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From Map To Compass: The New Way To Do Strategic Planning


This article was written in collaboration with Carina Cortese

Strategic planning needs to change because our world has changed.

We’ve long assumed the world we operate in (and our path forward in it) looks like this:

  • Set a goal.
  • Create linear steps toward that goal.
  • Walk the path, follow the road signs.
  • Arrive at our destination.

We think our best path forward is to follow a map.

In reality, the world we operate in (and our path forward) is nothing like that. In fact, those who continued to believe that was the case were the ones who struggled most throughout the pandemic. The companies, entrepreneurs, creators, employees, and team members who accepted the unknown and non-linear path forward were the ones who learned, adjusted, and moved forward effectively.

Instead of a map, what we really need is a compass.

Strategic planning is not (or should no longer be seen as) an annual exercise, driven by process, that starts with the company and tries to anticipate the future. It should not be a “means to an end” that provides leaders and executives with comfort, gaining clarity over what is “known.” It should not be a strategy that gets set forth at the beginning of the year and then precisely executed in the 12 months that follow. And it should not be written out, in unnecessary detail, and compiled in company documents as thick as a hardcover book.

The past year and a half has taught us that strategies “on paper” are a waste of time when the world changes in a way you didn’t expect.

Instead, strategic planning should be a habit. It should start with the customer and the impact (not the company). It should seek to design the future (not try to anticipate it). It should require the leaders’ bravery in order to achieve that end state and vision (not provide leaders comfort). It should be built by testing, day after day. It should be iterative, flexible, “antifragile” (as Nassim Nicholas Taleb would say), and the entire summation should be able to fit on a single page. 

The end of the year is approaching, which means many companies are beginning their strategic planning efforts. 

If this is you, then I encourage you to reflect on the following:

1. How can you transform strategic planning from being a yearly exercise into a rapid-fire, moment-to-moment flywheel?

Strategic planning exercises are most often treated as an opportunity for taking stock: what’s happening inside the organization? What’s happening outside the organization in the market? Which direction are macro winds blowing? Is the company properly positioned? And so on.

But are these really questions best answered once per year? How about once per quarter? Or once per month? What would your company look like if these questions were instilled into the fabric of your operations, and employees were empowered to ask, examine, and make decisions based on current signals (and not the state of affairs 6 months ago).?

To prevent being blindsided by unforeseen business and market dynamics, it’s worth considering how to transform strategic planning into a more flexible, build-test-learn cycle that happens more often, across more levels of the organization.

2. How are you gathering insights from your employees and your customers to inform your path forward?

If strategic planning for your company looks like the executive team in a conference room for two days, it’s also worth considering the blindspots this approach may be creating.

For example, who else in the organization may have perspectives you should include in your discussions? What would customers say about the direction of the company? Are decisions being made top-down, or are insights being considered from less conventional angles and avenues? 

One of the biggest benefits of yearly strategic planning exercises is the alignment it creates within leadership teams around a shared view of the future, along with a high-level outline of the milestones required to get there. But keep in mind, alignment in the wrong direction isn’t very valuable alignment at all! How can your leadership team ensure your compass heading is informed by the experiences of your employees, your customers, your other stakeholders—and more broadly—reality? 

3. Can you build in regular moments to consider the future from a place of divergence and imagination?

Strategic planning is too often an exercise in deduction, planning, and operationalizing that is limited by what’s already known, instead of open to (and designed for) the possibilities of the unknown.

Executives, company leaders, and stakeholders love when plans confirm existing biases. It feels good for the conclusion for a strategic planning session to be: “We were right all along.” And sometimes, that’s certainly true. But over time, this confirmation bias becomes an echo chamber that makes it very difficult to see the forest from the trees, and contextualize whether the company is truly on a trajectory of making a long-term difference.

Instead, it’s worth making the time to consider the impossible—or, at the very least, the improbable. What would the company do if everything it assumed to be true no longer was (as things were during the height of the pandemic)? How would the company remain relevant if, due to unforeseen circumstances, its primary offering suddenly became commoditized? What wants, needs, and desires of customers are hiding in plain sight, or have been previously ignored or deprioritized? And even better, what are the bold questions we can ask ourselves, which would lead to bold visions of a world we want to create, which in turn lead to bold moves we will make as an organization?

And even if the conclusion of the conversation, or the two-day exercise, is that the company is doing the right things and on the right trajectory, then at least you stress-tested the thinking and didn’t simply accept the truth that exists today as the same truth that will exist tomorrow.

This is what strategic planning does at its best: it sets your compass bearing with both the aspiration of the destination and the reality of the terrain in mind. So you and your teams can make the journey, together—regardless of what you encounter along the way.

Because maps are a thing of the past.

There’s an old saying that if a company doesn’t like change, they won’t have to worry about it for long. I am a speaker, change agent, and Partner at SYPartners—and I'm on a mission to help companies not just embrace change, but get good at it. I focus on transformation, innovation, organizational design, and culture advising leaders at companies including Calvin Klein, Adobe, Google, Etsy, Capital One, and Dropbox. Previously, I was the CEO of NOBL Collective, a global organizational design and change consultancy. I have founded and led an Innovation Department, advised Fortune 500 companies as a service designer, and explored communication and decision-making as a psychology researcher. In previous careers, I performed as a stage actress and taught high school math. I hold an MS in Organizational Learning and Change from Northwestern University and a BA from the University of Pennsylvania. I am a visiting lecturer at Northwestern and Parsons. I live in Manhattan with my husband and 5 year old daughter, and moonlight as an improv student at the Upright Citizens Brigade.

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