Leaders have a deciding problem

Here's a number that should bother anyone whose job is developing leaders. At the average Fortune 500 company, managers spend about 37% of their time making decisions, and they reckon 58% of that time is wasted. McKinsey put real figures on it: more than 530,000 days of lost working time a year, and roughly $250 million in wasted labour costs (McKinsey, "Decision making in the age of urgency," 2019, surveying 1,259 leaders). Only one in five of those leaders said their organisation was actually good at making decisions.

If you run learning and development, you've almost certainly tried to fix this. Decision-making frameworks, pre-mortems, RACI charts, "disagree and commit," the whole shelf. Some of it helps at the edges. But most of it quietly assumes the problem is process (people aren't following the steps) when the real problem sits one level deeper. It's a definition problem. Your leaders, like nearly everyone, have never agreed on what a good decision actually is. And you cannot train people to do well at something they can't define.

Let me show you the trap, then show you a way out that's older than most religions and fits a leadership team better than anything invented in a business school.

We measure decisions by the one thing we don't control

Ask a leader if they made a good call and watch what they do. They check the result. Did the hire work out? Did the launch land? Did the reorg stick? We define "good choice" by the outcome, which feels like common sense until you sit with it for a second.

Say you hire Ms Smith for a role in accounting. Smart process, good references, the team liked her. Six months in she makes an error that costs the company a pile of money and a bigger pile of trust. Now everyone says, "we made the wrong choice." Did you, though? Or did you make a sound choice that ran into an outcome you were never in a position to guarantee?

This is the bit people skip. When we choose, we're really trying to do two impossible things at once. We're trying to (1) see the future and (2) lock in our preferred version of it. Neither is available to us. The Stoics worked this out a very long time ago: some things are up to us and some things aren't, and outcomes mostly aren't (Epictetus, Enchiridion 1). You can choose to hire well. You cannot choose that Ms Smith stays sharp, honest, and healthy for the next three years.

I use a daft little example in the workshop to make this stick. You want chocolate milk, so you drive to the shop. You've genuinely chosen to move toward an outcome. But that outcome needs the shop to have stock, your car to start, the roundabout to stay accident-free, and your own heart to keep beating while you grab your keys. You chose none of those. And yet, almost every time, you get your chocolate milk. That's the cruel part. Everyday outcomes cooperate so reliably that we start believing we control them. Then a genuinely high-stakes decision lands, the kind your senior people actually lose sleep over, and the illusion shatters at the worst possible moment.

What broken decision-making looks like on a team

When leaders believe a good decision means a good outcome, and they can feel they can't guarantee the outcome, they don't get more rigorous. They get evasive. Three moves show up again and again, and L&D folks will recognise every one:

They trust their gut and dress it up as experience ("twenty years in this industry, I just know"). They reach for consensus, not because the group is wiser but because shared blame is lighter to carry if it goes sideways. Or they delegate the call downward, distancing themselves from a result that neither they nor the poor soul they handed it to could actually control.

None of these are decision-making. They're insurance policies against being blamed for outcomes. And a leadership team full of them is a team that looks collaborative while quietly refusing to own anything hard.

The fix: make "good" objective by moving it off the outcome

Here's the move the whole workshop turns on. If you judge a decision by its outcome, you're judging it by something the decider doesn't control, which is both unfair and useless. So stop. Judge the decision by the deciding. Judge it by whether the leader reasoned well given everything that was actually theirs to work with.

That sounds soft until you give it structure, and the structure is where this stops being a nice idea and becomes a tool your team can use on a Tuesday. It comes from Panaetius, a Stoic philosopher, preserved for us in Cicero's De Officiis (Book I, sections 107 to 121), where it's laid out as four roles, or personae, that every person occupies at once. I've ported the language out of the toga and into the boardroom, but the bones are 2,300 years old and they've held up better than most things published last quarter.

Every leader, in every decision, is playing four roles simultaneously:

Human. You're a reasoning creature, and your first job is to reason honestly rather than rationalise. This is the role that asks "given that I owe everyone fair, honest dealing, what does that actually require here?" It's the one most leaders skip, and it's the one that keeps the other three from quietly drifting into self-interest.

Individual Nature. Your particular temperament, talents, and blind spots. If you avoid conflict, you'll be tempted to handle a hard call softly and quietly and tell yourself it's kindness. If you're decisive to a fault, you'll want the problem gone by Friday. You can't fight your nature, but you can name it before it names your decision for you. Your strengths are tools to deploy on purpose, not just risks to manage.

Circumstantial. What the situation actually handed you. The deadline, the market, the team you have rather than the one you wish you had. This isn't an excuse ("my hands were tied"). It's the board you're playing on. It constrains you in some directions and hands you room in others, and good leaders read both.

Commitments. What you actually said yes to. Your title, your mandate, the people who report to you, the promises baked into the role. And a hard rule lives here: never commit to delivering things you cannot choose. You can promise to manage someone fairly. You cannot promise the board a number you haven't earned.

A good decision is one that honours all four roles well. Not one that produces a good outcome (you can't control that), but one a fair, clear-eyed person playing all four roles could stand behind. That's an objective standard. It's defensible. And critically for you, it's shared. When a whole leadership team uses the same four roles, "I have a bad feeling about this" turns into "this fails on Commitments, here's why," which is a conversation you can actually have in a room.

Does it survive contact with a genuinely ugly situation?

That's the right question, and it's most of what the workshop is. Frameworks are easy when the case is clean. So we don't use clean cases.

Picture a senior leader, well-liked, been with you for years, who's been hiding that a major initiative is failing. They fudged the numbers in the last two reports. You only just found out. They're also going through something genuinely brutal at home. The board wants real figures next week. The team doesn't know yet. And everyone is watching how you handle it.

Run it through the four roles and the apparent contradictions start to resolve. Human: you owe the team the truth and a leader who won't tolerate doctored numbers, and you owe this person compassion and a chance to respond. Both. Individual Nature: if you're conflict-avoidant, notice the pull to bury this; if you're a hard charger, notice the pull to fire by Friday. Circumstantial: you found this early, which means you control the sequence and the framing, that's leverage, not just constraint. Commitments: you promised this person fair management, and you promised the organisation real numbers, and when those collide you don't get to pretend only one exists.

The verdict that falls out isn't a compromise. You give the board the real figures, no softening. You tell your report first, face to face, before anyone else hears it. They keep their job with clear conditions and support, because hiding a failing project under personal strain is a correctable mistake, not a firing offence. Every part of that is defensible on reasoning rather than on guilt or fear. A wise, fair person would do exactly this. The roles only looked like they were pulling apart. Done properly, they point the same way.

Why this belongs in front of your leadership team

You're not buying a motivational hour. You're buying a common language for how decisions get made, one that outlasts the workshop by years rather than weeks. After it, when two of your VPs disagree, they're not trading gut feelings and seniority. They're asking which role the call is failing and why. That's the difference between a team that argues and a team that reasons.

I run a small number of these a year, in person or remote, half-day or full-day, built around the real decisions your team is sitting on right now (not theoretical ones). It's the actual framework, taught properly, by a working philosopher who's spent years adapting it, with time to practise under pressure and someone in the room willing to say "that bit there isn't reasoning, that's rationalisation." That last part is the whole job, and it's the part a slide deck can't do for you.

If your leaders are spending a third of their time deciding and wasting more than half of it, the cheapest fix on the table isn't another tool. It's teaching them what "good" means before they choose.

Want to talk about running this with your team? Book a call with me here. Tell me what your leaders are deciding badly, and I'll tell you honestly whether this is the right fit.