Finding Strategic Insight in Unexpected Places

by | Nov 22, 2022 | Strategic Planning

It often seems that strategic insight comes from the most unexpected places or moments.

You could be in the shower when the idea for how to revamp a social media campaign hits you. Or perhaps you’re out walking your dog when you suddenly realize the solution to a thorny client problem.

It’s a great reminder that problem solving and strategic insight aren’t limited to board rooms or cubicles.

Which is why a recent BBC profile of artist Annie Nicholson inspired us so much. In mid-2021, during some of the most difficult days of the pandemic, Annie created an ice cream van and started touring her local area in the UK. Sounds ordinary so far.

But the unexpected insight Annie brought was using ice cream to launch conversations about grief, something many people find hard to discuss even with their closest friends. Annie explained to the BBC how she encouraged customers to open up:

In the packaging of the ice cream we’d have questions around grief and loss, and how you’ve managed 2020 and the pandemic… questions to prompt people.

And people responded. They shared personal stories and spoke about tough topics. For those struggling, Annie also referred them to professional resources.

Here at Funding for Good, one of the things that struck us about the grief ice cream truck was how it created intentional opportunities for unexpected conversations and insights.

As nonprofit leaders, whether we’re working with our board, staff, or the community we serve, being open to hearing about thorny challenges and inspiring ideas can yield incredible insights. And ultimately, it can help our organizations achieve even greater impact.

How can nonprofit leaders be more intentional about creating opportunities for finding unexpected strategic insight for our organizations?


Ask Questions and Show that You Are Listening

At the ice cream truck, Annie started by simply asking people questions as she scooped their ice cream. Sure, some folks might have been taken aback at first, but many more discovered a new space to talk about hard topics.

As leaders, we can do the same:

  • Asking substantive questions. This means going beyond the surface level questions we often rely on in the workplace. But one caveat: only ask questions if you’re ready to listen and engage.
  • Listening with intention. Too often, leaders ask staff, board members, or community members for input on topics where they’ve already made up their minds. This is a waste of everyone’s time and undermines trust. Instead, consider asking questions about the topics you’re actively grappling with. If you’re also looking to build consensus within your organization, listening is key to navigating different perspectives and finding alignment.
  • Valuing wisdom from diverse sources. It’s easy to get caught up in the credentials of a source rather than what they’re saying. For example, do you give more weight to the recommendation of your communications consultant rather than your communications director, even though they’re saying the same thing? Having a second opinion is always useful, but so is learning to value the wisdom as much as the source.


Facilitating CONSENSUS BUILDING Conversations


Use Intentional Opportunities to Generate Strategic Insight

Consider combining traditional tools used in evaluation—such as surveys, interviews, and focus groups—with intentional opportunities for more open conversations. One great way to do this is investing in a strategic planning process. With strategic planning, you’ll bring in a facilitator who is an expert at asking thoughtful questions and guiding conversations to get at deeper insights, rather than remaining at the surface level.


Reward Strategic Insight

Acknowledging strategic insight is critical to generating more in the future. Rewards can be simple and free. For example, you might give a shout-out to a team member’s recent insightful contribution at an all-staff meeting or take the time to explain to a board member how their input helped shape a new strategy.

When people see that their insights are making a difference, they’ll be that much more energized to contribute more.

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