The Strategic Planning Process Isn’t About Planning. Here’s What It Really Is.

By Erin Sedor | Black Fox Strategy

A CEO slides a binder across the table. It’s thick. Professional. Color-coded tabs, executive summary up front, appendices in the back. She tells me about the retreat that produced it — three days offsite, a facilitator they liked, good energy in the room. The team left feeling aligned. That was eighteen months ago.

She tells me what happened next, which is what always happens next. The binder went back to the office. A few goals got picked up. Most didn’t. The priorities that felt so clear in the retreat started competing with each other the moment real operations kicked back in. New problems surfaced that the plan didn’t anticipate. The team drifted back to their silos. The binder migrated from the desk to the credenza to the shelf behind the door.

Now she needs a new plan. That’s why I’m here. She wants to know my process, my timeline, what a project would look like. She’s ready to do it again — bigger, better, with the right framework this time.

I listen. I appreciate the honesty about what didn’t work. And then I do something that catches most of my clients off guard.

I push the binder to the side.

Not because the work wasn’t real. It was. Not because the team didn’t try. They did. But because that binder — no matter how much effort went into it — isn’t going to help us with what we need to do now.

It’s then that I ask the only question that really matters:

What are you trying to solve?

The answer is where strategic planning actually begins. Not with the binder. Not with the SWOT. Not with the mission statement review or the three-day offsite agenda. It begins with the thing that’s keeping you up at night and the courage to say it out loud.

And yet, most strategic planning processes never get to that conversation at all.

The Box-Checking Trap

Here’s what happens in most organizations. The calendar says it’s time for strategic planning. Someone books the conference room. The facilitator dusts off the last plan, updates the dates, reviews the mission statement, runs through a SWOT, and asks everyone to come up with goals for the next three years. The team complies, because that’s the script. Three days later, there’s a document. Everyone feels productive. And within 90 days, the plan is sitting on a shelf while the same problems that existed before the retreat continue to run the show.

This isn’t planning. It’s theater.

Only 2% of leaders are confident they’ll achieve 80–100% of their strategic objectives. Eighty percent feel good about crafting strategy, but only 44% feel good about implementing it. That’s a 36-point confidence gap between the planning event and the doing that follows — and it tells you everything about what’s wrong with the way most organizations approach the exercise.

The gap isn’t between planning and execution. It’s between going through the motions and actually solving something.

Here’s the brutal truth: that plan everyone felt so good about? It’s usually built on a lie. Not because people set out to deceive. But because the process itself was never designed to surface what’s actually going on. When planning starts with “let’s review our mission” instead of “what’s broken, and what will it cost us if we don’t fix it,” you’re building on a foundation of assumptions that nobody has tested.

Strategy Is Problem-Solving. Full Stop.

Every organization that needs strategic planning has a problem to solve. Every single one. If they didn’t, they wouldn’t need a new plan — they’d just keep doing what’s already working.

Sometimes the problem is obvious: revenue is declining, talent is leaving, a market disruption is bearing down. Sometimes it’s more subtle: growth has plateaued, the team feels misaligned but can’t articulate why, or the organization has outgrown the infrastructure that got it to where it is. And sometimes — often, in fact — the problem is the pile. The CEO sitting across from me with competing priorities stacked so high they can no longer see the horizon. That pile is not a planning challenge. It’s a diagnostic one.

The question is never “what should our five-year goals be?” The question is “what is actually happening in this organization, and what must change for us to get where we say we want to go?”

That’s not a subtle distinction. It’s a fundamentally different starting point. And it demands a fundamentally different process.

What a Problem-Solving Strategic Planning Process Looks Like

If strategic planning is problem-solving, then it helps to know how problem-solving actually works. And this is where my deep roots in enterprise risk management shaped how I approach strategy.

Risk management has a well-established process for solving problems, built on five core disciplines: Context, Collaborate and Observe, Investigate, Prioritize, and Respond. When you see it laid out, you’ll notice something: it looks nothing like a typical strategic planning retreat. And that’s the point.

Context is the most overlooked and misunderstood discipline in business management — and the most crucial skill in problem-solving. Its purpose is deceptively simple: define the scope and boundaries of what you’re assessing so the work and its outcomes are well anticipated and understood. When you fail to pin down the assumptions and boundaries of the issue, the process becomes unwieldy and the outcomes miss the mark.

The context questions that change everything are the ones most strategic planning processes never ask: What is actually happening versus what we think is happening? What are the applicable requirements and constraints? And — the one that forces all the dots to connect — how do all of these things ultimately affect the goal?

That last question insists that you understand the impact of what you’re seeing before you start building solutions. Without it, you’re guessing. And most strategic plans are, in fact, very expensive guesses.

Layer this over strategic planning, and context becomes about ensuring the health and vitality of the organization — clearly defining what is most important to its purpose, growth, and evolution. That scoping work gives context for everything that follows: what we investigate, what we prioritize, what we build.

The remaining disciplines work in concert. Collaboration and observation are continuous — not steps you complete and move on from, but a cooperative, multi-dimensional dialogue that brings perspective you cannot find otherwise. Investigation combines identification, analysis, and evaluation into a single fluid effort, developing deep understanding of why problems exist and what they’re connected to. Prioritization is where investigation yields clarity about what matters most, preventing organizations from trying to do everything at once. And Response is where outputs are directed into a plan with clear expectations for action and outcome — implementation that’s been earned through rigorous diagnosis, not assumed through box-checking.

Harvard Business Review research identifies four core errors that consistently undermine strategic effectiveness: not understanding the problem, not understanding the organization’s capabilities, not understanding immovable pressures, and not understanding the cultural landscape. Every one of them is a diagnostic failure. They happen before the plan is ever written, and they happen because the process wasn’t designed to surface them. Context is the missing link. It always has been.

When I recognized that the same contextual intelligence discipline that made risk assessment effective was completely absent from how most organizations designed strategy, the Essential Strategy Formula started to take shape. Purpose, Growth, Evolution, Equilibrium — these dimensions are a contextual framework. They force you to define what you’re actually working with before you start building on top of it. And they demand double-loop learning — not just “are we executing the plan well?” but “is this even the right plan? Are the beliefs driving it still valid? Are we solving what actually needs to be solved?”

When I tell clients that my workshops are some of the hardest work they’ll ever do, I mean it. Not because I enjoy making people uncomfortable, but because solving a real problem requires confronting things that box-checking never touches.

Why Problem-Solving Changes the Room

There’s another reason problem-solving produces better strategy, and it has nothing to do with frameworks or process design. It has to do with people.

Think about how a typical strategic planning retreat works. The CEO presents the vision. The facilitator walks through the SWOT. Department heads offer updates. Goals are discussed — often with the senior-most voice carrying the most weight. People contribute where invited, defer where expected, and leave with a plan that mostly reflects what leadership already believed going in. The room is polite. The process is orderly. And a significant portion of the intelligence available in that room never makes it to the surface.

Problem-solving engages teams in a way that check-the-box planning cannot.

This isn’t because people don’t care. It’s because the structure of the process actively discourages the kind of contribution that matters most. There’s a well-documented pattern called Authority Bias — the tendency to over-trust the opinions of authority figures and defer to them even when the data points in a different direction. In a planning process organized around hierarchy, the CEO’s instinct on market direction carries more weight than the operations manager’s firsthand knowledge of what customers are actually saying. Not because the CEO is wrong, but because the structure of the room makes it socially costly to challenge them.

Layer on the Chilling Effect, and the damage compounds. After a leader publicly dismisses a concern or visibly favors a particular direction, the entire room recalibrates. People stop surfacing problems. The leader interprets silence as alignment. It’s not alignment. It’s fear wearing a professional smile.

Problem-solving disrupts all of this — not through force, but through design. When the organizing question is “what are we trying to solve?” rather than “what do we want to achieve?”, the dynamic in the room shifts. Suddenly the operations manager’s ground-level knowledge isn’t peripheral — it’s essential. The finance director’s concerns about sustainability aren’t pushback — they’re diagnostic data. The team member who’s been quietly watching a process fail for two years isn’t a dissenter — they’re the person most likely to identify the root cause.

People invest differently when they know the work is real. They push harder. They listen more carefully. They leave with ownership of the plan — not because they were told to own it, but because they helped build it from something honest.

The Courage to Break Things

Fifty percent of middle managers can’t name even one of their company’s top five strategic priorities. That’s not a communication problem. It’s a signal that the priorities themselves are either too numerous, too vague, or too disconnected from the work people actually do. And no planning process that starts by reaffirming the existing plan will ever surface that reality.

Strategic planning done right is an act of intentional disruption. It challenges the status quo — not for the sake of disruption itself, but because the status quo is precisely what’s preventing the organization from reaching its potential. It requires naming the sacred cows, surfacing the uncomfortable truths, and breaking down the things that won’t work so you can build the things that will.

Organizations are living systems — complex, adaptive, and deeply interconnected. They don’t respond well to formulaic approaches any more than a living organism responds well to being treated like a machine. Dr. Danah Zohar, whose work on Quantum Management Theory gave language to what I’d been seeing in practice for years, frames the core problem clearly: organizations built on mechanistic thinking — predict, control, repeat — cannot thrive in a world defined by uncertainty, rapid change, and interconnectedness. The planning process itself has to reflect the living nature of the system it’s trying to serve.

What You’re Really Choosing

Every time your organization approaches strategic planning, you’re making a choice — whether you realize it or not. You can choose the comfortable path: dust off the last plan, update the language, set new targets, and produce a polished document that satisfies the board and changes nothing. Or you can choose to solve something.

Solving requires honesty. It requires sitting with your leadership team and naming the thing that everyone feels but nobody says. It requires a framework that doesn’t just organize goals but creates the context to evaluate whether those goals are even the right ones — a framework anchored in Purpose, Growth, and Evolution, held in dynamic Equilibrium, where every priority is tested against its impact on the whole.

And it requires facilitation that doesn’t let you off easy. Strategic planning should push you. It should surface the tensions you’ve been managing around instead of through. It should leave you exhausted in the best possible way — the way you feel after doing work that actually matters.

The CEO who sat across from me and admitted they couldn’t sort their competing priorities? They didn’t need a better plan. They needed a better process for solving the right problems. And once we had that conversation — the real one, not the polished one — everything else started to fall into place.

The plan was the output. The problem-solving was the point.

So the next time your calendar tells you it’s time for strategic planning, start with the only question that actually matters:

What are we trying to solve?

If you can’t answer that — or if the answer is “we just need to update the plan” — you’re not ready for strategic planning. You’re ready for the conversation that comes before it.

Ready to stop planning and start solving? Let’s talk. Reach out at erin@erinsedor.com or visit ErinSedor.com.

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Erin Sedor is an executive advisor and strategic performance expert with 30+ years helping organizations build strategy that actually works. She is the creator of Essential Strategy and the Quantum Intelligence framework for conscious, adaptive leadership