Strategic Planning: One Year From Now, What Will You Wish You Had Done Today?

7 hours ago
6 min read

Strategic Planning

One Year From Now,

What Will You Wish You Had Done Today?

Most strategic planning sessions begin by looking backward. What happened last year? What worked? What didn't? Where are we today? What are our strengths and weaknesses?

Before long, the walls are covered with flip-chart paper and enough sticky notes to wallpaper a small condo. There's value in understanding where you've been, but I've found that some of the most powerful strategic planning conversations begin somewhere entirely different.

Start in the future. Then look backward. Ask your board and leadership team one simple question: One year from now, what will you wish you had done today?

The room changes.

The Future Has a Way of Clarifying Things

When leaders focus exclusively on the present, everything feels important. Staffing is important. Fundraising is important. Programs are important. Technology is important. Marketing is important. Board development is important.

Congratulations. You've just identified everything.

Strategy requires something harder: deciding what matters most. When I facilitate strategic planning sessions, I sometimes ask people to mentally move themselves one year into the future.

Imagine we're sitting together again. Twelve months have passed. Some things went well. Others didn't. Now ask: What decision would you regret not making when you had the chance?

Suddenly, priorities begin separating themselves from the noise.

Regret Is an Underrated Strategic Tool

Nobody likes regret. That's precisely why it's useful. Regret forces us to consider the cost of inaction, something strategic plans frequently overlook. Boards are usually pretty good at asking, "What could go wrong if we do this?" They're considerably less disciplined about asking, "What could go wrong if we don't?" That's a dangerous blind spot.

Maybe you've been discussing a capital campaign for three years. Perhaps everyone knows a struggling program needs to be redesigned. Maybe your organization has outgrown its facility, technology, leadership structure, or even its business model.

Doing something carries risk. But so does waiting.

The Status Quo Isn't Standing Still

Boards often treat the status quo as the safe option. It isn't. Choosing not to make a decision is still a decision. Delaying an investment has consequences. Keeping an underperforming program consumes resources. Ignoring a leadership problem affects morale. Postponing fundraising leaves money unraised and relationships undeveloped.

I've watched organizations spend enormous energy analyzing the risks of moving forward while barely discussing the risks of standing still. Sometimes it feels like the safest strategic recommendation would be: Everybody remain perfectly still and hope the world cooperates.

Unfortunately, the world has terrible manners. Costs rise. Donors change. Staff leave. Opportunities disappear. Community needs evolve. Competitors grow.

Time doesn't preserve the status quo. It changes it.

Start With the Destination

One of the best ways to improve a strategic planning session is to temporarily stop talking about today's problems. Instead, describe the organization you want to see one year from now.

What has changed? What are you doing better? What problem has finally been solved? What opportunity did you seize? What are your donors saying? What are employees experiencing? What does the board feel proud about?

Make the picture concrete, then work backward. If that's where you want to be twelve months from now, what needs to happen in the next nine months? Six months? Ninety days?

Now you're not creating a wish list. You're building a route.

The Best Strategic Planning Sessions Create Tension

Some of the best strategic planning sessions I've facilitated have a moment when the conversation becomes uncomfortable. That's usually a good sign.

Someone realizes the organization can't accomplish everything it wants. A cherished program may need to change. Money may need to move. The board may need to become more involved in fundraising. Leadership may finally have to make a decision it has postponed.

Strategy without tension is usually just agreement around things everyone already supports. Real strategy involves choices and tradeoffs.

If your strategic plan allows every program, priority, committee, initiative, and board member's pet project to continue exactly as before, I'm not sure you've created a strategy.

You may have created a very diplomatic to-do list.

Let People Think Before They Talk

Here's a simple technique I use in strategic planning sessions: Don't immediately throw an important question to the whole room.

Give everyone a few minutes to think and write independently: One year from now, what are the two things you will most regret if we haven't addressed them?

This matters because groups influence people. The board chair speaks first and suddenly six people discover they have remarkably similar opinions. The CEO mentions fundraising and—presto!—fundraising becomes everyone's biggest concern.

Independent thinking surfaces issues that might otherwise disappear. Then put the answers on the table. That's when the interesting conversation begins.

Look for Patterns, Not Perfect Agreement

You don't need everyone to give the same answer. In fact, you probably don't want them to.

What you're looking for are patterns. If nine people independently identify leadership succession, pay attention. If half the room mentions financial sustainability, don't bury it beneath twelve other priorities. If several people believe the organization is missing a once-in-a-generation opportunity, explore why.

At the best strategic planning sessions, the goal isn't to manufacture consensus. It's to surface what people genuinely believe, identify the issues with the greatest strategic consequence, and help leaders make choices.

And don't automatically dismiss the outlier. Sometimes the person standing alone sees something everyone else has missed.

Turn Regret Into Action

This exercise only matters if you convert the answers into decisions.

Take the top three or four issues and ask: What specifically must happen? Who owns it? What resources are required? What's the first step? When will we know we're making progress?

This is where strategic planning stops being philosophical and becomes useful.

"Improve fundraising" isn't a strategy. "Identify 25 new major-donor prospects and secure introductions to 15 of them by December" starts looking like one. Clarity creates movement.

Takeaways

Don't automatically begin strategic planning by looking backward. Sometimes the clearest view comes from the future.
Ask leaders what they will regret not addressing one year from now.
Evaluate the risk of inaction as seriously as the risk of action.
Remember that maintaining the status quo is still a strategic choice.
Let participants think independently before important group discussions.
Look for patterns, but don't automatically dismiss minority viewpoints.
The best strategic planning sessions force choices and tradeoffs rather than producing longer wish lists.
Convert strategic priorities into specific actions, ownership, timelines, and measurable results.

Final Thoughts

Strategic planning is ultimately about the future, yet organizations spend an astonishing amount of time staring into the rearview mirror. History matters. Data matters. Understanding today's reality matters. But none of those things tells you what you're willing to do next.

Sometimes the most powerful strategic question isn't "What should we do?" It's "What will we regret not doing?"

Move yourself one year into the future and look back at the organization you're leading today. What decision do you wish you had made? What opportunity do you wish you had pursued? What problem do you wish you'd had the courage to address?

Then come back to today. And do something about it.

Tom Iselin

Rated One of America’s Best Board Retreat

and Strategic Planning Facilitators

About the Author

Tom Iselin is recognized as one of America’s leading authorities on high-performance nonprofits. He has built nine sector-leading nonprofits and two software companies, written six books, sits on multiple boards, and has been rated one of America’s Best Board Retreat and Strategic Planning Facilitators. His work on nonprofit strategy, board leadership, and culture has been featured on CNN, Nightline, and in Newsweek.

Tom is the president of First Things First, a firm specializing in board retreats, strategic planning services, fundraising strategy, and executive coaching for nonprofit CEOs.

Board Retreats & Strategic Planning

If you’re looking for a board retreat facilitator or strategic planning facilitator who has been in the trenches and understands real-world nonprofit challenges, Tom can help your board gain clarity, build alignment, and create an actionable plan that improves performance and impact. His sessions propel organizations to the next level of performance and impact . . . and they're fun!

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