October 19, 2026

Stop Planning the Perfect Reorg—Run a 90-Day Operating Sprint

Most mid-market CEOs don’t wake up thinking, “You know what I’d love? Another reorg.”

And yet, when growth exposes friction—missed handoffs, confused roles, delayed projects—the conversation almost always drifts to structure:

  • “We probably need to reorganize.”
  • “Let’s redraw the org chart.”
  • “Maybe we need a new layer.”

If you’ve ever survived a reorg, you already know the pattern:

  • Months of planning
  • Endless versions of boxes and lines
  • Big announcement
  • 90 days later, the same issues are back—just with new titles

You might ask, “Do I really need a reorg—or can I test changes with a 90-day pilot?”

If org charts actually fixed execution, you’d only ever need one.

In my experience, reorgs create theater. Operating sprints create proof.

You don’t need the perfect new org chart.
You need a 90-day operating sprint that shows your business can actually run differently.

Why Big Reorgs Fail Mid-Market Companies

In $20M–$150M organizations, classic reorgs almost always run into the same problems:

  1. They’re designed at the wrong altitude.
    • The conversation is all boxes and reporting lines.
    • Very little time is spent on how work actually flows.
  2. They ignore capacity and change fatigue.
    • Your best people are already overloaded.
    • Now you’re asking them to “transform” the business on top of their day jobs.
  3. They move slower than the business.
    • By the time you’re ready to roll out the new structure, the reality on the ground has already shifted.
  4. They’re hard to unwind if you get it wrong.
    • You’ve changed titles, comp, and reporting lines.
    • Walking it back is politically painful—so you live with a bad design.

So you end up with a familiar outcome:

New boxes. Same bottlenecks.

What Is a 90-Day Operating Sprint?

A 90-day operating sprint is a contained experiment where you:

  • Pick one critical slice of the business
  • Redesign how work flows in that area
  • Test the new design for 90 days
  • Measure whether it actually created better outcomes

No company-wide reorg.
No 200-slide “transformation” deck.

Just one focused proof point:

“We can run this part of the business differently—and it works.”

Where Operating Sprints Fit in Your Operating Model

Here’s how I frame it for CEOs:

  • Strategy says: “This is where we’re going and how we’ll compete.”
  • Operating model says: “This is how work needs to move to make that real.”
  • Operating sprints say: “Let’s prove it in one place before we try to do it everywhere.”

You can still change structure.
But you do it after you’ve learned what works in practice, not before.

Choosing the Right Area for a Sprint

Not every part of the business is a good candidate for your first sprint.

Look for a value stream that is:

  • Critical to your strategy (e.g., quote-to-cash, order-to-install, implementation, service)
  • Cross-functional (touches at least 2–3 teams)
  • Painful but fixable (people can name the problems, even if they don’t know how to fix them)

Ask your team:

“Where do we feel the most friction that our customers would also recognize?”

That’s usually your sprint.

Inside a 90-Day Operating Sprint

Here’s a simple structure I use with clients. You can run a lighter version internally.

Phase 1: Diagnose (Weeks 1–3)

  • Map the current flow of work in that area
  • Identify:
    • Bottlenecks
    • Rework
    • Confusing handoffs
    • Decisions that always get stuck
  • Talk to the people who live there every day:
    • “Where does your work go to die?”
    • “What do you fix over and over again?”

Output: a brutally honest view of how things actually work today.

Phase 2: Design (Weeks 4–5)

  • Define what “good” would look like 12–18 months from now
  • Design a lighter, clearer version you can test in 90 days:
    • Fewer handoffs
    • Clear owners for key steps and decisions
    • Simpler metrics

Ask:

“If we could only change three things in this flow over the next 90 days, what would they be?”

Phase 3: Test (Weeks 6–12)

  • Run the new design for a defined set of customers, projects, or regions
  • Keep the experiment visible:
    • What we’re testing
    • How we’ll know it’s working
    • Who to talk to when something breaks
  • Track a small set of metrics:
    • Cycle time
    • Rework
    • Customer escalations
    • Team capacity / burnout

Phase 4: Learn and Decide (Week 13)

  • What worked?
  • What didn’t?
  • What do we keep, kill, or extend to the rest of the business?

This is where you decide whether any structural changes are needed—and which ones are justified by real evidence.

CASE SNAPSHOT: From “We Need a Reorg” to “We Need a Sprint”

A CEO came to me convinced they needed a full reorg:

  • Customer experience was inconsistent
  • Implementation projects were always “just barely” on time
  • Sales and ops were blaming each other

The default recommendation on the table was:

  • New org design
  • New VP role
  • New reporting lines

Instead, we picked one area: the journey from signed deal to go-live.

In the 90-day operating sprint, we:

  • Mapped the current process across sales, solutions, and implementation
  • Found 7 handoffs, 3 of which added zero value
  • Clarified who owned:
    • Kickoff
    • Timeline commitments
    • Scope changes
  • Created a simple weekly cross-functional huddle to clear blockers

Within 90 days:

  • Average implementation time dropped
  • Internal escalations dropped
  • Customer feedback improved

Then—and only then—we made a small structural change:
We created a single owner for that value stream, with clear decision rights.

The CEO got what they really wanted:
Better execution, less noise, more confidence.

Without putting the whole company through a year-long reorg.

How Do You Know You’re Ready for an Operating Sprint?

You’re ready if:

  • You can clearly name one area where:
    • Customers feel the pain
    • Your people are exhausted
    • You’re not sure whether it’s a people, process, or structure problem
  • You know a reorg would be:
    • Politically expensive
    • Slow to implement
    • Hard to unwind if you’re wrong

You’re not ready if:

  • You haven’t decided what you’re optimizing for
  • You’re hoping the sprint will magically solve a deeper leadership or culture issue you’re avoiding

Operating sprints don’t fix everything.
They do give you honest data about what works before you bet the company on a big design.

Where to Start: A 90-Day Experiment Instead of a Reorg

If you’re already thinking about changing structure, don’t ignore that impulse.

Just start smaller and smarter:

  1. Name the real problem.
    • In one sentence: “The part of the business that keeps me up is ______.”
  2. Choose one value stream that reflects that problem.
    • Quote-to-cash
    • Order-to-install
    • Implementation
    • Service response
  3. Frame a 90-day operating sprint.
    • Who’s involved
    • What you’re testing
    • How you’ll know it worked
  4. Commit to deciding, afterwards, what (if any) structural changes are actually required.

Well, you might be right that “we just need a reorg.”

But in my experience, if you can’t get one area of the business running better in 90 days, a new org chart won’t save you.

Let’s Make This a Conversation

If you’re staring at the same problems and everyone’s quietly whispering “reorg,” you’re not alone.

You don’t have to put the whole company through a structural earthquake to make progress.
You can start with one focused operating sprint and learn your way into the right design.

If this describes you, schedule 30 minutes on my calendar and we can talk about:

  • Which part of your operating model is the best candidate for a 90-day sprint
  • How to frame a sprint that doesn’t overwhelm an already tired team
  • How to use the results to make smarter, lighter structural changes

Not ready for a conversation yet? Take one value stream, and use this as your roadmap for a 90-day experiment before you redraw a single box on your org chart.