Jessica Powell, the former Google vice president who wrote The Big Disruption and told you how to quit your job, is here to answer your common but tricky work questions. Check back every other week for more management advice with a tech inflection, and send your own work conundrums to askjessica@medium.com. (Your name will not be used.)
When it comes to hiring, we tend to look at people’s resumes, where they went to school, and their last few jobs. But none of that reliably predicts how people will do in a role. The interview is supposed to help, but a lot of times I feel like I’m just judging whether this is a person I want to have a conversation with. As a manager at a fast-growing startup, I really want to recruit people who are resilient and have a high tolerance for ambiguity. How do I vet for that in an interview?
My favorite way to test for resilience and tolerance for ambiguity is to conduct interviews on the top of our building, and at some point push the person off the roof. (It’s not that high.) Then, when they ask from down below whether I can call an ambulance, I call down, “I don’t know…can I?” I watch how they respond. Do they stand up? Call an ambulance? Understand that this is a metaphor?
If they smile and brush off their mildly broken bones, I can tell I’m dealing with a winner. They’re hired!
But I get that’s not always practical — some people work in skyscrapers! — so let’s talk about other approaches you can take to suss out whether a candidate possesses these qualities.
Resilience
No interview question is perfect, and even if it is, your interviewee may be scared of appearing vulnerable in front of you. So don’t expect to suddenly get a tearful recollection of a painful life moment when the interviewee overcame extreme adversity. That said, I’ve found that gently probing a candidate’s self-perceived weaknesses and missteps are an effective way to suss out a person’s resilience. And by that, I don’t mean the cliched question of “What’s your weak point?” (Answer: “I’m a perfectionist. I care too much!”)
You have to be a bit sneakier than that.
Here are some questions that I like. Bonus: many of them help you gauge more than just resilience.
Q: What is the most important strength you bring to this role? Give me an example of how you used it in the past. What was the result? Can you describe a time when this strength did not lead to success?
Q: What is your biggest professional regret, if any?
Q: Tell me about a time you were embarrassed and how you got past it.
Q: Some people tend more easily to put responsibility or blame on others, and some people tend to put it on themselves. Where would you see yourself? Can you give me an example of when this happened?
Q: What are you most afraid of, careerwise? Have you ever seen this fear tested?
Q: What would your current co-workers say is your greatest strength? Your greatest weakness? (Note: you may still get a few “My greatest weakness is that I’m a perfectionist”-type answers, but flipping the script and asking the candidate about how others perceive them does tend to yield more truthful answers.)
Q: Tell me about your experience at WeWork? (Just kidding.)
Ambiguity
Resumes can be more helpful when you’re vetting for the ability to thrive in a high-ambiguity environment, a place where goals and funding and the whims of the founder may change from one day to the next. A person who comes from a background where the ground is always shifting (e.g. a startup) likely has some aptitude for succeeding in this kind of workplace.
But not everyone comes from a startup, and there are lots of life experiences that speak volumes about a person’s ability to thrive in an unstable environment. That kind of stuff isn’t usually on a person’s resume, nor is it necessarily appropriate to be discussed in an interview.
Nevertheless, there are still questions that can help uncover this theme. I think the best questions are the ones that let you, the interviewer, see the world as your interviewee sees it — to understand what they most value in their work environment and career, and see how they approach complex problems.
Q: Do you love your routines or do you like to do things on the fly? How much structure do you like in your work day?
Q: Where was your favorite place to work and why? (Use this question to then probe about size and work culture, knowing that a preference for smaller and/or fast-moving companies with broad and/or vaguely defined roles may suggest a certain flexibility in rolling with the punches).
Q: Tell me about a tricky situation related to your boss, employees, or peers, and how you dealt with it. What did you do, and what would you do differently next time?
Q: Tell me about a project you saw from concept through to execution. What were the challenges? What did you do to make it a success? If you did it again, how would you improve it? If it failed, what did you learn?
Q: If you weren’t in your job, what would you be doing? If you could work on anything, with unlimited resources, what would you do? What if you were not constrained by money? What if you couldn’t fail?
None of these questions are perfect, nor is there a correct answer. Just because someone tells you they want the majority of their day to be highly structured, doesn’t mean they wouldn’t thrive at your insane startup. They might just use structure to help organize the chaos you and your company keep throwing at them.
You have to triangulate multiple answers to build a clearer picture of your candidate. For example, that same highly structured candidate may also tell you an impressive story about how they handled launching their product when two warring departments wanted ownership over it. That suggests an ability to navigate politics and a potential lack of clear direction from the top. It also may suggest an interpersonal style that works well with others. You probably want that person working for you.
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January 02, 2020 at 07:09PM
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How to Know if a Job Candidate Can Handle Working at a Startup - Forge
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