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Navigating Ambiguity as a Strategic Leader

Skyler Holloway
April 22, 2023

Leadership is most valuable when the path forward is hazy. During these times, the best leaders consider all available information, test their intuitions, and inspire their teams to forge into the unknown. Having led teams in business and being an outdoor leadership guide, I pondered the tenants of leadership, both metaphorically and pragmatically, as I traversed the Wind River High Route. Here are a few keys to success next time you find yourself leading in a remote environment or charting a new path on your next team project at work.

Identify your current position

The first step in backcountry navigation is knowing where you are. Maps aren’t particularly helpful if you can’t identify your location. If your workgroup is building product roadmaps or setting next-year forecasts, having a keen understanding of the current status is crucial. Unfortunately, we often gloss over the important step of identifying our current position, opting instead for the more exciting work of setting a vision. Similarly, metrics don’t mean a lot without comparables, either from past benchmarks or competitor trends. In either case, don’t miss the chance to take stock of your present status before you start moving.

Direct is best

When confronting a hard-to-read valley or obscured talus field and trying to select the best course of navigation, oftentimes the team will be presented with incomplete information. Sure, when we can see the terrain perfectly, we could all likely pick the best route. But, in the absence of concrete direction, a decision must be made. In business, similar situations often occur. So, if a preferred route is indiscernible, I like to think, “Direct is Best.” Go for it- head on. Approach the challenge at hand directly and don’t try to sidestep it. The lessons you learn or information gleaned from a direct approach can guide adjustments in your course, but you’d never gain those insights without taking a bold approach first. Often moving even a little bit gives us an improved vantage point from which to recalculate our bearing. Don’t succumb to analysis paralysis, move in a direction you think best and gather data along the way!

If it feels wrong, it probably is

In backcountry navigation, as in life, if something feels wrong, it likely is. If the big terrain feature your map shows isn’t where you think it should be, STOP. Consider that you are off course or haven’t pinpointed your current location correctly (see tip one). It’s human nature to allow confirmation bias to talk us into ignoring gigantic cues that we are off track. We can often reason our way to an incorrect assessment because of this. It happens to the best of guides and certainly plagues business leaders as well. Similarly, if you are navigating a decision or course of direction at work and your current progress doesn’t align with your plans, take a moment and reassess. Be open to the idea that perhaps you are wrong and need to recalculate your direction. A willingness to listen to your doubts and reassess could save lots of ill-spent time or effort.

Check your bearing

Alpine weather can change quickly, in some cases caused by weather patterns such as orthographic lift. Orthographic lift occurs when an air mass is forced from a low elevation to a higher elevation and results in weather drastic changes that provide no forewarning by developing slowly on the horizon. This can result in a quick loss of visibility and becoming disoriented. Not knowing where we are and not being able to see is about the worst situation we can find ourselves in in the mountains or business. As I’ve gained experience, I’ve learned that operating of a compass bearing in times of strong visibility means that staying on a pre-set bearing is simple if the visibility is lost. This approach has saved me from unnecessary effort many times on the trail, and in business.

In business, this could mean KPIs and a clear strategy to achieve these. Or, it can mean establishing core values that drive decision-making and goal-setting at a more granular level. But, when lost outdoors or submerged in the fray of daily ‘fires’ at work it can be difficult to set your core values. So, take the time and effort to consider and set your personal and team core values now. When times are calm, leaders should put in hard introspection to determine what matters so that they have clear guidance during times of crisis or uncertainty.

Practice makes perfect

Navigation is a skill set, just like guiding your business or team. Accurate, successful, navigation is something to be practiced and intentionally honed over time. There are varying degrees of skill and no matter how accomplished one may be, these skills can be improved, or at the very least refreshed. The leadership of teams in business is similar to backcountry navigation. Do you truly know exactly where you are? Are you willing to take action as a leader to move and methodically gather more information? Are you able to listen to your doubts or reconsider your assumptions? Do you have a deep understanding of your core values and know how they show up in your daily actions? Practice makes perfect. Get out there and spend some time navigating while things are relatively clear so that when the inevitable ambiguity arises you’ll be ready!

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