How to manage someone who thrives without structure

The simplest way to manage someone who thrives without structure is to agree on a small number of firm outcomes and deadlines, then leave the method up to them, with short, regular check-ins. They tend to be flexible, quick to respond and at ease with changing plans. A tight process can smother those gifts, while no process at all can leave them, and you, stranded on deadline day.

Who we are talking about

People who score lower on conscientiousness tend to be spontaneous and comfortable leaving things open. It says nothing about how much they care or how smart they are. Consider Dev, a sales rep who can rescue a wobbling client relationship over one coffee, but whose CRM entries are a work of fiction. Or Tess, an events coordinator who stays calm when the caterer cancels at noon, and whose inbox has 4,000 unread emails.

If you are a natural planner, your instinct may be to add more process. Sometimes that helps. Often it just gives them more things to forget.

Mistakes managers often make

Mistake one: treating all deadlines as equal. If every date is urgent, none of them are. Sort tasks into "this date is real because a client or regulator depends on it" and "this date is a preference". Then be unbending on the first group.

Mistake two: long, weekly status meetings. They are likely to wing them. Try a ten-minute check-in twice a week with the same three questions: What got done? What's next? What's stuck?

Mistake three: reading late as careless. Sometimes it is, but more often the task was unclear, or dull, or sitting behind five more interesting ones. Ask before you assume.

Mistake four: hiding the real due date. Inventing fake early deadlines tends to get found out, and then nothing you say counts. Give the true date, plus a checkpoint halfway through.

Tools that tend to stick

Don't hand them your system. Ask them what has ever worked, even once. Some might use a phone alarm, a sticky note on the laptop or a voice memo to themselves on the way to the car. Odd is fine. Results are what you are paying for.

It can help to make the tedious stuff smaller and closer to the fun stuff. If Dev updates the CRM by dictating into his phone in the car park right after each client visit, it might take him 90 seconds. If he has to log in on Friday afternoon, it may never happen. You could also pair them with a detail-minded colleague for the last ten per cent of big projects, as long as that colleague is recognised for it and isn't quietly cleaning up after them.

A conversation about a missed commitment

Stay specific and keep it forward-looking. Here is one way:

"The proposal went out two days late, and the client noticed. You're the person I want on this account, so I'd like to fix how we get there. Walk me through what happened in the last week. And what's one thing we can set up so I see a draft by the Wednesday before?"

Then let them propose the fix. A plan they invent is one they are far more likely to follow.

Give them the right work

Look for places where things change fast and few days look alike. Launches, client emergencies, pitching, troubleshooting, first drafts and open-ended experiments may all suit them. When something breaks at 4pm, you will be glad somebody on your team doesn't need a plan to start moving.

Be honest with them about how the work is judged too. If promotion depends on documentation, tell them plainly, and well before review time, so they can get help.

Related reading

The same trait at home appears in how to love someone who is relaxed about plans, and in families we look at how to plan with a sibling who runs late. Spontaneity often overlaps with being outgoing, so you may also want to read about managing someone high in extraversion.

Your people can tell you how they work best, if you ask well. Get a Field Guide written for the people in your life.

Managers tend to assume their own way of getting organised is the right one. Check yours with the Core Personality Expedition, which covers conscientiousness along with the four other big traits.