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Question of Week

Buying or selling a business comes with plenty of questions. Each week, we'll highlight a question we've received from a business owner or buyer and provide our expert answer. Chances are, if one person is asking it, many others are wondering the same thing.

How Do I Know If It's the Right Time to Sell My Business? Sarah Moose Jaw, Saskatchewn August 2 2026

Thanks Sarah

If you've ever stood in your office staring out the window and wondered whether it's time to sell your business, congratulations—you've joined a very large club.


The truth is that most business owners don't wake up one morning and suddenly decide to sell. The idea usually sneaks up on them. It might start with a difficult employee issue, another government regulation, a customer complaint that arrives five minutes before closing, or the realization that your "temporary" 70-hour workweek has lasted 15 years.


Many owners think the best time to sell is when they're completely finished with the business. Unfortunately, that's often the worst time to sell.

Buyers don't like desperation.


If you're exhausted, profits are declining, key employees are leaving, and you're counting the days until retirement, buyers can usually sense it. They may not know what's wrong, but they know something feels off.


The best time to sell is usually when the business is doing well.


Think of it this way. If you were selling your house, would you list it after the roof started leaking, the furnace quit working, and the dog chewed through the kitchen cabinets? Probably not.


Businesses work the same way.


Buyers are purchasing future opportunity. They want to see strong financial performance, stable operations, reliable employees, and room for growth. They are often willing to pay a premium for businesses that appear healthy and well-managed.


There are also personal considerations.

Perhaps you want to retire.

Maybe you're ready for another challenge.

A change in partnership business or personal

Maybe your spouse wants to travel while you're still young enough to enjoy airport food and hotel mattresses without requiring a chiropractor afterward.


There is no perfect age and there is no perfect time.


The real question is whether your business is ready to be sold.

Ask yourself:

  • Are profits stable or growing?
  • Could the business run without me for several weeks?
  • Are my financial records organized?
  • Do I have documented systems and procedures?
  • Is there a management team in place?
  • What does my business look great from the outside in?

If you answered "no" to most of those questions, don't panic.


Many successful business owners are excellent operators and terrible documenters. They know how everything works, but it's all stored in their head like a giant filing cabinet.


The problem is buyers cannot purchase what's in your head.

They need systems, procedures, and evidence that the business will survive after you're gone.


The owners who achieve the best outcomes usually begin preparing 6 months to three years before they actually sell. They improve profitability, clean up financial statements, reduce owner dependence, and strengthen management.


When they finally decide to go to market, buyers see a valuable business.

Not a job disguised as a business.

That's a huge difference.


The smartest question isn't, "Am I ready to sell?"

It's "Would a buyer be excited to buy what I've built?"

If the answer is yes, you may be closer than you think.

Animated woman thinking about business selling questions.

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