Planning

Payout or Annuity

Do you take the payout or defer it for another day? Do you elect the over-scheduled board member or wait until they can focus on your cause? Do you ask the donor for a campaign gift even when they suggest they can do something more significant in a few years? Do you launch the new program with numerous gaps or continue assembling a more complete team before activating? Do you grab headlines with a sensational claim or send a press release after you have completed a remarkable level of service?

Each scenario above is too vague to answer definitively but represents generative questions. They are worth pondering; each serves as a proxy for the real-time decisions we need to make. Trying out a new tactic during a training session offers immediate feedback and is more effective than waiting for a competition. If we delay until the race to deploy a new strategy, our results are often hampered by our lack of preparation. Train today so our capabilities are evident, and we are prepared when the spotlight focuses on our enterprise.

Does Imagining Happen?

When do you and your team spend time imagining? Is it scheduled or happen organically? What is the mindset when it takes place? Is there a location where it seems most productive?


An organization with a headquarters building containing an open lounge with extraordinary mountain views overlooking an iconic river insisted we meet in the conference room, sequestered in the interior of the building. When I inquired about the location of the blue sky thinking session, the response was that all meetings take place in the conference room. The venue selection hindered the opportunity for generative thinking before the gathering commenced.


How might we embrace a culture of sense-making without starting from a place of tradition and hierarchy?

Direction vs Destination

What destination have you selected? What direction are you currently headed? Sometimes, we must head opposite our destination, but we are still on course. During the New Year’s resolution phase of the calendar, it can feel that we have planned poorly; however, do not confuse destination and direction. If the journey is a priority, we deploy our wayfinding skills to keep moving, even when the best route suggests we revisit paths already traveled.

Wrong Route

Somebody planned to climb Mount Massive in Colorado’s Collegiate Mountain Range. They discovered the Highland Trail was not the correct way to the summit and left a note (graffiti) for their hiking companion to save them the experience of repeating their mistake.

What wrong turns have you made? How do you share your trail knowledge with others? What mistakes are worth leaving for others to encounter on their own, and which require notification in your judgment?

How might we point out what is worth noting and not be a constant flashing amber light of ‘caution everywhere?’

Horizon Lines

What horizon line has our focus? The houses sitting on the closest ridge? The mountains in the mid-ground? Is it the sunset taking place in the background? Depending on our mindset and the intended impact of our journey, one of these horizon lines might be more appropriate than the others. Is our expedition team aligned around the same horizon line? It might impact the supplies we procure in advance, the team we assemble, and the speed with which we proceed.

Future Me

Future me benefits when current me acts thoughtfully. Before a trip, I might make the bed with fresh sheets, clean, and leave a reasonable supply of food for my return. Current me might unpack my bag completely and leave items in easy-to-find locations so future me can pack without stress for the next adventure. Current me can wax skis, clean bikes, dry out muddy running shoes, place new batteries in the headlamp, and repair a small leak in the tent, so future me launches with a higher degree of success and enjoyment.

What actions and decisions can your current team make that would set up the future team for a higher degree of impact? How often has a topic or barrier been raised that never gets resolved, knowing it will ultimately be decided once it is an emergency (burning platform)? Have you served an organization that inherited disruptions that could have been avoided by the team that proceeded your tenure? What if your gift to the board/staff/members that follow is to wrestle with the obstacles they will encounter? Even if we cannot make definitive progress, we can leave a record of how we tried to iterate and what succeeded and failed.

My hope is that current you assumes a force for good mindset so future you can focus on the work that matters.

Blazing the Way

Somebody had to figure out how to put in the first path. Then it the trail was updated and perhaps improved. Maybe another individual found a better route. Eventually, a group decided to construct a road. It was not easy, but now buses, cars, and cyclists pass without considering the obstacles.

What paths have you blazed or improved? What is their impact? Does anyone notice anymore? If they are well-designed, perhaps the purpose is not to point out what was near impossible during construction.