Strategy is a Practice, Not an Event
You know the feeling. It’s 4:30 PM on a Friday, and you are sitting in a rented boardroom surrounded by the remnants of a catering lunch, half-empty coffee cups, and walls completely papered in neon sticky notes. As an Executive Director, you look around the room at your tired team. You feel a fleeting surge of inspiration, but beneath it lies a heavy, quiet knot of anxiety in your stomach.
Your phone is buzzing with missed emails. You carry a deep, exhausting guilt over how hard your staff is already working, and a persistent performance anxiety about letting your funding partners down. You pack up the messy rolls of chart paper, knowing they have to be translated into a formal document, but there are still so many unanswered questions: How on earth are we actually going to execute this? When do we find the time to communicate it to our community? How do we evaluate if it’s working, and what happens when we inevitably need to adjust the plan so we don’t burnout our people?
If you have felt this friction, you are not alone. This is the most common approach to strategic planning in North America—and unfortunately it’s not very effective.
The Data on Strategy
Research synthesized by the Harvard Business Review and long-standing studies by Harvard Business School researchers Robert Kaplan and David Norton consistently reveal a staggering reality: between 70% and 90% of strategic plans fail to achieve their intended outcomes.
When we look beneath the surface of this statistic, we find two distinct layers of friction:
The Technical Challenge: Traditional planning lacks an operational lifecycle. The plan leaves the boardroom without a designated framework for how it will be communicated internally, no defined metrics for evaluation, and no mechanism for real-time adjustment. Instead, milestones are often stacked heavily into one year creating an immediate, unsustainable bottleneck.
The Adaptive Challenge: We are operating under the influence of a deeply ingrained North American corporate culture that equates "busyness" with impact and "slowing down" with failure. We rush through a single planning day because facing the reality of our limited capacity triggers intense discomfort and scarcity-driven fear. We avoid building evaluation and adjustment rhythms because, subconsciously, we fear they will expose our gaps and make us look unsuccessful to our beneficiaries, boards or donors.
The Equity and Inclusion Impact
This event-driven approach isn’t just an operational risk; it can actively eliminate marginalized leaders and equity-deserving groups who are already navigating systemic barriers. When an organization adopts a rigid, corporate-pacing model, it inherently prioritizes institutional speed over human well-being. By dumping a massive checklist of goals into one year, leadership teams create an overwhelming mental pile-up. Staff are forced to constantly juggle a mountain of new strategic initiatives on top of their demanding day-to-day jobs.
For diverse leaders—including those who are neurodivergent, disabled, racialized, or working within marginalized spaces—this unrelenting, artificial pressure can trigger rapid, systemic burnout. Traditional planning fails to account for diverse processing styles, differing access needs, and the heavy emotional labor often carried by equity-deserving staff.
Furthermore, for organizations walking the path of Indigenous reconciliation or deep community advocacy, a rushed, top-down execution timeline completely bypasses the relational, community-centered pacing required to build genuine safety and deep trust. If a strategic plan cannot be safely paused, re-evaluated, and adjusted based on grassroots feedback, it ceases to be an equitable framework. Instead, it becomes just another top-down mandate that forces conformity over connection.
Coaching Reflections
Before rushing to fix your planning process with another tool, take a moment to step back and examine the underlying mindsets driving your organization.
When you look at your current strategic goals, are they a realistic reflection of your team’s day-to-day capacity, or are they an over-packed wishlist driven by the fear of not doing enough? What are you afraid will happen if you choose to do less, but do it deeper?
Who on your team is currently designated to coach your strategy forward, and what is one small boundary you can set this week to protect your team from a front-loaded timeline?
The Practice: Designing the Operational Lifecycle
To shift from a static document to a living practice, you must replace the "planning day rush" with a clear, ongoing operational lifecycle:
Paced Execution (Estimate Effort First): Before writing a single goal into stone, calculate what strategic activities will actually cost in time, energy, and money. Work directly with your implementation team to map out who, when, and how much can realistically be achieved each year.
Transparent Communication: Build a clear communication plan. Ensure front-line staff understand exactly how their daily work connects to the larger strategy, and keep community members actively engaged in the narrative.
Continuous Evaluation & Adjustment: Create a recurring, quarterly, and psychologically safe space with your team and your board to look at data, celebrate small wins, evaluate progress, and—most importantly—safely adjust the plan in real time based on changing realities.
Moving From Spark to Sustained
Strategy takes time. Not in a vague, philosophical sense, but in a literal, day-to-day operational reality. Your plan will not materialize tomorrow, and when leaders try to force it to, the human cost is incredibly heavy.
This is exactly why my consulting work naturally evolves into fractional partnerships. Organizations rarely need help just starting—they need a structure for sustaining. Once a leadership team experiences the profound relief of having a dedicated partner who holds the strategic, operational, and financial dimensions of their work all at once, the isolation lifts. They realize they no longer have to carry the crushing weight of execution alone.
What would change for your organization if your strategic plan became a predictable, supported practice rather than a source of underlying anxiety?
