How to Spot a Bad Boss Before It's Too Late

Photo from Sebastian Hermann on Unsplash

How to Spot a Bad Boss Before It's Too Late

The best way to avoid working for a terrible manager? Don’t start working for one in the first place. But how can you tell if a potential boss might be a nightmare? Here’s an example from my own experience.

I once interviewed for a leadership role in data and data science at a fast-growing fintech startup. The interview had been rescheduled multiple times, which I figured was fine—hiring managers are busy. When it finally happened, it was scheduled for 6 PM on a Thursday. Tip: Always ask for a morning interview if possible—people are usually fresher and less grumpy.

The interviewer was the Chief Technology Officer (CTO), let’s call him Dave. I thought, “Great! This guy should know his stuff.” But things started to go sideways right away.

Dave called me on his cell phone to say he’d be late because he was waiting for an Uber. Not a great start, but I decided to stay positive. When he called back, the conversation went something like this:

Dave: “So, tell me about yourself.”

Me: “I have over 15 years of experience in data, building teams...”
(I kept it short—about 20 seconds, as I was well-practiced by then.)

But before I could finish, Dave interrupted.

Dave: “Great, great. I’m not a coder, but I love pair coding with analysts. I ask lots of questions and give lots of feedback. It works really well.”

Internal monologue: “Really? Do your analysts love having the CTO hovering over their shoulders?”

Then, while I was still processing this, Dave started talking about himself.

Dave: “I’ve started lots of companies, but this one’s different—it’s really taken off. I co-founded it with two friends; they’re the CEO and CFO. We run a tight ship.”

At this point, Dave paused to give the Uber driver directions: “Make a right here. Don’t go straight; it’ll be a nightmare.” Then he jumped back into the conversation.

Dave: “What have you done to set up data warehouses and reliable reporting?”

Me: “I’ve been hands-on as a data engineer and DBA. I’ve built databases, optimized performance, set up backups, scaled operations—pretty much everything data-related.”

Dave: “That’s what we need! Look, I’ve got to go—I’ll talk to you later.”

And just like that, the call ended.

The next day, the recruiter who arranged the interview called to say Dave liked me and wanted me to come in for another round. But I told the recruiter I wasn’t interested—this startup wasn’t the right fit for me.

Why? I got the feeling I wouldn’t enjoy working for Dave. He seemed more like a micromanager than a strategic leader. Great CTOs remove obstacles and drive meaningful projects. Dave, on the other hand, sounded like he’d spend his time hovering over my work.

In the end, I trusted my gut and walked away. Sometimes, the best career decision is saying no. I hope the Uber driver got a good tip but somehow I doubt it.