History remembers the doers. 🫡

No matter how strong your strategic plan is on paper, its success or failure depends on how well it’s implemented.

Failure? we’re not gonna let that happen. 😤

You need someone to show you how to anchor your plan to reality. We’re here to do that.

In this article, we’ll go through the five steps to operationalize a strategic plan:

  1. Determine the destination by mapping out OKRs and goals for the organization as a whole.
  2. Set the course by developing an actionable plan to reach the goals you’ve set out.
  3. Begin your journey by executing your plan.
  4. Monitor your progress and adjust as necessary.
  5. Wrap up the project with a recap and debrief.

First, let’s break down strategic planning itself by looking at its five key stages.

What are the five stages of strategic planning?

The five steps of strategic planning (which perhaps you followed to get to this point), look something like this:

  1. Set out OKRs and mission objectives.
  2. Gather and analyze intel.
  3. Formulate a strategy.
  4. Implement that strategy.
  5. Monitor and adjust.

First, you determine where you want to end up. On a large scale, ask yourself “where is the organization headed?”.

Second, you take stock of where you’re at right now. You might perform a competitive landscape analysis to determine the state of your competitive environment. You might conduct a SWOT analysis, or a hybrid of SWOT, PEST, and all the other four-letter acronyms you can think of.

Third, you’ll formulate your strategy. That means putting together the building blocks of how you’re going to get from where you are now to where you want to be (as defined in step one with your OKRs and mission objectives). You’ll do that in light of what you learned in step two.

Fourth, you’ll implement the strategy, carrying out the plan you formulated in the last step.

Finally, you’ll monitor and evaluate progress as you go.

(Note: when there's a lot on the line, it's also useful to pressure test your strategy against various unfavorable scenarios. Business war games have you bring folks together from across the business to do just this.)

What does it mean to operationalize a strategic plan?

So that’s strategic planning in a nutshell. But we’re here to talk about operationalizing your strategic plan. So where do the two meet?

Operationalizing your plan is all about putting it into action. That might make you think this is only to do with strategic planning’s step four: implementing your strategy. But you’d be wrong. 🙊

Truly operationalizing your plan means working it into your day-to-day operations, making it a part of everyday business processes, and allowing it to penetrate the foundations of the business.

To do that, create your plan with the understanding that people are actually going to have to put this to work.

That means fitting into the plan considerations like:

  • How much extra capacity each department has.
  • Which individuals are qualified to perform which tasks.
  • What obligations people will put to one side while they work on this new project.

It also means appreciating the finer practical details. For example, structuring incentives, and communicating reasons why to task doers. Without adequate incentive and understanding, motivation will lapse, and your grand plan will drift off course and behind schedule.

Finally, it means you can’t get bogged down in details that’re way out in the future. Strategizing to the smallest detail three years in the future is a colossal waste of time; chaos will ruin your plan before you get there.

Instead, imagine you’re driving through the fog with headlights on full. Right in front of you, you can see things pretty clearly. Way out in the distance, it’s all mist. In between, you’re seeing in low resolution.

You and the gang. Carrying out your strategic plan.

Structure your plan the same way. This will save you time up front, and keep your focus where it needs to be: bearing the critical milestones in mind, but staying practical about what needs to happen right now to get you where you want to go.

Note: A great time to gather much of this information is while you're facilitating your next strategic planning session. Having everyone in the same room is the perfect time to get feedback and nurture buy-in.

Operationalize your strategic plan in five steps

Time to take action. Here are those steps again:

  1. Determine the destination by mapping out OKRs and goals for the organization as a whole.
  2. Set the course by developing an actionable plan to reach the goals you’ve set out.
  3. Begin your journey by executing your plan.
  4. Monitor your progress and adjust as necessary.
  5. Wrap up the project with a recap and debrief.

1 - Determine the destination: map out OKRs and goals

How big should your plan be?

Keep it simple. Ambitious, but simple.

Remember, too: the further into the future the plan gets, the less rigid it must be. Focus on the few things you can control in the near-time, and have faith that you and your team will be smart enough to handle inevitable bumps in the road.

First up: develop a project charter, defining at a high level the work to be done. That means getting clear on the final destination, or the end goal for the project. Split this “final destination” into several OKRs (Objectives and Key Results) at this stage. With those in mind, map out the following:

  1. Create metrics to measure success. You need KPIs to act as yardsticks of success on your way to meeting your OKRs. These should be realistic and achievable, and constitute measurable progress towards your laid out progress towards goals.
  2. Create key milestones. Outline critical milestones in the project. This will help you gauge progress and help break down the plan into manageable seasons.

With OKRs, metrics of success, and key milestones mapped out, you’ve already taken the first few concrete steps toward operationalizing your project.

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2 - Set the course: develop an actionable plan

Creating a great strategy is only one part of the problem. The real challenge is in the execution. Taking the plan from a mental exercise on the drawing board to a set of steps that people can start getting done is the essence of “operationalizing”. You’re translating concepts for success into concrete steps. 🕺

Though this part of the process doesn’t fully encapsulate what it is to develop an actionable plan, this is the section where the most work needs to take place to set up the rest of the project for success.

For that reason, we’ve crammed this section with more advice than any other.

Making your plan actionable

So what should this plan look like?

Remaining on the high-level for a second, you’re going to want to develop a budget for the overarching plan. A risk management plan too.

However, the bulk of ‘operationalizing’ is people-focused. Taking your plan from high-level strategy to low-level action points means focusing on the people involved. Start breaking things down into chunks to make the lofty goals more manageable.

That means subprojects with their own timelines. Break these subprojects into tasks and subtasks, each with its assignees and collaborators, and clear guidance as to what success on the task looks like.

Happily, you might notice this sounds familiar. That’s because you (probably) use project management software every day. If you do, figuring out how to get your strategy off the whiteboard and into your project management software—in a format that team members are already used to—is the goal.

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Avoiding the pitfalls

But there are pitfalls. Think about the last time you were snapped out of flow-state by a notification for an administrative task with a due date of… today?! And you were making such good progress on that project. 😡

It’s frustrating, but it’s not just you that gets turned off by inconsiderate due dates and workloads.

To get buy-in on this project for the long-term, you’ll need to work with other departments in a way that’s compassionate. If your managerial fur bristled at that, then remember this is the best way of getting what you want.

So, what to do?

Do some reconnaissance on your project’s future stakeholders. By now, you should have some sense of how much work will be required of each of them. Do they have the capacity to take on that much new work? If not, you’ll have to ask them to drop or delay some other project to get yours done.

For that, you’ll need to speak with whomever they report to and agree on a reshuffling of their workload.

Communicating the plan

This brings us to communication. Communication, on the whole, is one of the most important parts of this process.

Communicating with people ahead of time makes them feel more valued and prepares them for the work to come. It also gives them a chance to voice any concerns or grievances before they have a chance to fester.

Meeting and communicating ahead of time gives everyone a chance to work together to set expectations around deadlines, workloads, and existing commitments. Not to mention a chance to chime in on what metrics and KPIs should be used to measure project success.

When you can give people a clear ‘reason why’ before they can ask, “What’s the point?”, they’ll be far more likely to push through mundane tasks in service of the overall effort.

People tend to get lost in the weeds as large scale projects (like strategic plans) wear on. Consider what you’ll do to motivate the troops at key stages, reward big wins, mitigate failures, and learn all you can from the mishaps you can’t avoid.

3 - Begin your journey: execute your plan

With everyone aware of what’s about to happen, and the plan in place, there’s nothing really left to do except… let it happen.

As tasks roll into inboxes, teams will complete them, and your plan will already have begun its long march to victory.

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4 - Weigh anchor: monitor your progress

Of course, you can’t let the entire, multi-month process unfold on its own without any oversight at all. That’d be madness. 😉

Instead, you’ll want to perform ‘health checks’ at various milestones along the way (preferably a good few weeks before each critical juncture).

This way, nothing takes you by surprise. Even with the wind in your sails, it pays to keep a hand on the rudder—to steer your ship as you sail it toward success.

The scope of your project will guide how regularly you monitor, but it’s common sense to check-in with key individuals at regular intervals. Sparse cliff notes as updates in daily or weekly reports, a standup meeting perhaps bi-weekly, and then a more in-depth look once per month. Then, each quarter, take a deep dive with a rigorous, all-hands meeting.

Finally, be sure to make any necessary adjustments in line with what you find from these health checks.

5 - Bring the ship in: debrief and recap

That’s it. You start with an overarching strategy and, once you’ve outlined the broad strokes of what you want to achieve and how you’re going to get there, you make the strategy actionable.

A plan is made practical by making it about the people. Operationalizing is all about getting the various facets of your business pulling in the same direction towards a common goal.

While, yes, that means integrating with your org’s favorite processes, tools, and software, it primarily involves communicating and working with the people who will be making your plan happen. That means outlining the necessary steps, tasks, timelines & deadlines, deliverables, and people responsible.

Once the plan is made practical, you’ll launch the project and check in with key stakeholders more frequently, holding more in-depth meetings with the whole team less frequently, but before critical milestones. You’ll use what you learn from the mistakes you and the team make to improve the process, correct course, and continue making way to your destination.

That process will guide you all the way to the finish line. 🏁

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