Every so often, an interviewer comes along who refuses to settle for the expected answer. Sometimes based on curiosity, sometimes frustration with the guest, sometimes based on great research, but always from a place of genuine desire to deliver a great experience — that interviewer won’t accept anything but your best.
One such interviewer is Ryan Hawk, host of the long running podcast, The Learning Leader Show (330+ episodes; more than twice the number of my show, Unthinkable). He’s talked with the likes of Seth Godin, JJ Redick (an NBA player, for the unfamiliar), Brian Koppelman (writer/creator of Billions and Rounders), Julie Zhuo (head of design at Facebook), Beth Comstock (former CMO of GE), and more. I was thrilled to get the chance to appear myself on episode #321. Ryan and I, both longtime interviewers, immediately hit it off both on and off the mic.
So then a thing happened.
Ryan asked about me coming on as a recurring guest to deconstruct topics near and dear to our hearts, going deep and nerding out, without the higher stakes of trying to promote anything like my book. “Learning happening in realtime,” he said. (I love that.)
Below, I also wanted to answer a question from one listener of the show that Ryan received right before I published this. This comes from Casey Collins, who said:
I work for one of the largest auto insurance companies as a casualty adjuster and was recently selected to take part in an accelerated leadership development program and have an opportunity to start a mentorship with some senior level leaders. I want to make sure I come prepared to these meetings and get the most out of these conversations. I'm struggling with finding questions to ask them because I don't know what I don't know. How have you worked past this mental block when talking to someone you know is further along their career and they can help you but you simply don't even know where to start and how any of it applies to you?
To Casey, I’d of course first send my congratulations for being a part of that program. Second, I’d break my answer into three parts:
Yes, sometimes, you just have to put in the grunt work and throw time at a problem. In this case, when interviewing someone whose world you don’t fully understand, research their careers, find appearances in the media or past internal memos or content they’ve personally published. Find trend pieces on the general topical area, written in reputable sites. That could mean trade publications or national or local media, or blogs, podcasts, and video series from industry luminaries. What’s happening “out there,” and what are people saying about it?
With all that in mind, find out where you're intrigued or even disagree with someone else’s assessment. Figure out what your knowledge gaps are that your mentor could help with. In other words, establish a baseline of content and context, then let your natural curiosity and other emotions (frustration, confusion, etc.) guide you towards questions and conversation with the other person.
A quick example: You might recognize that the classic upward mobility inside a corporation requires that you move from individual contributor to manager. Okay, that's the convention or best practice, but (to the mentor), how much did you find that people management is required of you to ascend to your position in this industry, compared to being really great at the job as a practitioner? And how did you make that transition between the two successfully, seeing as they're not the same skills?
Another example: Everyone in the industry seems to be buzzing about XYZ trend. Is that something you’ve thought about and do you think it will affect my career as I progress? How did you work through other cycles of hype for a given industry trend before? How do you parse what’s worth studying and what’s overblown?
2) Reflection Questions
Once you get beyond the first category, there are some basic questions you can try that I’ve pulled from my time as a show host interviewing guests. The point of these and others like them is to get the other person to pause and reflect. You want to push them beyond easy, knee-jerk answers, because when they’re being mindful and fully engaged in the response, they’re likely giving their best, not-often-heard answers. (Great for creating content like a show. Great for chatting with someone you hope to learn from, period.)
What's something you wish you knew sooner?
What's something you always assumed when you were younger that didn’t turn out to be true — or what did others always tell you that wasn’t true? What about the inverse? What’s some advice you got early on that changed you for the better?
What did you read or watch that helped you grow? Anything you're reading now you'd suggest?
What were the roles you moved through to get to where you are? Can you walk me through what caused you to make the change or get the promotion? What were the top 1-3 things you learned in each?
Any big mistakes you made that you’re willing to share?
What's something they never tell you that you learned through experience?
3) Brutal Honesty
Lastly, lay your cards on the table. You’re hungry and want “it” (maybe define “it” for the other person), but you don’t know what you don’t know. However, that mentor DOES know what you don't know. So just be honest: "What questions should I be asking? What questions didn't I ask that you think are important for me to explore? What do you look for in a longer-term mentee?"
It’s fine and maybe even expected that you know you want better — or can maybe articulate what “better” means — but have no idea how to get there. Nobody does. We’re all just hacking away at the jungle and talking to others who have been hacking away, trying to reach that mountain peak in the distance.
Good luck, Casey, and to anyone reading this, here’s to having productive, transformative conversations by mastering the art of the interview. It’s a skill that serves you in content, in career, and in life.
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