Startup Hiring Mistake: Idealistic Pessimists
And what you really want, skeptical optimists
You’re going back and forth over if you made a hiring mistake. This person is constantly pointing out problems. They’re real problems, important risks, things you hadn’t noticed yourself. But nothing moves forward. When this person is in a product conversation, the team gets stuck. Whenever you give them a specific task, they handle it well. They’ve clearly got skill. But you’re sitting on a decision to let them go. And you can’t quite do it because they’re skilled and uncovering real issues.
I’ve been in this situation more times than I’d like to admit. For mission-driven startup teams with rigorous hiring practices, the most common hiring mistake is keeping skilled idealistic pessimists around, often because they look so much like skilled skeptical optimists.
The difference:
An idealistic pessimist locks you in place behind the appearance of wisdom.
A skeptical optimist moves you forward, willing to be wrong together.
At a startup, you often hire people passionate about something (the idealistic part) even if it’s not exactly your mission. But you run into trouble when that idealism is locked into a specific worldview or implementation. Any deviation isn’t going to be something they could ever see working out (the pessimism).
A contrived example:
Someone has an idea: “We could use AI to generate content to serve more people.”
Idealistic pessimist: “We can’t use AI to generate content. What if it hallucinates?”
This is a legit risk. The team sees it, and it stops the conversation.
A skeptical optimist says, “We can, if we handle hallucinations.”
This keeps the conversation going. It doesn’t even require the person finding the problem to have a solution. Now the team is discussing how to handle it: creating a solid set of evals, watching metrics on a test with 1% of your traffic, etc.
It’s not about finding a way to go along with everything though. That’s why you need more than an optimist. You need a skeptical one. Someone who’s going to go deep. Someone who can see success with you. Someone who can see issues, and find ways to derisk things early. Or even to find ways to avoid the risk entirely.
What about other kinds of pessimists? Some kinds of pessimism help, especially curious pessimists in roles where adversarial thinking is the job (security, reliability, compliance, QA, finance, legal). The danger shows up when idealism locks that pessimism to one “right” solution and shuts the team down.
Are you saying pessimists can’t be skilled? No. Raw skill seems to be distributed relatively evenly across both idealistic pessimists and skeptical optimists. But skeptical optimists can actually harness the skill to solve open-ended problems. At best, idealistic pessimists begrudgingly solve tightly scoped problems. They feel productive, but they freeze when it matters most.
So you start trying to fix it. You tell yourself it’s a coaching problem, or a clarity problem, or a process problem. And it’s hard to see, because a lot of surface traits overlap.
Both idealistic pessimists and skeptical optimists:
Ask hard questions
Find failure scenarios
Seek to improve themselves
Can be skilled at their craft
Get labelled as “troublemakers” sometimes
Are seen as wise because of their ability to detect risk
That overlap is why you hesitate, but you start to see these differences:
So what do you do?
First, soul searching.
Then, if it still makes sense, let them go.
Soul searching:
If you use “idealistic pessimist” as shorthand for “person who makes me uncomfortable,” you’re the problem.
Are your mission, values, incentives, and behaviors incoherent? Have you communicated them clearly?
Do you play these games: stakeholder-driven product development, feature-driven roadmapping, guess-the-estimate bingo, inconsistent decision making, toxic deadlines? If so, you create incentives for pessimism.
If you’re far enough along to need roles where adversarial thinking is the work, scrutinize your organization’s communication and how you design, build, and operate to make sure people are in the right places.
Letting them go:
I believe people can grow, though growth on this particular item takes too long for a startup to tolerate. I’ve tried multiple times and haven’t been able to turn it around fast enough. I’ve tried coaching them to own the problem, tried to help shift the behaviors above, tried to pull apart the idealism or the pessimism. I think it’s possible, but it is a long process, often six to twelve months. Each time, I’ve parted ways with an idealistic pessimist across companies, the team has been much happier and productive afterward.