As a Canadian business owner with a company generating between $5 million and $50 million in annual revenue, deciding to sell your privately held enterprise is a big step. In this mid-market segment, share sales are common. They let buyers acquire the entire entity — including assets, liabilities and tax attributes — while often giving you favorable tax treatment, such as access to the lifetime capital gains exemption.

But the share purchase agreement that governs the deal is complex. As an M&A advisor with experience guiding owners through these transactions, I've seen how certain elements become negotiation battlegrounds. These points can affect your proceeds, risk exposure and post-sale life.

Drawing from market insights and deal trends in Canadian private M&A, here are the 10 most heavily negotiated elements in a share sale. Understanding them can help you prepare, set expectations and work with your advisory team to maximize value while minimizing liabilities. Every deal is unique, influenced by factors like industry, buyer type (strategic versus financial) and economic conditions. But these areas consistently draw attention from both sides