Create options, create momentum. How stuck leadership teams move.

Leadership teams get stuck for a small number of repeating reasons. Most of them look like analysis problems but are actually options problems. The team isn't missing a smarter answer. It's missing a wider set of plausible answers to choose from.

I see this most often inside executive coaching engagements with senior leaders in Toronto and across Canada. A CEO will tell me "we've been going back and forth on this for months," and the conversation that follows is almost never about the analysis. It's about how few credible alternatives the team has actually generated. This essay is about why that happens, what to do about it, and where it fits inside coaching work.

When a CEO tells me a team has been going back and forth for months, I almost never ask what they've decided. I ask what other options they've considered and ruled out. Nine times out of ten the answer is two: the one they want and the one they're against. That's not a decision. That's a referendum.

Two-option decisions are bad for predictable reasons. They polarise the team. They turn the conversation into a defence of conviction rather than an evaluation of evidence. They obscure the strongest counter-argument because nobody is incentivised to develop it. They produce decisions that don't survive the first surprise after launch.

The conversation a leadership team needs in those moments is not a smarter argument for option A. It's a wider field. Putting a third and fourth credible option on the table changes the structure of the discussion, even if the team eventually picks option A. The presence of credible alternatives forces option A to defend itself against something other than option B.

Real options work means putting at least four credible paths on the table (including ones that make people uncomfortable) and forcing the team to evaluate each on the same criteria. The discomfort is the point. The fourth option is almost never the one chosen, but generating it changes the conversation about the first three.

Concretely: schedule 90 minutes. The first 30 are option generation only. No debate. Each leader writes down two paths they think are credible, including the one they don't want. The facilitator collects them, dedupes them, and writes them on the whiteboard without attribution. You should end up with at least four credible candidates.

The next 30 minutes are evaluation. Pick three criteria the team would defend to their board. Cost, time, risk. Or strategic fit, execution risk, optionality. Score each path against the same criteria. Don't let the conversation drift into advocacy.

The last 30 minutes are convergence. Now you can debate. But the debate is now about evaluation, not conviction. That changes the social dynamics in a way that's hard to overstate.

Options work doesn't just produce a better decision. It produces a faster one. A team that's been stuck for months will move within two weeks of seeing a wider field, because suddenly the conversation is about evaluation instead of conviction. Evaluation is shared work. Conviction is a fight.

The momentum compounds. Once a team has done one options session and seen it work, the next stuck decision tends to surface as "let's run a four-options session" instead of three more weeks of arguing over two. The team has a shared move it can call when it gets stuck. That's worth more than any individual decision.

There are two situations where the fourth-option technique doesn't help.

First: when the real problem is trust, not analysis. If two leaders fundamentally don't trust each other's judgement, generating more options just gives them more ground to fight on. Trust problems need different work, usually direct, structured conversations between the two people involved, often with a coach in the room, before any team-level decision-making can move.

Second: when the decision genuinely is binary. Some decisions are. Whether to acquire a specific company. Whether to fire a specific person. Whether to enter a specific market. In those cases, the discipline isn't generating more options. It's making the binary call and committing to it. Trying to generate four options when the decision is genuinely two-way produces theatre.

Knowing the difference between an options problem and a trust problem is most of the work. A coach who has been in those rooms before can usually tell within twenty minutes which one is in front of you.

If your leadership team is stuck on something that should have been decided a quarter ago, the move is simple. Schedule 90 minutes this week. Generate four credible options together with no debate yet. Evaluate them against the same three criteria. Then converge.

Run the first one yourself. If it works, you have a new shared move. If it doesn't, the failure mode usually points to what's actually in the way (trust, information, or a binary call you're avoiding), and that diagnosis is worth more than any framework.

Inside an executive coaching engagement, this technique tends to surface in month two or three, once we've worked through the leader's own decision-making patterns and they're ready to bring the move into the team. If you want to talk about whether coaching would help with a specific stuck decision, an intro call is 30 minutes and there's no obligation.