The Business Owners Holiday Checklist
For many entrepreneurs, taking a proper summer break feels impossible. But stepping away is vital for you, your health, and your family. It’s even beneficial for your business, especially if you are planning towards an exit at some point in the next 3 years. A business that is dependent on the owner could lose up to 40% of its value or require onerous tie-ins over several years post sale.
Here’s your essential checklist to prepare your business so you can enjoy that well-earned downtime, worry-free.
Lock in Your Second-in-Command
You can’t relax if no one’s steering the ship. Delegation is hard, but an essential skill to master.
👍 Good: Identify a trusted senior team member who can handle key decisions. Brief them thoroughly and give them temporary authority. Your phone will thank you.
✅ Better: Develop and empower your senior leadership team so that they are competent at running the day-to-day without deferring to you. Not only will this make holidays a breeze, but it will add significant value when it is time to sell up.
Client Comms? Get them Covered
Your clients need to know you’re away… but the business isn’t on hold.
👍 Good: Schedule an email update and ensure someone is available to respond. Confidence is everything.
✅ Better: Work to transition all of your client relationships to another contact in the company. The longevity of your business depends on those clients not jumping ship when you’re no longer there.
Crisis Plan = Peace of Mind
Because stuff happens.
👍 Good: Have a simple crisis procedure ready. Who gets called? What’s urgent versus what can wait? Make it crystal clear. Emergencies feel smaller when there’s a plan.
✅ Better: Have a clear escalation policy that operates all year round. Empower those in leadership positions to deal with smaller issues but have clear definitions of when something requires more senior involvement. This will not only free you up to think more strategically but will give any future acquirer peace of mind that what they are buying will not be a constant headache.
Cash Flow Eyes On
The numbers keep moving even when you’re on the beach.
👍 Good: Forecast cash flow for the holiday period and set alerts for anything unusual. No one wants a financial surprise while ordering cocktails.
✅ Better: Implement monthly management accounts and make sure that it’s more than just you watching the numbers. Although it does require some investment, the pay off is more consistent reporting and the ability to get more people on board with how the numbers work for your company. When it comes to selling your business, they are a highly valuable tool that will pay considerable dividends in negotiations on things like surplus cash.
Tighten Up the Tech
Because systems glitch.
👍 Good: Before you go, double-check that your IT, security, and comms are solid. Automated backups, secure access, and clear passwords save headaches.
✅ Better: Implement strong redundancy and back-up policies, especially if your business is reliant on technology. This is just one of the ways that you reduce risk. Lower risk is not just good for your blood pressure, but good for acquirers too – low risk = high value…
Out of Office – The Right Way
An out-of-office email isn’t just polite… it’s professional.
👍 Good: Be specific about your return date and who to contact in your absence. Keep it confident, not apologetic.
✅ Better: Work towards a situation where you are not the main point of contact for anything or anyone outside of your own organisation. If the day-to-day runs without you, any future acquirer will see a low-risk business that will require little intervention.
Set Boundaries (And Stick to Them)
Decide how ‘off’ your holiday really is.
👍 Good: Will you check emails once a day? Only answer urgent calls? Make the rules — and hold firm. You’ll recharge faster.
✅ Better: Running a business is a 24/7 activity, if you’re not doing it, you’re thinking about it. But eventually you will need to find your ‘off ramp’. Starting to implement a regular routine where you don’t check emails, don’t take calls and invest in something you love will help to ease that transition. Once a month, once a week, whatever works for you.
Pipeline Progress, Even When You’re Sunbathing
Leads and deals shouldn’t stall.
👍 Good: Automate follow-ups and keep your CRM humming. Delegate active negotiations where possible. Momentum means money.
✅ Better: There’s nothing more attractive to an acquirer than a business that is demonstrably growing and has potential for more. Think about how you can build that momentum into your business model and make sure you leave something in the tank for any acquirer.
Staff Know the Score
Your team needs clarity, not chaos.
👍 Good: Hold a quick briefing so everyone knows their role, key dates, and what success looks like while you’re away. Confidence breeds competence.
✅ Better: Regular team briefings and a clear management structure helps to keep everyone clear about roles and responsibilities. It’s also something buyers like to see… a well organised business means a low risk acquisition which will attract a higher value.
Future-Proof with Big Picture Thinking
A holiday is the perfect time to reflect. Is your business truly sale-ready? Could it run without you permanently? M&A success depends on that. Use the quiet moments to think bigger.
Ready to escape the office and think about building your exit plan? Speak to an experienced M&A Director at Entrepreneurs Hub.
We’re entrepreneurs and business owners like you, so we understand that selling your business is a difficult decision. So, we’ve built this offer to make things as easy as possible:
- A brief conversation, just to confirm we are able to help – your time is precious and so is ours…
- A 90-minute consultation with an experienced M&A Director where we will explore your business and your goals and give you our honest, unfiltered opinion on saleability and next steps…
- A fully researched and evidence-based valuation exercise (if appropriate) that will give you a benchmark valuation range that you can base real decisions on…
- A follow up discussion to discuss actionable next steps, whether or not you decide to work with us!
Email us at enquire@entrepreneurshub.co.uk to book your initial confidential discussion.
Are you a business owner looking to sell your company?
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FAQs – Selling Your Company
What is the best way to sell a business in the UK?
At Entrepreneurs Hub, we talk about five key areas that make the difference between success and failure when selling your business. Read more…
How much can I sell my business for?
Determining your business’s value is more than just calculating a number it’s complex with key factors, that said the basic equation is actually quite simple. Read more…
How long does it take to sell a business in the UK?
The timeline varies depending on the complexity of the deal and how ready the business is for sale. On average, the process takes around twelve months – sometimes less, sometimes more.
While preparing your business for sale, Entrepreneurs Hub conducts in-depth research to identify potential acquirers. You’ll have the opportunity to review and approve this list before we make any approaches. Once the business is fully prepared – often the most time-consuming step, we begin marketing it. Typically, you’ll start seeing initial interest within a few months, with follow-up meetings happening shortly after.
As these meetings progress – coordinated and facilitated by Entrepreneurs Hub, you’ll begin receiving initial offers. At this stage, we’ll help you assess the strategic fit between your business and potential buyers. When you decide to move forward with an offer, an exclusivity period begins, during which the acquirer conducts Due Diligence (DD).
The DD phase typically lasts two to three months, depending on the complexity of your business. Once complete, the sale is finalised, and you’ve successfully sold your company.
What’s the quickest way to sell a company?
Selling a business quickly is possible, but speed shouldn’t come at the expense of value or deal security Read more…
When is the best time to sell a business?
Selling your business is a major milestone, and the start of an exciting new chapter, whether that means new ventures or a well-earned retirement.
In our experience, the best time to sell is when you don’t need to – when your business is performing well – not necessarily tied to the calendar. That said, timing can still play a role.
Timing the Market
Strong economic conditions, sector growth, and buyer confidence boost valuations. Don’t wait for a “perfect” market – a well-prepared, well-performing business sells in any climate.
Plan Ahead (12–18 Months)
The best outcomes come from early planning: clean financials, solid forecasting and growth potential.
Spring & Autumn Are Active Periods
The M&A market is typically busier in spring and autumn while summer and winter tend to be slower due to holidays and year-end distractions. However, the unpredictability of deals and negotiations makes this hard to target. We do deals all throughout the year – the key is to work with someone who can keep driving the deal forward whenever it happens.
Financial Year- End
Selling your business well is a long process and aiming for your financial year-end milestone is a virtually impossible task. But it is worth bearing your financial year in mind as buyers will want to review the most up-to-date accounts available.
The best time to sell is when your business is ready, and you are too. With the right preparation and positioning the right timing follows naturally.
What’s the best way to sell a business online?
Yes, you absolutely can sell a business online. Many platforms specialise in connecting business sellers with buyers. Read more…