2. The Exit Roadmap That Does Not Collapse

A timeline you will actually follow, not one that lives in a dusty drawer

Problem Statement.

Many owners swear they have an exit plan. Somewhere there is a spreadsheet, a whiteboard photo, a note in a notebook that says something like “sell in three years”. Yet the years slide past. The plan ages quietly while you deal with staff, customers, tax and life.

When you finally speak to a buyer or adviser, things feel rushed. Financial clean up, legal tidy ups, systems work, leadership changes and personal planning all pile on at once. That pressure often shows up in the deal as lower value, tougher terms or a sale date that moves further away just when you wanted it closer.

What An Owner Might Say

“We said we would be sale ready in eighteen months. Four years later I am still here, still promising myself next year.”

“I have a long list of things we should do before selling. I just never quite know what comes first.”

“We did a strategy day that spat out a big roadmap. Everyone felt good. Then the document went into a folder and real life took back over.”

Why It Happens

Exit plans often start as wish lists rather than schedules. People throw every good idea on the page. Tidy the numbers, fix the contracts, sort the leadership, upgrade systems, improve margins, grow recurring revenue. The list looks clever although no one checks whether a normal human team could actually deliver it alongside day to day work.

Timeframes are usually reverse engineered from mood. You pick “three years” because it feels far enough away to be safe, not because you have mapped what the work really requires. There is no clear link between tasks, dependencies or capacity. The first unexpected event such as a staff departure, a wobbly quarter or a family issue blows the plan off course.

Accountability is fuzzy. The owner supposedly owns the roadmap, yet is also the busiest person in the building. Managers nod, agree something should happen, then return to the fire in front of them. There is no simple rhythm to review progress, reset priorities or say no to distractions.

In my view a lot of owners also carry quiet anxiety about what the exit might mean for identity and life. It feels easier to talk about selling than to commit to a real date. So the plan stays conveniently vague, hoping that one day everything will line up by itself.

What To Do About It

Think of an exit roadmap as a practical project plan, not a glossy poster. The goal is a sequence of steps you can execute with the team and capacity you actually have.

Start with a clear horizon. Pick a target window rather than a single magic date. For example “we want the option to sell any time from late twenty six onwards”. That language matters. It reminds you that you are creating an option, not a promise to sell whether you like it or not.

Next, pick a timeframe for serious preparation. For many SMEs twelve to twenty four months of focused work is enough to tidy key value drivers without burning everyone out. Work backwards from your window and mark that period in your calendar. This is your runway.

Break the work into a small number of streams. For example

• Financial clarity and value
• Risk, legal and housekeeping
• Customers, revenue quality and growth story
• Operations and people
• You as the owner and your life after exit

Under each stream list three to five specific outcomes that would make a buyer more confident. That might include clean normalised earnings, a basic risk register, reduced single customer dependence, a working management reporting pack, or a short personal plan for your next chapter. Keep the language plain.

Now build a simple timeline that runs in quarters rather than weeks. For each quarter, choose only a handful of priority milestones across the streams. Ask a hard question. If we could only achieve three things this quarter that move us closer to sale readiness, what would they be. This forces trade offs and keeps the plan from bloating.

Assign clear owners for each milestone. Name a person rather than a department. Then ask those people what they will stop or pause to make space. Without that conversation, everything becomes extra work layered on top of full plates, which is exactly how roadmaps end up in drawers.

Translate big milestones into the first few concrete next steps. For instance, “improve working capital” turns into “run a debtor ageing review next week, choose one change to our credit terms, start a trial with new rules for new customers from next month”. Your exit roadmap should quickly touch the ground in visible actions.

How To Keep The Momentum

A good roadmap lives or dies on rhythm. Put a recurring exit readiness session in the diary. Monthly suits many owner managed firms. Ninety minutes with the small group who own key milestones is usually enough. The agenda stays simple.

• What did we say we would do last month.
• What actually happened.
• What do we commit to for the next month.

Capture decisions in a one page tracker. Traffic light colours help. Green for done, amber for in progress, red for stuck. This is not corporate theatre. It is visual honesty that stops everyone pretending progress is happening where it is not.

Expect the plan to change. Markets move, staff leave, health throws surprises. When something big happens, do not junk the roadmap. Recut it. Decide which milestones to delay, which to drop, which to bring forward. The ability to re plan calmly is one of the quiet skills buyers respect. It shows the business can adapt without panic.

Protect your own energy as part of the plan. Mark in holidays, recovery time and non negotiable family events. If your roadmap assumes you will sprint flat out for two years you already know it is fiction. Many exits stumble not because the plan was bad, but because the owner was exhausted before the real work began.

Share a high level view with your leadership team so this does not feel like a secret project. People cope better when they can see where the business is heading and how their work this quarter fits the bigger picture.

Golden Nugget.

“A good exit roadmap fits on one page, survives contact with real life and still makes sense on the day a buyer finally calls.”

How RegenerationHQ can help.

RegenerationHQ works with owners who want a roadmap they can actually walk, not a consultant diagram that gathers dust. Support often begins with a practical readiness review across financials, risk, customers, operations plus your own life plans. From there, RegenerationHQ helps you shape a simple timeline, choose the few moves that really lift value, assign sensible owners and create the monthly rhythm that keeps everything moving.

Within a wider Exit Prep Programme the roadmap becomes the backbone. It links work you are already doing with targeted changes that buyers and lenders actually care about, so that by the time you choose to sell you are stepping into a process you have prepared for, rather than rushing through a door that happened to be open.

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.