The situation
By the time Mai called our office, her son Mohamud had already spent close to a year trying to negotiate his separation from Edgardo directly, without a lawyer, and the one piece of the file neither of them could agree on was a block of minority shares Mohamud held in a mid-sized engineering firm where he worked as a sales director. The shares had come to him years earlier as part of a compensation package, a small percentage stake with no seat on the board and no say over whether the company paid dividends or reinvested its earnings instead.
Mohamud and Edgardo, a professional engineer, had built a household income in the range of one hundred fifty to three hundred thousand dollars a year between them, along with equity in their home and a modest set of joint investments. Most of that was straightforward to divide. The shares were not. Edgardo's position, repeated across months of kitchen-table conversations, was that the shares were worth whatever the company's most recent internal valuation said they were worth, a number used for tax purposes that assumed a full, controlling sale of the business. Mohamud's position was that the number was fiction, since he could not sell his shares to anyone outside the company, could not force a dividend, and had never received a payout in the eight years he had held them.
Neither side moved. Mohamud, uncomfortable with confrontation and increasingly exhausted by a negotiation that circled the same disagreement every few weeks, had started talking about simply agreeing to Edgardo's number just to be done with it, even though it would mean handing over cash or other assets against a value he did not believe the shares actually had.
Mai, watching her son's stress mount over months of visits and phone calls, was the one who eventually said the negotiation needed a lawyer in it, not two people who loved each other once trying to guess at company law from opposite sides of a kitchen table. She made the appointment herself and brought Mohamud in, later than either of them would have liked, to finally get an answer grounded in something other than each side's own certainty.
Part of what had kept Mohamud from seeking advice sooner was a genuine belief that lawyers would make the split worse, not better, turning a difficult but civil conversation into an adversarial one. He and Edgardo had managed to divide the furniture, agree on a schedule for their shared dog, and split the joint investment accounts without much friction. The shares felt like the one sticking point in an otherwise workable process, and Mohamud kept hoping one more conversation would resolve it. By the time Mai intervened, roughly ten months of that pattern had passed, with the disagreement no closer to settled and both men increasingly frustrated with each other over a number neither of them could actually verify on their own.
The legal question
The question at the centre of the file was a familiar one in family property disputes involving private company shares: what does it mean to value an asset that has a number on paper but no real way for its holder to access that number in cash. Ontario's family property regime requires shares like Mohamud's to be included and valued as part of the property divided at separation, but valuation is not the same as liquidity, and the two had been treated as identical throughout the informal negotiation.
A controlling shareholder can typically sell the business, direct dividends, or otherwise convert paper value into cash more or less at will. A minority holder without board influence, in a private company with no public market for its shares, usually cannot do any of those things unilaterally. The company's own valuation, prepared for tax and internal compensation purposes, had been built on assumptions, such as a full sale of the business, that had nothing to do with what Mohamud's specific slice was actually worth to someone in his position, holding a small non-controlling piece with no exit available.
This distinction matters because it affects both the number itself and how any resulting payment gets structured. A share that cannot be sold quickly should usually be valued with a discount reflecting that illiquidity, and a spouse who is asked to pay out the value of an asset they cannot easily convert to cash has a legitimate interest in spreading that payment over time rather than producing it all at once. Edgardo's position ignored both points, treating the internal valuation as a clean, liquid number and expecting Mohamud to satisfy it as though the shares could be sold tomorrow.
There was also a question of what evidence would actually resolve the disagreement. Neither side's own opinion was going to settle it. What the file needed was an independent business valuation, prepared specifically for the purpose of a family property division rather than borrowed from the company's tax filings, and a clear-eyed look at the shareholder agreement itself to confirm exactly what restrictions applied to a sale or transfer of Mohamud's shares.
There was a fairness argument running underneath all of this that both men were, in different ways, gesturing at without naming clearly. Edgardo's underlying worry was that Mohamud would quietly keep an asset worth far more than he was admitting, walking away from the marriage with a hidden upside. Mohamud's underlying worry was the mirror image: that he would be forced to pay out real money today against a value he might never actually see, since the shares could sit dormant for years without a dividend or a sale opportunity. Both concerns were legitimate in the abstract. Resolving the file meant finding the number that actually reflected Mohamud's position, not the number that felt safest to either side emotionally.
What we did
- Reviewed the company's shareholder agreement to confirm the restrictions on Mohamud's shares. The agreement barred any sale to an outside party without board approval and gave the company a right of first refusal at a formula price well below the internal valuation Edgardo had been citing, confirming in writing, for the first time, what Mohamud had been arguing verbally and without documents for months.
- Retained an independent business valuator experienced in minority interests in private companies. Rather than relying on the company's internal number, we engaged a valuator to produce a report specific to Mohamud's actual holding, applying a discount for both his lack of control and the shares' limited marketability under the agreement's transfer restrictions, rather than the full enterprise value assumed by a sale of the whole business.
- Compared the independent valuation against the figure Edgardo's side had been proposing. The gap was significant, and having two defensible numbers side by side, one grounded in the restrictions that actually applied to Mohamud's shares and one borrowed from an entirely different purpose, gave us a concrete basis to move the negotiation away from competing assertions and toward evidence.
- Explained the discounted valuation to Edgardo's side in terms tied to the shareholder agreement itself, not just our client's preference. Because the restrictions were contractual and documented, this was not a matter of opinion. It reframed the conversation from a dispute over what Mohamud wanted to believe to a dispute over what the governing document, which Edgardo had never actually read, said in writing.
- Negotiated a structured payout rather than insisting on a single revised lump sum. Given that Mohamud's own liquidity was limited by the same illiquid nature of his shares, we proposed dividing the corrected value over a period of years, secured against other assets, so Edgardo received the full agreed value without forcing Mohamud to liquidate other property to fund an immediate payment.
- Addressed the company's right of first refusal as part of the settlement terms. Because any future sale would still be constrained by the company's formula price, we built language into the separation agreement acknowledging that constraint, so neither party was later surprised by a discrepancy between the agreed value and what the shares could actually fetch if Mohamud ever sold them.
- Brought both accountants into a joint conversation to reconcile the tax treatment of the payout. Structuring the division to minimize unnecessary tax consequences for both sides required coordination beyond the family law file itself, and getting the accountants speaking directly to each other, rather than relaying figures through two lawyers, avoided a second round of disagreement layered on top of the first.
- Documented the whole valuation methodology in the separation agreement itself. Rather than leaving the reasoning behind the discounted figure unrecorded, we set out in the agreement how the number had been reached, including the discount rate applied and the restrictions relied on, so neither side could later reopen the question on the basis that the figure looked unexplained or arbitrary.
The outcome
Edgardo's side ultimately accepted the independently valued, discounted figure rather than the company's internal number, once the shareholder agreement's transfer restrictions were laid out plainly and confirmed by a qualified valuator. It was not the number Edgardo had spent months insisting on, and it represented a real concession from the position taken at the outset of the informal negotiation.
It was also not the outcome Mohamud might have hoped for either. The discounted value was still a meaningful sum, and paying it out over a structured schedule meant carrying an ongoing financial obligation for several years rather than closing the book on the shares in one transaction. Neither side walked away with everything they wanted, which is generally the sign of a genuine compromise rather than a clean win for one party.
What the structured schedule did accomplish was proportionality: Mohamud paid out a figure that reflected what his shares were actually worth to him, not an inflated number borrowed from a valuation built for an entirely different purpose, and he did so without being forced to sell other assets under pressure to raise cash quickly.
The joint conversation between accountants also mattered more than either side expected going in. Structuring the payments to land in a way that avoided an unnecessary tax hit for Mohamud, without shifting an unfair burden onto Edgardo, took several rounds of back and forth once actual numbers were on the table, and it was the kind of detail that a purely informal negotiation between two separating spouses would never have caught.
Mai's decision to push her son toward proper legal advice, months into a stalled negotiation, is what turned an unresolved standoff into a settlement both sides could actually live with, even if neither would call it a complete win. The shareholder agreement had been sitting in a drawer the entire time the two men argued informally; it took a lawyer reading it, rather than either spouse guessing at what it said, to move the file to a documented, defensible number both sides could sign.
What you can learn from this
- A share's value on a company's internal or tax valuation is often not the same as its value to a minority holder with no control and no market to sell into. Ask what discount applies before agreeing to a number.
- Read the shareholder agreement before negotiating over private company shares in a separation. Transfer restrictions and rights of first refusal are contractual facts, not points of opinion.
- An independent valuation prepared specifically for a family property division carries more weight than a number borrowed from a company's tax filings or compensation records.
- If an asset cannot easily be converted to cash, a structured payout over time is often fairer to both sides than insisting on a single lump sum.
- Informal negotiation between separating spouses can stall indefinitely on a genuinely technical question. Bringing in advice earlier, rather than after months of disagreement, usually shortens the path to resolution.
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