Sharpen the Questions: Individuals

Get to Alignment Faster through Hard Questions

Nearly two decades ago, I went through multiple interviews at eBay for a business role. At the end of each interview, the interviewers asked me if I had any questions for them. I would ask, "If you had a magic wand that would let you say anything you wanted to [then-CEO] Meg Whitman, what would you say? What would you want to fix?"

Every interviewer gave the same reply. They said they wished that the company was less consensus-driven, more innovative, and more fast-moving. This was during a time of tremendous growth for eBay, so I was somewhat surprised to hear this. Now, with the benefit of hindsight, it's clear that each of those employees had the same perspective on issues that would later catch up with the company. I ended up joining PayPal, when it was still small and nimble, in part due to the eBay interviewers’ response to my question. 

The answers you receive are often shaped by the questions that you ask. If you ask someone a generic question, such as, “How do you feel about the company?, you will receive a generic response, one that typically doesn’t provide you with valuable information. If you ask a more specific question, however, you will get a clearer, more insightful answer.

There are many realms of our lives and work where we can learn to be sharper in the questions that we ask. When I say “sharp,” I'm not talking about being rude or dismissive; I'm talking about being precise and targeted with your questions, so that the answers you receive give you the information you're actually seeking. 

In my last post, I shared strategies for sharpening your questions in group settings to help you get to alignment. In this post, I'll discuss ways you can leverage more effective questions in one-on-one settings in order to get clearer, more useful answers.  

Start with the answer 

When asking important questions, it’s common to default to a generic, “How are you?” style of query, where the answer is almost an afterthought. However, if you want to ask sharper questions, the best place to start is not with the questions themselves, but with the answers you’re seeking. What sort of response are you looking for? What information do you hope to gain? 

Remember that the type of question you ask can determine the type of answer you get. A lot of leaders will leave the stage or finish a talk and ask, “How did that go?” The issue with this type of question is that there’s an implicit request for a judgment or a verdict. The majority of people will be reluctant to respond, “That went badly,” or, “It was just okay.” Instead, they’re likely to reassure you that it went well, even if there were areas of improvement. 

We used to joke that “How did that go?” was the standard “tell-me-something-positive” question, so I would always answer that the meeting or presentation went well. I have found that if you’re looking for real feedback, a more productive question might be, “What is one thing that I could have done better?” By turning the question into one where the answer is steeped in curiosity rather than judgment, you are much more likely to get a useful response, one that will help you improve next time.