Udbjørg Management
Mar 27

On Hiring: A Guide for Startup CTOs

How I approach job ads, outreach, interviews, and candidate communication when building a technical team.

Hiring is one of the most important things you do as a CTO, and one of the easiest to treat as somebody else’s problem.

It isn’t.

The recruitment process is a candidate’s first experience of how your company communicates, makes decisions, and treats people. If the process is vague, slow, or slightly chaotic, they will quite reasonably assume the job is the same.

I want trust-based teams. That means the trust has to start before somebody signs a contract.

Start with the actual job

Before writing an ad, work out what problem you need this person to solve.

Not which fashionable tools you would like them to know. Not a copy of the last job ad with another seniority level pasted into the title. What will they be responsible for, and what should be better six months after they join?

A useful job ad should explain:

  • what the company is trying to do;
  • what the team owns;
  • what the person will spend their time on;
  • which skills are genuinely required and which can be learned;
  • how the hiring process works; and
  • the salary range.

The last point should not be a surprise at the end of four interviews. Being open about salary saves everybody time and sets a much better tone.

I also try to read the ad for accidental gatekeeping. Long lists of requirements make people screen themselves out, often even when they could do the job. Tools such as Gender Decoder and Joblint can help find questionable wording, but a tool is not a substitute for asking a few different people to read the ad.

And take old ads down. A job listing that has been sitting untouched for months makes the company look asleep.

The pitch

For important hires, I like the CTO or VP of Engineering to be part of the first contact. A personal message shows that hiring is not just a ticket handed to recruitment.

The message does not need to be clever. It needs to answer three questions:

  1. Who are you?
  2. What is the company trying to do?
  3. Why are you contacting this person?

For example, I used a version of this while at TwentyThree:

Hi, I’m Magnus, VP of Engineering at TwentyThree. We’re working to humanise digital experiences, and we need an engineer to help move our monolith towards a more modern architecture. Your experience looks relevant. Would you be interested in a short conversation about the challenge?

It is short, specific, and sounds like it came from a human. That already puts it ahead of most LinkedIn messages.

Three ways to run recruitment

I have used three basic models.

Do it yourself

You find people, write to them, screen them, and run the process. You keep control and build the relationship directly, but it takes a surprising amount of time. It also only works if somebody treats recruitment as real work rather than the thing they do after everything else.

Let a recruiter do it

A recruiter handles sourcing and the process. This gives you time back, but it can create distance between you and the candidate. If the recruiter cannot explain the work, the team, and the reason the role exists, you will get more candidates but not necessarily better matches.

Do it together

The recruiter handles the machinery while you and the team stay involved in outreach and conversations. This is usually my preference. A good recruiter brings reach and discipline; the people doing the work bring context and credibility.

Whatever model you use, agree on who owns each step. Otherwise both sides assume the other person is following up, and the candidate hears nothing.

Keep the flow simple

You do not need an impressive recruitment system on day one. A board in Trello, Asana, a spreadsheet, or the tool you already pay for is enough. Make the stages visible and keep only the information you actually need.

A simple flow could be:

  1. New candidate
  2. First conversation
  3. Technical or practical conversation
  4. Team conversation
  5. Decision
  6. Offer or rejection

For each stage, define the purpose. If two interviews ask the same questions, one of them can probably disappear.

Before the interviews, decide what you are trying to learn. Afterwards, collect written feedback before everybody discusses the candidate. This makes it a little harder for the loudest opinion in the room to become the team’s opinion.

I am not a fan of interview processes designed as endurance sports. Every extra step should earn its place.

Use the team, but give them a job

Candidates should meet some of the people they may work with. It gives the team useful input and gives the candidate a much less polished view of the company.

But “meet the team” is not enough of an interview plan. Give each participant an area to explore: collaboration, technical judgement, product thinking, or something else that matters for the role. Teach people how to interview and how to write useful feedback.

Be careful with the phrase “culture fit”. It can easily become “feels like us”, which is a good way to hire the same person repeatedly. I would rather ask whether the person can work well in the environment, add something to the team, and succeed with the support we can realistically provide.

Also leave time for the candidate’s questions without the hiring manager in the room. They are evaluating you too.

Communication is part of the interview

Tell candidates what the process looks like, who they will meet, and when they should expect an answer. Then keep those promises.

Sometimes a decision takes longer than expected. Fine. Say that. A short update is better than silence, even when the update is “we are still discussing it”.

Rejections deserve the same care. Be direct, be kind, and give useful feedback when you can. Do not send somebody through several hours of interviews and then finish with a mysterious template from a no-reply address.

The point is trust

Hiring is not separate from culture. It is the first demonstration of it.

If you want a team built on trust, show candidates how decisions are made. Let them meet the people they will work with. Be honest about the difficult parts of the job. Share the salary range. Answer when you said you would.

None of this guarantees the right hire. Hiring people is still messy and full of judgement. But it gives both sides a fair chance to make a good decision, which is a much better starting point than a polished job ad and five rounds of surprises.