Creating the Conditions for Strategic Success

Over the last few weeks, I’ve been interviewing leaders about their experiences with strategic planning. 

One thing that stands out from those conversations is how the conditions for success in the process were often established years before the official kickoff of their strategic planning. 

Success Enabler 1: Alignment on the current state

Alignment on the current state usually does not happen because of something trivial: Most people do not think about the organization’s strategy, how the whole system works, or what’s happening in the external environment on a regular basis. 

As one leader reflected on her organization’s strategic planning process, she told me, “I now realize […] how few people in leadership have to think across the organization.” 

She went on to describe how only a handful of departments in the organization—communications, legislative affairs, and development—regularly work with people across department lines to see the big picture. Those departments are also the only ones who regularly have to articulate to those outside what the organization is doing, and hear feedback directly. In other words, they’re the minority of employees who actually think about the strategy.

But if most people in your organization—even the leaders—aren’t thinking about the strategy day-to-day, or interacting with people outside of the organization, they can arrive at strategic planning with wildly different perspectives. And without a common foundation, it’s harder for a group to reason through why one idea or direction is better than another.

Of course, you can try to build a common foundation after you start a strategic planning process, but that’s hindered by the fact that it takes time for people to reason through new information and, where necessary, change their minds. It doesn’t happen in just a few hours, or over the course of a few meetings. 

The solution, then, is to have an always-on effort to build a common understanding–i.e., continuous collection of insights from employees, customers, and external stakeholders, sharing those insights widely, and collectively making sense of them.

Success Enabler 2: The ability to generate a healthy discussion in the organization

Often, once leaders arrive at a strategy decision, they turn their attention to convincing the rest of their organization that the strategy is the right one. 

In contrast, I spoke with the person who led the strategic planning process of a social justice nonprofit who described how their staff was on board with pursuing a bold new direction for the organization, even though the strategy hasn’t been finalized. 

She described why this acceptance of change was possible this way: “We've been doing a lot of work in the past couple years that we wouldn’t have thought was part of preparing for strategic planning, but it helped people practice the skill of talking about what they want their workplace to be.”

Specifically, there were several moments over the previous years in which leaders convened the staff to have critical conversations about staff wellbeing during the pandemic, about attrition, and about the support they needed. So by the time the organization arrived at the start of the strategic planning process, the team had both the skill and the culture to have a healthy debate about new ideas. 

And this paid off in terms of the quality of staff engagement. The leader said, “We got people's real thoughts—not people trying to guess what we thought the right answer was. […] And it was collaborative. Somebody would come up with something, and the next three comments would build on or respond to what their colleague had said. […] I think that the way people built on each other’s comments made it feel like a creative process for them, and not just like a feedback solicitation.”

Because these foundations take time to build, it’s worth investing in them today. Whether you foresee a strategy change down the line or just want to have a more strategic team, building these skills as a team will make strategic change much easier to achieve.