Answers
Straight answers to the questions I actually get asked.
No wind-up. Each one answers the question in the first paragraph and then explains the reasoning.
What does AI governance look like for a company that isn't a tech company?
Not a policy document. It is three decisions made before the build: what data the AI can touch, who owns its output, and how you will measure whether it works. Get those right and you can adopt AI aggressively.
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What does a fractional CTO actually do?
Owns your technology decisions and delivery on a part-time basis, without the cost of a full-time executive. The word that matters is owns: accountable for what gets built, what gets bought, and whether it worked.
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Fractional CTO vs full-time CTO vs IT consultant: which do you need?
Full-time when technology is your product and the work never stops. Fractional when the decisions are senior but do not fill a full-time calendar. A consultant when the problem is defined and you need hands, not ownership.
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How much technology leadership does a 50-person company actually need?
Less than a full-time CTO and more than nothing, which is the gap most 50-person companies fall into. Senior ownership typically starts at 5+ hours a week and scales with the involvement needed.
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When should a founder stop running operations out of spreadsheets?
When the spreadsheet only works because a specific person is watching it. That is the signal, not the row count, not the file size, and not how sophisticated the formulas have gotten.
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How do you know if a process is worth automating?
Automate a process when it is repetitive, stable, and expensive in a way you can name. If the process is still changing shape every month, automating it locks in a design you are about to regret.
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What should an AI agent be allowed to do in our business?
Enough to remove real work, but not more than the risk justifies. Let it act on its own where mistakes are cheap and reversible, require approval where they are not, and widen its authority only after it proves reliable.
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When should we build a prototype before committing to custom software?
When the problem is clearly worth solving but the right solution is not. A prototype should answer one specific business question before you pay for the full system.
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Quick answers
Questions about owning the technology function
The short version first. Open any question for the practical answer, without adding another page to navigate.
Do we need a fractional CTO or just a better MSP?
Usually both questions have the same root: nobody owns the technology function. A better MSP may close tickets faster, but it will not set your roadmap, manage your budget, or decide what should stay internal. A fractional CTO owns those decisions and holds the support model accountable.
Read what a fractional CTO ownsCan one internal IT person replace an MSP?
Sometimes, especially for day-to-day support and infrastructure work, but only when coverage and specialist gaps are handled deliberately. One strong internal hire may still need targeted partners for managed detection, backups, overflow, and after-hours support. The right answer depends on the work, the risk, and the coverage you need.
What does SOC 2 readiness take for a company our size?
It starts with scope, policies, access controls, vendor management, change management, and evidence that the controls are followed. Readiness commonly takes several months before the audit window. I lead readiness and internal oversight alongside an audit partner, including assigning control owners and keeping evidence moving.
How many hours a week is fractional leadership?
A typical engagement starts at 5+ hours a week for priorities, vendor and budget reviews, security oversight, and guidance for internal staff. The commitment increases when the business needs deeper involvement, such as an active build, MSP transition, or SOC 2 readiness. The monthly fee reflects that level of involvement and what I own, not a prepaid block of hours.
Read about the right leadership levelWhen should we hire a full-time CTO instead?
Hire full-time when technology is a large share of your budget, you are building a product that is the business, or you need someone present every day to lead a sizable team. Before that point, fractional leadership provides senior ownership and helps define the eventual full-time role clearly.
Compare fractional and full-time leadershipStart with one problem.
Bring me the thing that's eating your week. We'll figure out whether it's worth solving and what it would take.