Have you ever come out of a planning session that went genuinely well — good discussion, real engagement, everyone aligned by late afternoon — and then found yourself eleven months later wondering what happened to it?
You’re not alone. And nobody did anything wrong.
Some of it got done. A few things moved that mattered. But the plan hasn’t come up since about March, and if you asked your leadership team right now to name the priorities without looking them up, you’re not confident they could.
The usual response to a year like that is to plan harder next time. More analysis going in, tighter goals coming out, a better tracking system.
It rarely helps, because the reasons the plan didn’t hold were in place before anyone walked into the planning session.
There are three of them, and they’re the same three almost every time.
1. The group never found out what it actually disagreed about
Think back to a decision in that session that landed easily. Someone proposed a direction, a couple of people built on it, nobody objected. You checked for concerns, got a few nods, and moved on because there were four more things to cover before lunch.
Now think about who was in the room:
- The finance lead who thinks the growth target is unrealistic — and who’d have to say that to the person who proposed it
- The program director who suspects the flagship initiative has run its course, and who built that initiative
- The newest person at the table with a sharp read on why the last two initiatives stalled, and no idea yet whether this is a group where you say that in your first year
None of them are being dishonest. They’re doing what reasonable people do in a room with colleagues: agreeing in order to keep things moving, and planning to raise it later in a smaller conversation where it costs less.
Probing for disagreement is the job. After two decades of doing it, what I’ve learned is that there’s a ceiling on how well it works — and it isn’t a skill problem. Some things simply cost too much to say in front of the people they’re about.
So the group agrees. The plan gets built on that agreement. And it rests on something that was never really there.
You find out slowly. A priority everyone endorsed doesn’t get resourced. A decision gets quietly relitigated six weeks later. Someone says “I was never sure about that” in a meeting in August — and you realize they weren’t sure in October either.
What to do instead: ask before the session rather than during it.
Even a simple written question sent round a week ahead — what’s the thing we’re not talking about? — will surface more than the same question asked at the table. Writing is private in a way speaking isn’t, and people answer differently when nobody’s watching their face.
Two honest limits, though. Anonymity is only as real as people believe it is, and if the person collecting the answers is the person some of those answers are about, they’ll hedge. And someone has to read what comes back without getting defensive, which is harder than it sounds when it’s your own organization.
2. Nothing came off the list to make room
Here’s a test worth running at your next leadership meeting. Ask everyone to write down three of the organization’s strategic priorities. No looking anything up, no phones. Then compare.
In an analysis of 124 organizations, only 28% of executives and middle managers responsible for executing strategy could list three of their own company’s strategic priorities. (Sull, Sull, and Yoder, MIT Sloan Management Review)
Worse, a third of the leaders charged with implementing the strategy couldn’t list even one.
The instinct is to treat that as a communication failure. Send the plan round again, put it on the wall, open every meeting with it. Donald Sull, the MIT researcher behind that analysis, found the same impulse in the executives he studied — and discourages it. (Sull, Sull, and Yoder, MIT Sloan Management Review)
But you can’t communicate your way out of twelve priorities. People couldn’t name three because there were too many to hold.
And the reason there were too many is structural, not careless:
- Funding or revenue shifts, and something gets added
- Someone new joins the leadership team with an idea, and something gets added
- Feedback from the people you serve surfaces a need, and something gets added
- A genuinely good opportunity appears, and something gets added
Each one is defensible on its own. What almost never happens is the other half of the transaction — something coming off to make room.
So the list grows. And because a year has a fixed number of weeks and a fixed number of people, the list sorts itself out anyway, just not deliberately. Some things get done. The rest quietly fall away, usually the ones without a strong advocate rather than the ones that mattered least.
You end the year having made choices. You just didn’t make them on purpose.
What to do instead: before anything goes onto next year’s list, establish what’s already on it — the real commitments, not the plan. Then for every priority you want to add, ask two questions. What would it actually take? And what comes off to make room?
That second question is hard for a reason that has nothing to do with judgment. The things worth stopping usually have someone attached to them, which is why the conversation gets deferred and then never happens. The fix is to make the trade a normal part of the decision rather than a separate confrontation — and to decide it before anyone is attached to an answer.
3. Nobody checked what the choices depended on
This one is the quietest, and it costs the most.
Every strategic choice you make rests on something being true:
- A growth strategy assumes the people you serve still want what you’re offering
- A revenue plan assumes a channel, a funding source, or a price point holds
- A new program or product assumes you can hire the people to deliver it
Most planning processes do look at the environment. The usual output is a list of conditions — strengths, weaknesses, opportunities, threats — catalogued in a session and filed with the plan.
We’ve been rethinking how much that’s worth.
A list like that ages immediately. It’s a snapshot of one day, it isn’t connected to any particular choice, and so nothing about it tells you what to watch. It’s a picture of the environment when what you need is a set of tripwires.
The alternative is smaller and more useful. For each priority, know what has to stay true for it to work — and watch that, rather than watching the goal.
It’s a different question, and an earlier one. Are we on track tells you where you are. Is what this depended on still true tells you where you’re heading. By the time a goal is visibly missed, most of the year is already spent. The condition it rested on usually stopped being true months before the number moved.
This matters more than it used to, and the clearest recent measurement of it happens to come from the association sector. ASAE’s first State of Associations report found nearly 39% of association CEOs reporting a financial decline against only about 10% reporting an improvement. Research from Association Laboratory describes leaders reading a shift in relevance as though it were a gap in their own performance — treating the symptoms of a changing environment as a failure of execution.
That second finding is the one that travels. Whenever conditions move faster than plans do, the temptation is to work harder at the plan you have rather than ask whether it’s still the right one.
What this adds up to
None of the three are failures of effort. They’re what happens when a planning session is asked to do a job it isn’t built for.
A planning session is designed to produce agreement, and it’s good at that. What it can’t do, in a single day with colleagues in the room, is find out what a group won’t say out loud, work out what has to come off to make space, and test what each choice actually depends on.
Those three things are what our planning approach is built around. The first happens before anyone is in a session. The second is most of the day itself. The third continues through the life of the plan.
Three questions worth asking on your own
You don’t need us to start here. Ask your leadership team:
- What do we believe that nobody has said in a meeting?
- What came off the list last year to make room for what went on?
- For each of our current priorities — what would have to stop being true for that to be the wrong choice, and would we notice?
If those are uncomfortable to answer, that’s useful information.
If you’d like to talk about what a planning process built around those three questions looks like, let’s have a conversation. No pitch — just thirty minutes to see whether it’s a fit.
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