April 1st, 2026

The gap between a good IT services business and a great one is rarely talent. It's almost always clarity. Here's how to measure yours.

Twelve weeks ago, this newsletter started with a single observation: most IT services founders are not stuck because they lack ambition, talent, or clients. They're stuck because the structure underneath the business hasn't kept pace with the growth on top of it. The decision architecture. The operating rhythm. The GTM alignment. The margin discipline. The leadership depth that lets the business move without requiring the founder to be everywhere at once.

The themes in this newsletter have been variations on that one idea. And the question worth asking now is not whether the ideas are right — most founders already know what needs to change in their business. The question is whether anything has actually moved.

This issue is different from the others. It's a diagnostic. Ten questions across five pillars — strategy, execution, margin, structure, and leadership. There are no trick questions and no right answers. There are only honest ones, and they are more useful than the polished ones.

Most IT services companies don't have a revenue problem. They have a clarity problem — and clarity is the one thing you can build without a bigger budget, a new hire, or a better market.

The Five Pillars

Each of the five pillars corresponds to a theme this newsletter has covered. They are not independent — a business with excellent strategy and poor execution is just a well-articulated stall. A business with strong margin discipline and no leadership depth is one departure away from a crisis. The pillars reinforce each other, and the weakest one sets the ceiling for all the others.

Strategy. Do you know what you're building, who it's for, and what you're deliberately not doing? A strategy that can't answer those three questions in plain language isn't guiding decisions — it's providing cover for them.

Execution. Does strategy translate into action through a predictable operating rhythm with clear priorities, decision ownership, and a written accountability loop? If the same problems surface in every quarterly review, execution is broken.

Margin. Is the business becoming more profitable as it grows — or just bigger? Revenue is what you celebrate. Margin is what you live on. Pricing, scope discipline, and delivery efficiency are the levers.

Structure. Can the business run without you for two weeks? Does your leadership team make decisions, or do they coordinate with you before making them? Structure is the difference between a business and a job.

Leadership. Are the people around you growing into larger roles — or staying exactly where they were when you hired them? Leadership depth is what allows the business to scale past what one person can carry.

The 10-Question Assessment

For each question, answer honestly — not aspirationally. The point isn't to score well. It's to identify the one or two gaps that are setting the ceiling on your growth right now.

1. Can your leadership team name the top three priorities this quarter without checking a document?

Yes — without hesitation

2. Do you have a written decision log from your last leadership meeting?

Yes — reviewed at the next meeting

3. What percentage of your revenue is recurring and contracted?

Above 60% — and growing

4. Can your business operate for two weeks without you in client or operational decisions?

Yes — and it has before

5. Does every major initiative have one named owner with a real deadline?

Yes — one name, one date

6. Have you reviewed pricing with your bottom three margin clients in the last 18 months?

Yes — and had the conversation

7. Does your delivery team have pipeline visibility before deals close?

Yes — weekly

8. Do you have documented processes for onboarding, escalation, and billing?

Yes — followed consistently

9. Has your leadership team made a significant decision without you in the last 30 days?

Yes — and it was the right call

10. If a buyer evaluated your business today, what would be the first gap they'd find?

You can name it — and you're closing it

How to Read Your Results

If you answered “healthy” on eight or more, your business has strong structural foundations. The work now is compounding — deepening each pillar rather than building from scratch. The highest-leverage next step is likely enterprise value and leadership succession.

If you hesitated on three to five, you know where the gaps are. The question is which one is the most expensive right now — not the most uncomfortable. Start with the pillar that is most directly limiting revenue, margin, or your own capacity. Fix that one before moving to the next.

If you hesitated on more than five, the business is running on founder bandwidth rather than organizational structure. That's not a character flaw — it's a stage. The transition out of it is the most important work you can do, and it starts with one of the five pillars, not all of them at once. Pick the one that would change the most if it were stronger and start there this quarter.

The gap you can name is the gap you can close. The one you can't name is the one that closes you.

What Comes Next

This newsletter has covered twelve weeks of content across strategy, execution, GTM alignment, technology, leadership development, margin, enterprise value, and operational discipline. The ideas are not complicated. The execution is.

If any of the ten questions above surfaced a gap you've been aware of but haven't yet addressed — that gap is costing you more than you think. Not just in revenue or margin, but in the quality of the business you're building and the quality of the experience of running it.

The offer is simple. If you'd like a second set of eyes on where your business stands against these five pillars — an honest, structured conversation that tells you exactly where to focus and in what order — I set aside time for exactly that. No pitch. No methodology deck. Just a clear-eyed assessment from someone who has done this work with IT services companies at every stage of the growth curve.

Book your complimentary Strategic Business Assessment →

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JP Van Steerteghem

+1-617-548-3863

[email protected]

https://calendly.com/jvansteerteghem