Why Do You Want To Sell?

The most important question to ask a potential sellers

The most important question to ask a potential sellers:

"Why do you want to sell?"

Selling your business is a big deal. As the buyer it's critical you understand the driving force behind this decision.

There are 3 primary freedoms they are looking to achieve are: financial, time or travel


The business could be losing money causing a huge financial stress on the owner. This stress could lead to health and marriage issues. What started as a way to create extra income has turned into a money pit. 

The business could be very successful. At this point they are looking to cash out to fund the rest of their lives. 


Businesses, like children, need a lot of attention. Once the the owner has achieved financial freedom, they want time freedom. They put in years of hard work and now they want to retire, giving them freedom to spend time doing what they enjoy with people they love. 

Even if the business is running smoothly they know at some point it will hit a rough patch, forcing them to step in to get the business back on track.


Similar to time, some owners want to travel to Peru, go on a cross-country road trip with the family, or totally relocate to a new state. 

They may feel handcuffed by the business, not wanting to travel too far or for too long in case of an emergency.

The Questioning Framework

At first the seller will give you surface level reasons such as: 

  • I want to retire

  • I can’t dedicate the time / pursuing another opportunity

  • I’m relocating to a new state

The initial reason is just the tip of an iceberg. You need to dig deeper using follow up questions and challenging them.

Here is the framework I use:

  1. Why do you want to sell? 

  2. Congratulate them on their business success

  3. What are they doing next after selling?

  4. Challenge them on NOT selling & keeping the business

  5. Listen for the emotional reasons, dig deeper with why/what/how questions  

Me: Why do you want to sell? [1]

Seller: I want to retire

Me: That’s great! You deserve it after all these years in the business. Remind me, how long have you been in the business? 

Seller: 15 years

Me: That's impressive, you've built a great business. [2]

Me: What does retirement look like? Do you have any plans yet? [3]

Seller: Yes, my wife & I plan on traveling across the country

Me: That sounds awesome ( ask some follow up questions to get into details on the trip, where they are going, who they are going with, etc. get them excited about the new opportunity )

Me: I’m curious, why not keep the business so the cash flow can cover all your expenses while you travel the country? [4]

Seller: The business requires too much time & attention. I’m afraid every time the phone rings it’ll be a fire to put out or someone just quit. I want to relax and enjoy life.

Listen for emotional reasons, such as fear, stress it has been putting on them, worried about retirement, etc.

Why Challenge on NOT Selling

The sales process is like a pendulum. If you push hard to sell, sell, sell the prospect will often come back stronger in the opposite direction.

If you push with questions on why NOT to sell, they will often come back with all the reasons they WANT to sell.

Why not pass the business down to their children?

Why not sell to someone internally?

Why not list the business with a broker? (if you going direct to seller)

The goal is to get the seller to anchor down on selling. The process is so much easier once they are 100% committed to selling. A 50/50 seller is slow to respond and will waste your time, money & energy.

Deal Tracker

Some acquisitions take months or years to close. Put together a deal tracker to log all conversations & details:

  • Reason why are selling

  • What they are going to do after they sell

  • Reasons for not keeping the business

  • Cash flow, historical sales, estimated purchase price, etc

  • Next actions w/ due dates

We use Clickup but a simple Google doc works too

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Business with Beers

Every week on my podcast I bring you the stories of entrepreneurs about building their business, wealth & passive income.

See you again next week!


- Brian