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From one-on-one consulting to a program: what’s worth structuring

You can structure how a group works without deciding the answer to every case in advance.

6 min · read

When someone tells me they want to turn their consulting sessions into a program, I like to ask what they do when a session doesn’t go as planned. It’s easier to talk about the one that went beautifully: someone arrived with a clear problem, they worked on it, and the person left knowing what to do. But a difficult session reveals something that’s hard to put in a syllabus: the moment the expert realizes they need to change course.

That matters because when moving from one-on-one work to a group, it’s easy to structure what’s most visible: topics, explanations, exercises. It’s also easy to leave out what made the session work: someone hears what the person just said and decides not to follow the plan they came in with.

What repeats isn’t always the explanation

Imagine I’m working with a consultant who helps business owners stop reviewing everything their team does. Delegation comes up in many sessions. If we build the program around the topics that recur most often, the first module is easy to imagine: how to give clear instructions.

Now imagine two people who arrive saying the same thing: “If I don’t review it, it goes wrong.”

The first asks someone on the team to prepare a budget, then corrects it using criteria they’ve never explained. One day the important thing is staying under the limit. The next, it’s making sure every line item has documentation. The person preparing the budget has learned to send it for review before doing anything else. Here it makes sense to work on how the task is handed over and what a job well done looks like.

The second has someone who prepares good budgets. The trouble is that whenever a client asks a question, the owner jumps in to answer. Not because the team doesn’t know how, but because the owner has never said what they can decide without checking first. Give that owner another template for assigning tasks and they’ll fill it in perfectly, then jump in to answer the same email on Tuesday.

At first I’d have said both people needed to learn to delegate. Maybe they do. But if I’m helping them, I wouldn’t start in the same place. One needs to make their judgment visible. The other needs to decide what they’re willing to stop approving. That difference doesn’t show up when I ask what they want to learn. It shows up when we look together at the last task that ended up back on their desk.

I’d standardize the work, not the answer

I do see something we can structure. I’d ask everyone to bring a real task they tried to let go of and ended up doing or reviewing again. Bring the message assigning it, what came back, and the exact point where they decided to intervene. We can ask for that in advance and show an example so nobody arrives wondering what to bring.

Then I wouldn’t ask everyone to make the same correction. The consultant can help the first person spell out what needs to be in a budget before it’s ready. With the second, it may help to agree which questions the team can answer and when they do need to flag something. Both leave with something to try that week. They don’t need to leave with the same document.

I’d also make time to come back to what happened. Saying “I know how to give better instructions” is very different from showing up next week with a budget the team finished without waiting for your review. If it still came back to your desk, that doesn’t mean the exercise failed. We may be able to see something we couldn’t before: the instructions were clear, but the person didn’t have access to the information they needed.

That’s the kind of program I’d want to build. I know what we’ll do together, what each person can try, and when we’ll look at what happened. I don’t need to know what everyone will discover in advance.

Before recording anything, I’d try supporting people through it

I’d test that sequence with a small group before recording a course. Not just to see whether they liked it. I’d want to know where we can move forward together and where each case needs more attention than one session allows.

If three people arrive unable to name a specific task, they may not need another video about delegation. The first activity might need work; maybe we should help them choose a task before the meeting. If everyone understands the exercise but the consultant ends up doing a long individual review before anyone knows how to continue, I want to see that too. The program may need to reserve time for it. Or the problem we’re trying to solve may still be better suited to one-on-one consulting.

I’d rather learn that while we can still move a session or change a question. Once we’ve sold eight modules and a transformation that’s supposed to happen in eight weeks, it’s harder to admit the most useful part wasn’t module four. It was when someone looked at your case and helped you separate two problems you’d been calling the same thing for months.

So when I think about turning a consulting session into a program, I don’t start by asking what I could record. I ask what I want the person to bring, what we can decide together, and what they can try afterward. I want those things clear from the start. The answer to their particular case can wait until I know what it is.

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