I recently had the experience of joining and then leaving a startup. I won’t get into the details of the company, but let’s just say it rhymes it “kitty slapper.” I stayed a month, which was long enough to understand the culture of the company, the mission, and the people. In that time, it became really apparent to me that I’d joined the wrong company for me. Once I knew, I didn’t waste any time. I let the team know and transitioned out.

So, on one front, I think I did okay. When I knew it wasn’t going to work, I didn’t belabour it. I didn’t foolishly stick to my plan despite the evidence I had that it wasn’t going to work. A younger, more driven, and more naïve me would have pushed ahead trying to make it work at all costs. I did that at Facebook and mostly just gave myself more grey hairs.

Now, I wouldn’t pretend that I left Facebook in the most mature, conscientious way. No, in truth I was really frustrated and hurt when I left. Things weren’t adding up and my two separate chains of accountability were giving me incongruous feedback. If I’m honest though, I think there was a way forward for me there. It would have just required a lot of letting go of hard feelings and finding a new team to call home.  I wasn’t willing to let go of my goals or area of focus at Facebook. So, instead of moving away from security or quitting when it seemed like there was an impasse, I just kept grinding. I gritted my teeth and pushed forward. The result? I still quit a year later, even more frustrated and demoralised than the year before.

Okay, so I didn’t repeat that mistake this time. I recognised the way was blocked by unresolvable issues and I walked away.

But there’s room for improvement here. The question I keep coming back to since I left a couple weeks ago is how did I miss these signals in the first place? I’m a very, very seasoned interviewer. So much so that when someone is interviewing me, it typically works more like I’m interviewing them. So how the hell did I miss majorly important signals that would’ve prevented me from joining that company in the first place?

After another week of self-reflection, I think it comes down to just a few things.

#1 Don’t fall subject to the authority bias

One of my favourite books is The Art of Thinking Clearly by Rolf Dobelli. The chapter devoted to the Authority Bias poignantly sums up one place where I went wrong in joining the startup I just left:

The first book of the Bible explains what happens when we disobey a great authority: we get ejected from paradise. This is also what less celestial authorities would have us believe.

When I went for one of several interviews with the CEO, I noted a clear authoritarian streak in his communication. Shockingly (at least to myself in retrospect), rather than investigate this, I bowed down. I was excited about the company and scared of not getting to join it. So, even though I had signal that *already* was telling me something wasn’t right, I ignored it. This is probably a bit of confirmation bias on my part as well, but the fact that I didn’t take the opportunity to ask the hard questions I should have is something different. It’s the authority-fearing part of me (and I guess part of everyone) who is afraid of causing trouble — even when the consequences of *not* causing that trouble turn out to be much worse.

#2 Don’t let “winning” override making a smart decision

In the interview phase of this company, I sent over some outlines that explained how I would run a team doing the work I had been discussing with the leadership team. It was very technical (as one might imagine it ought to be if I’m being interviewed to be a lead engineer). Now, from the technical people, I got a thumbs up. In fact, after a month at the company, I can see that the outline I sent over was basically spot on. Yay me. The important part about this is that I also got told that my communication “wasn’t a successful one for informing business people.”

At this point, if I’m honest with myself, I let my ego get the better of me. Incredulity overtook me and I got caught up in a haughty, “Why would business people expect to be able to understand an outline explaining how to tackle a hard technical problem?” train of thought. Now — that question is actually the perfect question to ask. However, instead of facing the reality that I was having to ask such a ridiculous thing and walking away, I tried to “win” the debate. I should have just accepted that at this particular company the top of the food chain was obviously business people rather than engineers. I should have owned the reality that their expectation would be that I would communicate extremely complex things upwardly in some sort of digest format. That if I didn’t summarise complexity digestibly enough, the communication would be a failure and blame would be assigned to me.

But I didn’t do any of that. I got caught in the trap of “No way, I’m a great communicator — I’ll prove it!” I can see that now, but it was not at all obvious to me then. In fact, after being told that my hours of free effort devising a way to tackle a hard problem with a team were wasted because a business person didn’t understand it, I was nervous. I worried that I had screwed up my prospects of getting hired. I spent one night tossing and turning hoping that my failure hadn’t undone all the positive interactions I’d had prior. Silly me.

#3 Pay attention to all the signals you have

Going into this company, I had several reports that all was not unspoilt in the state of Denmark. I had some direct feedback from current employees and I had some very telling Glassdoor reviews. Did I weigh these correctly? Nope! Again, I let confirmation bias take over my reasoning. Rather than asking the hard questions about these things, I instead asked the questions that I knew gave my interviewers enough rhetorical space to give answers I’d accept.

For instance, I should have asked, “I read on Glassdoor that X, Y, and Z appears to happen at your company. Is that true? If so, how often? Has anyone left the company as a result?” That question leaves no room wriggling around. Instead of using the signal I had usefully, I instead asked questions like, “You guys have a bit of a reputation. How does that play out in the day-to-day running of the company?” This question gives *plenty* of room for subjectivity and soft answers. This is silly of me. Wasting a strong signal about a company — especially one that invalidates the assumption that it’s a good one to join — is about as rookie a mistake as one can make. 10+ years into my career, here I am making exactly that mistake.

#4 Checksum your intuitions about how your job will work

As I look back at my interview performances, I realise I didn’t bother to do something really important. I didn’t bother to check if the company worked in a sensible way relative to my expectations. I think my years at Facebook set me up perfectly for this. At a company like Facebook, even a “meh” team still produces a lot of great work, has amazingly talented people on it, and has plenty of remit to do their jobs well. It never occurred to me that these things might not be true at a different company. So, rather than asking straightforward questions like:

• If I need to coordinate with other teams in order to do my job well, what might that look like?
• What does the reporting structure look like for engineers?
• If I see an opportunity to improve processes across the engineering team, how can I push that forward?
• If I see an opportunity to improve processes across the company, how can I make them happen?

If I’d asked these questions and pushed for authentic answers, I would have known that I was barking up the wrong tree. But, I didn’t. I just assumed that every company works as well as Facebook by default.

Nope.