February 22, 2018

Strategic Planning: Tackling Your Lonely Mountain

Recently, we had the opportunity to run a condensed strategic planning workshop for the Washington County Watershed Alliance, a local nonprofit that serves as the mother-support-ship for the individual watershed organizations working across our county. I’m proud to say I’m an At-Large Board Member, so that makes me biased toward the organization, but the work was a reminder of just how easy it is for even the most passionate organizations to lose sight of their true direction.

This is why the most successful businesses and organizations use strategic planning. For the sake of clarity, here is the Wikipedia definition of strategic planning: “Strategic planning is an organization’s process of defining its strategy, or direction, and making decisions on allocating its resources to pursue this strategy.”


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A well-developed strategic plan that you use is an invaluable tool for driving your growth. That latter part, actually using it, is a surprisingly common sticking point, but even more than that, many business and nonprofit leaders mistake a collection of tactics for a strategy. They lurch from initiative to initiative without ever lifting their heads to see if they are still moving toward their goals. In other words, you have to look up from your hands as you climb to make sure that your route is still taking you where you want to go.

And that comparison is apt. A good strategic plan is like the beginnings of a mountain climbing expedition.

  • Step 1: Clearly articulate your purpose or your “why” (why do you believe it’s important or worthwhile to climb mountains?)
  • Step 2: Identify where you are today and where you want to go (what mountain peak do you want to summit, and where are you starting?)
  • Step 3: Craft a strategy that makes the most sense for your organization and for your goals (perhaps you free-climb to the summit to get there as swiftly as possible, perhaps you take a longer but less intense route, perhaps you develop an innovative technology that drops you off at the summit, and so on)

Notice that these steps don’t talk about the specific equipment you will use on your expedition, or the timing of your trip, or how much food you pack, or what camera equipment you bring along. Those decisions come after you make the big picture decisions. For example, a free climber uses almost no equipment at all except perhaps for a good pair of shoes and a bag of chalk, but he or she must be in incredibly good shape and have developed a high-level of skill to climb with no safety equipment. On the other hand, someone who opts to hike up the back side of the mountain might need supplies for a few days of camping.

You don’t make those individual equipment (tactical) choices until you make the general strategic situation: We are going to reach the summit by taking the longer but hike-able path because of our strengths in camping and weaknesses in rock climbing.

These big-picture steps may sound oversimplified, and that’s because they are.

Accomplishing these steps can be an incredible amount of work, and that process gets more complex as a business gets larger and the stakeholders more plentiful. For the Washington County Watershed Alliance, we condensed these three steps into a 3.5-hour sprint to cover the most fundamental high-points of each stage. In other businesses and organizations, we have seen this process stretch across multiple days (with each day fully dedicated to the strategic planning process) to be effective.

When you ask hard questions like what does a business believe or why does it exist (as Simon Sinek says, to generate revenue is not a why, that’s a result; you have to go deeper into the DNA of the business), you end up having hard discussions and getting to hard answers. It’s difficult, and that’s a big part of why this process is worth doing.

For this particular blog post, we are going to focus on steps 2 and 3 (the more concrete aspects of a strategic plan), so that you can pull your head away from the tactics and get a better view of where you want to go with your business or organization. If you want more insights into Step 1, pick up my book The Innovative Brand and Simon Sinek’s Start with Why.

One Plan to Rule Them All: A Hobbit’s Tale

Let’s pick up our mountain climbing metaphor and raise the stakes by dipping into the setting of Middle Earth. The Hobbit by JRR Tolkien is essentially a mountain climbing story (a rag-tag band of adventurers seeking great treasure in the Lonely Mountain). Like in business, they had other entities actively working against them, they faced unexpected problems and challenges, and the adventure was in its most dire moments when the members of the band started to disagree and dispute the best way to achieve their goal.

The adventure starts with Gandalf pitching his plan at the shire. He gathers his team, and they start to layout where they want to go and how they plan to get there. The whole team talked about the whole plan.

If you want the whole business (or organization) to grow, you should look at the whole business when you plan for that growth. That means looking at everything from your marketing to your customer service to your supply chain. If you don’t, it’s a bit like forgetting Bilbo Baggins, the team’s burglar, at the campsite only to remember later that you really needed someone who could sneak into a place undetected. When you’re motivated and busy though, getting lost in the momentum of your adventure is all too easy.

You have to take the time to sit down at the table with your dwarves, your hobbit, and your wizard and look at your map.

In this story, they knew where they wanted to go from the start, but the fact that so many people (using this loosely with dwarves and hobbits running about) have come together for the same adventure suggests that there was likely a lot of discussion that preceded the story. They identified a common purpose and emotional hook (their why; the loss of their home and their culture, potentially) and used that to pick the Lonely Mountain as their destination.

A nonprofit setting is more likely have a clearly definable and emotional unifying cause. Businesses have them too, but they are often hidden, unspoken, or forgotten, especially as a business grows and the culture evolves beyond Tom and Martha running the whole of the operation out of their garage.

For your organization, here are some tips that will help you pick your own mountain:

  • Run a strengths, weaknesses, opportunities, and challenges (SWOC) analysis to get a clear picture of where the organization is today.
  • As Jim Collins would say, get the right people on the bus. Bring together leaders from across your organization and talk about why you’re all in this work in the first place. Note: A strategy change may require kicking some people off the bus in favor of better cultural fits.
  • Be audacious. An outrageous goal that represents an immense challenge is a worthwhile starting point, and you might discover that you can actually accomplish it. Keep negativity out of this conversation. The devil has enough advocates and you don’t need them in the boardroom at this stage.
  • Look at the common threads of what you have done as an organization already and prioritize those activities by impact and meaningfulness.
  • As you talk about defining the goal, avoid drifting into tactics. Running a singular ad campaign that is heavy on absurd visuals and humor is not a strategy but redefining a brand so that it better connects with the YouTube and meme generation is a strategy (this example is Old Spice, by the way).
  • Refer back to your why and challenge your team to do the same. If the goals you are hearing in this process are not aligning with your why, your team may need to step back and start over or you may need to revisit and rework your why.

Once you pick your goal, you can start to build a strategy for getting there.

The Best Way to Claim Your Own Lonely Mountain

Remember, a strategy is about the overall goal. It’s your general approach to the game, not the specific plays you make. In the Tolkien story, they picked a destination and picked a route, recognizing the potential dangers along the way, and decided that their strategy for retaking the Lonely Mountain would hinge upon stealth and surprise.

Let me emphasize this point: What they chose to do is just as important as what they chose not to do. They didn’t assemble a huge team of dwarves to storm the front gates. They didn’t try to develop partnerships with other groups (such as the human town nestled nearby), and they didn’t announce their plan publicly.

Those are big strategic decisions, and what they did and didn’t choose to do are all tied to the group’s values and the realities of their organization. Some of those choices turned out to be smart (being sneaky rather than brash), but other parts, such as not forging partnerships with nearby locals, created much more turmoil for the adventure than perhaps was necessary.

For your real-life strategic planning, here are some points to consider as you develop your strategy:

  • Put everything on the table first so that you can make the elimination of an idea a conscious decision. It’s better for you to decide as an organization that partnerships, for example, are not a part of your strategy than for it to go unmentioned and become a wish-we-had-talked-about-this item.
  • Look at your SWOC analysis. How can you maximize your strength and minimize your weaknesses? What opportunity can you seize or challenge can you overcome?
  • What are you uniquely positioned to do that your competitors cannot easily mimic?
  • How well do you understand your target audience? What do they really respond to?
  • Stick to the big picture path rather than individual steps you will take. To test your strategy to see if it’s broad enough, see if you can come up with five or six tactics that would fit into it. If you can only think of one or two, you might actually have a campaign on your hands rather than a bigger strategy.
  • Review your most impactful activities in the past and identify common threads between them. You may find that what worked well in the past fits a theme that leads you to your “new” strategy.
  • Put your strategy in the context of your competitors’ strategies. Do you stand out? If not, go back to the drawing board.

Again, this is not easy. We’re talking about taking down a metaphorical dragon here. There’s a reason that most people leave the dragon alone in its lair. Taking on a dragon is difficult and rife with uncertainty, and that’s what makes it worth doing.

There and Back Again with Your Plan

Implementing your strategy is more of what we have talked about already: You need to stick to your strategy and use it to evaluate the choices you make as an organization. You need to zoom out and evaluate your strategy on a regular basis. Then, on an even more regular basis, you need to use your strategic plan to measure and evaluate your choices and progress. In a perfect world, each time you consider a new idea or initiative, you should ask yourself, “Does this align with our strategic direction?”

So, back in the shire, your plan was to get to the Lonely Mountain and reclaim it. If you make a choice that takes you in the opposite direction or too far sideways, you are starting to lose sight of your goal, which means you are probably deviating from your strategy.

If the answer to that question—Does this align with our strategic direction?— is not a resounding yes, that should make you hesitate. If your strategy is to differentiate your business from the competition by becoming a leader in your customer community, putting a bunch of money into a display ad campaign might not be the best fit, especially if it means doing less grassroots, organic activity.

Strategies change, and that’s a normal part of this process and a big reason why you should have these conversations with your team on a routine basis, but the point of this process is to have everyone in your adventuring party moving in the same direction toward the same goals. Your strategy might fail, or perhaps you reach the summit and need to choose a new adventure, and that’s okay. But you won’t ever know if the strategy was a good one if you never got the business aligned with it.

If you have more questions, shoot me a note.


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Image by Marco Hazard. Used with permission under creative commons license.

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