The Biggest Obstacles to a Good Business Sale And How To Fix Them

The Biggest Obstacle to a Good Business Sale Is Often YOU – the Business Owner

YES, YOU!

When it comes to selling a business, the single biggest obstacle is often not the economy, the market, or even the buyer. It’s the owner.

“How can that be?” you might ask. Let’s look at six of the most common mistakes owners make when selling their business – and how you can avoid them. Sidebar: Ready to See If Your Business Is a Freedom Machine?

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O.K. now let's look at the most common mistakes...

1. The Business Relies Too Heavily on You

If your business only works because you work, then buyers see risk. They ask: “What happens when the owner leaves?”

Fix it: Start transferring knowledge, responsibilities, and decision-making to managers and documented systems. A buyer should feel confident the business will keep running without you.

2. You Work in the Business, Not on the Business

Long hours may keep things afloat, but they don’t build a saleable business. Buyers want something scalable, not something tied to the owner’s stamina.

Fix it: Step back. Focus on strategy, systems, and leadership. A business that runs smoothly without you on the tools is far more valuable.

3. Systems and Processes Are in Your Head

If your processes only exist in your brain, the business is fragile. Buyers need to see consistency and repeatability.

Fix it: Document everything – from sales processes to supplier contracts. Think of systems as assets: the more robust they are, the more attractive your business becomes.

4. Key Relationships Belong to You, Not the Business

If clients and suppliers only deal with you, then the business has little value without you. Buyers see this as a major red flag.

Fix it: Broaden the relationship base. Involve other team members in managing key accounts. Encourage clients to see the business as their partner, not just you.

5. Family Members or Friends in Key Roles

While loyalty is admirable, having family or friends in pivotal positions can worry buyers. They may fear those people will leave when you do – or that their roles aren’t based on performance.

Fix it: Professionalise your team. Ensure roles are filled by qualified people, not just trusted ones. If family members are genuinely the best fit, make sure their roles are clearly defined and justifiable.

6. You Can’t Let Go

Perhaps the toughest obstacle of all. Many owners see their business as their “baby” – something they built, nurtured, and grew. Letting go feels personal, not commercial. But holding on too tightly can cause you to reject good offers or sabotage negotiations at the last minute.

Fix it: Prepare yourself emotionally, not just financially. Have a vision for life after the sale – whether it’s retirement, another business, or personal pursuits. The more you can see a positive future beyond ownership, the easier it is to let go.

The Bottom Line

Most business sale problems don’t come from the market or the buyer – they come from the owner. The good news? These obstacles are fixable.

Start preparing early. Systemise your operations. Shift relationships to the business. Clean up your financials. And most importantly, prepare yourself for the transition.

Remember:
A business that is ready to sell is also a business worth keeping. But if you’re not prepared, the biggest deal of your life could easily slip through your fingers.

Ready to See If Your Business Is A Freedom Machine or a Job?

Take the quick quiz - Is Your Business A 'Freedom Machine' Or A Job? – it’s a quick, free tool that gives you a personalised score.

👉 Click here to get your score