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By Randall Kaplan
The interviewer closes the notebook and asks whether we have any questions. We’ve spent the last half hour trying to demonstrate that we belong there. Now we get an opportunity to find out whether the job belongs in our future.
That opportunity deserves more than a question we found on a list five minutes before the meeting. The answer could change whether we want the position, what we negotiate, or how we prepare for the next conversation. A good question helps both people understand the work more clearly.
Our goal is to leave knowing something we could not have learned from the company’s website. That starts with deciding which uncertainty we actually need to resolve.
A job description might say that we’ll manage important client relationships. It may say very little about what is currently difficult about those relationships. Are customers leaving? Are accounts growing faster than the team can support? Does the company need someone to rebuild trust after a problem?
We could ask, “What would you most want the person in this role to improve during the first few months?”
That question connects the position to a real need. If the answer is still broad, we can follow it with, “What would you see happening differently if that improvement were successful?”
Now we’re beginning to understand what performance means. We may also discover that different people define success differently. That is useful information to explore before accepting responsibility for it.
Every company can describe its culture in appealing language. Collaboration, ownership, and excellence sound good. The more revealing question is how those ideas show up when something goes wrong.
For example, we might ask a prospective teammate, “Could you describe a recent project where priorities changed and how the team handled it?”
The answer can tell us how people communicate, who makes decisions, and whether disagreement is welcome. We’re listening for a sequence of actions, not grading someone’s ability to recite company values.
We should also give the person room to be candid. A demanding project does not automatically indicate a bad workplace. The useful distinction is whether the team recognized the problem and responded constructively. If every challenge is described as somebody else’s fault, that deserves further conversation.
The right question also depends on who is across the table. A recruiter may explain the interview process and employment logistics. A manager can discuss expectations and resources. A teammate can describe the daily work.
When we ask each person about something they directly understand, we tend to get more useful answers. We also demonstrate that we’ve considered their role instead of treating every meeting as the same interview.
Extreme Preparation® includes that distinction. Before the meeting, we can connect each important uncertainty to the person best positioned to address it. Our notes might identify the manager for decision authority and a teammate for how work moves between departments.
This gives our curiosity direction without turning the conversation into an interrogation.
Our next question often matters more than the one we prepared. If the manager says projects stall during approvals, we could immediately move to our next topic. Or we could ask what typically causes the delay.
That follow-up may reveal the most important challenge in the role. Perhaps responsibilities overlap. Perhaps a senior leader reviews every detail. Perhaps the team is missing information when it requests approval.
Each answer describes a different job. Listening carefully helps us understand which one we’re actually considering.
A coach or trusted colleague can help us rehearse this skill. After answering our prepared question, they can introduce an unexpected detail and see whether we notice it. The exercise is about following the meaning of the answer rather than racing through our notes.
We don’t need to ask every question in one meeting. Near the end, we can identify the most important issue that remains unresolved and ask how we might learn more about it during the process.
Afterward, our notes should distinguish what we heard from what we inferred. “The team described two recent priority changes” is evidence. “The workplace must be chaotic” is an interpretation that needs more context.
An interview is an evaluation in both directions. The questions we ask should help the employer understand our judgment and help us decide whether this is work we want to do. When those questions reveal the real responsibilities behind the title, they’ve earned their place in the conversation.
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.