4. Time Your Sale to the Market Not to Your Mood

Pick the window that gives you leverage and the buyer confidence you want

Problem Statement.

Owners often decide to sell because of feelings rather than timing. You feel tired. You are over staff issues. A health scare rattles you. A big birthday arrives. In that moment the urge to get out can feel stronger than any market logic.

Buyers and banks do not care much about your mood. They care about trend lines, sector sentiment, interest rates, deal activity and whether your numbers have had time to mature. If you hit the market in a weak window with flat or choppy results, you hand leverage to buyers. You still may sell, although often with more compromise than you hoped.

What An Owner Might Say.

“I know the last two years were rough although I just cannot do another one.”

“We will put it on the market then see what happens. I am ready to be done.”

“Sure the economy is wobbly. I just want my life back.”

Why It Happens.

Running a business is emotional. You ride through recessions, pandemics, staff departures, customer dramas, government changes. At some point even the most resilient owner hits a wall. When that happens, timing questions feel academic. The only clock that matters is your own energy.

Most owners also only sell once. You do not have a mental map of market cycles or deal flow. You hear snippets. Someone got a great multiple three years ago. Someone else struggled last year. Those stories rarely include context about sector trends, interest rates or how clean their numbers were at the time.

Short term pain looms large. A single ugly year can colour your whole sense of the business. You forget that buyers will look at three to five years of performance. If you leave just as recovery starts, they may enjoy the uplift that should have belonged to you.

Advisers sometimes avoid hard conversations about timing because they do not want to sound like they are telling you how to live your life. They help you sell when you say you are ready. That is fair. It also means owners occasionally move straight from “I am fed up” to “let us list it” without a sober look at where the business sits relative to the market.

What To Do About It.

While you wait for the chosen window, do not sit on your hands. Use the time to make the business more sellable.

Strengthen earnings quality. Clean up personal costs, document normalisation adjustments, prove cash conversion, improve debtor days a little, tidy any rough tax positions. Buyers pay more readily for profit they can see, explain and fund.

Reduce visible risk. Work on key customer concentration, supplier dependence, health and safety housekeeping, simple cyber hygiene and any obvious compliance gaps. You will not fix everything although even partial progress shows momentum.

Lift your leadership bench. A buyer is more relaxed when they can see a team that runs the show without you in every meeting. Promote sensibly, document responsibilities, get second tier leaders presenting numbers and plans.

Build or refine your basic sale tools while the pressure is low. That includes a short overview deck, a clean buyer reporting pack, a draft data room structure, a first pass at your “known issues and how we are addressing them” list. When the window opens, you will be ready in months rather than years.

How To Keep The Momentum.

Timing is not a one time decision. Markets shift. Life changes. You need a way to review without obsessing.

Set a simple check in rhythm. Once or twice a year, sit with your key adviser or accountant and ask the same handful of questions. Has the business become more or less attractive to a buyer. Has my personal appetite for ownership changed. Has the funding environment for deals my size improved or tightened. Based on those answers, does our target window still make sense.

Share the broad horizon with your partner or whānau. They live with the emotional and financial consequences as much as you do. Knowing that you are aiming to exit in, say, three years with regular reviews can ease tension. It turns exit from a vague dream into a plan that can flex.

Watch for mood driven decisions. If you catch yourself saying “I am done, I do not care about price”, treat that as a signal to talk rather than to sign. Sometimes health or crisis means a fast sale is exactly right. Sometimes it means a holiday and a fresh look at the numbers would serve you better. Trusted advisers exist partly to hold that mirror.

Golden Nugget.

“Sell when your business is ready and the market is listening, not just when you have had a bad week.”

How RegenerationHQ can help.

RegenerationHQ partners with owners who want to exit on purpose rather than in a rush. That includes helping you step back from the day to day and look at timing through three lenses, your life, your business and the wider market.

Support can include a practical readiness review that highlights what buyers and banks will see today, where an extra twelve to twenty four months of focused work could add value, which risks truly need attention and which are fine as they are. From there RegenerationHQ helps shape a simple timeline that fits your energy, your family picture and your financial goals, then walks alongside you as you get the business into shape for that window.

The result is not a guarantee of perfect timing. No one has that. It is a sale that feels like it happened in a season you chose, with numbers and narratives that support the price, rather than a hurried decision made on a bad Friday afternoon that you spend the next decade second guessing.

If you want a steady guide beside you while you get ready for one of the biggest decisions of your working life, RegenerationHQ is ready to help you walk that road with clarity and confidence.