Can I rant for a moment?

The way most organizations develop their strategy is a useless paper-pushing exercise that makes me want to rip my hair out. It’s vanilla, formulaic, one plus one equals two, and as a result, most business strategies are utterly devoid of wisdom. What a giant waste of time.

And a huge lost opportunity.

Great strategic planning is less vanilla and more Rocky Road or Raspberry Ripple. It’s full of twists and turns and serendipity. It can be frustratingly one step forward, two steps back. But as you keep at it, something powerful emerges… insight!

I love facilitating this kind of strategic planning because I thrive on the challenge of looking at a forest of complex, dynamic, seemingly unrelated trends and finding a unique path through trees that will get a company further, faster than its competition. It’s invigorating.

Why Your Strategy Process Isn’t Creating insight

So, what keeps you in the mundane, incremental, ho-hum form of strategy? The overarching theme is that you’re trying to do strategic planning the same way you review last month’s financials or the way you evaluate the new performance management process. You treat it like a task that you need to work through efficiently. It’s not going to work. Evaluate your strategic planning process and be honest with yourself about whether you’re doing one or more of the following insight killers.

Are You Trying to Do Strategic Planning Too Quickly?

Strategic planning is not something you can fit into a two-day meeting once a year. You need time to follow tangents. You need to let ideas marinate. So ideally, strategic planning is a series of two-day sessions over four to six months. That leaves room to process what’s happening and wend your way through a few dead-end trails before finally seeing the sun coming through the trees.

Boring person going over data at a flip chartAre You Trying to Make Strategic Planning Too Orderly

I find that strategic planning processes are often stewarded by people who crave order and precision. They like project plans and Gantt charts, and detailed agendas. Insight does not come when called. It’s fickler than that. Sometimes, you’re on step 3 of the process when you realize you missed something fundamental at step 1. If your Director of Strategy refuses to let you back up the bus, you’ve left insight in the dust on the side of the road.

Are You Only Looking Internally?

A strategic planning process should gather steam by looking at the world outside your organization and all the possibilities it offers, rather than with people droning on about the current state inside your company. It usually starts with at least the intention to view the world from some distance. Still, it quickly devolves to the point that participants are talking about internal strengths, weaknesses, or constraints. If you only look within your company, you’re not going to find much that’s new. The best you’ll get out of a strategic planning exercise full of navel-gazing is a glorified continuous improvement process.

Do You Have the Wrong People in the Room?

Here’s another issue. You might feel like you’re pushing a rope because you don’t have the right people in the room. You need to have strategic thinkers or else you’ll be incrementalized to death. If you’re choosing your strategic planning invite list based on people’s formal roles, you might be missing the brand of thinking that will help you create a breakthrough. And to put an even more cynical lens on it, if you’re only inviting people who benefit from the status quo, they might be reluctant (or downright resistant) to ideas that would disrupt the good gig they’ve already got.

Are You Forcing Your Strategies Into Fixed Categories?

I am continually flabbergasted by the lack of creativity in the strategic planning frameworks of the massive global strategy firms. To be fair, I haven’t worked with these firms directly, only with the people who have left these firms to work in internal strategy roles. But man, are they ever rigid and narrow in their thinking. Every strategy has two boxes reserved for growth and operational excellence. Wow… growth… shocking! Shiver-me-timbers! Knock me down with a feather. You paid $6 million for a strategy that says you have to grow?!? Zoinks. Growth is an outcome or a goal, not a strategy!!!! How will you create growth that’s different from what you’re doing today? Where will you grow that’s more advantageous? How will you grow that will allow you to capture market share? OF COURSE, YOU HAVE TO GROW, but growth is not a strategy!!!

Fire any strategy facilitator who comes with a pre-populated template, fire them. There’s no insight to be gained in having the same categories as everyone else. There’s no strategy in that kind of strategic planning.

How to Improve a Strategic Planning Process?

So, how do you turn your strategic planning process into an unfettered, electric, insight-fest? Try the following:

Add New Information

If your strategic planning process is feeling a little dull, go in search of new information you can inject into the conversation. Ask around. Who’s heard or read something that blew their mind? What are your professional services vendors serving up in white papers or research briefs? Which of your competitors has released a new video or a vision of the future? Ideally, you’re looking for something a little shocking–something to shake things up. It doesn’t matter if it’s true or will actually pan out; it only matters if it inspires some new thinking.

Insert the Voice of the Customer

Another way to get out of your heads and find fodder for new thinking is to engage with customers or prospects. What are they wrestling with? What trends are they paying attention to? And even better than talking to single customers (who might tend to drag you into a tactical conversation about minor irritants), what about immersing yourself in your customer’s industry associations or advocacy groups. What do they imagine for the future? What are they not imagining that they could be?

Team standing around a wall covered in post-it notesMake More Connections

The most exciting strategic insights come from connecting two things you thought were unconnected. There are many ways to do this. One would be to ask each person around the room to connect two trends and discuss the intersection in the Venn diagram. Where is there an opportunity or threat in combining those two trends? (I have so many client flip charts from 2018 and 2019 that have both “pandemic” and “just-in-time supply chain” written on them. Imagine what would have happened if they had made the connection and understood the threat of just-in-time supply chains in a locked-down world before 2020!)

Ask More Open-ended Questions

Tactical conversations tend to converge quickly. Every time someone asks a question, others are quick to provide an answer. Try doing a few rounds where each statement needs to be followed with 3-5 questions before anyone is allowed to answer. For example, if someone says, “Eighty percent of our customers’ employees want to work at least three days per week from home,” don’t let someone say, “we need to offer more security services for remote workers.” Instead, force the team to come up with the best questions that the idea provokes. Maybe, “What does the typical home office computing setup look like?” “How savvy are remote employees about the security risks on their laptops?” “What are the most material risks companies face with having workers access files remotely?” Then you can decide the order in which you’ll start to tackle these questions. (And as you can see from these questions, it’s not likely that you’ll have the information to answer the questions in the room. Good thing you’re not trying to build a strategy in two days. You’ve got time to go collect some new data.)

Ask, Why Not?

It’s tough to have the patience to reach insight if people in the room are jumping to all the reasons why something is not possible. I love the approach my daughter’s grade three teacher took. She let the kids say anything defeatist they wanted as long as the sentence ended with, “Yet!” If one of your colleagues responds to your suggestion with the reason it can’t be done, add a “yet.” Then ask. “It can’t be done yet. What would it take?” If you’re striking off every potential strategy because one person has one reason it won’t work, you’re not going to have many options left. Go back to the impossible, and the improbable have another kick at the can.

If you want your strategic planning process to have more rich insight, you’ll need to feed it with new fodder and then fantasize, follow, and flesh out, before filtering.

You know you’re there when you hear someone audibly, almost awkwardly, exclaim one of the following in front of the whole team:

  • Wow! I never thought of that! 😃
  • A-HA! THAT would make all the difference. 🤩
  • YES!!! Yes! Yes! Yes! 🤗

One last litmus test. If the hairs on the back of your neck haven’t stood up at some point, you’re not done. You haven’t achieved insight. Keep going.

And now in handy-dandy poster version (click to download).

Further Reading

Your Strategy Should Serve Two Purposes

Are you helping or hindering with strategy? A Quiz

Running a great strategic meeting