%20(1).png)
By Randall Kaplan
At 24, I moved to Los Angeles with $3,000 in the bank. I was fired five and a half weeks after starting my career and went through three jobs in eight months doing work I despised.
I wanted a different future, so I wrote 300 cold letters to CEOs. Those letters generated 80 meetings and eventually led to a job as Assistant to the Chairman of a Fortune 500 company.
That was a turning point in my career. It also illustrates the question I’d put at the center of any decision about career coaching: what will we do differently because of the work?
We can spend months discussing how stuck we feel. A worthwhile coaching engagement should help us examine the problem, prepare a response, and take action we can learn from. That is how we begin evaluating whether the investment makes sense.
Before we evaluate coaching, it helps to understand where we’re getting stuck. “I need a better job” may express the frustration without identifying the problem.
If applications are going unanswered, we may need to examine the roles we’re pursuing and how we explain our experience. If interviews consistently stall, the issue may be how we communicate in the room. If we can’t choose a direction, we may need to understand our priorities before sending another application.
Each situation calls for different work. When we can describe our obstacle clearly, an introductory coaching conversation becomes more useful. We can discuss the actual challenge instead of speaking in general terms about success.
For example, we may be consistently reaching final interviews without receiving offers. “I need more confidence” may be our explanation. A closer look might reveal that we spend most of each answer describing the background and very little explaining our own contribution.
A useful coaching exercise would be to record an answer to a real interview question and examine it together. Where did the answer become unclear? Which detail established our value? What follow-up question would an interviewer reasonably ask?
Then we could prepare a stronger answer using the same truthful experience, practice it, and compare the two recordings. We’d have evidence of what changed instead of relying only on how encouraged we felt after the session.
That is an illustration, not a promise that better answers will produce an offer. It shows the kind of concrete work we should be able to discuss before committing to an engagement.
Extreme Preparation® connects the outcome we want to the details that could help or hinder it. We study the opportunity and the people making the decision, challenge assumptions, anticipate difficult questions, and rehearse different scenarios. We also prepare how we’ll listen, communicate, and follow through when the conversation is over.
For a final interview, that means understanding what still needs to be resolved about our candidacy. It might be our ability to lead, our reason for changing industries, or a gap in experience. Our preparation should address that uncertainty honestly with relevant evidence.
The work goes beyond sounding polished. We’re preparing to respond when the interviewer probes the part of our experience we find hardest to explain.
Before paying for coaching, we should understand what the engagement includes and what it requires of us. That means clarity about the focus, fees, schedule, preparation, and work between sessions.
We also need realistic expectations. A coach can help us prepare for a promotion conversation or evaluate a transition. The employer still controls the hiring or promotion decision. A promise of a guaranteed outcome deserves scrutiny.
Our own commitment matters just as much. If we discuss an important conversation but continue avoiding it, the discussion has not yet changed our situation. The value develops as we apply what we learn, observe the result, and return ready to examine what happened.
A useful engagement should have an agreed point for reviewing progress. The evidence will depend on the problem we brought into it.
We may be explaining our accomplishments more clearly. We may have tested assumptions about a career change and narrowed our options. We may finally have held a conversation we had been postponing for months.
Other resources can help too. A mentor, trusted colleague, alumni career service, or focused course may address a specific need. Coaching makes more sense when we understand the support that is missing and can see how the proposed work addresses it.
That gives us a practical way to judge the decision: whether the help fits the problem and leads to action we can evaluate.
For 25 years, I’ve coached hundreds of entrepreneurs, business owners, and executives. I bring my experience building companies, investing, and navigating my own career to that work.
The Extreme Preparation® methodology I created asks us to go deeper into the opportunity, the obstacles, and the details that can change an outcome. Our research has to inform our decisions; our rehearsal has to improve our performance; and our follow-through has to carry the work beyond the conversation.
If you’re ready to examine what’s holding you back and put that level of preparation into your next move, you can explore working 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.