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By Randall Kaplan
As our responsibilities grow, the consequences of our decisions grow with them. A conversation we put off affects the team. A decision we keep making ourselves prevents someone else from developing. A habit that once helped us succeed may begin limiting what we can accomplish.
Those moments can be difficult to recognize from the inside. We’re busy doing the work, solving the immediate problem, and moving toward the next deadline. There may be very little time to step back and examine how we’re leading.
That is one reason an executive coach can be valuable. The right relationship creates room for honest examination and deliberate improvement. That choice deserves the same care we would give any important professional decision.
“I want to become a better leader” is a good place to begin. But it becomes much more useful when we can explain what is happening in our day-to-day work.
Perhaps our team waits for approval on decisions it should be able to make. Perhaps a colleague leaves every difficult conversation unsure of what we expect. Or perhaps our presentations are thorough, but nobody seems clear about the decision we’re asking them to make.
Those details give a prospective coach something meaningful to explore. They also help us recognize whether the person is listening carefully or reaching for advice before understanding the situation.
An accurate description of the problem puts us in a stronger position to choose someone who can help us work on it.
An impressive biography can get our attention. During an introductory conversation, we can learn more by describing one specific challenge and asking how the coach would approach it. We’re asking to understand the process, not expecting a complete solution before an engagement begins.
For example, we may be considering promoting a strong salesperson into management. A useful question would be: “What would you want to understand before helping me prepare for that decision?”
The response can reveal a great deal. Does the coach ask what the management role requires? Whether the salesperson wants to manage people? What evidence we’ve seen of their ability to develop others? Or do they move directly to advice without examining our assumptions?
Relevant experience matters because it can inform better questions and judgment. Training and credentials deserve consideration too. But we should leave the conversation understanding how this person would help us think through the decision in front of us.
Extreme Preparation® gives that work depth. We investigate the situation and the people involved, separate evidence from assumptions, anticipate resistance, and prepare for more than the outcome we hope to see. Then we rehearse the conversation and consider what support the decision will require afterward.
In the promotion example, that could mean examining the role, discussing the candidate’s ambitions, and preparing for the possibility that management isn’t what they want. It also means thinking through what happens to their existing accounts and how the team will be supported during a transition.
Now coaching has something concrete to work on. We can examine the evidence, hear our reasoning challenged, and rehearse the conversation before another person’s career is affected by it.
The prospective coach should be able to explain how their approach moves from discussion into work we can apply.
There is another part of the decision that deserves attention: whether we can be honest with this person.
We need to be able to admit that a meeting went badly or that we avoided a conversation. We also need someone who can challenge our explanation without dismissing our perspective.
That balance becomes visible in small ways. The coach asks a follow-up question before offering an opinion. We disagree, and the conversation remains productive. A difficult observation comes with reasoning we can examine.
The practical boundaries matter too. Before the engagement begins, we should understand confidentiality, fees, session frequency, and expectations between meetings. If an employer is paying, everyone should be clear about what information will be shared with the sponsor.
Progress becomes easier to assess when we agree on what improvement would look like. For a manager learning to delegate, that might mean clearer ownership, fewer unnecessary approvals, and better feedback from the team.
Those changes give us something concrete to discuss at an agreed review point. We can evaluate whether the approach is helping and where it needs to change. A promotion or business result may follow, but neither is something a coach can guarantee.
The strongest choice is someone whose experience is relevant, whose approach we understand, and with whom we can do honest work.
For 25 years, I’ve coached hundreds of entrepreneurs, business owners, and executives. My work brings the perspective of a serial entrepreneur, Akamai co-founder, and investor to the opportunities and difficult decisions my clients face.
Extreme Preparation® is the methodology I created and refined to help people pursue those opportunities with greater depth and precision. The work reaches from research and scenario planning to rehearsal, execution, and follow-through, including the human details that can determine how our preparation is received.
If you’re facing a consequential leadership decision or preparing for greater responsibility, you can explore coaching with me here.
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.