You've sat through the offsite. You've read the strategy deck. You've nodded along to the transformation roadmap. And somewhere in the back of your mind, a question is forming that nobody in the room seems willing to ask out loud:
"This all sounds right. But what do we actually do on Monday morning?"
It's the most common question in organizational life, and the most commonly ignored. Frameworks are abundant. Methodologies are everywhere. What's rare is honest guidance about where to begin — not in theory, but in your specific organization, with its specific problems, its specific politics, and its specific constraints.
The answer isn't "implement everything at once." That's the organizational equivalent of trying to fix a house by renovating every room simultaneously. It produces exhaustion, cost overruns, and a family sleeping in the garage.
The answer is: start where the pain is sharpest.
Diagnose Before You Prescribe
Most change efforts skip the diagnosis. Leadership identifies a symptom (revenue is down, stakeholders are disengaged, execution is failing) and jumps straight to a solution (digital transformation, reorganization, new KPIs). The solution may be excellent. But if it doesn't address the actual root cause, it's expensive irrelevance.
Before you do anything, answer one question: Where does alignment break down in your organization?
Not "where are we underperforming?" That's a symptom. The question is where the connections fail — between why you exist and what you choose to focus on, between what you choose and what you're capable of, between what you're capable of and what stakeholders actually experience.
Four patterns show up in virtually every organization. Each points to a different starting place.
Four Entry Points
If the problem is purpose confusion, start with why you exist.
The signal: ask five leaders why the organization exists and you get five different answers. Strategy conversations go in circles because there's no shared foundation. Initiatives multiply because there's no filter for deciding which ones matter. People work hard but can't explain how their work connects to any larger purpose.
The starting move: get leadership in a room and ask the uncomfortable question. Not "What's our mission statement?" but "If we ceased to exist tomorrow, what specific thing would the world lose?" Collect the answers. Don't debate. The divergence that surfaces is the most valuable strategic insight your organization has never confronted.
If the problem is strategic drift, start with choices.
The signal: the organization has a strategy document, but nobody uses it. Resources are spread across too many priorities. Every initiative gets funded at 60%, and nothing produces results. Leaders can't articulate what the organization has explicitly chosen not to do.
The starting move: take your current portfolio of initiatives and ask, for each one: Does this directly serve the reason we exist? If we stopped doing it, would the people we serve be worse off? The initiatives that fail both tests are consuming resources that should go to the ones that pass. One honest "no" is worth more than a hundred aspirational "yeses."
If the problem is execution failure, start with capabilities.
The signal: the strategy is clear, but execution consistently falls short. The plan calls for digital transformation, but the infrastructure is legacy. The strategy assumes new markets, but the skills don't exist. Leadership commits to outcomes that require capabilities nobody has assessed, let alone built.
The starting move: pick one strategic priority and ask, "What must we be genuinely great at to deliver on this?" Then honestly assess your current state. Not what you have on paper. What actually works. The gap between "what the strategy requires" and "what the organization can actually do" is where execution dies.
If the problem is outcome disconnect, start with the stakeholder experience.
The signal: capabilities exist, but stakeholders aren't seeing the value. Dashboards are green, but the people you serve are disengaged. Operations are efficient by every internal measure, but the experience of being on the receiving end is fragmented, confusing, or irrelevant.
The starting move: ask your most important stakeholders what their experience actually looks like. Not a satisfaction survey. A conversation. What works? What doesn't? Where do they feel processed rather than served? The gap between their description and your internal metrics reveals exactly where delivery has drifted from purpose.
Your First Cycle Is a Proof of Concept
Here's what doesn't work: spending six months building the perfect framework, analyzing every dimension, producing comprehensive documentation, and then launching a transformation program that touches everything at once.
Here's what does work: a small, fast, focused first cycle that demonstrates value in your specific context.
Weeks 1-2: Diagnose. Talk to stakeholders. Talk to front-line staff. Talk to frustrated leaders. Where are the disconnects? Which of the four patterns is most visible? You're not doing comprehensive research. You're finding the sharpest pain.
Weeks 3-6: Focus. Based on what you found, go deep on one thing. If strategy is the problem, draft the strategic choices for one business unit or program — including what you'll stop doing. If capability is the problem, map one critical process and assess its gaps. If delivery is the problem, blueprint one key service from the stakeholder's perspective. Produce something tangible.
Weeks 7-12: Prototype. Implement one change based on what you've found. Not a transformation. A single, measurable improvement. Redesign one handoff. Introduce one outcome metric where only activity metrics existed. Align one team's priorities with the strategic choices. Measure the result.
This isn't a full transformation. It's a proof of concept. Its purpose is to demonstrate that asking better questions produces better answers in your specific environment.
The result should be concrete enough to show skeptics and compelling enough to earn the right to do more.
Build the Case by Speaking to Pain
The biggest barrier to changing how an organization thinks isn't disagreement with the approach. It's the question: "Why do we need this? We already have a strategy."
Don't answer that question with a methodology presentation. Answer it with the problems leaders already feel.
If the problem is lack of focus: "We're spread across too many priorities and nothing gets the investment it needs. We need a way to force choices."
If the problem is execution failure: "Our strategies look great on paper but don't produce results. Something breaks between the boardroom and the front line. We need to see where."
If the problem is initiative churn: "We launch a new priority every quarter but none of them stick. We need a way to sustain commitment through execution."
If the problem is measurement confusion: "Our dashboards are green but our stakeholders aren't happy. We're measuring the wrong things."
Start with their problem. Then show how a better discipline addresses it. The most effective case for a new approach isn't an argument. It's a question that reveals a gap leaders can feel but haven't been able to name.
Find the Frustrated
You can't change how an organization thinks by yourself. And you shouldn't try to start by converting the most skeptical leaders. That's a recipe for exhaustion and failure.
Instead, find the people who already feel the pain of misalignment. The program director whose initiatives keep getting derailed by competing priorities. The operations manager whose team is measured on activity instead of outcomes. The strategist whose plans never survive contact with organizational reality. The front-line leader who knows exactly what stakeholders need but can't get the organization to listen.
These people don't need to be convinced that a problem exists. They need a framework for solving it. Start with them. Run your first cycle with their problems. When it produces results, they become your advocates.
Success with allies creates the evidence that eventually persuades skeptics. One concrete improvement in one part of the organization is worth more than a hundred theoretical arguments at the executive level.
The Discipline, Not the Document
Here's the thing that takes most people by surprise: the value isn't the strategy document. It's not the capability map. It's not the stakeholder analysis or the governance framework or any individual artifact.
The value is the capacity to navigate whatever comes next.
An organization that has practiced this discipline — sensing what stakeholders need, making explicit choices, assessing capability honestly, designing delivery from the outside in, and learning from the result — handles the next disruption fundamentally differently from one that planned once and executed until the plan expired.
The first disruption produces panic. Dozens of ideas, no criteria for choosing, months of paralysis.
The second disruption, if the discipline is in place, produces something qualitatively different. A structured assessment. A nuanced response. Weeks, not months. Not because the environment got easier, but because the organization got better at responding.
That capacity isn't something you buy. It's something you build — one cycle at a time, starting with the first imperfect attempt and improving from there. The first cycle will be rough. That's the point. The value isn't in the first cycle's output. It's in what you learn about doing the second one better.
The Question That Starts Everything
You don't need a consultant. You don't need a six-month initiative. You don't need executive buy-in for a comprehensive transformation program.
You need one conversation.
Pick the gap that's costing your organization the most. Gather the people who feel it most acutely. Ask the question that nobody has asked out loud:
- "Why do we exist?" (if the problem is purpose)
- "What are we choosing not to do?" (if the problem is focus)
- "What can we actually deliver on?" (if the problem is capability)
- "What does this feel like from the other side?" (if the problem is experience)
The answer — or more likely, the disagreement — will tell you exactly where to start.
The framework is a lens. The picture is yours to see. And the first step is yours to take.
This post is drawn from Closing the Strategy-Execution Gap, a self-paced course that follows one institution from crisis to adaptive capacity — and shows what the first cycle looks like when the discipline is real.