Nine Simple Questions I Learned To Ask That Transformed My Career

The true mark of expertise is knowing when you need to learn more before deciding how to act.

Nine Simple Questions I Learned To Ask That Transformed My Career
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Early on in your career, you’re focused–quite reasonably–on skill acquisition. To get ahead, you need to get good at something. But once you’re an expert in a certain area, something funny happens: You may start asking fewer questions, worried that it’ll be seen as a weakness–an indication that you don’t really know what you’re doing. The more expertise you pick up, the more you have to lose, and the fewer questions you ask.


Like a lot of people, I spent the early part of my career trying to demonstrate my expertise and prove myself. It often felt uncomfortable, but I didn’t feel like I had many alternatives. Plus, it seemed to be working: Before long, I became the head of a department, managing 12 direct reports. To improve my management skills, I took a three-day coaching course with the Coaches Training Institute, and looking back, it’s no exaggeration to say that the experience shifted my entire career from that point forward.

Why? Because I learned how to ask questions again–not just any questions, but the kind that impel others to step back and assess a situation from a new perspective. My ability to ask questions transformed me from an uncertain new manager to a confident leader–a skill that I now consider one of my best career assets.

Related: Three Simple Questions This GE Exec Asks To Solve Big, Complex Problems


These are a few questions that I’ve learned can help managers, mentors, leaders–really just about anyone–get right to the heart of a problem more quickly and build the types of relationships that turn regular colleagues and clients into trusted collaborators.

Three Open-Ended Questions To Uncover What Matters

Earlier this year, software developer Justin Weiss joined me on my podcast, Indiedotes. He told me he wasn’t quite as happy as usual, but he wasn’t sure why. So he decided to pause and check in with himself, by asking a few important, open-ended questions like, “When am I happiest?” and, “What is it that I want to do now?” After mulling these over, Weiss decided he needed to let go of his management position and go back to focusing on the technology. He eventually found a new job that let him focus on programming again.

As a coach, I’ve learned that it’s easy to give advice and offer suggestions based on my own experience. But sometimes, information and recommendations aren’t what’s needed most. Often, somebody just needs help understanding how they feel about their own circumstances and options. This way, they can make their own informed decision about a potential new job or shifting roles within a company.


These are three open-ended questions that can steer you or others toward the fundamentals that are sometimes easy to lose sight of:

  • What do you really want?
  • What’s ultimately most important?
  • How can I best support you?

Three Questions To Prepare For Tough Conversations

Meeting with your boss can be nerve-wracking. So can going on a job interview, where you know you’ll be judged, not just by what you say to a hiring manager, but the questions you ask them as well. Showing up with no questions might signal that you’re not interested in the job or that you haven’t spent much time preparing. Similarly, when you’re presenting an idea to your boss, you’ll want to be ready to field their questions, but coming up with a few of your own can also help you make sure you get all the information you need.

So before an interview or big meeting, spend an hour or so preparing your questions. But don’t just draw up a list of questions you want to ask the person you’re speaking with. Do that, too, but take a little time as well to think about the purpose of the meeting and gaps in knowledge you have.


Here are a few questions to ask yourself before going into a tough conversation with somebody else:

  • What do I want to get out of this meeting?
  • What information do I lack going into it?
  • Where do I feel uncertain?

Related: 7 Interview Questions That Can Help You Land Your Dream Job

Three Questions To Help You Talk Less And Listen More

Listening sometimes feels hard, especially as you advance in your career and it becomes an ever more crucial job skill. In my experience, this has proved true working with clients, too. You want to prove that you’re smart and worth taking seriously–to demonstrate that what you have to offer is valuable. What’s more, many of us have been trained to think that, as experts, our value lies in giving advice.


But sometimes talking less so you can focus on listening can unearth hidden information, and help you deliver even more value than by doing the reverse. When I’m vetting a prospective coaching client, I’ll practice asking questions before actually offering any advice. The same habit works when you’re a manager or mentor trying to sort out an issue in the workplace. Don’t ask just one or two questions, either, before weighing in–continue to ask clarifying questions until you’re sure you’ve unearthed the most pressing underlying problem. Only then should you start offering advice.

These three questions can help you listen more intently before jumping in with your own two cents:

  • What would success look like?
  • What’s most important about this project?
  • What concerns you most about this project?

Even the most skilled consultant, coach, or manager will hit a point where they just won’t know what to say. Maybe you’ve never faced this particular situation before, or it’s just an especially complicated challenge. Your first instinct might be to say nothing, or chime in with a remark that isn’t very helpful (even if it’s accidental). But in times like these, remember that it’s your curiosity that got you here–the questions you’ve asked that have helped you build up your expertise and credentials in the first place.


When you don’t have ready advice, it’s the perfect time to ask questions. No matter what your job title might be, or how pressured you feel to come up with a wise solution on the fly, try reaching for one of these nine questions first, depending on what the situation might be. Chances are that the answers you’ll hear will be more helpful–to both of you–than anything you could say.