How do I know you’ll be a great co-worker when I’ve never worked with you?

Every day, I am searching for new members of my team or extended team. As Co-CEO of a growing senior services company, I can’t co-lead effectively unless there are great people with whom we can share the work.

What do I mean by “great people” for our team? My answer here is not different from the ones that other CEOs at Valley firms often give: smart, energetic, committed, willing, motivated, pleasant, mature — these are some adjectives we’d like to check off in our interview process. The emphasis changes depending on who is speaking, what the job entails, what the company culture is like, and so forth. And I’d say further that most hiring managers I know don’t care what gender, age, ethnicity, national origin, sexual orientation, and other attributes candidates have. We just want them to be great to work with, and to deliver excellent work.

So how do I figure out whether they would be both before I actually start working with them? Well I can’t. Even the very best in the hiring business only get it right half the time, according to an excellent organizational consulting firm I have moonlighted for and co-written with. What I can do is aggressively weed out the ones that I know won’t work out. Here are some notes from actual candidates I have interviewed and vetted. These would not have worked out.

  • The gunner who wanted too much: A young man who had just graduated from a top 50 college wanted an entry-level Business Development role. I liked his sense of hustle and his answers to my questions were sharp and insightful. I didn’t think much of it when he referenced right at the outset that he was looking at a few other things. Good candidates often parallel process several opportunities. But then, when I eventually extended a verbal offer, he very clearly wanted to use it to drum up competing offers. He also wanted a significant bump over what I had offered (because, he hastily explained, his new landlord required that he make a certain amount), as well as equity (from a company that does not have an equity plan). It was too many asks, and I realized that he wanted way more than this company could give for someone of his profile — namely an unproven without a track record of success. I also realized that he didn’t understand the nature of the job I was offering him: the opportunity to work on real projects that matter, and have significant responsibilities and learning experiences that would pay off over his career. It was a poor fit. I passed and wished him well.
  • The woman who wanted too little (and too much): This woman was a recent mom who had left a fairly high-powered job at Fortune 1000 firm. I liked her. She was easy to talk to. She also gave crisp, clear descriptions of projects she had worked on and assignments that had ended successfully. But there was a catch: She only wanted a part-time job that was also flexible. She also did not want to have any set meeting times. Plus, she wanted to be a remote employee. It was tough to imagine onboarding a new person and getting her integrated into a team without the aid of face time, regular meetings, or even the promise of a certain minimum number of work hours in a day. Perhaps this was a roundabout way of saying she was not interested in working with my team. Perhaps she didn’t really want to work anymore, and this was her way of testing herself. I do understand the allure of motherhood, and that new moms often don’t want to go back to work right away. But I don’t know of any company that could agree to the terms she laid out unless the work didn’t matter very much, or she was the only person in the world who could do it. Either way, it would not work for us.
  • The both/and woman: Before I tell this story, I’ll say this. Folks who are stuck in jobs they don’t like often have a love/hate relationship with them. On one hand, the job pays the bills and has been ok enough to stick around. On the other hand, there are aspects of the job that cause one to yearn for something more, and to troll Craigslist in search of alternate realities. And in between, there are usually some things that amount to adverse incentives: the flex time, the loose discipline, the lack of standards, the low workload, the easy street, the list goes on. These feel nice to have, and can make a bad job oddly sticky. The woman who came in to interview was quite impressive in her fearless approach to understanding what the job was and whether she would be successful at it. She was both expressive and direct. She described the frustration of being at a firm where she wasn’t learning anything, and had no real responsibilities. (The new job would have had plenty of both goods.) But when presented with the option to join the team, she hesitated. She wanted to take the extended vacations she had planned. She wanted my partner the other co-CEO to train her on weekends and nights, when she gallantly offered to come in to work (between her two vacations). She wanted more money. And so on. I had prepared an offer letter, but never sent it. I finally tired of her many asks, and rescinded my verbal offer. In the final analysis, she wanted to keep the perks of her job while adding the challenges of a new one. Her decision required a tradeoff — one that she ultimately did not want to make. Too bad.

Whenever we say no to a candidate, I wonder if we are letting someone go who actually would be a great new member of our team. We learn about the false positives in the hiring business, but not the false negatives. I am aware that the three people I have profiled here could have been awesome. But in the moment of truth that always comes in major decisions on work, life, and love, all three ended up showing me what they valued most in that moment. And it was not an opportunity to join our team.


4 thoughts on “How do I know you’ll be a great co-worker when I’ve never worked with you?

  1. Achieving the optimal point in the false positives and negatives curve is really difficult, and this article was very helpful in untangling some of the nuance behind those decisions. It’s even harder at a smaller company where each additional person has such a large impact on the culture, and there aren’t as many data points to draw from. Great post!


    • Great point! Smaller offices do need to be more careful. The impact of an integration is huge — as is the impact of a departure if a new recruit doesn’t quite work out. It’s important to make sure that the folks on the team know the parts they play, on both ends. A continuous dialogue among the team about its values and norms is important to building and reinforcing a strong culture.


  2. This is true – from an applicant’s perspective I’m always thinking why can’t they just give me a chance; from an employer’s perspective, it can mean an annual six figure investment and every dollar is agony for a while! And all of this based on 3-4 conversations/hours with this person. Sure is risky business!


    • Sure is. And we really don’t have much choice but to make those decisions based on limited information! That said, I think there can be a difference in outcome if you dig really hard in the short time that you have. It is all too easy to get lazy and not check the obvious places for clues about the person: LinkedIN, Facebook, Google, and so forth. Whether or not you find information that helps, you’ll know that you tried your best to fully vet your new recruit. And that is something you can both control and trust.


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