This article was originally published in Emergence: The Journal of Business Agility in December, a magical time of year when many find themselves locked in stuffy conference rooms breathing recycled air and agonizing over a 2023 strategy. Speaking of which… how’s that going? Smooth sailing so far? (😉) With Q2 nearly here, we thought it was time for a check-in—and course-correction for those who need it.

Strategic planning is a corporate ritual akin to RIFs, annual budgeting, and performance management. Loosely defined, strategic planning is a (likely annual) process in which leaders determine where an organization is headed and lay out a roadmap to get there.

Sometimes this planning happens during a weeklong offsite; other times, it takes place over a series of extended sessions. Regardless of the context, the content stays the same: Loads of data are gathered, slides are revised (and revised), and wish lists are honed and packaged by the fat end of the pyramid. Then, those at the top represent the work of those they manage, sometimes Hunger Games-style, as they negotiate with cross-functional peers.

There are two main problems with this pattern. One, it fails to imagine possible futures and lean into divergent thinking before a team converges on exactly what it will do. There’s too much emphasis placed on the “plan” and not enough on the future itself; leaders get together and immediately move to discussion, debate, and consensus-building around what they’ll “do” rather than what “could be.” The focus is almost entirely on debating the milestones, deadlines, and ownership.

The other typical headwind: skipping critical conversations about how an organization’s ways of working need to change in order to make use of its new strategy. Most strategy falls apart not because the plan is terrible (though many are), but because the process avoids answering questions like:

1. What roles must be added, shifted, or shed so we have the right capabilities and capacity?
2. What decision-making authority do various roles and teams need to execute elements of the plan?
3. How do money and time resources need to be reallocated?
4. What operating rhythm of meetings is needed to keep the execution work moving and to be sure we’re retrospecting and learning as we go?
5. What tools will make the day-to-day work visible and transparent to the organization?

Don’t get me wrong, nailing a strategic plan after days of debate and too much coffee is a great high. It’s easy to believe an organization is moments away from becoming shiny and new. A bright, lucrative future where ambitions are realized, the market responds, and dreams come true? Yes, please!

But feelings of accomplishment and certainty fade away when these lofty fantasies make contact with reality: The company hasn’t changed. And that beautiful, well-interrogated, fussed-over strategic plan we committed to? It’s a shared deception.

I once worked with the executive team of a famous non-profit. To say they didn’t trust each other is an understatement. They asked me to spend a day with them unpacking a strategic plan created by a fancy, overpaid consultant. I suggested digging into the team’s ways of working — a.k.a. how they thought about role clarity, authority, meeting rhythms — to see how and where those things would have to change in order to execute the plan. The team insisted they didn’t need that work; they just needed to lay out a detailed roadmap of how to achieve the building blocks, within the pillars, under the umbrella (or some such nonsense on the animated PowerPoint they’d shelled out for).

We did their thing. They loved it. High fives were flying. Absolutely nothing about their ways of working changed and they remained mystified when, 18 months later, the “new strategy” hadn’t come to life. A strategic plan (bought or homegrown) is like a diet book or a gratitude journal, providing initial hope and then serving as a reminder that nothing changes unless you change.

What would have changed if that team had dug into the how? First, they would have noticed that the CMO and her team had minimal digital experience or interest and that a major thrust of the plan would require a reorientation from print to social media. Second, the CEO was assuming the Head of Product was going to make a major pivot in her organization’s focus based on one of the pillars. (Spoiler alert, she wasn’t.) And third, their existing meetings were about event planning and fundraising; without shifting the content of those meetings, none of the strategy-related work would be discussed week over week.

A strategic plan that’s continually steered and buoyed by experimentation can be one of the greatest tools of organizational agility. But mediocre strategic plans that lack vision and imagination — and that focus only on the what, not the how — are likely to capsize. An inflexible plan is the opposite of wind in your sails; it’s an anchor holding you back from responding to and interacting with the environment.

Learning How to Sail

Now that we know there’s room to do better with strategy, let’s explore a short stack of practices that will serve you to steer your team, department, cross-functional team, or project on different time scales. Deep breath, there’s a metaphor.

Strategy Is Like Sailing

I grew up in Connecticut on Long Island Sound and spent a lot of time on boats as a kid. From our town’s beaches, four smokestacks were visible on the Long Island shore. They were the only clear markers on a cloudy day. Think of your strategy as those smokestacks; it’s where you think you’re headed.

Even if you’ve never been on a boat, you probably know enough about water and wind to know that sailing in a straight line isn’t a thing. There is no “shortest line from point A to point B” when you’re dealing with tides, shallows, and wind. These factors aren’t obstacles — they’re part of the environment. The environment slows us down, blows us off course, or gives us speed to shorten our journey. Sometimes, these externalities even tell us our original destination was wrong. (There’s a pie shop a mile east of the smokestacks?) We keep one eye on the destination, but we adapt to and with the environment along the way. This is where strategy and steering come together.

Essential Intent: The Point On the Horizon You’re Aiming For

To define team strategy in a way that’s enduring, visionary, and flexible, our crew at The Ready uses a simple Mad Lib created by Greg McKeown in his wonderful book Essentialism. Creating an Essential Intent (or EI) helps us think both big and small, and ultimately define an intention (not a plan) that’s both concrete and inspirational. The practice of defining an Essential Intent avoids several common pitfalls in strategic planning:

1. Having a motivational purpose or vision with no path to operationalize it
2. Having clarity on OKRs, goals, or initiatives with no coordination around long-term intent or cross-functional implications
3. Having both of these things without feedback loops between them

Now that you’re fired up to craft an EI, a plea: Do not start with grinding on the statement. You will end up with something fine but uninspired. A few years back, my colleague Ali and I created a workbook to help clients draft a compelling EI they could get team feedback on. Even though clients consistently rail against sitting down with a cup of coffee and taking 20 minutes to fill in these prompts, it always delivers when they do. To get a copy of this workbook, email: getstarted@theready.com.

You need to tap into insight to be inspiring; if you take the time and space to imagine the winds, rocks, and weather you may be navigating, those smokestacks will become visible. If you stare at a blank sheet of paper and try to jam out a brilliant statement because you are too smart for a creative process, they may prove elusive.

But, the tl:dr of the workbook (should you skip that bit) is this Mad Lib:

Essential Intent = Verb + Population + Outcome + Date

Verb: What is the priority thing you do?

Population: Who is your priority customer?

Outcome: What is the most important thing the customer gets?

Date: By when?

Even/Overs: How to Decide Which Routes Not to Take

When charting a course, you have an ocean’s worth of options. You’ll adapt along the way, but you have to make hard trade-offs for the essential aspect of the Essential Intent to mean something. Enter prioritization.

An even/over statement is a phrase that helps identify what priorities will cost. These statements prioritize one good thing even over another good thing and can be used to make difficult decisions. When my husband and I were buying our first home, we fell in love with our mid-century dream house in a beautiful, desirable neighborhood…that wasn’t within walking distance of anything. Our even/over became “walking distance even/over dream houses,” and, though it stung in the moment, it helped us avoid compromising on what was most important.

Once you have your EI, think about what you’ll trade off — the routes you’re intentionally not taking this time — to bring it to life. Aim for no more than three even/over statements for the quarter. And remember, an even/over should be just as valid when reversed.

Here are some examples:

Strategic Trade-Offs

• Growth even/over Revenue
• Market Share even/over Growth
• Quality even/over Speed

Product Trade-Offs

• Exclusive even/over Mass Market
• Amazing Customer Service even/over New Product Features
• Revenue Growth even/over User Growth

Cultural Trade-Offs

• Collaboration even/over Focus
• Progress even/over Perfection
• Candor even/over Harmony

Used as heuristics, even/overs guide decision-making and help you make conscious trade-offs that bring your EI to life.

“An inflexible plan is the opposite of wind in your sails; it’s an anchor holding you back from responding to and interacting with the environment.”

90-Day Outcomes: How and Why We Tack

Sailing in a dead-straight line toward smokestacks won’t get you there. There will be wind, currents, and weather that you can either avoid or take advantage of by tacking, a maneuver in which a sailboat heads into the wind so the direction from which the wind blows changes from one side of the boat to the other. From above, tacking looks like zigzagging, and it’s how all vessels reach their destination. Each quarter’s worth of 90-day outcomes is a zig or a zag along the route.

Once you have your EI and your even/overs, get the team together to determine outcomes for the quarter. Outcomes aren’t the same as objectives; they aren’t a mile marker to be achieved, but an impact you are trying to have. They help a team determine what shorter-term impact will lead to the EI or, equally important, tell a team that the EI needs to change. Spot the differences below:

Objectives & OKRs

• Specify the work we aim to deliver
• Assume conditions won’t change
• Define the “how” of work
• Measure whether a plan comes true

Outcomes

• Articulate the impact we intend to make
• Assume we will deliver through experimentation
• Define the “why” of work
• Measure based on impact

Here are some example outcomes:

• Budgeting process redesigned that allows us to steer quarterly
• Every employee enabled to easily access the information they need when they need it
• Customers so delighted by site experience that time spent on page increases by 40%
• One out-sized bet placed in a specific customer segment
• Cross-functional, autonomous teams established as the default way of organizing around work

Projects: How to Trim the Sails

Trimming the sails are small adjustments you make to take advantage of wind conditions. They aren’t big swings like tacks, but finer tuning to optimize the journey.

You’ve identified an Essential Intent (smokestacks); you have 90-day outcomes (tacking moves); and you have even/overs (trade-offs for the route). What’s missing are the day-to-day connections. Projects sit at an altitude above tasks but below 90-day outcomes; they’re chunks of work designed to help deliver outcomes.

This is where feedback loops come into play. Even with the most enlivening EI, the smartest outcomes, and the clearest trade-offs, if the day-to-day work doesn’t shift, you’ll never be on course. And if what’s learned day-to-day doesn’t feed the next suite of 90-day outcomes, E/Os, and EI, that’s also a miss.

“We keep one eye on the destination, but we adapt to and with the environment along the way. This is where strategy and steering come together.”

Be a Fleet, Not a Cruise Ship

Being good at either strategy or execution is a false binary. If you aren’t willing to shake the “Strategy is a plan” mindset, then your job adds up to driving compliance and alignment. Said differently (and keeping our metaphor in mind), you’re signing on as the captain of a cruise ship — to steer a lumbering vessel from predetermined port to predetermined port.

But if you shift away from that mindset and toward one that believes strategy is instead a series of hypotheses, then your job becomes experimenting and discovering. From that perch, the more learning, the better. You get to help guide a fleet of ships — where every boat, every function, and every team (not just the ones at the top of the house) — can and should chart its own strategic course. When a fleet of smaller boats are all sensing and responding to the environment, overall organizational agility increases dramatically.

Now, pull up the proverbial anchor and set sail.

The Ready is a future-of-work consultancy committed to changing how the world works—from business as usual to brave new work. We help organizations remove bureaucracy and adapt to the complex world in which we all live. Learn more by subscribing to our podcast and newsletter, checking out our book, or reaching out to have a conversation about how we can help your organization evolve ways of working better suited to your current reality.