As a CEO, there were more than a few times where I felt outrageously overwhelmed by the sheer number of requests hitting me every day — from members, partners, and especially employees.
But honestly, a lot of it was my fault.
I had never clearly taught my (very young) team how I expected them to approach problem-solving, or how to communicate when something needed my attention.
So I sent them this message, along with a framework:
As we continue growing as a team, I want to share some thoughts about problem-solving approaches and expectations.
Below are five levels of problem-solving maturity, along with what they mean for different roles within our organization.
The Five Levels Explained
Level 1: Problem Identification
What it looks like: “Here’s a problem.”
➔ Simply raising an issue without context or proposed solutions.
Example:
“This member is frustrated.”
“This core group wants a new facilitator.”
Appropriate for: Entry-level roles, new hires in their first 60 days.
Level 2: Problem with Context
What it looks like: “Here’s a problem and here’s the background.”
➔ Providing details around why the issue matters.
Example:
“This member is frustrated because another member skipped two meetings. It’s starting to hurt group retention.”
Appropriate for: Early-career individual contributors.
Level 3: Solutions-Oriented
What it looks like: “Here’s the problem, context, and potential solutions.”
➔ Presenting the issue along with 2-3 considered options.
Example:
“Bob Bobbertson is frustrated with Sara Thompson’s absences.
Solutions to consider:
- Reaffirm core group expectations,
- Remove Sara from the group,
- Send Bob flowers and hope he chills out.”
Expected for: Mid-level managers, experienced ICs.
Level 4: Recommended Action
What it looks like: “Here’s what I see, and here’s what I think we should do.”
➔ Coming with a well-thought-out recommendation and implementation plan
Example:
“Bob is frustrated because Sara’s been absent. I recommend removing her from the group despite short-term disruption. Others have flagged the same issue — the feedback is linked here. Would you like to give me the greenlight, or would you prefer to see other options?”
Expected for: Senior managers, directors
Level 5: Proactive Execution
What it looks like: “Here’s what I’ve done about it, and here’s how I’ll keep you informed.”
➔ Taking ownership and initiative while maintaining appropriate communication
Example:
“Based on our guidelines, I removed Sara from the group. I’m following up with Bob and Sara individually and reviewing onboarding to prevent future issues. Next update Tuesday.”
Expected for: Senior directors and above.
Role-Based Expectations
Then I went on to tell my team, here are the minimum expected levels based on role:
- Entry-level / Junior roles: Levels 1–2 acceptable during onboarding
- Mid-level ICs: Level 3 minimum
- Managers / Senior ICs: Level 4 minimum
- Directors and above: Level 5 expected consistently
This was so helpful because if I had a director-level or senior-level person emailing me Level 1 or 2 comms, it’d be so easy to push back.
“Level 4 me, dog!”
Summing It Up
Most of the communication hitting me as CEO was Levels 1–3 — with the occasional 4, and a few Level 5’s sprinkled in here & there.
And that was okay — we had a young team.
(To be clear: most of the team kicked ass. They adapted fast and loved having clearer guidance.)
Giving the team this framework:
- Empowered them to pause, think, and own their recommendations
- Reminded them not every issue needed to be escalated
- Helped them build real autonomy and decision-making skills
I first shared this with my direct reports, we talked through it, and then they rolled it out to their teams. We covered it briefly at an all-hands too.
The goal wasn’t just to save me time — it was to help level up the whole company and make sure we approached problems with real ownership and solutions-first thinking.
If you enjoyed this blog post, sign up for my weekly-ish newsletter, Signal // Noise, where I share my honest notes on work, startups, life, and money. No bullshit or spam!
