A Verbal Yes on Conditions Nobody Wrote Down

The situation

The house was going to sell for roughly $480,000, and Joost, who worked as a hotel front-desk supervisor and had never administered an estate before, needed that number to hold. His aunt had left him as executor of a modest Toronto property, and the sale proceeds were meant to cover her outstanding debts, a small bequest to a cousin, and the remainder split between Joost and his brother Delroy, the estate's two named beneficiaries. There was no room in the numbers for the deal to collapse and no time to relist if it did.

The buyer, Winston, had made his offer conditional on financing, with a deadline by which he needed to either confirm his mortgage was approved or waive the condition and commit to closing. Joost had been told by the lawyer who first opened the file that Winston's agent had called to say the condition was waived, that everything was fine, and that the deal was moving to closing. That call happened four days before the deadline. No letter followed it.

The original lawyer on the file left practice partway through the transaction for reasons unrelated to Joost's file, and the estate's file was transferred to our office with roughly three weeks left before closing. When we reviewed what had actually been documented, we found the closing file contained no written waiver of the financing condition at all. There was a note in the file summarizing the phone call, written by a legal assistant, but nothing signed by Winston or his lawyer confirming the condition had been formally waived.

That distinction mattered more than it might sound. An agreement of purchase and sale that is conditional does not become firm just because someone says it is fine on the phone. Until a condition is waived in writing and delivered to the other side by the deadline the contract sets, either party can usually treat the condition as unmet and the deal as dead. If Winston's mortgage fell through in the following weeks, he would have grounds to argue the deal had never become binding, and Joost's estate would be left trying to relist a property with a shrinking window before beneficiaries expected their distributions. This is a common trap for first-time executors, who often assume that once an offer is accepted, the legal mechanics of a closing are largely automatic from that point forward.

What the review found

We started by pulling every document in the file and lining up dates against the contract's deadlines. The financing condition had a clear cutoff, and the phone call the previous lawyer's assistant had noted came before that cutoff, which was some reassurance. But a call before the deadline is not the same as a waiver delivered before the deadline in the form the contract required. Ontario real estate transactions generally expect waivers of conditions to be in writing, signed, and delivered to the other party or their lawyer, precisely so that disputes like this one do not happen months later when memories differ.

We also found that Winston's own lawyer's file, which we requested through the closing solicitor exchange that is routine before a deal closes, showed the same gap. Their file had no signed waiver either, only a similar internal note about a phone call. That told us the miscommunication was not one-sided. Both offices had treated the verbal exchange as sufficient at the time and moved on without following up, which is a more common gap in busy transaction files than either side likes to admit.

The harder question was what this meant for Joost. If Winston's financing had come through cleanly and he intended to close regardless, the missing paperwork was a formality we could fix retroactively with his cooperation. If Winston's financing had fallen through, or if he had cooled on the deal for any reason, he now had a real argument that the condition had never been properly waived and that he could walk away from the deal without penalty. We could not know which scenario we were in until we approached Winston's side directly, and every day we spent confirming the gap was a day closer to the closing date the estate could not afford to miss.

We also checked whether Joost, as executor, had done anything that could be read as accepting the deal as firm in a way that might help or hurt his position, such as incurring costs in reliance on the sale. He had begun arranging a moving company for his aunt's remaining belongings and had told the estate's other beneficiaries a distribution date based on the expected closing. None of that created a legal waiver on his side, but it meant the estate had real exposure if the deal unwound. Gaps like this one tend to surface only when someone with a reason to scrutinize the file closely, whether a new lawyer taking over or a dispute that forces a second look, actually goes looking for them.

What we did

1. Confirmed the mortgage status directly with Winston's lender contact, routed formally through his lawyer rather than through an informal call to the branch, because we needed a reliable, verifiable answer before deciding how hard to push on the missing paperwork. Going through counsel rather than approaching the lender ourselves also avoided any appearance of interfering with the buyer's own financing arrangements. This told us his financing had in fact been approved on terms close to what he had originally sought.
2. Requested a formal written waiver from Winston's lawyer immediately, framing the request as tidying up an administrative gap in the closing file rather than as an accusation that anyone had acted improperly. Approaching it as routine paperwork rather than as the opening move of a dispute made cooperation far more likely from a buyer who, on the facts we had, had no real reason to walk away from a deal he intended to close.
3. Documented the entire gap in a detailed memo to the estate's file, setting out exactly when the phone call happened, what the previous lawyer's note said, and what remained missing, so that if a beneficiary later questioned why the deal took an extra two weeks to firm up, there was a clear, contemporaneous record showing the delay was about paperwork we caught, not about any decision Joost made as executor.
4. Negotiated a short closing extension with Winston's side to give both offices enough time to exchange the missing documentation properly and without pressure, since rushing a signature under deadline pressure risked creating a second flawed or ambiguous waiver instead of a clean one that would actually hold up if the deal were ever challenged. A rushed fix would have solved nothing.
5. Obtained the signed, dated waiver from Winston in the form the agreement of purchase and sale actually required, and confirmed its delivery to our office in writing, closing the gap that had existed since the original phone call four days before the original financing deadline. Only once that document was in hand did the deal's status stop being a matter of interpretation.
6. Reviewed the rest of the closing file line by line for any other conditions handled informally by the previous lawyer, since one undocumented waiver raised the possibility there were others, and found one minor title matter that had also been resolved by phone without a written follow-up, which we then confirmed in writing as well so the closing file would not carry two unresolved gaps into the same transaction.
7. Advised Joost in plain, non-legal terms about what the estate's real exposure had been during the roughly two weeks the deal's status was genuinely uncertain, including what could have happened if Winston had changed his mind, so that Joost understood the risk himself and could later explain to the estate's beneficiaries, in his own words, why part of the distribution timeline had slipped.
8. Contacted the previous lawyer's former practice for the underlying notes on the phone call, which took two follow-up calls to track down after the office had already begun winding down its files. A first-hand written record of what was actually said on that call, even reconstructed after the fact, was better evidence than relying on a secondhand summary if the waiver's validity had ever actually been challenged.
9. Set a firm internal deadline for closing out the outstanding items and communicated it clearly to both Winston's lawyer and the estate's beneficiaries, so the extension did not quietly slide further the way the original deadline had. That gave the estate's distribution timeline a new, reliable date to plan around, rather than leaving Joost telling beneficiaries the sale would close 'soon' for a second time.

The outcome

The sale closed at the original price of roughly $480,000, with Winston's financing intact and the written waiver properly on file. In the end, nothing about the substance of the deal changed. Winston never had any real intention of walking away, and the gap turned out to be exactly what it looked like: two offices that treated a phone call as good enough and moved on.

The cost was in time and certainty, not dollars. The closing extension pushed the date back by about two weeks, which meant Joost had to tell the estate's beneficiaries that their distributions would be delayed, and he had to unwind and rebook the moving arrangements he had made in reliance on the original date. Those were real inconveniences for an executor who had no experience with this kind of file and had been told, in good faith by the previous lawyer's office, that everything was settled.

We were candid with Joost that this outcome was not a clean win. The estate absorbed a delay and some avoidable stress that a properly documented waiver, delivered on time in the first transaction, would have prevented entirely. What limited the damage was catching the gap early, verifying the buyer's actual financial position before raising it, and fixing the paperwork calmly instead of treating it as a confrontation. Had Winston's financing fallen through, or had he simply changed his mind about the purchase, the estate could have been facing a relisting process with none of the certainty Joost needed.

Delroy, as the other named beneficiary, took the delay in stride once Joost explained what had actually happened, but it was still an uncomfortable conversation for an executor to have in his first months handling the file. Joost later said the two weeks of not knowing whether the sale would hold were harder on him than anything else in administering the estate, including the funeral arrangements. That is a common reaction among first-time executors, who often expect the legal steps of a sale to be routine once an offer is accepted, and are unprepared for how much can still turn on a single undocumented phone call.

What you can learn from this