A co-managed meeting is less about pitching. It’s more about understanding how the current structure works, and where it’s under pressure.
The goal is to surface problems without making the IT director feel criticised.
Start with structure, not solutions
Try to avoid jumping straight into recommendations.
Instead, ask questions that help you understand how their environment operates.
For example:
How are responsibilities currently divided across the team?
Where does escalation become unclear?
What happens when priorities clash?
How often do you step back and review capacity?
These questions show you’re thinking about structure, not just support.
Explore pressure points carefully
You’re looking for signs of strain, but without being confrontational.
Ask:
Where does the team feel most stretched right now?
What tends to get pushed back or delayed?
Are there areas that rely heavily on one person?
Where does risk feel most concentrated?
This helps move the conversation from “we’re coping” to “is this sustainable?”
Understand how decisions are made
Co-managed deals involve more than one person.
Ask:
Who would typically be involved in a decision like this?
What would they need to feel comfortable moving forward?
This gives you clarity on the path ahead.
The simple rule
Ask questions that explore how things work, not what tools they use.
If the conversation feels calm, structured, and reflective, you’re doing it right.
That’s what builds trust.