There are many good sources online and in print for advice about what interview questions to prepare for and the best ways to answer them. Instead, I’m going to focus on what it means for our professional and self-development when we take the time to stop and answer our own interview questions.

Being a leader often means being in the position of hiring or promoting staff. The meaty part of this journey are the interviews, remote and in person. Each type of interview has typical questions that a well-prepared candidate will expect. Part of the fun of hiring is seeing how candidates respond to questions they didn’t expect. I know I’m not unique in that when I ask some of these trickier questions, I wonder how I would respond were the tables turned. Taking the time to delve into the intent of some interview questions is a professional development opportunity that I sometimes use in mentoring situations. Recently I decided to mentor myself by setting new goals around a few of these questions.

Do more of (what?!) Do less of (what?!)

One of my new favorite questions to ask comes in a double pair: What would your boss like you to do more of? What would your boss like you to do less of? After a long pause, candidates usually respond to the former by saying something about spending more time with direct reports or out with the customer – spend less time on administrative tasks. The latter question typically gets the same kind of response. Of course, this is really an EQ question to see how honest someone is about critical feedback they receive from their boss. And truly, based on most people’s tendency towards conflict avoidance – sometimes this might be the most honest feedback they have received.


I recently had the opportunity to answer a similar question. I surprised myself by taking the easy way out – something about setting too high of expectations for myself and my direct reports and being too optimistic about timelines. But if my boss were truly being honest with me, what would she like me to do more or less of? Getting an answer to these questions means taking deliberate action: a deeper dive into self-reflection and the courage to ask them of my boss, which I have done. The trick here is to give someone time to consider a response. Just like when giving feedback, it’s helpful for the other person to know you’ve got a “gift” for them; when asking for feedback, it’s most helpful to give the other person time to reflect on a response.

The second part of that double-paired question is this: What would your direct reports like you do more of? What would your direct reports like you to do less of? I know the challenge in asking these questions is getting past the stock answer of “I’d like more of your time” to “I’d like you to acknowledge my work more.” Got that one. Hit like a ton of bricks because it was true in a very different way from “Give me more of your time”.

What New Skills Have You Developed in the Last Year?

Recently I was part of a large group hire. This was my first experience hiring over a dozen staff at one time. This extraordinary opportunity allowed me to repeatedly observe the same question being answered hour after hour, day after day, for an entire week. Our old standby questions served us well, as we expected. However, we added a new question that was particularly intriguing: What new skills have you developed in the last year? While there were some stock answers that emerged, what shocked and inspired me was the breadth of experiences that people had sought out in the past year for self-development. From things like learning a new instrument to learning a new language to learning how to better manage themselves in tense situations, candidates revealed more than I would have expected about their character and the human need to strive. I was humbled. I also became curious about how I would answer this question for myself.

I’ve been in my current position for over four years now. At about three years in, I felt I knew pretty much all I needed to know to do my job well. Rather than being in an intense learning curve that is typical when new to a position, I had come to the point where I felt I was simply doing things I’d done before – different projects and sometimes different people, but essentially the same process. The year before I had taught a master’s level class for the first time, but that was more than a year ago. If I were answering honestly for myself, and just went back 12 months, what would I say? I didn’t like my answer. So I got to work.

Learn How to do (what?!)

With this new challenge before me, the first thing I had to do was decide what I wanted to learn next. I decided I wanted to learn more about how to buy a business. There are surprisingly few new books on the topic. Most advice out there is about how to start a new business or grow an existing one. Note to self: another book on how to buy an existing business is a gap that needs filling in publishing – opportunity alert! However, my task was not to write a book about an unfamiliar topic; it was to find out how to buy an existing business. I finally found one good source that was a kind of primer on buying a business. I read it and was surprised at how much I didn’t know about the process. My husband has started four different businesses, so I thought I would have a better handle on how it works than I did. The main “aha” for me was learning about the different kinds of businesses to buy and how to determine the best fit for different personalities and skill sets. Of the many lessons espoused by this author the most intriguing were about patience and due diligence, which I think are the hardest to put into practice. It was easy for me to see how people jump in too quickly to entrepreneurship – it sounds so sexy and exciting at first. Then the reality of understanding tax liabilities, structuring the purchase, negotiating non-competes, spending capital as opposed to bringing in a paycheck – takes hold. I learned that buying a business is hard work, harder maybe than I thought at first. The strong temptation for me to skip over some of the trickier aspects of the different approaches was enlightening. Not only was I learning something new about buying a business, I was learning that I had a tendency to want to find an easy way to a hard thing. Interesting insight into my character.

The next thing I did was to start interviewing a couple of small business owners to learn about their experience starting and running their small businesses. The challenge for me in these situations was to really listen to what they were saying about themselves without trying to turn their experiences into something I could relate to. Again, I was surprised at the strong pull that relating to them had for me. The realization that the people I was interviewing had taken very different paths for their lives than I had was sobering. What is it that gives someone the mindset and courage to start something themselves? And the related question for myself: what kind of mindset do I have about my future? What courageous steps am I taking to bring that future to fruition?

business-card-427511_640Taking interview questions that help me learn about others before I hire them and asking myself those same questions gives me the opportunity to self-reflect. It is a sure path to awareness about myself, my behavior, and my mindset. For me, it is also a path to action.

Another powerful set of interview questions to answer about any job, including the one currently occupied, is: Why this? Why now? Why you? Time for more self-reflection.


Recommended Reading:

The complete guide to buying a business / Fred S. Steingold

Interesting subject but slightly dry reading. The author goes to great lengths to provide guidance and navigation for the uninitiated. A truly helpful primer.

Finding meaning in the second half of life / James Hollis

I learned about this book from reading Brene Brown . The premise – that we can’t escape where we came from – that choices we think we make about a profession or a mate for example – are inextricably linked with our upbringing – feels fatalistic. The more I read, the more convinced I became that the author was on to something. Even making the deliberate choice to behave other than we were parented is proof that we can’t escape the impact of the events of our childhood.