Recently, Scott Burgmeyer and I were working with a leadership team to help them refresh their organizational strategy. We completed the groundwork—environmental scans, industry research, and deep-dive stakeholder interviews. With a clear view of their current roadblocks, we brought the leadership team together for a two-day, in-person strategy session.
At BecomeMore, our approach isn't about walking into a room and hand-delivering a pre-packaged template of answers. We believe in a facilitative method—drawing out the deep institutional knowledge, needs, and solutions directly from the people who live the business every day.
As we facilitated the discussion, several heavy, honest themes rose to the surface from the leaders in the room:
If you have ever sat in a leadership seat, those frustrations hit close to home. Throughout my career—whether leading my own consulting firm since 2009, serving in executive roles, or owning and running a $15 million logistics and agronomy business — I have heard and experienced variations of these exact pain points in almost every boardroom.
The day after that session with our clients, I went out for a bike ride on a trail I love. It’s one of my favorite ways to clear my head—clicking my shoes into the pedals, turning on some music, and setting my watch to track my metrics.
Although I knew the trail, I hadn't ridden it in a couple of years. The trees had grown thicker, and suddenly, squirrels and rabbits started darting out onto the path directly in front of my tires. I didn't want to flip over the handlebars into the brush, so I had to instantly shift my focus. I couldn't just get excited about the long-term destination down the road; I had to look at the immediate few feet right in front of me.
Soon after, I realized the terrain was completely flat compared to my last hilly ride. My gear was way too light. I was spinning my wheels at a fast pace but barely gaining ground. To get momentum and distance without completely exhausting myself, I had to find the right gear for the current landscape.
Later came a crossroad. A sign warned: "Cross traffic may not stop. Use caution. Slow down and look before crossing." I didn't want to slow down. I had built up great speed and wanted to maintain my numbers. But I also knew that in a battle between my bike and a cement truck, I would lose. I tapped the brakes, verified the intersection was clear, and then moved forward.
To get back up to speed, I relied on data. I checked my watch for my average speed, current pace, and distance. It kept my mental game sharp because I knew exactly where I stood relative to my halfway point. But as the heat climbed and my energy dipped, I had to calculate when to pause for a water and snack break to refuel my resources for the remainder of the ride.
As I pedaled home, it hit me how that trail ride mirrored the exact challenges our client’s leadership team was facing. True strategy isn't a static document you file away; it lives in the execution.
Here are the four strategic parallels every leadership team needs to navigate:
1. The Short-Term AND Long-Term Balance
Like the wildlife darting across my path, unexpected operational issues will always jump out in front of your organization. You cannot ignore them, but you also cannot lose sight of the horizon. Strategy is never an either/or proposition between daily operations and future vision; it is a both/and discipline.
2. Matching the Gear to the Landscape
If your team is putting in massive effort, burning out, and yet failing to move the needle, you are likely in the wrong gear. Strategic alignment along with process improvement ensures that your organizational energy translates into maximum distance with optimized effort. If you ignore the landscape, you wear out your best people and miss the destination entirely.
3. Navigating the Crossroads
In business, there are critical moments where you must intentionally slow down. When facing major market shifts, structural changes, or regulatory hurdles, hammering down with your eyes closed and hoping for the best is a liability. Pausing to confirm it is safe to cross isn't a loss of momentum—it's risk management.
4. Relentless Measurement and Resource Allocation
We cannot manage what we do not measure. Relying on guesswork leaves us blind to whether we are actually reaching our destination. True strategy requires real-time indicators to gauge the pace, alongside a clear-eyed understanding of when and where to inject resources—time, money, and talent—so the team doesn't run dry before the finish line.
While the business world calls it "strategic planning," the reality of leading an organization feels much more like strategic adapting while executing. The value isn't just in the plan you create; it’s in building the organizational capability to adapt, pivot, and shift gears safely when the landscape changes.
What area of your current organizational strategy feels like it's spinning its wheels in the wrong gear? Are you slowing down at critical crossroads before moving forward?