, or more complicated than it needs to be.
The coach can respond with a likely objection and help us examine how we handle it. Do we explain the expectation? Do we listen? Do we retreat from the point as soon as the other person becomes uncomfortable?
We should have room to try again. A better second attempt is useful evidence of learning, especially when we can identify exactly what changed.
The purpose is to leave more prepared for the real interaction. Insight matters most when we can carry it into a decision or behavior outside the session.
Before the session ends, we should understand our next action and what we’ll learn from it. That might be holding a conversation, testing a delegation agreement, or gathering information that would change a decision.
We also need a realistic time to act. A commitment that has no place in our week is easy to admire and postpone.
At the next session, we can return with what happened, including anything we avoided. That honesty allows the work to build. We’re developing our ability to prepare, act, examine the result, and adjust. The value of coaching grows when that sequence continues between the meetings, where our leadership actually takes place.
Randall Kaplan is a serial entrepreneur, investor, and executive coach. He’s a co-founder of Akamai Technologies and the founder and CEO of JUMP Investors, which has invested in more than 100 early-to-late-stage companies, including Google, Seagate, and Lyft. For 25 years, he’s coached hundreds of entrepreneurs, business owners, and executives. He created Extreme Preparation® to help people pursue their boldest ambitions, overcome the obstacles standing in their way, and change the course of their careers, businesses, and lives.
He also interviews some of the world’s most successful people, including Mark Cuban, Tony Robbins, Mike Tyson, David Solomon, and David Rubenstein, on his podcast In Search of Excellence, which has reached as high as #3 in Entrepreneurship and #10 in Business on Apple Podcasts.