Letter 020 - Why I (Strive To) Only Hire People Who Can Disagree With Me
A simple, concise perspective on hiring
*Going on honeymoon later this week post-quasi elopement! I’ve promised myself to not do any work + avoid internet, so I’ll probably write a few essays and bulk publish them once I’m back in mid-June*
First, some background
When I built out my own personal framework for interviewing + hiring, I thought deeply about what I didn’t like about interviewing when I was earlier in my career. One of the biggest things that bubbled up to the top for me was the feeling of walking on eggshells. I was trying to please every interviewer… to “make a good impression” … to “build rapport.”
I tip-toed on eggshells effectively enough to secure full-time offers, but then as I spent more time at work, I started to notice a trend: oftentimes the most difficult people were in leadership positions.
I really, truly struggled with this, particularly in the first couple of years of work where this guy, let’s call him Jamie, was revered in the office by everyone. He walked around like he owned the place, and everyone alluded to him as quite literally, “The Chosen One.” (can’t make this shit up).
And then, a realization
But as I started to get closer to him…to watch him operate, I realized why people were so enamored with him — he was downright brutal in meetings. …And could get better results than any other manager —> made him look very good in the eyes of senior management —> the rest is history (this person is now a very senior executive at a large company).
I couldn’t bring myself to adopt this guy’s playbook, but I wasn’t going to just ignore the lessons in his interim and long-term success. There was something Jamie was doing — he was not shying away from conflict. He was in fact embracing conflict, head on, without any fear. Some people call this being brash, some people call it being aggressive, some people call it being bold. Call it whatever you want, but the ability to disagree with others is of paramount importance to high-performing teams. It’s just that Jamie went about it in a rather off-putting way.
This is when I discovered the power of mixing candor with genuine kindness and empathy. I basically said, “How can I be as or more effective than this guy…but not be an asshole?”
I started testing different ways to operate…
I started testing this out — being warm but also openly disagreeing with others… After some failed runs, I started to tune the way you present disagreement, and before long I was getting the very same opportunities Jamie had gotten, but without the trail of figurative destruction behind me.
I tell this story because I basically always try to hire not-Jamie’s. I want to work with people who are kind, welcoming, but very willing to disagree. Over the years, after so many hundreds of mini projects, you start to uncover patterns around when the very best work is done, and it was almost always with people who embraced disagreement, both on the receiving and giving ends.
I’ve had this guideline in the back of my head for probably the last five years, and I know it has served me well, simply by measuring the number of high-likelihood-of-failure projects we’ve all executed together that have somehow…. turned out to be home runs.
How to apply this guideline
A quick note on execution: applying this rule requires a pretty thorough interview process, a process deep enough to get to the point of highly dynamic, back-and-forth conversation. The way I’ve typically done this is by either:
Presenting a current challenge our business is facing and asking for the candidates thoughts across several dimensions, and/or
Then ask them to argue the opposite case, and gauge how deep they can go on why to not pursue a certain path
Asking them questions like, “what is something you think most people would disagree with you on?”, or
Directly asking for feedback, either on the interview process or even on how I could’ve provided a better experience
Critically, you must capture one, material piece of feedback either for you or your company. This is the real gauge — if you’re thinking about how we could be better before Day 1, that bodes well for Day 1000 on the job, after you’ve helped us upgrade our capabilities as an organization
The deeper point here
However you might implement something like this, let me be very clear on the actual root intent here. The point of this is to ensure you’re hiring people who can, at the very least, simulate a variety of perspectives, assess multiple options, and communicate various options effectively, without succumbing to the pressure to agree or go with the flow of the team. In other words, find people who can challenge groupthink… It is this see-sawing between options that leads to more thoughtful planning and realization of goals.