Strategy and execution are usually treated as two separate worlds. One happens in workshops and slide decks, the other happens in the mess of the real organisation. And that’s exactly where the trouble starts.
What if implementation actually starts in strategy discovery, not after the strategy is “done”?
What usually happens today
Strategy is typically built in a small room by a senior few or built in the ‘Strategy Team’, then revealed to the company as a finished answer. The delivery teams see it for the first time in a slide deck roadshow, an offsite or an all‑hands email. They’re expected to nod along, ask a few questions at the end and then “take it away” and make it happen.
At that point, execution is treated as a downstream phase, even planning is done later. “The front line teams will develop their plans when the strategy is approved”. Then, when results eventually stall, the post‑mortem turns into a blame game of “unrealistic strategy” vs “poor execution”. Strategy points at poor adoption and inconsistent delivery. Execution points at goals that don’t reflect reality. Everyone is technically right but everyone is missing the point. And it leaves the organisation at the start of a marathon slog to deliver what it set out.
Why the ‘usual’ creates problems
When strategy is treated as something separate from execution, you almost guarantee problems before it’s been announced:
Wrong Assumptions: the capacity, capabilities and customer reality weren’t really tested, built and designed with the people closest to the work. The numbers added up in the spreadsheet but they never will in the field.
Ownership is low: Teams feel “done to”, so they comply but don’t commit. They do as much as they can but because they don’t truly understand where the strategy comes from or how it’s supposed to work, they struggle.
Rework explodes: Initiatives are re‑scoped, delayed or quietly killed once they hit operational constraints. The work happens twice, once in the strategy room, once again when someone finally asks, “Can we actually do this?”
Cynicism grows: “We’ve seen this show before” becomes the default attitude to any new strategy. Each cycle gets a little harder because belief has been eroded. It becomes a fancy tick box exercise and people go back to what they were doing before.
The organisation ends up running two separate conversations, one about what we want and one about what we can actually do. Unfortunately, the second comes too late, nothing aligns and no one is clear on what to do next. This is what running in ‘hard mode’ looks like.
Implementation really starts in strategy
Implementation doesn’t start when the strategy is signed off. It begins the moment you decide who is in the room, what questions you ask and what you treat as fixed constraints versus variables.
Discovery can be pure research, the interviews, data, market analysis. Or it can be seen as codesign, involving the people who sell, deliver and support customers (and sometimes customers themselves) to shape the direction of the business. When you bring execution voices into discovery and design, you surface risks and practicalities early, when they’re cheap to respond to. You hear things like “That would add two weeks to onboarding” or “We can’t sell that promise with the systems we’ve got” before they’re printed on a slide or more importantly, signed off by the board.
For most leadership teams, this feels uncomfortably early to involve execution teams. It can feel messy, slower, and less “strategic”. It feels constraining. But the benefits are clear through sharper choices, more realistic plans and teams who already see themselves in the strategy before it’s announced. By the time the “strategy” is shared, many people feel like they designed and importantly, that they’ve already started implementing it because by this time, they are.
How to design strategy as the first phase of execution
1. Use proposition design as the first mile of implementation
A high‑level strategy is useful. But until it turns into a clear value proposition, it’s still too abstract to deliver. Translate the direction into something concrete:
- Who are you for
- What problem you solve
- Why you over alternatives.
Force yourself to write down the specific promise you are making to a specific customer(s). Make the proposition specific enough that sales, marketing and product can see what they would actually need to do differently on Monday morning. If they can’t picture conversations, campaigns or features changing, it’s not yet actionable.
Then stress test the proposition with real customers, existing deals and current delivery capabilities. Where does it hold up? Where does it snap? Let what you learn feed back into refining the strategy, not just the messaging. This is what makes proposition the first mile of implementation, not just a branding, marketing or communication exercise.
2. Codesign with the people who deliver
Strategy lands differently when the people who have to live with it helped build it. Involve sales, marketing, product, operations and customer success. Where it makes sense, bringing in and get input from real customers in the strategy and proposition working sessions. Not as a token “input” stage but as genuine co-design.
Use real examples as the raw material, recent wins and losses, live opportunities, customer stories. Talk about actual accounts and journeys, not just segments and personas.
Ask explicitly: “What would have to change in your world for this to be real?” and “What are we underestimating here?”
Capture objections and concerns as design inputs, not as “pushback” to be managed later. If something sounds hard or unrealistic, challenge it but use that as a clue to refine the direction, not something to ‘smooth’ over later with comms.
3. Design for constraints and feedback loops
Most strategies fail not because the ambition is wrong but because the constraints appear too late. Put real constraints on the table early including budgets, capacity, skills, tech stack, compliance and risk. Name them and make them visible in the room where choices are being made. Usually, this means involving and engaging the people at the coal face who know the detail, not just the C suite who speak on behalf of their teams.
Decide what’s genuinely non-negotiable and where you have room to run structured experiments before being iterated and defined. This means treating the first cycle of execution as part of the strategy process and then establishing ways in which the organisation can learn to refine the strategy further.
4.Make the first 90 days part of the strategy
Whilst developing a strategy shouldn’t be a planning exercise or a shopping list of actions (see article), if your strategy can’t survive being turned into a 90‑day plan, it isn’t ready.
Outline the first 90 days of implementation in the strategy. What are the key initiatives, simple milestones and a few critical measure? This doesn’t need to be a full programme plan as it’s the first step, not the whole journey.
Agree who leads what and where cross‑functional collaboration is required, for example, sales–marketing, product–ops, or commercial–compliance. Make those joins explicit.
Keep this deliberately light but concrete enough that everyone can picture “day one” after sign‑off. People should come out of the strategy conversation with a clear sense of “what happens next”. Use this 90‑day plan as a living test of how executable the strategy really is. If you can’t agree it, that’s a signal to go back and refine the strategy, not simply add more stuff to the plan.
This is potentially one of the biggest failings we see in strategy and proposition design, not developing the initial roadmap as part of the process that gives people clear actions to take.
What changes when you work this way
When you treat strategy as the first phase of execution, the feel of the whole organisation starts to shift. Strategies stop dying quietly in a SharePoint folder. More of them make it to delivering real customer impact without endless rework and reinvention. You still iterate, but you’re iterating on something that was built with delivery in mind.
Time from decision to first visible results shrinks, and the handover gap narrows as there is less “figuring it out” after the fact. Leaders get fewer nasty surprises from the front line, because constraints and risks were surfaced much earlier. The conversations at review time are about trade‑offs and learning, not about basic feasibility.
Teams talk about “our strategy” rather than “the strategy”, because they helped shape it. They can see their fingerprints on the choices and the proposition.
Over time, the organisation builds a repeatable pattern for turning intent into action, instead of treating each strategy cycle as a one‑off event. Strategy and execution stop blaming each other and start behaving like one system. This shifts the organisation from running in ‘hard mode’ to ‘easy mode’.
The bottom line
If implementation is expected to start after strategy, you’ve already built in a gap between them. The shift is simple to describe but not always obvious when you’re doing it. It’s shifting from ‘strategy as a document’ to ‘strategy as the first phase of execution’ and designing with that mindset.
So, where in your current strategy cycle could you pull implementation thinking up into discovery? How can you structure your strategy and proposition design process to include executors and the key insights they’ll bring?
This is the work we do with B2B organisations, connecting strategy, proposition and delivery so the organisation can actually live, breathe and deliver the choices they make.
