I’m Joe Schiavone. Last time, we talked about roadmaps, remember? The best ones are built to come apart on purpose and the goalposts are already moving while you’re still drawing the diagram.
A bunch of you reached out after that one (thank you, by the way), and the question that kept landing in my inbox was some version of this:
“Modular roadmap, sure. But what actually executes it?”
Fair question indeed. And the honest answer? Whatever you inherited.
Most CIOs don’t get handed a flawless “don’t change a thing” roadmap. They get handed a box of parts — some labeled, some not, some with the instructions missing entirely, and at least one piece you’re pretty sure came from a different box found in the back of a server room somewhere.
Welcome to the role. Some assembly required.
You’ve Received An Inheritance — No, Not The One From Aunt Millie
Here’s the thing nobody tells you when you take a CIO seat: the strategy you “have” isn’t really a strategy. It’s a manifesto answering — how did we get here?
Layer one: decisions made by the CIO before you
Layer two: decisions made by that CIO’s consultant
Layer three: a board mandate from 2019 that nobody questions anymore because the people who agreed to it have all moved on
Layer four: a vendor relationship that exists because someone went to college with someone
Layer five: a governance committee that meets every other Thursday, and nobody is entirely sure what it governs
You pop the lid and start sorting parts. Some snap together. Some don’t fit. Some look like they belong but are glued to something they shouldn’t be glued to.
And naturally, you’ve got a board meeting in six hours where you need to explain how the whole thing is going to deliver an AI strategy, a cost reduction, a security posture upgrade, and a possible carve-out. All of it, by the way, before Q4.
No pressure.
Sound familiar?
It Even Came With A Manual …
Sort of.
There’s always a slide deck — I love a good slide deck — there’s always a slide that says “Five-Year Roadmap” in nice 32-point font with five colored boxes and arrows that mostly go in the right direction. Someone presented it. It got applause. ELT got teary eyed. It got laminated. It now lives in a SharePoint folder nobody opens.
The deck is the box art, not the manual. The real magic is whatever happens when you try to make the thing do something it wasn’t doing yesterday; this is where the agility of your “strategy” reveals itself.
Which brings me to a story.
Picture This (Cue Flashback Music And Distant Gaze)
I had a divestiture pending. SEC approval in motion, deal mechanics under wraps, and a tight read-in list — a handful of leaders who knew what was coming and a much larger organization that didn’t. You know how this goes. You can’t pre-stage the way you’d want to. You can’t engage the broader teams. You’re sketching the separation in the margins, leaning on whoever’s already read in, and quietly hoping the plan holds together long enough to do the real work when the business officially gives the thumbs up.
Approval lands. Clock starts.
You’ve got 90 days to divest, button up the TSAs, and hand over a rather large plane that is still very much in flight.
We do what good teams do. Stand up the workstreams. Map the dependencies. Sequence the cutovers. Build the TSA scaffolding. Communicate, communicate, communicate. Day 30, on track. Day 45, mostly on track. Confidence is building. The so-called strategy, the inherited one, the one nobody had stress-tested at this scale — looked like it was going to hold.
And then …
Some Parts Sold Separately
The acquirer comes back to the table.
Turns out the core operational platform — the brains of the manufacturing system, the thing actually running production — wasn’t in their plan. They didn’t have a path to stand up their own. They didn’t have a replacement strategy. They didn’t have time. And they wanted to stay on ours.
Small problem …
We weren’t decommissioning that platform. We were still in this line of business. The system we were being asked to share was the same system running our operations — same code, same data plane, same backbone.
The TSA, to its credit, didn’t overpromise. It didn’t have to. Because to get the deal closed, we had to step up.
So now the puzzle isn’t: How do we hand off a system? The puzzle is: How do we keep them running, on our infrastructure, fully segregated from everything we still need to operate, without compromising either side — and do it inside a divestiture clock that’s already ticking down?
This is the moment the inherited M&A playbook showed its breaking point. Governance was built for sequential decisions, not simultaneous ones. Vendor contracts assumed clean separation, not extended cohabitation. Security architecture was built for “us” and “them” — not “us, them, and a wall down the middle of the same house.”
So, we pivoted. Tiger teams stood up against each pressure point — segregation architecture, data isolation, identity boundary, support model, contractual reframe. Embedded leadership inside each tiger team with decision authority on the spot, not a queue back to a steering committee that met every other Thursday. TSA scope was reopened and rewritten to cover a relationship nobody had drafted for. A little luck — because honestly, you don’t pull something this hard inside 90 days without some.
It worked. They stayed operational. We stayed operational. The wall held. The deal closed.
But here’s the thing I want every CIO reading this to sit with for a minute:
The reason it worked was because we took the original strategy, that framework, apart in real time and reassembled it around the problem.
The decks didn’t save us. The governance committees didn’t save us. The architecture diagrams didn’t save us. The ability to disassemble and reassemble — that saved us.
That’s what a modular strategy and flexible framework is actually for. Not to look right on a slide. To come apart on purpose, when reality demands it, without breaking.
And if you’re sitting in a sell-side seat right now thinking divestitures are the easy half of M&A — guess again, they’re not. The seller absorbs more operating-model stress than most playbooks admit. You’re handing over a plane in flight, keeping your own plane in the air, and discovering mid-flight that some of the parts you thought belonged to one plane are actually load-bearing on both.
To Be Continued …
So that’s the box. Inherited, mislabeled, glued where it should have been jointed, and somehow still expected to deliver an AI strategy, a cost reduction, and a deal by Q4.
Knowing your carefully designed strategy needs to come apart is one thing. Knowing how to design one that’s built to come apart on purpose, under pressure, without breaking — that’s a different conversation entirely.
Part 2 is where we get into it even more: Batteries Required (Discipline Sold Separately). See you there.
