Where many CIOs’ strategic visions fall short

Setting direction is the first task of leadership. That’s because, by definition, you’re only leading when others are following. Leaders, that is, are supposed to say, “Follow me!” Those who are supposed to follow have every right to ask, “Where to?”

“I don’t know” is not an answer likely to garner energetic enthusiasm. But even if you have a better answer, you aren’t done answering questions. Like, for example, the logical follow-up: “How will we get there?”

When CIOs set direction, they need to articulate a vision — a compelling account of a future state that is, in most respects superior to the way things are today. Then they need a plan — a recounting of the work that will have to get done to turn today’s reality into tomorrow’s improvements.

And that isn’t sufficient either: Just because you describe a vision for the future, that doesn’t automatically mean it’s a good idea.

Turning vision on its head

Somewhere in all this a CIO who wants to lead successfully needs to make the case for change. They (you) need to describe the problem the vision will solve or opportunity it will pursue — and describe it in convincing and verifiable terms.

To be strategic — this is, to be worth the leader’s time and attention — the problem should be daunting; the opportunity being chased had better warrant the investment and risk that achieving the vision will require.

Is that all there is to thinking strategically? A big problem or opportunity, plus a vision, plus a plan? Of course not. But it’s a start.

Start with the vision. From a strategic perspective the vision has to be a simple-looking thing. Everyone who looks at it has to be able to grasp it quickly and intuitively. Also, it has to be clear, on the same at-a-glance basis, how the vision will solve the big problem or opportunity it’s intended to address.

And it has to be plausible.

Therein lies the problem with many strategic visions: They stray beyond the line that separates simple from simplistic. For the description to be quickly and easily grasped it must be too simple to be buildable. Someone has to turn it into something that can be built — specifications, Agile-style user stories, or something else that provides enough detail to make the vision real.

Which highlights a hazard of thinking strategically: Vision is essential, but the steps needed to ensure it goes beyond plausible to being realistic happen in the wrong sequence — and have to happen in the wrong sequence. Leaders have to “sell the problem” first. Then they have to sell their vision. Only then can they go through the steps needed to determine whether their vision can work.

Red-teaming for risks

All of which can lead an unwary leader into a cognitive rabbit hole.

Leaders articulate a vision. Then they have to sell the vision. To sell it they have to commit to it. And they have to commit to it before they can know whether it will actually work.

And if it turns out that it won’t actually work?

Dropping a vision after publicly committing to it isn’t easy. Having put their name on the vision, most leaders will expend time, effort, and political capital trying to find a way to make it work, even if the only ways to make it work are, from an engineering standpoint, a hopeless mess.

“I guess I was wrong about this. Sorry to have wasted your time,” is a phrase few leaders are willing to utter.

Smart leaders know how to avoid the worst of the rabbit holes. One formula that works in a wide variety of circumstances is the Red Team / Green Team gambit.

How it works is to appoint two small teams to research the incipient vision’s viability. The Green Team is charged with enumerating all the reasons to move forward with the vision — all the potential benefits to be had by investing in it.

The Red Team has the obverse assignment: to spot all the vision’s risks, potential flaws, and ways it’s likely to implode with unfortunate consequences.

Give each team a week to investigate, then bring them together. More likely than not, the right answer — the vision’s viability — will be immediately apparent to all concerned, saving the visionary leader considerable embarrassment and the organization the distraction of chasing ideas that are, while superficially appealing, unworkable.

And if the right answer isn’t apparent? Wise leaders fall back on the earliest forms of artificial intelligence: They consult a dart board, tossed coin, and Magic 8 Ball to resolve the remaining doubt.