But first, to get a sense of where I’m headed with this article, this is what I tell founders who ask me about Fractional CTOs:

You should be as uncomfortable with a fractional CTO running your tech as you would be with a fractional CEO running your business.

I am compelled to write about this because it’s too easy. It’s too easy to be a mediocre fractional CTO. Companies come to us with great need, they see a sort of salvation in our words and then within a year, maybe even months, the relationship has gone to hell.

Feel free to click the back button if this isn’t your experience. Or better yet, leave me a comment to share the values and principles that have served you well in helping your client meet their goals through your fractional services.

Why does a fractional CTO engagement go sideways?

Consider the reasons for being pursued by a company in desperate need of your services:

  1. they lost (or fired) their CTO who left a vacuum in the leadership suite
  2. they never had a CTO or any real leadership of their technology organization
  3. they are suspicious or concerned about their current technology organization’s productivity, velocity or quality
  4. they need to expand their capacity to produce deliverables that their current technology organization doesn’t have the time, expertise or appetite for

Having an acute understanding for the context by which you were invited into the system can drastically help you provide the value the organization needs. It is the lack of understanding this context that creates several pitfalls for you to step into. Yes, even in broad daylight.

Here are few complex problems that you might be walking into and I provide you with some steps towards resolution if you find yourself stuck in there already.

The Messiah Complex

Promise the world to a hungry crowd who will lap up anything you say! Especially if they are faced with a sudden and unexpected change in their organization. They have the cash, they have the desire and they want YOU!

The temptation here is to promise a ride free of any (or mild or medium) hiccups as you help them transition into a new dispensation. Trust me, you are doomed to fail. No system is able to accept a newcomer consultant type unless that consultant is there for a very short time.


  1. Define a very short period of time (less than 3 months)
  2. If you plan on staying longer, advocate for an “Interim CTO” title and then define a slightly longer period of time.
  3. Focus on velocity over re-inventing systems. They are in a lurch, you’re not there to “go back to the drawing board”. As a fractional CTO, jump in, focus on picking up where the other left off and deliver results early.

The Coaching Complex

So many fledgling startups have no clue what they’re getting into when they dream up their first SaaS company. If they are lucky, they have been exposed to the lean startup methodology and are on their way to saving a LOT of money towards building their product.

In flies the fractional CTO who gets to design the blueprint for the technology organization and “coach” the founders as they try desperately to get a product off the ground.


  1. Don’t. Charge. Them. A. Single. Dime. Yup, now how do you feel now about coaching young founders?
  2. Don’t give them the impression that you’re seriously considering joining them if you have no intention of doing so.
  3. As a fractional CTO you are occupying a critical function to the brand new startup. The choices and the decisions you make will make or break them. Take it very seriously and spend 20% more time than you originally committed to.

If a startup can’t afford a CTO, then the fractional CTO should not be charging them anything.

Something I tweeted https://twitter.com/etdebruin/status/1522457895345922048

The Expert Complex

So courageous and ignorant to point the finger at another’s work when we are void of fully understanding the system in which that work was accomplished. But yes, you’ll be the “expert” to shine the light on how things were supposed to be done.


  1. Do one thousand interviews so that you can understand absolutely everything about the team, the system, the culture in which the work that was accomplished.
  2. Don’t trust yourself. Be suspicious of your conclusions.
  3. Be fully in service to the team, and not the work. You’ll be gone in a few months, and the team will remain. How will the feedback or recommendations you give be in service to the humans you leave behind?

Velocity and Value over Time and Materials

A Fractional CTO position at the executive level needs to focus on getting in, delivering value and getting out. If this is not your intention, then I would highly recommend you call the position you are advocating for an Interim CTO position.

Remember that you may understand what you are there to do, but there are many C-Suites who don’t fully understand the role of CTO. It is up to you to help educate them.

  1. Fractional: project based, value delivery with great velocity $$$
  2. Interim: people based, management delivery over longer period of time $$
  3. Mentorship: project based, expertise sharing over short period of time $
  4. Coaching: people based, development through partnership over longer period of time $$

I am a huge fan of Fractional CTO Engagements

I tell any CTO of an established startup or organization to go for it when a fractional engagement comes their way. There is a tangible improvement in your CTO role at your own company when you are out there learning how to solve other projects within companies and domains that you don’t know.

This is my preferred view of when to do fractional engagements: when the CTO is gainfully employed and doesn’t really need the gig for any other reason than helping out or learning new things quickly.

This is all I have to say about this.

I could be wrong.