The time I hired a con artist


A prehistoric con artist

Back before job applicants included bots and North Korean operatives as standard, we inadvertently hired a con artist as Textio's first director of information security. Let's call him Jason, because that is the name he was using at the time.

When I say "con artist," I'm not talking about someone who exaggerated their achievements a little bit. I'm talking about someone who fabricated his mother's death, his daughter's kidney failure, and an altercation with an unhoused person at a CVS. Someone who was, in the era before remote employment was popular, simultaneously employed by Textio in Seattle and a community hospital in Alaska. It is one thing to defraud a VC-backed startup. It is quite another to defraud a non-profit medical facility.

Jason was an extreme case, but you've likely worked with more con artists than you're aware of. So how does this happen?

Just enough value to make you believe

You might be reading about Jason and thinking, "That would never happen to me. I am too good an interviewer to make this kind of hiring mistake!" You might be right.

But Jason was impressive. His interview was fantastic, his domain knowledge exceptional. He showed up as a team player; even before his first day of work, he came in on the weekend to help set up our new office. He called in for sales meetings from the hospital (well, from the "hospital") with his daughter and her failing kidney. During his first weeks with us, he seemed capable and committed.

Six weeks later, things had unraveled. But before Jason vanished with his laptop, sign-on bonus, and disappointment that we had declined to give him access to the company bank account, he contributed some real value at Textio. He created info sec resources for the whole company to use. He helped close sales deals. He even introduced our first-ever new hire background check program (oh, the irony).

Like every good con artist, Jason gave us just enough value to make us believe.

The everyday con artists walking among us

Hopefully, you have not worked with many Jasons before i.e. sociopathic criminals. But there's another workplace con artist that is much more common. Unlike Jason, they aren't breaking any laws.

Many years ago, I managed a guy we'll call Ben. Ben was assigned to work for me during a company reorg. My manager had recruited him into our team and was excited about him joining.

In my first few weeks working with Ben, I was impressed. I saw what my boss saw. Ben was smart, outspoken, and always willing to express a contrarian take. I aligned him to the most strategic work on the team and I was interested to see what he would create.

The first thing Ben did was question the assignment itself. "It makes no sense to build this now," he explained. "We will end up redoing it later. First, we have to make these other decisions."

I saw his logic and felt validated in my decision to assign him this important work. But a few days later, after we had worked through the questions he had raised, he found another reason not to proceed. In fact, every week he found a new reason. He had to go to a design workshop. He needed to help a colleague meet a big deadline. Finally, wouldn't it make more sense for another teammate to take this item so that he, Ben, could move on to this other very important item?

Every individual excuse made sense in isolation, so they were hard to argue with. However, it soon became clear that he was never going to complete the assignment. Or any assignment. Because every time we got within striking distance of him having to dive in to produce something, he found an excellent reason that someone else should do it.

Spotting the everyday con artist

Everyday con artists have plenty of talent. They typically start out in positions of influence with peers. It can take time to recognize the con, but here are a few common patterns:

  • They never finish anything. They always transfer work to a colleague before the work is complete, arguing that some new assignment makes more sense for them.
  • They don't stay anywhere long. There are many valid reasons that people end up with low-tenured stints on their resume. The everyday con artist has many low-tenured stints, over a period of years.
  • If you hold them accountable, they become combative. They generally succeed at slipping from thing to thing. If you try to hold them accountable to a deliverable with a deadline, the veneer of logic slips away. They get agitated and contentious. As soon as they can, they quit.

If you watch closely, you will see how they use slipperiness as a strategy; they talk a good game, but they manage to avoid doing any real work.

The bottom line: The everyday con artist can be even more damaging to a team in the long run than the straight-up criminal. They seem credible, so people default to seeing them as cultural role models.

Once you recognize the con, you won't be able to unsee it.

Kieran


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Every week, I write a deep dive into some aspect of AI, startups, and teams. Tech exec data storyteller, former CEO @Textio.

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