Most entrepreneurs do not spend years building a business thinking about inheritance tax, trust structures or deferred consideration mechanics. They think about growth customers, hiring, funding, the product, even survival, in some cases.
Tax planning usually sits somewhere in the background, something to revisit “when things settle down” or when a transaction starts to feel real. The problem is that by the time many founders start thinking seriously about these issues, some of the best opportunities have already narrowed.
We regularly work with entrepreneurs who say some version of the same thing after a sale: “If I’d understood this earlier, I would have done things differently.” Not dramatically differently. Just earlier, calmer and with more joined-up thinking around the business and their personal affairs.
Here are seven of the issues we see most often and how we step in to help.
1. Waiting until a deal is on the table
A surprising number of entrepreneurs assume tax planning starts once lawyers and buyers are involved. In reality, that is often the point at which flexibility starts disappearing.
Some of the most effective planning opportunities, particularly around trusts, ownership structures and succession, work best when they are implemented well before a transaction is in sight. Not because they are aggressive, but because they need time to become part of the commercial reality of the business.
This has become even more relevant with the changes to Business Property Relief (BPR) from April 2026. Many business owners are now reviewing whether existing structures still achieve the inheritance tax outcomes they originally intended.
For entrepreneurs who may want to pass value to the next generation in future, now is a sensible time to review:
- Whether shares should be transferred into trust over multiple years
- Whether existing shareholder structures still support long-term succession plans
- Whether family members are involved in the business in the most tax-efficient way
The irony is that the best time to plan is often when nothing urgent is happening at all.
2. Extracting profits inefficiently
Many founders evolve their business much faster than they evolve their remuneration strategy. What started as a simple combination of salary and dividends can become inefficient as profits grow, family circumstances change, or new investments emerge outside the business.
We often find entrepreneurs extracting profits in ways that made sense years ago but no longer reflect where they are now financially, or the changes to tax rates since the plan was implemented. Sometimes relatively small changes can improve overall tax efficiency significantly over time.
That may involve:
- Reviewing the balance between salary, dividends and pension contributions
- Making better use of spouse or family tax allowances where appropriate
- Repaying or restructuring director loan accounts
- Considering whether surplus profits should remain inside the business at all
These reviews rarely feel urgent. But the cumulative impact of not doing them can be surprisingly expensive.
3. Leaving too much cash trapped in the company
This is particularly common in successful founder-led businesses. Over time, surplus cash builds up inside the trading company because there has never been a reason to move it elsewhere. At first that feels sensible, but then gradually the business becomes part trading company, part investment vehicle, without any deliberate strategy behind it.
That can create complications later. It may affect BPR or Business Asset Disposal Relief (BADR) availability, increase exposure to commercial risk, or simply make long-term personal planning harder than it needs to be.
In some situations, entrepreneurs benefit from separating personal wealth from trading risk earlier. Practical options might include:
- Moving excess cash into a holding or investment structure
- Funding pensions more strategically
- Using Family Investment Companies for long-term investment planning
- Reviewing whether retained cash levels remain commercially justifiable
The goal is not necessarily to extract everything immediately. It is to ensure the structure evolves alongside the success of the business and cash is in the right place at the right time.
4. Assuming existing trusts or family structures still work
Entrepreneurs are usually very good at adapting commercially. Their personal structures, though, can often be left untouched for years; trusts established a decade ago, shareholdings that no longer reflect reality, Family Investment Companies that were set up with clear intentions but have not been reviewed since.
None of this is unusual; businesses evolve quickly and structures rarely keep pace naturally. But legislation changes, families change and priorities change. For example, entrepreneurs should regularly review:
- Whether trusts still align with their intended succession plans
- Whether shareholder arrangements remain commercially sensible
- Whether Family Investment Companies are still being used as intended and should these shareholdings be reviewed
- Whether wills and estate planning documents reflect current asset values, ownership structures, and up to date wishes
Regular reviews are less about creating complexity and more about making sure old planning still works in the real world.
5. Focusing on the headline deal value instead of the tax mechanics
Entrepreneurs, understandably, focus on valuation during a sale process, but sometimes the detail sitting underneath the headline number matters just as much. Deferred consideration, earn-outs and loan note or equity arrangements can all create unexpected tax consequences if they are not reviewed carefully from a personal perspective alongside the transaction itself.
We occasionally see situations where founders are surprised by:
- When tax becomes payable
- How deferred proceeds are treated for capital gains tax purposes
- The tax implications of remaining involved post-sale
- Or how multiple payments across tax years affect overall exposure
Those issues are often avoidable when personal tax advice is brought into the process early rather than treated as a separate workstream towards the end. This can simply include an estimated cashflow considering tax payments, allowing exiting shareholders to prepare for liabilities.
6. Avoiding succession conversations because they feel “too early”
For family business owners especially, succession planning is often postponed because it feels emotionally difficult rather than technically difficult. There is usually a sense that there will be more time later. But the earlier these conversations happen, the more options tend to exist around ownership transitions, inheritance tax planning and properly preparing future generations to take the business forward.
Good succession planning is rarely about handing over control overnight. More often, it involves gradually creating flexibility over time. That might include:
- Gifting shares progressively rather than all at once
- Creating different classes of shares for different generations and needs
- Introducing family governance structures early
- Using trusts to separate economic benefit from control
- Reviewing whether the current ownership model still supports the family’s long-term intentions
With changes to inheritance tax reliefs, many entrepreneurs are reassessing whether existing plans still achieve the outcomes they want for both the business and the family behind it.
7. Spending years preparing for the deal, but not life afterwards
One of the quieter challenges after an exit is that entrepreneurs often move very suddenly from building wealth to managing wealth, and that transition is not always straightforward. There can be pressure to invest quickly, make gifts, support family members or establish new structures immediately after a transaction completes. But decisions made too quickly in that period can be difficult to unwind later.
The entrepreneurs who tend to feel most comfortable post-exit are usually the ones who thought about the bigger picture beforehand. That often means considering:
- What role future investments should play
- How wealth should be structured for family purposes
- Whether trusts or Family Investment Companies are appropriate post-sale and provide the right control
- How inheritance tax exposure may change after liquidity is created
- And what long-term objectives the wealth is actually intended to support
The best post-exit planning usually starts before the transaction begins, rather than after it has completed.
Planning early creates breathing space later
The entrepreneurs who tend to feel most confident after an exit are rarely the ones who pursued the most aggressive planning. More often, they are the ones who started conversations early enough to preserve flexibility later on, even where action was not actually taken.
At HaysMac, our Entrepreneurs and Private Business specialists within the Private Client Tax team work closely with founders, shareholders and family business owners to help them navigate growth, wealth and long-term planning with confidence.
From succession planning and trusts to investment structuring, profit extraction and pre- and post-sale planning, we provide joined-up advice designed to protect value without distracting from the business itself.
Whether an exit is imminent or years away, early planning can make a significant difference to the options available later. If you would like to discuss your current structure or future plans, our team would be very happy to talk.
