Opportunity Moves Fast; Don’t Let Strategy Box You In

One of the great comforts of strategy is that it gives us a plan. We study the environment, make choices, align resources, establish measures, and create a shared understanding of where the organization is going.

Then the environment changes.

That doesn't, by any means, make the strategy wrong. It does, however, expose an important challenge leaders must overcome: The more confidence we place in a plan, the easier it can become to defend the assumptions behind it—long after new information is telling us otherwise.

During my conversation with Jared Freeman, President/CEO of OnPath Credit Union, we talked about leading when certainty is increasingly difficult to come by. Jared described a willingness to take calculated risks, move before every answer is known, study what is happening beyond financial services, and challenge his teams with goals that may initially seem impossible.

Taken together, those practices point to an important leadership discipline: Strategy should create direction while leaving room for discovery. 

Know Which Assumptions Your Strategy Depends On

Every strategic plan contains assumptions, whether they are explicitly named or not. We make informed assumptions about what members will value, how competitors will behave, what technology will enable, where growth will come from, and what our organizations will be capable of delivering. Those assumptions can become dangerous, however, when they gradually begin to feel like facts.

Leaders can reduce that risk by identifying the assumptions that matter most to the success of the strategy and revisiting them deliberately throughout the year. Ask the question, "What evidence would tell me an assumption is weakening?" Decide which external signals deserve attention. Discuss what you would do differently if one of your core beliefs about the market proved incomplete.

This creates a different kind of strategic conversation. Instead of asking only, “Are we executing the plan?” leaders also ask, “Are the conditions that shaped this plan still true?”

Both questions matter. 

Look Beyond Your Competitive Set

One of Jared’s particular observations was related to how he thinks about keeping OnPath relevant; he looks at trends and practices in other industries and examines what attracts consumers. “I don’t want to just be a credit union; I want to be a good business,” Jared noted. “What are other businesses in other industries doing that consumers are gravitating towards? Because I think the answers that lie ahead, in terms of how we stay relevant, may not be found in the credit union space today.”

Benchmarking against peers tells you where your credit union stands today. It's important data, but it's often much less reliable at showing you where member expectations may be headed next.

Members aren't separating their experiences neatly by industry. The ease of one interaction changes what they expect from another in a completely unrelated industry. A new standard for personalization, access, responsiveness, or convenience can become familiar remarkably quickly, even when it originates far outside financial services.

This makes external curiosity a strategic skill worth practicing.

Leadership teams can intentionally bring signals from outside the industry into strategic discussions. The goal is not to imitate whatever appears newest or most innovative. Instead, ask what those developments reveal about changing human behavior. What are people becoming accustomed to? Where has friction disappeared? What once seemed exceptional and now feels routine? Then consider which of those shifts could eventually matter to your members.

That expands the field of vision before circumstances force the point. 

Make Ambition Expose Your Assumptions

Jared also shared OnPath’s practice of setting what the organization calls “impossible goals.” Teams across different functions are challenged to imagine outcomes beyond what their current ways of working would normally produce.

When a goal is only incrementally larger than last year’s, the natural response is usually to improve what already exists. Work a little faster, increase productivity, and refine the process. A sufficiently ambitious goal creates a different conversation because the existing system can no longer produce the answer.

There is a key lesson here that goes deeper than setting stretch goals. Choose an important strategic outcome and ask: What would have to be true for us to achieve something dramatically better than our current trajectory?

That question exposes assumptions quickly. For example, a process everyone has accepted for years may suddenly look negotiable. A capability gap becomes more obvious. A technology limitation moves higher on the agenda. A partnership that had never been considered becomes worth exploring.

This connects directly to the concept of “elastic leadership”: creating enough tension and flexibility for an organization to stretch beyond its current way of operating and discover what else might be possible. I explored that idea in a CUbroadcast conversation on elastic leadership, including how leaders can use tension and uncertainty to create space for adaptation, creativity, and growth.

The point is not to populate the strategic plan with unrealistic targets, but to occasionally create enough distance between today’s performance and the desired outcome that the organization has to think differently about how the work gets done.

Even when the “impossible” result remains out of reach, the thinking it produces can change what the organization considers possible.

Match the Level of Certainty to the Decision

Jared traced some of his own leadership approach to advice from an early CEO who wanted him to make decisions, knowing that an imperfect decision could usually be corrected. Today, Jared talks about the paralysis that can occur when leaders become too afraid of being wrong.

At the executive level, that makes you wonder: How certain do we actually need to be?

The answer should vary considerably depending on the decision.

Some choices carry consequences that are expensive, difficult to reverse, or potentially damaging to members and the organization. They warrant rigorous analysis and a high standard of confidence.

Other decisions are far more reversible. They can begin at a limited scale, generate information, and be modified as leaders learn more. Requiring the same level of certainty for those decisions can create an unintended cost: The organization learns more slowly.

Leaders should become deliberate about distinguishing between the two.

Before extending the decision-making process, ask what additional information would materially change the choice. Consider whether the decision could be structured as a smaller test. Determine what would trigger expansion, revision, or exit.

That turns uncertainty into something you can manage instead of something you have to eliminate. 

Leave Room for the Strategy to Get Smarter

The strongest strategies provide clarity; they help people understand where the organization is placing its bets and why those choices matter. But they should also be capable of getting smarter.

That requires leadership teams to be willing to challenge their own assumptions, bring unfamiliar perspectives into the room, pursue ideas without guaranteed outcomes, and revise their thinking as new information emerges.

Jared’s leadership journey offers a useful example. Early in his career, someone gave him room to make decisions before he had every answer. Today, he describes applying that same willingness to learn through action—taking calculated risks, looking outside the traditional boundaries of the industry, and asking teams to imagine possibilities beyond what their current systems would suggest.

Strategy gives the organization a destination and a shared sense of purpose. Leadership determines whether the organization can recognize new information along the way and use it.

We know that opportunity moves fast. Let's make sure our strategies leave us enough room to see it coming—and enough freedom to respond.