I heard from a friend the other day who had an offer in hand from one company but was very upset. Her first choice had been stringing her along for a month. My friend is very experienced in tech. She’s worked at a lot of notable startups, so I was surprised that she was confused.

It was a perfect match. She’d met the CEO twice, had interviewed with many members of the team and knew she was exactly what they needed but…

…still no offer!

I instantly understood that this situation had nothing to do with her. The company wasn’t making her an offer because they had no idea what they were looking for in a candidate. They would only come to realize this much later in the process and would be unable to make a decision before they actually knew what they wanted.

Hiring is a huge decision for a young company and even more so if they are hiring for a role they do not understand or have never done before. Consider this from the CEO’s perspective: In an early stage startup each hire significantly reduces your runway. It is a big decision. An individual team member can greatly impact the culture of the company, the direction your product goes, or your engineering culture. This is why many smart people say that extreme reference checking is the only way to get critical hires right. Startups have this adage that you need to be either really good at hiring or really good at firing. I think you need to be good at both. (Few people are.) These are hard problems to solve.

When you’re interviewing with a startup, it’s important to understand what they do know and what they don’t know. Have they hired and fired for this role before? Do they know what the role entails? Do they need help and guidance to define the problem space? This can be an opportunity to set yourself apart from other candidates.

If you find yourself asking: Why is this not moving forward? It’s probably start up shit.

It probably has nothing to do with you. If you’re going to work in this environment you are going to deal with this a lot. The most important thing is to understand the startup. What they know, what they don’t know, and what they think they know that they don’t know.

How do you know if this type of indecision is affecting you?


(1) Do you know what you are looking for in a candidate for this role?

(2) Do you have 3 and 6 month goals for this position?

(3) How will you judge success in this role?

(4) How long has this position been open?

(5) How many people have you interviewed for this role?

What should you do if the CEO does not know what they are looking for?

Educate them–

(1) Here’s how my approach differs from other common approaches…

(2) Here are some things I would look for in a candidate if I were hiring for this role…

(3) When developing this role in the past here are some metrics that I have used to judge performance. […] Do you see any of those being a fit for how you do things here?

Good luck. Startups are hard.