How to Diagnose What’s Actually Broken in Your Business
A practical diagnostic for founders when everything feels off.
Did you know? I’m writing a book, and just launched its pre-sale! The First-Time CEO: 50 Conversations on Leading While Becoming will include 50 podcast conversations with modern leaders, hosted by me, reflections on building an AI startup as a first-time CEO, and some of my most-read newsletters. Pre-order your copy and follow my progress as I write it in public!
P.S. Wanna get some evergreen publicity? Choose a Founding Membership Pack instead of just the book!
There is a particular kind of confusion that only founders experience.
The numbers are not disastrous. The product is not obviously bad. Customers are still there. The team is still shipping. And yet—nothing quite clicks. Effort goes in, progress comes out thin. Meetings multiply. Optimism becomes procedural.
This is the moment when founders often mistake motion for diagnosis.
Before adding strategy, hires, or capital, there is a quieter, more consequential task: figuring out what is actually broken—not what is loud or irritating, or what feels embarrassing, but what is structurally misaligned.
This is not a motivational exercise. It is an inspection.
The Diagnostic Frame: Three Systems, One Problem
When a business feels chaotic, the issue almost always lives in one (or more) of three systems:
The Product System – what you’ve built and how it’s used
The Metrics System – what you measure and what moves
The Human System – how decisions are made and work is coordinated
Most founders default to fixing the most visible one. Diagnosis requires checking all three—systematically.
Let’s tackle all three one by one.
1. The Product Check: Is It Solving a Real, Repeated Problem?
Ask these questions without defending the product:
Can users describe the value without your vocabulary?
Is there a single, repeatable “aha” moment—or many vague ones?
Do users return because they need the product, or because they are being reminded to?
Red flag: Usage exists, but urgency doesn’t.
Likely issue: The product solves an interesting problem, not a necessary one.
What to look at first
Activation rate (not sign-ups)
Time-to-value
Repeat usage tied to one clear job-to-be-done
2. The Metrics Check: Are You Looking at the Right Signals?
When everything feels noisy, first-time founders and CEOs often track more. The move here is the opposite: track fewer, sharper metrics.
Start with these, in this order:
Unit economics
Do you clearly understand what it costs to acquire, serve, and retain one customer?
Churn (behavioral, not just logo churn)
Where exactly are people disengaging?
Acquisition channel ROI
Which channel works without heroic effort?
Velocity of iteration
How fast can you test, learn, and change direction?
Red flag: Metrics look “fine,” but no decision feels obvious.
Likely issue: You are measuring outcomes without understanding drivers.
3. The Team Alignment Check: Is the System Thinking or Reacting?
Misalignment often masquerades as execution failure.
Ask, plainly:
Can everyone name the current top priority the same way?
Do teams know what good looks like this quarter?
Are decisions slowed by consensus—or rushed by avoidance?
Red flag: Everyone is busy, but ownership feels blurry.
Likely issue: The system lacks shared clarity, not effort.
The Decision Tree: Keep, Pivot, or Kill
Once you’ve diagnosed, you need a decision—not a debate.
Use this simple tree:
KEEP
Core metric is improving
Users demonstrate real pull
Problems are executional, not structural
PIVOT
Users exist, but value is mispositioned
One metric moves while another collapses
Learning velocity is high, outcomes are not
KILL
No meaningful pull after repeated iterations
Churn remains high across cohorts
Progress depends on constant justification
If you can’t confidently place an initiative into one of these three, you haven’t finished diagnosing.
The Diagnostic Tool (Save This)
When things feel off, do this in one sitting:
Write down what you think is broken (one sentence).
Identify which system it belongs to: product, metrics, or team.
Pull one primary metric tied to that system.
Talk to three users or team members about that specific issue.
Decide: keep, pivot, or kill—then set a review date.
Clarity compounds faster than effort.
The Diagnostic Playbook: A Practical Guide for When Your Business Feels Off
When your business feels off but you can’t tell why, guessing gets expensive.
Grab a practical diagnostic playbook I created for moments like that! It shows exactly how to identify what’s broken across product, metrics, and team, and how to decide what to keep, pivot, or kill without panic. It’s a tool you can use the moment compounding stops.
Upgrade to paid to get access to The Diagnostic Playbook: A Practical Guide for When Your Business Feels Off, and to future no-BS guides, field notes by the experienced CEOs, and more.
#CEOCheck
Before you change strategy, ask yourself:
What am I assuming is broken without evidence?
Which system am I avoiding looking at?
If I had to kill one initiative this week, which would it be—and why?
If you can answer those honestly, you’re no longer guessing.
You’re leading.
Hit reply to share your answers. I read every email!
Let’s Connect!
For more authentic content on leading companies for the first time, follow me on LinkedIn and Instagram, and The First-Time CEO podcast on Spotify, YouTube, and Apple Podcasts. Here you can find more information about me and my career.