Good Times and Good Stories from Informational Interviews

I have a philosophy that something good comes from every first date:  a good time, or a good story, or very occasionally, both. As a job-seeker, I've come to think of informational interviews in the same way. I've been surprised at how much I can learn about a leader and his or her organization just from a single conversation over coffee. An hour is barely enough time to get even a rough sense of a company's product, business strategy, and technical challenges. But it's more than enough time to establish a baseline understanding of a someone's personal style and the likely culture of their organization. People tell you who they are very quickly, if you're listening.   

Earlier this year, I met with the CTO of a medium-sized startup over coffee.  The informational meeting had been arranged by his head of HR a week earlier, to explore the possibility of my joining to lead a new analytics initiative.  As he invited me into his office, fifteen minutes late, he said, "Ok, so, I can't remember...what role are you interviewing for, again?"  He motioned toward the whiteboard as he scrolled through something on his phone.  "Has someone already put you through your technical paces, or is that for me to do?"  

My mission was accomplished before I even sat down. There was no path through the next 45 minutes that could convince me to join his team. I don't expect a red carpet and champagne, but I do expect common courtesy and at least a pretense of enthusiasm, from a team considering hiring me. Forget about my personal feelings—who wants to join a group of people who conduct business this way? How would I ever recruit quality people to join my own team, in such a place? 

Manners aside, the phrase "putting you through your technical paces" irritated me. I fully expect to have technical conversations during an interview.  I have little patience, though, for processes that run these in an adversarial and/or generic way. What "paces" was he going to put me through without knowing a single thing about who I was or why I was there? I assume that recruiting processes that test narrowly for the skills listed in a job description are also searching narrowly in the space of solutions to their technical and business problems. I assume they're missing out on opportunities in all cases.  

In the course of a 45-minute conversation with this CTO, I didn't learn a single personal fact beyond where he grew up. I don't actually care whether he has a family, or is a chess master, or breeds goldfish, or commutes from the moon. But I do care that I end up in a professional environment where I can be successful, and I need a way to assess that. What drew this guy to the company, and what keeps him there? What excites him? What inspires his team? How does his work fit into his life with the people important to him?  

Establishing a baseline level of humanity and some kind of personal connection as part of an introductory meeting should happen without effort, particularly for people in leadership roles. Instead, this CTO took ten minutes—twenty percent of our time together—to explain to me a piece of technology that I am aware of but have never used. He didn't think to ask which concepts were already familiar to me, and didn't listen when I tried to interject to save us both time. I learned a lot in those ten minutes, though not about the technology.  

That startup could go public tomorrow at a zillion-dollar valuation and I'd have zero regrets about not pursuing the opportunity.  It's the right place for someone, but not the right place for me. 

Contrast this with a similar meeting I had over coffee with the CEO of a different mid-sized startup.  As we settled into our chairs, I mentioned that I have an infant.*  Over the next hour, the CEO wove into the conversation a handful of stories that drew a picture of an amazing and family-friendly company culture. He spoke about both his children and his wife's career with pride. He talked about close friendships born at work and gave concrete examples of supportive behaviors on his teams. He mentioned the quirky family-oriented schedules of some of the company leaders, and spoke in the same breath about these individuals' value to the company.  

We spent most of our time discussing his company's technical challenges and business model (both compelling) and how my skills might fit together with these. But what I most remember was the growing feeling that I wanted to work for this guy. His values and his company's obviously aligned with mine, and we were both able to confirm this in our initial conversation because he prioritized it.  

When we parted, he proactively offered me the options of a shortened interview loop or a pumping break in the middle, to accommodate my breastfeeding if necessary. He did this without scrunching his face up, or laughing uncomfortably, or apologizing for any awkwardness (indeed, there was none).  I have arranged breastfeeding accommodations before, but I've never had options brought up to me proactively, and certainly never by a man. It was so refreshing to talk with someone who so obviously got it.  

I would have joined his team on the spot, given the opportunity. I did interview, but was not offered the role. (I've been pushing myself slightly beyond my comfort zone, and in this sense the experience was a success.) Nevertheless, the sensitivity and sincerity of this CEO and the culture of the company he created, which was crystal-clear and consistent during my interview loop, was such that this became my gold-standard interview experience. I recommend this place enthusiastically to tech friends, and look forward to watching their success. It will not be accidental. 

What's the lesson? Well, people convey a lot about who they are in a first conversation, and not through words alone. When someone represents an organization that I am considering joining, who they are matters to me. It matters so much that, when I discover a new opportunity these days, I read the bios of the leadership team before I even look at what problem the company is solving, or how, or why.  People and culture are what differentiate good vs. great opportunities to me. As such, I'm happy to keep on showing up for those first meetings—collecting my good times and good stories, and in this case a few new friends, too—until I find a great match. 


 *I used to avoid mentioning my kids in interviews, for fear that my interviewer would (inaccurately) assess me as less committed to my work.  Now, I go out of my way to mention them early. They're my best tool for identifying and avoiding places where family is perceived as a liability.