I was recently at a board meeting where a group of executives from a small financial services company gathered to discuss AI. This wasn’t just an idea - they were committed to making investments in something tangible. Like many, they were drawn to the concept after noticing announcements made by competitors. They’d made a remarkable move by staying in tune with the market. They understood the changing landscape and gathered their most experienced directors for this meeting.

The meeting was productive, to say the least. Each division leader was tasked with creating a roadmap. Towards the end of the meeting, each leader was asked about their approach. They were able to walk through their plans in incredible detail. They congratulated one another, headed back to their teams, and began creating the plan.

When “Yes” Does Not Mean “Yes, We Can Do It”

Then it struck me. The executives, though brilliant, were creating a plan in isolation. They could provide the roadmap to product–market hypotheses, experimentation, prototyping, and launch. The members at that meeting were clearly more innovative than most. However, they developed a plan isolated from other parts of the business. There was little input from IT, marketing, or the people servicing their products.

I asked one of the division leaders what his team thought. He said they were thrilled with the initiative. That success, however, was short-lived. The technical teams realized the company lacked the infrastructure to execute the “AI initiative.” They also encountered errors that were unrecognizable during the trial phase.

So their plan eventually hit a roadblock. That’s normal. The surprising part was that they planned in isolation. The more brilliant the plan appeared, the less they sought validation from others.

Here's what's happening: The more consensus an idea gets, the more one feels confident planning it alone. It can be misinterpreted as a sign to continue. But a “yes” in such cases is only a half-truth. A “yes” from an IT department does not mean “yes, we can do it.” Similarly, when a marketing team says, “Yes, AI is a game-changer!” it doesn’t mean the company can actually deliver it.

Planning is a Team Sport

Adding the word “strategic” in front of planning has perhaps made it worse. People have come to take “strategic planning” to mean “a plan that’s limited to the strategy table.” That might work in some instances, but it rarely proves successful in large companies where the product depends on several departments. Too often, plans are formulated at the top, and it’s expected that the rest of the organization will implement them.

Even though this top-down approach never goes as smoothly as planned, it remains the primary method companies use to encourage employees to adopt technology. Here’s what it looks like: A new initiative is created by top management teams. Employees are told that the new way of working will bring opportunities. If they show resistance, it must be overcome through a mix of frameworks and surveys. If the technology isn’t adopted, the company reframes it as a compliance issue.

How does this top-down approach lead to isolated planning? Well, if you look at those activities, you’ll notice that the process can be carried out by a single person. That’s what I’ve repeatedly seen. That one person carries out the plan with minimal contact from others. They accept the “yes” and ignore those who say “no”. They continue down this track due to fear of uncertainty or, at worst, the fear of being wrong. In doing so, they avoid valuable feedback and miss out on the opportunities to improve the success of the plan. Those working in competitive industries know this well - they view every piece of feedback as a chance to outshine competitors.

If we want initiatives to succeed, we must treat strategic planning not as a solo project, but as a team sport. After all, no one wins alone. We often call it “strategic planning” because it’s formulated at the boardroom table, but that doesn’t prevent the planning process from being collaborative and problem-driven. The planning, no matter how brilliant, will fall short if developed in isolation. To succeed, we must consider the contributions of other teams - whether it’s IT, marketing, operations, or frontline employees - and what roles they play.

By Terryel Hu, Ph.D.

Keywords: Digital Transformation, Leadership, Management

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