I’m Glad I Hired One Of My Startup’s Biggest Skeptics

According to one founder, your ideal first employee will probe for weak spots as diligently as any investor.

I’m Glad I Hired One Of My Startup’s Biggest Skeptics
[Photo: Maximkostenko/iStock]

My startup just welcomed its first-ever hire since our launch, and he is not impressed with us.


He shouldn’t be–we have so much to do to turn our early milestones into sustainable, long-term success. It is a little weird to interview somebody who doesn’t care a whole lot about what you’ve accomplished so far, and doesn’t mind saying so. But even so, I’m glad that our first new team member arrived as one of our biggest skeptics. Here’s why.

You Want Your Earliest Job Applicants To Grill You

Tommy and I were old colleagues and had spoken a few times about UserMuse, so when we sat down to really discuss him coming on board, I felt unusually prepared. He was prepared, too, though, with questions like these:

  • “How are you engaging the buyers?”
  • “What percent do you think will never come back?”
  • “What are the biggest challenges you’re hiding behind the user growth?”

That’s how the conversation went–every business metric or insight I offered was countered by a frank question about why it mattered. The subtext was usually, “Tell me why this isn’t going to fail.” A few times, it was, “Tell me why you aren’t going to give up when things go sideways.”

It felt more like an investor pitch than interviewing a potential hire. Then again, there ideally shouldn’t be much difference between the two when you get right down to it.

Related: This Is Why Your Startup Will Fail

Convincing somebody from scratch of the value of a new business shouldn’t be easy. They force you to articulate that in new ways. Sometimes they ask questions for which you have no answers. For founders, this can trigger defensive instincts (“Do you even understand what it took to get to this point?”), but it’s extremely, critically important to fight the urge to push back.


After all, once you’ve clawed your way to wherever you are, it’s natural to feel pride in the accomplishment. A good first employee won’t care about what got you here, only about what’s next–and if you fall back on your defenses, you’re missing a chance to let them help you progress. They have no sacred cows and no attachment to how you did things yesterday. They stand on the shoulders of whatever came before.

Assuming they fit the culture, you need people with this attitude; you just have to be willing to listen and let them push you.

Don’t Shield New Hires From Your Toughest Challenges

If you’re confident you’ve found the right person to add to your core team, treat them like a grown-up from day one. Make sure they’re aware of the biggest problems you’re facing today–especially the hairy ones for which you don’t have answers yet.

Every company in the world is facing big challenges right now. You’re adding people to your team to help solve those problems, whether the issues stem from growth or a lack of it. You give your startup’s newest employees (and your business) the best chance to succeed if they all know where to train their sights.

Related: Here’s What To Do When Your Startup’s Customers Get Mad At You

Something unfortunate happens to a lot of companies as they grow, and it happens quickly in my experience: The on-boarding process, intended to help people get up to speed on how the business works and what everyone does, morphs into a marketing pitch. The company’s problems are minimized or avoided, and the team feels obligated to paint the rosiest picture of the business they can.


That’s dangerous to everyone involved. The worst thing you can do to a capable person is convince them that everything is a certain way for a reason. They should be questioning everything that doesn’t make sense, not trying to rationalize why the status quo is actually just fine after all. You and the founding team may have learned to live with certain things while you fought more pressing battles, but that doesn’t mean the new folks should.

Don’t spin gaps or deficiencies as things you did deliberately. There are times when it might actually make sense to bullshit people, but this is absolutely not one of them. Don’t make your new employees cut through marketing-speak to figure out for themselves where the bodies are buried. You’ll waste time and undermine your own credibility as a leader when they figure it out for themselves.

To me, the ideal first employee is eager to join the team and dying to fix things you’re not doing well. If you find someone like that, give them what they need and let them get to work.

About the author

Christian Bonilla is the founder of UserMuse, which curates market research panels for enterprise software companies. He posts frequently on UserMuse's blog