I'm looking to take on fractional CTO work and have been thinking about the sort of companies I'd like to work with and how I'd like to work with them. "Fractional CTO" could easily mean 100 things to 100 different people. That's fine! Hiring an individual at that level has to be based on deep, solid communication from the start. Let's set an AI baseline.

I couldn't have said it in a drier, more boring, almost human-like way. Thanks, Chatty! Ok, so what should your conversations with a fractional CTO cover?

Firstly, if you need a full-time CTO, don't hire a fractional CTO.

Engage with a fractional CTO. Sure. Be upfront and explicit about your needs and wants. If a short-term or part-time "tour of duty" might work, hash it out together. The fractional CTO may be open to becoming full-time after a period. Or perhaps the fractional CTO can give you 100% of their attention, but not at a traditional "full-time" commitment level.

This engagement can be complex to navigate. How much time, attention, and availability the position will demand is only sometimes apparent. A seasoned CTO will not take this lightly. Especially one that has made the mistake of underestimating a big task (i.e., every CTO ever).

Find out why this CTO wants a fractional position. Make sure this sits well with you. It could be a desire to work less, which may mean stronger work-life boundaries. They may be looking to experience more variety across industries. That could bring exciting cross-pollination of ideas. Preserving optionality to pursue other work; it's not uncommon but certainly comes with its own risk. In this case, especially, you should start an open dialog about the eventual transition out.

All employment will end. Discussing this at the start of a relationship may be unfamiliar or uncomfortable, but a mature leader will welcome the openness and honesty. It will engender trust and mutual respect.

A CTO, fractional or full, will become part of your company. If they're fractional -- which is increasingly common but may need to be better understood -- how will you communicate their role to your C-suite? To investors or board members? To your existing teams and new hires? Everyone must know why you're working with a fractional CTO. You avoid breeding resentment if the role is well articulated and the fractional CTO appears committed to the team and mission. The team must see how much they can learn and benefit from the experience and insight of a veteran CTO. Conversely, you should hire a CTO that expects to learn from the team and grow with their new role in your company!

Are you a founder? Do you want a founder-style CTO? A young company has much learning and growing (pains) ahead of it. Each company blazes its own trail. There is no playbook. Would you prefer a traditional CTO, one who rose through the ranks of big cos with enormous headcounts and P&Ls? Or one who cut their teeth in the trenches of tumultuous and scrappy startups? Who is the CTO that can work with you today and get to tomorrow with you? You both need to evolve or have the range to make this portion of the journey together.

A CTO needs to be on the inside with the leadership. They are responsible for driving back office (i.e., internal) and front office (i.e., customer-facing) technology and innovation. They must grok the founder's vision, align with the cross-functional goals of the company, and understand the marketplace you're operating in. This process will take some time. It should take some time. You want a CTO with boundless curiosity. Curiosity that drives exploration, learning, connection, and action.

If you can't discern anything else, assess their curiosity. It's a straightforward, leading indicator that you've found an individual who will proactively come to understand what you need, bring solutions and innovations without being asked, inspire the team, and -- most importantly? -- they'll be fun to work with.

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PS: Looks like you can hire a fractional CTO on Gumroad