There are three simple dimensions which neatly separate most fractional CTOs:
- Engagements: Few, or Many?
- Playbooks: Runner, or Builder?
- Experience: Engineer, or Leader?
Some combinations of these work particularly well, and I’ve seen them succeed over and over again. The two stand out combos are:
- Many Engagements (10+ simultaneous clients), Playbook Runners, with multiple decades of Tech Leadership
- Few Engagements (1-2 simultaneous clients), Playbook Builders, with multiple decades of Tech Leadership
From the CEO/Board perspective the key decision is the use of “Playbooks”; from the CTO/fCTO perspective the key is instead the number of parallel “Engagements” the person wants.
Playbook Runners
These are the ‘productised’ CTOs: they have a single, known, pre-baked, solution to each of many problems, accumulated over a long career of deploying similar solutions in similar ways over and over again, refining them each time, until they are highly polished.
This CTO will walk into any org and hit the ground running delivering measurable uptick in various OKRs.
The role won’t tax them mentally, since each company is a minor variation on the pre-made playbook; as a result, they can efficiently handle many simultaneous clients, spending a small amount of time with each, and delivering a large amount of value.
Playbook Builders
These are the ‘problem solver’ CTOs: they approach each company as a new and unique bundle of challenges, and assemble solutions quickly from the pieces of their prior experience, accumulated over a long career of deploying similar solutions in similar and different ways, adapting them each time, until they deeply understand the ‘why’ and the ‘how’ of each approach.
This CTO will immediately see the underlying problems in any org and work to fix them first, triggering an avalanche of improvements that ripple-through the org, effecting underlying change.
The role requires deep engagement, and time spent understanding each team and product in detail, to spot the key issues and craft solutions to them. As a result they can’t afford more than a few simultaneous clients, as they need the time and energy to really dive into the weeds with the CEO/team.
CEOs: Which candidate is for me?
If everything’s going great and your biggest challenge is efficiency: reducing the $ spend per $ gained … you probably want a Playbook Runner. You want someone with many other clients – it’s a positive that they’re not too engaged with your business, it ensures they’ll focus on cheap wins and efficiency improvements, on dictating solutions to you that you’ll follow slavishly — because those solutions represent common practices.
If there’s uncertainty in your business, and your biggest challenge is jumping in the right direction: diversify the product portfolio, invest/de-invest in core areas — or if your org is underperforming versus your reasonable expectations — you probably want a Playbook Builder. You want someone to diagnose the subtle problems that are holding your org back, frame tightly-defined solutions, and then stick around to shepherd them through to completion.
CTOs: Which role is for me?
Personal preference comes first, but if you’re sitting on the fence, then a few pointers may help you decide:
- If your work history is operations-heavy (DevOps, Infrastructure, Deployment, Project Management, etc) – you probably have ‘efficiency’ built-in to your mindset already, and processes that are ‘simple’ to you (because you’ve done them similarly or the same many times over) may be ‘difficult’ and highly valuable to others.
- If your work history is product-heavy (Innovation, Product Development, Engineering Architecture, etc) – you probably love problem-solving, and your extensive library of successes – and failures – gives you the ability to instantly diagnose and solve problems that others have to spend time investigating in detail.
- Would you consider the 5-10 year commitment (from arrival to exit) of a full time CTO role ever again? If so, and you still enjoy pouring your energy into businesses, that energy is invaluable to orgs that need detailed customised help from an expert.
- … Alternatively: if you’ve reached a point in your career where you’re happy with your achievements, and your involvement with businesses now is more for fun and giving back, then a focus on “many clients, same problems” will help you spread your influence as wide as possible, for the least possible tax on your energy and time.
- If you like the idea of a ‘productised business model’ CTO – doing the hard work once, then charging for it many times over – you should form those into playbooks and start selling them / access to them (via you).
- If you like the idea of an ‘interim role that becomes permanent’ – starting with a company smaller/earlier stage than would challenge you, but helping them grow to the point where it becomes exciting – then this is a great opportunity to take one and figure-out new playbooks that will shape this org you later hope to take a leadership role in.