Family business succession across borders — where does doing it myself start to cost money?
Some of it, yes — and we will say so on the call if that is the honest answer. The parts that are worth paying for are the ones where a missed election, a missed deadline or an unverified threshold costs more than the fee: freezes, family trusts and share reorganisations that are efficient domestically can create taxable events or reportable structures abroad.
What if I have already filed and got it wrong?
That is a common starting point. We re-derive the position, identify whether an amendment or a disclosure route is the right vehicle, and tell you which one preserves the relief that is still available. The order matters more than the speed.
How long will it take?
It depends on the documents rather than on us. Once the pack is complete most filings turn around inside a fortnight; anything that needs a certificate from a tax authority runs on that authority's timetable, which we tell you at the start rather than at the end.
Can I freeze my company shares if my children live abroad?
You can carry out the reorganisation, but the question that matters is what the other country makes of it. A freeze is designed to fix the present value in the founder's hands and let future growth accrue to the next generation, and domestically that is achieved without an immediate tax cost. A system abroad may not recognise the same deferral, may treat a step in the reorganisation as a realisation, or may treat the resulting structure as reportable by the successor who lives there. Establish where each intended successor will be resident before the steps are designed, not after they are executed.
Will a family trust create reporting for my children overseas?
It often will. A family trust is an ordinary part of a domestic succession plan, and in a number of other systems a beneficiary or trustee who lives there carries reporting obligations in respect of a foreign trust, sometimes substantial ones. Those obligations can attach to people who had no say in the structure and who may not know it exists. Before a trust is settled or a beneficiary class is drawn, it is worth listing where each likely beneficiary and trustee will live, and treating the answer as a design input rather than something the successors discover later.
Does the other country recognise a Canadian rollover?
Recognition is decided by the other system on its own terms, and it does not follow from the deferral being available here. The two questions are genuinely separate: whether the reorganisation defers tax under domestic rules, and whether the country where a successor or a shareholder is resident treats the same transaction as a realisation. Where the answers differ, the result is tax arising in one place with no matching event in the other, which is usually the worst version of the outcome. That analysis belongs at the planning stage, because the sequence of steps is often what determines it.
Should the freeze happen before or after my son emigrates?
The order matters, and in a cross-border plan it frequently matters more than the structure itself. A step carried out while a successor is resident in one country can have an entirely different character from the same step carried out after the move, both for the tax that arises and for what has to be reported afterwards. There is no general rule about which side of the departure is better, because it depends on the destination system and the assets involved. What is general is that the question should be asked while both orderings are still available.
What happens to a family trust when a beneficiary moves abroad?
The trust does not change, but its consequences do. A move can bring a beneficiary within a foreign reporting regime for the trust, can affect how distributions to that beneficiary are treated, and in some structures can bear on the residence or administration of the trust itself where trustees are involved. The move is rarely reported to anyone who would notice the tax consequence, so these situations usually come to light years afterwards. A review at the point a beneficiary or trustee relocates is far cheaper than the correction that follows from leaving it.
Can one child take over the business while the others live abroad?
That is a common shape and it can be done, but it puts two different problems in the same plan: transferring the operating business to the successor who is here, and providing fairly for those who are not, without handing them an interest that creates reporting where they live. Those pull in different directions, since the instruments that equalise value among siblings are often exactly the ones a foreign system treats as a reportable holding. The workable plans usually separate the two questions and solve each on its own terms.
Do Canada and the United States share tax information?
Yes, through more than one channel. The treaty has an exchange-of-information article that supports both routine and on-request exchange. Separately, an intergovernmental agreement has Canadian financial institutions identify US-reportable accounts and report them to the CRA, which passes them to the IRS, with the reverse flow for Canadian residents. Most other country pairs use the Common Reporting Standard for the same purpose. See FATCA reporting.
What happens if I have not filed for several years?
Missed years are handled as one package, not one at a time, because the route chosen for the first year determines the relief available for the rest. Each country has a disclosure or relief programme with its own conditions, and entering the right one — before the authority contacts you — is usually what keeps penalties down. Filing quietly outside a programme forfeits that protection. See catching up on missed returns.
