Usually, everyone focuses entirely on the science of selling a business—the numbers and data, the legal documents, and the technical due diligence details. This all matters, of course.
But the real story of business sales almost always unfolds in the emotional undercurrents.
After more than two decades of active deal-making, here is my take on the psychological and human elements—the "art part"—that have a far bigger impact on a small business sale than most people ever plan for or realize.
In Australia, businesses are bought and sold in two distinct environments, and human psychology plays out very differently in each.
1. The Listed Marketplace
Think of popular public platforms like Seek Business or Eden Exchange. I regard them as a digital lolly shop for small business buyers. Here is a quick look at how this marketplace typically rolls:
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The Cycle: An owner wants to sell quickly, so they approach a traditional business broker. The broker takes the listing (the more listings they hold, the better for them) and undertakes some limited, basic preparation.
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The Strategy: The owner pays to advertise to a broad target market, but it is often a lucky dip scatter-gun approach.
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The Reality: The listing goes live. Initially, you get a few casual inquiries, but then they dry up.
Where there has been no upfront work done to identify a pool of the most likely buyers, your sale price is the only lever left to pull. When inquiries slow down, a price drop becomes the broker's recommended strategy. This rarely helps, meaning the owner’s time is burned while the stress of not selling climbs.
There are two primal emotions at play in this public arena:
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Hope: Sellers list their businesses at an artificially high price, often unencouraged by brokers, just to "test the market." Innocently, they think, Why not? It feels good... you never know... Then time slips away and reality bites.
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Trust: Sellers trust that mass advertising alone will do the heavy lifting. No matter how glossy the advertisement is or how many "hits" the business-for-sale site gets, it rarely surfaces the right strategic buyer.
What to Do Differently in the Listed Market:
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Run the Pub Test: Dig deeper to find out what similar businesses are actually selling for. Ask yourself the ultimate objective question: Would I realistically pay this price for my own business if I were an outsider?
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Be Realistic About Timelines: Even if you set a fair market price, you must allow ample time for qualified buyers to arrange funding and due diligence. It is fine to test the market for a short period at 20% above your target price, but listing at 50% above is simply wasting precious market momentum.
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Don't Just Rely on Adverts: Actively compile a list of highly likely, logical buyers and execute a proactive, discreet approach to target them directly.
2. The Off-Market World
In B2B and industrial sectors, this is where the majority of valuable deals happen. However, off-market transactions are occurring across professional service and knowledge-based sectors with increasing frequency.
The off-market framework moves quite differently:
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Larger corporate players or private equity firms quietly monitor the industry and approach target businesses directly.
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The business owner is often flattered or blindsided by the unexpected interest.
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Financial and operational information is either over-shared too early out of excitement, or defensively withheld—both of which can be immediate deal-breakers.
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The power dynamics instantly feel lopsided to the business owner.
The core emotions at play here shift to:
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Power: Corporate buyers definitely bring commercial clout. However, sellers frequently forget that they hold immense leverage too—they own the asset the buyer wants.
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Ego: Everyone brings ego to a negotiation table. You need to use it wisely; mismanaged ego routinely ruins perfectly viable deals.
What to Do Differently in the Off-Market World:
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Rebalance the Power: Ask the buyer tougher, better questions right from the first contact. An acquisition inquiry is not a one-way job interview; you are evaluating them just as much as they are evaluating you.
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Humanize the Deal: Acknowledge each other's distinct strategic objectives and intent early. There are disciplined, high-quality acquirers out there who will work transparently with a founder to construct a transaction that works genuinely well for both parties.
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Keep Advisors Under Control: Do not let your advisors overplay their hand or inflame your ego, especially if you and the buyer need to work together productively during a post-sale transition period.
"Some advisors intentionally feed unrealistic hopes or stoke unnecessary conflict. The best advisors challenge your thinking, ask the hard questions, and keep the process grounded."
A 4-Step Emotional Preparation Checklist
If you are planning an exit, you must prepare your mindset alongside your financials:
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Accept the Trade-Off: Understand that there is always a direct trade-off between achieving a premium price and your time to settlement.
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Be Honest with Yourself: Know exactly why you want to sell, and ensure you are genuinely ready to hand over the keys.
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Define Your Non-Negotiables Early: Establish a clear list of non-negotiable deal terms—including personal or cultural expectations—long before negotiations start. Knowing what a good deal looks like to you reduces transaction anxiety later.
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Choose Truth-Telling Advisors: Choose professional advisors who are committed to keeping you accountable, not just agreeable. Ask them directly: "Will you tell me the hard truths, even when I don't want to hear them?"
The Bottom Line
It isn’t fluffy or soft to accept that emotions like hope, fear, trust, ego, and power heavily dictate how we, our advisors, and potential buyers behave. In fact, it is deal-critical.
If you are planning a business sale, or advising an owner who is, it is time to start actively mastering the art part of the transaction—not just the spreadsheet science.
All the best, Michael
Your Next Step: Get an Objective, Grounded Sounding Board
Selling your business is likely one of the most emotional financial milestones of your career. Navigating the competing tensions of price, ego, and timeline requires an advisor who keeps the process completely grounded in reality.
Whether you are trying to benchmark a realistic valuation for the listed market, or you've been approached out of the blue by an off-market buyer and need to rebalance the power dynamics, let's talk.
Call me directly or drop me a line for a plain-speaking, completely confidential advisory discussion.
Talk confidentially with Michael
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