The Gambler

In Part 1, I argued that hiring a CTO starts with clarity about the problem you are solving. This piece assumes you have already crossed that threshold and are now evaluating candidates.

A common mistake at this stage is treating attributes as personality traits rather than systems. Strong CTOs are not great because of who they are on a good day. They are effective because they build processes that make good behavior repeatable, especially under stress.

The attributes below matter, but what matters more is whether candidates have built durable ways to practice them.

Ability To Change Altitudes

Strong CTOs can operate deep in the details and then move up a level without friction.

More importantly, they build mechanisms that keep them grounded in reality without requiring constant heroics. Concretely this looks like: regular design reviews, incident retrospectives & followups, clearly defined escalation paths, etc.

Ask not only whether they can go deep, but how they ensure they stay sufficiently connected to the details as the organization scales.

Ensure that they also have the ability to define a technical vision and a roadmap to realize it. The best CTOs should have experience doing this on multi year timelines. This is a great barometer for this attribute because it requires someone who can take high level goals and ensure that they get accomplished from low level work.

High-Tolerance Context Switching

The CTO role requires constant context switching. What distinguishes strong CTOs is that they do not rely on personal stamina alone. Again you want to understand what systems they’ve built to reduce cognitive load as much as possible. Some common techniques:

1. Do they have a very clear priority list and framework to prioritize work?
2. How do they delegate work? Is it well-defined and do they require a common update template?
3. Do they track their personal work well? CTOs who have written artifacts can usually resume their work more quickly after interruption.

If a candidate frames context switching as a personal superpower rather than something they actively manage, that is worth probing.

Precise Communication

Strong CTOs communicate clearly across the organization. This could be in the form of written updates via email or Slack. It could be a recurring project status update to investors or executives. They need to talk to peers, reports, or customers 1-1 or in groups.

Are they able to respond to questions they don’t know the answer to yet? How do they deal with high pressure situations where they may get peppered with questions? Do they get frustrated easily if they are continually pushed?

You need to ensure that they have a mental model for maintaining alignment when the org grows beyond what 1-1 conversations can support.

Strong Opinions, Weakly Held

You want a CTO with opinions, but not dogma.

You can glean a lot from candidates by how they describe their process of testing their hypotheses. Have they run experiments before with development processes on teams? How did they pick the metrics to track? Did they look at qualitative data? When something didn’t go as expected, how did they react?

This is less about intellectual humility in the abstract and more about whether they have built processes that make changing their mind normal rather than exceptional.

Product and Customer Orientation

Many technical leaders claim to be customer focused. Fewer can explain how they stay that way.

Strong CTOs have explicit processes to stay close to customers. The best ones are constantly chatting with customers. They make time every week to review support tickets or sales calls. They have weekly cadences with the GTM teams to ensure the roadmap is on track and any insights gleaned from the sales process make their way back to engineering.

Ask how they ensured customer exposure when they became more senior. Vague answers are a red flag.

Motivation Through Others’ Success

At scale, the CTO’s impact comes through others.

Strong CTOs invest in hiring systems, career frameworks, and coaching structures that allow teams to grow without constant intervention. They measure success by how little they are required to unblock day-to-day execution.

If a candidate’s examples center primarily on their own output, that is a warning sign. Especially when you are looking at early stage CTOs, a common failure mode is someone who just wants to remain an engineer but with the compensation of a CTO.

Comfort Making Hard Decisions

Hard decisions are inevitable. Someone who has made a hard decision before knows the importance of gathering as much information as possible beforehand. Did you weigh the pros and cons of all positive alternatives? Did you think about the consequences?

Once they’ve committed to the difficult decision, how do they actually execute on it? Have they ever been in a situation where the other party/parties blow up?

Ask how they have made difficult calls in a way that preserved trust and execution velocity. Candidates will often waffle on this but you need to push for a real example where they had to push a tough decision that they may not have agreed with themselves.

Low Ego

Low ego is not just a personality trait. It is observable in how someone runs meetings, invites dissent, and documents decisions.

Strong CTOs create environments where disagreement is safe and changing course is expected. They model this behavior consistently.

This is something your engineers and potential reports will be able to ferret out much more easily than you, given the power dynamic imbalance between them and the candidate.

Persistent Curiosity

Great candidates will be peppering you and everyone that interviews them with tons of questions. It doesn’t matter if they are a salesperson, engineer, C-level exec, or an investor, they’ll have a million questions.

The best CTOs (and really any C-level exec) are the ones that go deep everywhere and understand every part of the business. As the company grows, they delegate this responsibility to others but they still exercise it here and there. They provide their reports with a mental model on how to ask useful questions.

Curiosity that survives scale is almost always intentional.

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The best CTOs are not defined by isolated traits. They are defined by the systems they build to express those traits reliably over time.

In Part 3, I will cover how to evaluate these attributes and their underlying processes in interviews, without relying on vague signals like seniority or pedigree.