STRATEGY

Strategic Planning: Work the Maze Backward

John Bailie

October 22, 2025

Ask a child to complete a maze in an activity book. If they are the savvy sort, they will likely begin at the part marked “end” and not at the place marked “start”. Through direct experience, children learn that it’s easier to complete a maze successfully when you do it in reverse.

This was a lesson from my strategic planning mentor. Like a child staring at a maze, when an organization has a vision for how it wants to expand, evolve, or level-up, there’s usually a spaghetti plate of twisting routes between “where we are now” and “where we want to be”.

In this early stage of change, leaders face the dual challenge of too many options and lots of potential dead ends.

Leaders who like a challenge – and dislike uncertainty – will tend to plunge ahead and trace their path by instinct. That feels bold and exciting, but we typically wind up with a lot of tracing, erasing, and re-tracing of paths through the labyrinth of change.

We’re also likely to become myopically focused on overcoming the immediate obstacles in front of our face and lose sight of whether our overall direction is taking us toward the intended destination.

A wilderness survival expert once told me, “As soon as you suspect you’re getting lost, go back to the last waypoint where you knew your precise location.”

This is sound advice for life as well as managing strategic change in an organization.

It’s a simple instruction. However, ego will conspire to drive most people forward anyway. They will tell themselves, “When I top that ridge, make it out of this valley, or find that lake, I’ll know where I am. I’m not really lost.” All the while, they move deeper and deeper into unknown terrain until they lose their bearings completely. They might make it out, but they’re unlikely to arrive at the destination they intended.

It takes discipline to stop, think, and act strategically. It also takes humility.

Children are often much better at mazes than adults. They have less ego. Children assume that mazes are hard. They don’t feel pressure, like adults do, to make the task look easy. So, they’re more likely to think it through first and look for an advantage. Children also know that there are traps built into every maze and take them seriously.

However, those traps are really designed for those working from start to finish. When we work from the end backward to the starting point, we bypass most of the dead ends, distractions, and paths to nowhere.

In strategic planning, like that smart child, start with the desired end-state or goal in mind.

Then, work backward from that destination using time-horizons: 10-year > 3-Year > 1-Year > Quarterly > Today.

Finally, focus on the disciplines (repetitive behaviors and commitments) that will keep us on the right path as we go. These disciplines aren’t necessarily sexy, exciting, or even particularly new to most of us, but they separate the finishers from the lost:

• Ingrain a regular rhythm of strategy meetings
• Set understandable KPIs
• Learn how to say “no” faster to interesting pathways and ideas that will distract us from our goal
• Spend time learning how to better present progress and data to the team through better design and creativity (three memorable graphics beats the best spreadsheet)

We must have the discipline to commit. Commit to reaching the end. Like a long trek through the wilderness, finish pretty or finish ugly – just finish. The point is to get there.

If you are feeling “lost in a maze” of dead ends, distractions, and paths to nowhere, schedule a complimentary call. I can help you find that waypoint to reorient your path forward.