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You’ve defined what you need in a leader, you’ve worked hard to narrow the pool to a handful of interesting and interested options. By the time you reach interviews, the stakes are high. At this stage, many founders default to the wrong signals.
They test for familiarity instead of judgment. Comfort instead of ownership. Pedigree instead of grit.
Let’s look at your first technical lead/CTO. What actually matters.
Ask technical and product candidates to walk through how they would build the first version of the product.
Where would they start? What would they de-risk first? What assumptions would they want to test with customers before writing too much code?
You are not looking for a perfect plan. You are looking for clarity of thought under uncertainty.
Strong candidates can explain what they’d build, but also what they would not build yet, and why.
Founding CTOs make constant tradeoffs. Speed versus quality. Learning versus scale. Flexibility versus focus.
Ask about decisions they regret, shortcuts they took, and things they killed early. These answers are as revealing as success stories.
If someone cannot articulate tradeoffs, they will struggle at this stage.
Even if they are building solo today, they will have to recruit soon.
Ask how they have built teams before. How they hire. How they handle disagreement. What former teammates would say about working with them. Who has worked with them more than once and would do it again.
Then actually check references in a meaningful way. Not “would you rehire them,” but “what was it like to build with them when things got hard.”
Over-optimizing for domain expertise. Many great CTOs learn a domain quickly if the problem is clear. Over-constraining here often leads to settling elsewhere.
Hiring a big-company CTO for a zero-to-one role. Leading inside structure and creating it from scratch are different skills.
Confusing research orientation with shipping orientation. Deep thinkers are valuable, but only if they want to put work into the world - and are ok putting it out when it is far from perfect.
Letting the process drag. Strong candidates read this as a signal about how decisions get made. Hiring with rigour doesn’t mean waiting weeks between steps. Provide transparent updates and frequent communication at every step.
Founding roles require transparency. The upside should be real, and the risk should be acknowledged.
Trying to make an early-stage role sound safe helps no one.
The right person is not looking for safety. They are looking for a bet that makes sense. If you are offering meaningful founder-level equity, then it is reasonable to expect lower cash compensation. Otherwise, you need to be prepared to pay at market levels.
Be honest about the unknowns and risks, and the supporting tools and staff (or lack thereof). If this scares someone away, better that then having them surprised and disappointed when they get started. The opportunity and upside will inspire the right person to lean in.
Hiring initial leaders is one of the most critical decisions a founder makes. Do this well and you won’t just hire someone who executes, you’ll add a multiplier who shortens the learning cycle, accelerates momentum, and makes the company possible.
Read more insights from our team.
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Founded by Kristina McDougall in 2013, Artemis has grown to become Canada’s most trusted boutique executive search firm for startups.
We recognize that our work takes place on the traditional lands of the Attawandaron, Anishinaabeg, Haudenosaunee, and Mississaugas of the Credit. We honour Indigenous stewardship and commit to embedding reconciliation into our work, holding ourselves and our clients accountable.
