Aspect Legal Managing Partner Joanna Oakey features in Bsale Magazine, unpacking a challenge she sees far too often in SME business sales:
When a “tax-effective” or supposedly “smarter” deal structure quietly turns a sale into something more complex, risk-heavy and emotionally draining than anyone expected.
In the article, Why the ‘Smarter’ Deal Structure Often Makes a Sale Feel Harder, Joanna explains how well-intentioned advice — particularly around share sales versus asset sales — can create unintended consequences when advisers overlook the broader legal and commercial realities early in the process.
She draws on real transaction experience to show how structure decisions influence:
Risk allocation
Buyer appetite
Due diligence intensity
Emotional strain on both sides
Her core message is simple: a technically clever structure doesn’t automatically produce a smoother sale.
If you choose structure without considering risk, buyer expectations, and deal dynamics, you often make the transaction harder — not smarter.
For many business owners, the structure of a sale is framed as a technical decision. But as Joanna explains, structure directly affects:
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the scope and intensity of due diligence
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the warranties and personal exposure a seller carries
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the buyer’s risk appetite and negotiating behaviour
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and ultimately, how smooth (or painful) the sale process feels
Drawing on a real-world transaction, the article highlights a common scenario.
A sale that should have been straightforward becomes difficult — not because of the business, but because expectations were not set early.
Joanna’s key message is clear.
Deal structure is not just about tax outcomes. It is also about risk, process, and the lived experience of the sale.
For business owners, accountants, and advisors, this is a timely reminder.
The “best” structure on paper is not always the best structure in practice.
If you’re planning a business sale — or advising someone who is — this is essential reading before structure decisions are locked in.
JOANNA OAKEY
Managing Partner Award-Winning Commercial Law Firm, Aspect Legal
Podcast Host – The Deal Room Podcast & Talking Law
Best-selling Author – Buy, Grow, Exit: The Ultimate Guide to Using your Business as a Wealth Creation Vehicle
As an award-winning commercial lawyer and Managing Partner of Aspect Legal, Joanna Oakey has advised thousands of businesses and their owners.
She works with them at every stage — from acquisition, to growth, to exit.
If you’d like more info on anything Joanna has discussed in this article, get in touch with Joanna via:
LinkedIn, Email ([email protected]) or visit : AspectLegal.com.au
