Now that I’ve said my piece around what a boon it is for you to help the seedlings of our ambition take root via generous listening, I now want to give you license to temper that generosity.
Because sometimes, when we’re dreaming of what might be and what we’re playing for, it resembles what the phrase “pie in the sky” has come to mean, namely “the prospect of future happiness which is unlikely ever to be realized”.
Naturally, chasing the impossible is obviously worth avoiding. But beyond the frustration of fruitless efforts, let’s map the terrain of the more insidious parts.
First, chasing pie in the sky feels good. It feels exciting and perhaps even self-important to be up to such a lofty goal, so long as one looks past the reality of Herculean effort and/or major aligning of stars that will be required. That begs our thinking to be increasingly unrelated to reality.
Second, it lets us off the hook. If a goal is way out of range and we fall short of it, well, it’s hugely ambitious! Surely no one would fault us for failing to produce a miracle or profoundly change the world. The problem here is that it was all thoroughly out of our hands, so we never have to look in the mirror about what was OUR role in why we fell short. We have put the responsibility for the outcome somewhere other than with ourselves.
Third, pie in the sky goals generally devolve into a “forever task”. We can talk about it with you on a regular basis without ever making even a plan to make actual headway. Whether we admit it or not, we’re just waiting for the world to change. This is no way to play the game of life with intentionality or velocity1And to be clear: being coached by you, where we are pursuing meaningful outcomes, SHOULD be an experience of intentionality AND velocity!.
So, if you hear us being too ambitious in our dreaming of what we’re playing for? Don’t let us get excited about something we’ll ultimately fail at, no matter how feel-good it is. You don’t get to just blithely nod and smile. Part of your job is to be our spotter that we remain related to reality. Sometimes that means you need to burst our bubble; you need to be willing to be a buzz-kill.
You might be wondering: who am I to say?
That we are chasing pie in the sky is a judgement call, for sure, but you don’t have to make it. You can turn it on us and our judgement by asking “Are you prepared to give your word to what it will take to get there?” And if we say yes, either as some blind reflex or with the steely conviction of one who has thought it through, then have us make a plan… right then and there.
The plan needs to have two parts: broad strokes, and next steps.
Broad strokes means an overall vision of how this could all plausibly happen.
Next steps means distinguishing actions we’ll be able to take between now and our next session with you that move us along consistent with those broad strokes.
And if we manage to create those two parts, and they ring to you as plausible, it’s no longer pie in the sky.
One or more Actions (or an Action Project) allows your client to create the specifics of those next steps, broken up into tasks each with their own due date and reminders. And this ensures the plan is clear, unambiguous, won’t get lost, and is easy for you and your client to track with what’s done and not done.
A Whiteboard is the perfect place to capture those broad strokes. It’s readily revisited by you and your client, and readily updated over the weeks and months (while still preserving the record of earlier drafts, allowing you both to see how the plan has evolved over time).
Notes:
- 1And to be clear: being coached by you, where we are pursuing meaningful outcomes, SHOULD be an experience of intentionality AND velocity!




