October 19, 2026
October 19, 2026
How to choose a fractional CTO
Questions to ask before you hire a fractional CTO, including how they’re paid when the right answer is to build nothing.
Questions to ask before you hire a fractional CTO, including how they’re paid when the right answer is to build nothing.
Choose someone who has run a system like yours in production, who spends your first meeting asking about the business, and who earns the same whether or not you build anything. A website won’t tell you any of that, so you have to ask.
I’m a fractional CTO, so read this knowing that. These are the questions I’d ask from the other side of the table.
Ask what broke on their watch
Ask about something that failed while they were responsible for it, like an outage, a migration that ran long or a senior hire that didn’t work out. Someone who has run a platform will have several of these and will tell them in detail, including what they changed afterwards. If every story is a success, they’ve either been lucky or they’ve been advising from a distance.
They should also be able to read your codebase and judge it. Reviewing your engineers’ work or a vendor’s proposal only counts for something when the reviewer could have built it.
Find out how they’re paid when the answer is no
Some fractional CTOs are the front door to a development agency. The advice can still be sound, but they earn more when you build. Ask what happens to their income if they tell you to buy an off-the-shelf tool instead.
I run a build team, so this question applies to me as well. I deal with it by charging for a diagnostic up front. The recommendation is paid for whether or not a build follows, which leaves me no reason to push one.
Check they know the rules your business runs under
Lending, insolvency and professional services each carry obligations that shape technology decisions, such as the credit information rules in the Privacy Act, AML/CTF requirements and privilege on legal files. Someone new to them learns on your time and at your risk. Ask what they’ve built under those rules and listen for specifics.
Notice who does the talking in the first meeting
In a useful first meeting you’ll do most of the talking. They should want to know where the business is stuck and what you’ve already tried to fix it. If they arrive with the answer before they’ve heard the problem, it’s probably the answer they give everyone.
Be honest about how much of their time you need
A fractional CTO gives you a day or two a week. Some businesses outgrow that, usually once technology becomes the core of what they do and the decisions come daily. A good fractional CTO will tell you when you’ve reached that point and help you hire a full-time leader, even though it ends their engagement.
Ask references what went wrong
When you speak to a founder they’ve worked with, ask what the CTO got wrong and how they dealt with it. Everyone gets something wrong over a long engagement, and how they handled it tells you more than praise does.
If you’re choosing one for a business in finance, lending, insolvency or professional services, here’s how I work.
Choose someone who has run a system like yours in production, who spends your first meeting asking about the business, and who earns the same whether or not you build anything. A website won’t tell you any of that, so you have to ask.
I’m a fractional CTO, so read this knowing that. These are the questions I’d ask from the other side of the table.
Ask what broke on their watch
Ask about something that failed while they were responsible for it, like an outage, a migration that ran long or a senior hire that didn’t work out. Someone who has run a platform will have several of these and will tell them in detail, including what they changed afterwards. If every story is a success, they’ve either been lucky or they’ve been advising from a distance.
They should also be able to read your codebase and judge it. Reviewing your engineers’ work or a vendor’s proposal only counts for something when the reviewer could have built it.
Find out how they’re paid when the answer is no
Some fractional CTOs are the front door to a development agency. The advice can still be sound, but they earn more when you build. Ask what happens to their income if they tell you to buy an off-the-shelf tool instead.
I run a build team, so this question applies to me as well. I deal with it by charging for a diagnostic up front. The recommendation is paid for whether or not a build follows, which leaves me no reason to push one.
Check they know the rules your business runs under
Lending, insolvency and professional services each carry obligations that shape technology decisions, such as the credit information rules in the Privacy Act, AML/CTF requirements and privilege on legal files. Someone new to them learns on your time and at your risk. Ask what they’ve built under those rules and listen for specifics.
Notice who does the talking in the first meeting
In a useful first meeting you’ll do most of the talking. They should want to know where the business is stuck and what you’ve already tried to fix it. If they arrive with the answer before they’ve heard the problem, it’s probably the answer they give everyone.
Be honest about how much of their time you need
A fractional CTO gives you a day or two a week. Some businesses outgrow that, usually once technology becomes the core of what they do and the decisions come daily. A good fractional CTO will tell you when you’ve reached that point and help you hire a full-time leader, even though it ends their engagement.
Ask references what went wrong
When you speak to a founder they’ve worked with, ask what the CTO got wrong and how they dealt with it. Everyone gets something wrong over a long engagement, and how they handled it tells you more than praise does.
If you’re choosing one for a business in finance, lending, insolvency or professional services, here’s how I work.
