Don’t do OKRs just yet.

The most common type of injury for OKR coaches? Being blown up in a Silo Explosion💥

Luca Cipriani
3 min readMar 28, 2024

Last week, I visited a client of mine*, a growing software consulting firm with a little over 30 FTEs.

During the discovery process, they insisted on immediately starting with OKR workshops to define their objectives for the upcoming semester.

That’s often the case, that’s why I developed a strict onboarding flow.

But this time, it wasn’t enough.

*(Yes, I am an actual OKR coach not another wannabe newsletter writer 😉)

My mandatory checklist

Before agreeing to run an OKR workshop right away, I had the top management — 5 managers in total — fill a mandatory checklist. Here is what I wanted to know👇

1. Do they have a shared vision for the company?

2. Do they have a shared mission for the company?

3. Do they have a shared north star metric for the company?

Clients HATE it when I pull out the OKR pre-requisite list :)

From what came to me I could already tell that there was some degree of misalignment between the 5 managers on these key questions.

I suggested to start with a North Star + Vision workshop instead, but they were eager to work on their OKRs, and they convinced me to join them for an OKR workshop the following week

The marketing lead assured me that they had done an extensive work on vision and mission already, and the whole company was onboard.

Blown up in a silo explosion 💥

So, how did the workshop go?


While Marketing had a clear idea of what the Mission, Vision and North Star looked like for the company this wasn’t clear to the other top managers — which had their own versions of course.

This is actually quite normal in a “silos” company, which is optimised for productivity versus collaboration and knowledge sharing.

Fixing the silos approach is not just necessary for my workshop to run smoothly, it’s paramount to the roll out of OKR to the whole company.

🤝 By definition OKRs are not owned by this or that department, but they require collaboration between different departments to get to the key result effectively. This cannot happen in a “silos” company.

The most common type of injury for OKR coaches: being blown up in a Silo Explosion💥

My report

For OKR coaches, this type of event is not the exception; it’s the norm. That’s why I have a habit of sending detailed reports after “derailed” workshops like this one.

It’s important to highlight both what they need to work on towards OKR readiness as well as the qualities they already have, that will favour OKR success.

In their case:


✅ Positive leadership dynamics, with open, frank, and clear discussions among leaders regarding problems and proposed opportunities.

✅ Openness and inclination towards change, useful for rapid adoption and understanding of new management tools.


❌ Limited alignment on the company’s Vision, Mission, and Values.

❌ Siloing, with the company organized vertically to optimize productivity. There are so few opportunities for cross-departmental collaboration that could enhance staff engagement and creativity, facilitating the achievement of shared goals.

Remember: as an OKR coach your value add is not just in the OKR rollout. Preparing the company for what is going to happen is an extremely delicate and valuable effort for you to take on.

Nerd out links

  • Read how Microsoft uses its own products to deploy OKRs effectively.
  • Read my analysis of the innovative UK scaleup policies.
  • Copy some well written OKRs.

🤝 Thinking your OKR strategy might need a tweak? Let’s talk about it. You can always hit me up on LinkedIn, or follow me there for more content like this.

Ciao for now, 👋



Luca Cipriani

I’m an OKR coach for scale-ups and the Head of Engineering @ Jimdo (formerly CIO @ Arduino).