He could have refreshed the strategy in thirty minutes. He booked two half-days instead.

A CIO I work with told me recently that it was probably time to refresh his technology strategy for the next two to three years.

Then he said:

“I could probably do it in about 30 minutes using AI. But that won’t add value long-term if I don’t bring my team along with me.”

He is right about the thirty minutes.

Most leaders reading this could open a chat window this afternoon and have a credible three-year technology strategy before the end of the day, complete with key themes, capability gaps, a phased roadmap, and an executive summary written and branded in the company’s style.

It would look professional, and I’d say that a fair amount of it would hold up to scrutiny.

But … it would probably then just sit in a folder and not be looked at again.

The document isn’t the hard part

Producing an artefact like this is rarely the constraint.

Large organisations have been turning out beautiful looking strategy documents for decades, usually at considerable cost, and most of those just gathered dust.

What has changed recently though is the price and speed.

When a strategy refresh costs six figures and eight weeks, you are forced to think about how you will use it. When it costs a prompt and thirty minutes, that pressure disappears.

The cheaper the artefact gets, the more tempting it is to skip the part that makes the strategy document most relevant.

AI doesn’t know about the acquisition

Ask your preferred AI model to build your technology strategy and it should do a competent job on the shape of it. What it cannot see though is your actual organisation.

It doesn’t know that a large acquisition is about to absorb your integration capacity for the next eight months.

It doesn’t know which future capabilities are really lacking in your current team.

It doesn’t know that two of your leaders have been fighting over the same territory for a year, or which stakeholder relationship is so fragile that it needs to be taken into consideration regarding sequencing a new platform rollout.

But your people know all of this.

They know the detail, they know their teams, and they know what is actually possible between now and the end of the year.

A strategy without that context is a well-formatted guess.

What transformation executives say when the benefits don’t land

I have spoken with hundreds of Transformation executives over my career, and I’ve spent years as a Transformation Director myself.

When people in these roles talk candidly about the times the benefits didn’t land, the reasons typically cluster in the same three places:

1. The human side.

2. Alignment on what really mattered.

3. Buy-in to go above and beyond, and to hold the course when things got hard.

Two half-days, and what they’re actually for

This seasoned CIO therefore took two half-days out with his leadership team.

He knew better than to present a well-crafted strategy to them.

Instead, they’re building it together.

His people bring what they think the strategic direction should be and what the priorities need to be.

The room debates, prioritises, and locks it in together.

He is there to frame the constraints and make the calls that only he can make.

Two half-days is not a small ask of a leadership team that is already stretched. He has (wisely) decided though that it’s cheaper than the alternative: him creating a strategy quickly in isolation that his team are not fully behind to deliver when things get hard (which invariably always happens).

When I ran the change management function at a large organisation, I came back again and again to something really simple: people appreciate things being done WITH them rather than TO them.

The test arrives about six months later

Several years ago I worked with a CIO and his leadership team on a significant change to their technology operating model. A full refresh of the strategy, a rebuild of how the technology team worked with business stakeholders, and a deliberate shift of skills and investment toward data and information security.

This was well before data and cyber became the board’s headline risks.

It was forward thinking at a time when few organisations were thinking in this way.

We invested serious time in that leadership team co-designing what it would look like.

Then it went live and the teething issues arrived, as they do in any change regarding who the business works with inside technology. People became unsettled. The path of least resistance was sitting right there.

But the leadership team held.

Every one of them stood behind the new operating model, because they were the ones who had designed and helped build it.

People defend what they help build.

The thirty minutes is real. Use it somewhere else.

None of this is an argument for slowing down. I use AI daily and it makes me faster at work that used to take me hours.

The opportunity is in where the time you save gets reinvested.

Let the model do the first draft, the research, the scenario modelling, the tidy-up.

Then take the hours you just got back and spend them in the room with the people who will have to hold the course when the budget tightens and the noise starts.

The leaders getting the most out of AI right now are the ones being ruthless about which parts of the work should stay human to a large extent.

Getting proper buy-in to your strategy is one of them.

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Tina Paterson is the founder of Outcomes Over Hours. She partners with tech leaders and their leadership teams to deliver the right outcomes faster and easier.

Because humans who strategically leverage AI will always win.

How I make my Substack articles

I do the thinking. Claude is my sparring partner, and sometimes it pulls my thinking into a first draft. Then I speak my own version over the top using Wispr Flow (which is ~4x faster than typing) and I tweak it until it sounds absolutely like me.

Because humans who strategically leverage AI will always win.