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Decision-making
By Advisorly · 9 min read

How to Make Hard Decisions: A Working Process

The decisions that keep you up at night rarely get easier by waiting. A repeatable process for the calls that actually matter.

You have been turning the same decision over for two weeks. Maybe it is whether to fire a senior person who is well liked but no longer pulling their weight. Maybe it is whether to kill the product line that pays half the bills but is quietly dying. You know it matters, you know the cost of getting it wrong, and that is exactly why you keep pushing it to next week.

The problem is not that you lack information. Most hard decisions stay hard because you are trying to feel your way to certainty that will never arrive. The trick is not to remove the difficulty. It is to have a process you trust, so that when you decide, you can live with the call even if it turns out badly.

Why hard decisions feel different

A decision is hard for one of a few reasons, and naming the reason changes what you do next. Some decisions are hard because the stakes are high and the outcome is irreversible. Others are hard because the options are close in value and you keep flip-flopping. And some are hard only because they carry emotional weight, a person you like, a project you built, a bet you made publicly.

These are not the same problem. A close call between two roughly equal options is not worth agonising over, because the whole point is that either choice is fine. An irreversible high-stakes call deserves real deliberation. Once you know which kind you are facing, you know how much time to spend. Spending three weeks on a decision that a coin flip would settle is its own kind of failure.

There is also a version of hard that is really just fear wearing a suit. You already know the answer. You have known for a month. What you are avoiding is the conversation, the awkwardness, the admission that you were wrong earlier. That is not a decision problem. That is a courage problem, and no framework fixes it. You just have to do the thing.

Write down the actual decision

Start by writing one sentence: "I am deciding whether to X or Y by [date]." This sounds trivial. It is not. Most stuck decisions are stuck because the question itself is fuzzy.

Consider Harlow & Reed, a 40-person accounting firm that spent months debating "what to do about the junior team." That is not a decision. It is a mood. When the two partners finally sat down, they found three separate questions hiding inside it: whether to raise starting salaries, whether to change who does client-facing work, and whether to let two underperformers go. Each had a different answer and a different deadline. The fog was not in the situation. It was in the framing.

Give yourself a deadline in that sentence, and make it real. A decision with no deadline is a decision you have chosen to avoid. If the deadline is genuinely far off because you are waiting for information that arrives in March, fine, but then the decision this week is simply "wait until March," and you can stop carrying it around.

Get the options on the table, including the ones you hate

The most common failure in hard decisions is a false binary. You have framed it as "keep the office or go fully remote," and you spend weeks fighting over two options when there were always five. Hybrid three days a week. A smaller office. Keep the office but sublet half. Move to a cheaper part of town.

Force yourself to write at least four options, even bad ones. The bad options are useful because they mark the edges of the space and they often contain a good idea in disguise. "Shut the whole thing down" is rarely the answer, but writing it down sometimes reveals that one part should shut down while the rest continues.

Include the option of doing nothing, explicitly, as a real choice with real consequences. Doing nothing is not neutral. It is a bet that the current path beats the alternatives, and it should have to earn its place like any other option.

Find the information that would actually change your mind

Here is where people waste the most time. They gather information that is easy to gather, feels productive, and changes nothing. They read another article. They ask another friend who agrees with them. Meanwhile the one fact that would settle the question sits untouched because getting it is uncomfortable.

Ask yourself directly: what would I need to know to be confident here, and what is the cheapest way to find it? If you are deciding whether to enter a new market, the useful move is not more desk research. It is a phone call to five potential customers. If you are deciding whether to keep an employee, the useful move is a frank conversation with them and their direct reports, not another month of watching from a distance.

Set a limit on this. Give yourself a fixed window, say five working days, to gather what genuinely moves the needle. When the window closes, you decide with what you have. Deciding with incomplete information is a skill worth building on its own, and there is a fuller treatment of it in deciding with incomplete information.

Run the numbers on the version you can quantify

Not every hard decision has a spreadsheet inside it, but more do than people admit. When money is involved, do the arithmetic before you consult your feelings, because feelings are terrible at scale.

Take a real case. A regional gym chain, Fulton Fitness, was deciding whether to keep a struggling location open. The emotional pull was strong: it was their second-ever site, the manager had been there nine years, and closing it felt like a betrayal. So they did the sums. The location brought in £18,000 a month in revenue. Rent, staff, and running costs came to £23,500 a month. It was losing £5,500 a month, or £66,000 a year, and membership had fallen for six straight quarters with no plausible turnaround.

The numbers did not make the decision easy, but they made it clear. Keeping the site open was costing them a full marketing budget every year to preserve a feeling. They closed it, redeployed the good staff to two nearby sites, and used part of the saved money to soften the manager's exit. The point is not that numbers always win. It is that you should know what the feeling is costing you before you decide to pay for it.

Where you cannot get a clean number, estimate the range. "Somewhere between £40,000 and £90,000 of upside, most likely around £60,000" is far more useful than a shrug. A rough number you can argue with beats a precise feeling you cannot.

Test the decision before you commit to it

Before you pull the trigger on something big, run two quick checks that catch most bad calls.

The first is the pre-mortem. Imagine it is a year from now and the decision has gone badly wrong. What happened? Writing the failure story in advance surfaces risks you were glossing over, and it is one of the most reliable tools in the whole business. It gets its own full treatment in the pre-mortem, and it is worth doing on any decision you cannot easily reverse.

The second check is to ask what advice you would give a friend in exactly your position. This sounds like a party trick, but it works because it strips out the ego and the sunk cost. You are far clearer about other people's decisions than your own, precisely because you are not defending your past choices. When the advice you would give a friend differs from what you are about to do, stop and find out why.

Decide, then commit in writing

When the window closes, decide. Write down what you chose, why you chose it, and what you expected to happen. This record does two things. It stops you relitigating the decision every time you feel a wobble, and it gives you something honest to check against later, so you can tell the difference between a bad decision and a good decision that got unlucky.

State the decision to the people affected plainly and without a hundred qualifications. Half-committed decisions leak. If your team can smell that you might reverse course at the first sign of trouble, they will hedge, and the decision never really gets tested. Commit like you mean it, while staying honest that you will change course if the facts change.

Where this goes wrong

The biggest failure is treating every decision as a hard decision. If you run this full process on what colour to make the invoices, you will exhaust yourself and never get to the calls that matter. Most decisions should take minutes. Save the process for the ones that are genuinely high-stakes and hard to reverse.

The second failure is using the process as a stalling device. People sometimes gather information forever, run endless pre-mortems, and canvass endless opinions, all to avoid the moment of commitment. If you notice yourself on the fourth round of "let me just check one more thing," the checking has become the avoidance. Set the deadline and hold yourself to it.

A third trap is confusing a good process with a good outcome. You can do everything right and still lose, because the world is uncertain and you were always making a bet. If you judge your decisions only by how they turned out, you will learn the wrong lessons, punish sound calls that got unlucky, and reward reckless ones that happened to pay off. Judge the decision by what you knew at the time.

The last one is quieter. Some people run the whole process, reach a clear answer, and then do not act, because acting means a hard conversation. The process is not the point. The decision is not even the point. The action is the point, and a decision you do not act on was never really made.

If you are carrying a hard decision right now, do the smallest piece today: write the one-sentence version of what you are actually deciding, with a date on it. Just that. Everything else gets easier once the question stops being a fog and starts being a sentence.

Free playbook

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The Hard Decision Playbook

A 7-step framework for working through the decisions that keep founders up at night.