Succession Planning

Transferring Your Business to the Next Generation — Without Handing a Third of It to the CRA.

Our office has extensive expertise in designing succession planning structures to facilitate optimal tax planning, long-term efficient use of capital and other business resources, while ensuring compliance with the Canadian Income Tax Act.

When a private company changes hands — to your children, to a key employee, or to a buyer you know personally — the Income Tax Act does not automatically treat that transfer the way you'd expect. Left unstructured, a sale or gift to a related party can be recharacterized as a taxable dividend instead of a capital gain, stripped of access to the lifetime capital gains exemption, or trigger an unexpected deemed dividend on redemption — turning what should be a rewarding transition into a costly one.

Succession planning re-engineers your corporate and share structure ahead of the transfer: choosing the right method for your situation, sequencing every step correctly, and documenting the transaction so it withstands CRA scrutiny.

This is not a simple share transfer you can do with a stock certificate and a handshake.
This is not a plan you can safely design after the transaction has already closed.
This is a citation-backed succession structure engineered around your corporation, your successors, and the outcome you're trying to protect.

How a Succession Planning Engagement Works

Every succession plan we design moves through three stages.

1

Comprehensive Succession & Tax Diagnostic

We start by fully mapping where things stand today, including:

  • Current corporate structure, share classes, and share capital
  • Fair market value (FMV), adjusted cost base (ACB), and paid-up capital (PUC) of your shares
  • Retained earnings, passive investments, and tangible property held inside the company
  • Whether your shares qualify for the Lifetime Capital Gains Exemption / QSBC status
  • Who your intended successors are, and their relationship, involvement, and readiness
  • Any other shareholders, and how a transfer affects their position

You can't design a tax-efficient transfer around a structure you haven't fully mapped first.

2

Succession Structure Design

Your plan is built as a fully documented package, selecting from the methods available to your situation:

  • Selection of a capital freeze, a qualifying intergenerational transfer, a structured buyout, or a combination of all three
  • A step-by-step transaction sequence, including any share exchanges, rollovers, or new holding entities required
  • Detailed footnotes citing the specific ITA provisions relied on
  • A figures appendix quantifying the tax outcome at each step

Every strategy is matched to your specific facts — not applied as a one-size-fits-all template.

3

Execution & Implementation Support

Your diagnostic gives you the plan. We support you and your successors through carrying it out:

  • Instruction letter for your corporate lawyer
  • Coordination with your successors, other shareholders, and family
  • A client-facing summary walking through the plan
  • Post-implementation filing support for you and the corporation

Your successors shouldn't have to interpret a technical memo while running the business.

The Tax Trap in an Unplanned Transfer

Without the right structure, transferring your business to family or a trusted successor can cost far more in tax than selling to a stranger.

When shares of a private corporation move to a related person — a child, a family trust, or a corporation they control — the Income Tax Act applies special rules aimed at preventing "surplus stripping": converting what would otherwise be a dividend into a lower-taxed capital gain. Here's how those rules can catch an unplanned transfer:

1

Dividend Treatment Instead of Capital Gains

A sale of your shares to a corporation controlled by a related party can be recharacterized so that the proceeds are taxed as a dividend rather than a capital gain — often roughly doubling the tax rate on the same dollar of value, and denying access to the capital gains exemption.

2

Paid-Up Capital Grinds

Where new shares are issued to a related party as part of the transaction, the paid-up capital of those shares can be reduced — "ground down" — to the paid-up capital of the shares given up, eliminating a return-of-capital option your successor might otherwise have relied on.

3

Deemed Dividends on Redemption

If shares are redeemed or repurchased by the company itself as part of funding the transition, the amount paid in excess of paid-up capital is deemed to be a dividend — not a capital gain — even where a sale to an arm's-length party would have qualified for capital gains treatment.

Left unplanned, a transfer to your own children can be taxed more heavily than a sale to a total stranger — the opposite of what most business owners expect.

Three Alternative Succession Planning Methods

Depending on your facts — your successors, your timeline, and how quickly you want to give up control — we typically design around one of these three approaches, or a blend of more than one.

A

The Freeze & Gradual Transfer

We use a section 85 rollover to exchange your common shares for fixed-value preferred shares, freezing the value of the company in your hands at today's number. New low-paid-up-capital common shares are then issued to your successor — directly or through a family trust — so all future growth in the business accrues to them from that point forward, while you retain the preferred shares, and the income and control rights attached to them, for as long as you choose.

B

The Qualifying Intergenerational Transfer

For a genuine transfer of your business to your children (or, depending on the structure, other qualifying family members), the Income Tax Act provides a path for the sale of your shares to a company controlled by them to be taxed as a capital gain rather than a dividend — provided specific conditions around control, management transition, and your successor's ongoing involvement in the business are met and properly documented. We test your facts against these conditions, structure the transaction to satisfy them, and file the required elections.

C

The Structured Multi-Year Buyout

Where your successor needs time — and often outside capital — to fund the purchase, we structure a buyout by a company owned by your successor together with arm's-length co-investors, with the purchase price paid over a multi-year schedule secured by vendor take-back notes. This lets your successor build up ownership and control gradually, brings in outside capital and expertise where needed, and gives you a documented, secured stream of proceeds rather than a single lump-sum sale.

Often, the right answer isn't just one of these — it's a coordinated combination, sequenced together as part of a single plan.

The Benefits of Succession Planning

A well-designed succession plan pays off in more than one way.

  • ✓ A tax-efficient transfer instead of one recharacterized as a dividend
  • ✓ More of your business's value staying with your family or chosen successor instead of the CRA
  • ✓ Continuity for the business, your employees, and your customers through the transition
  • ✓ A gradual handover of control on a timeline that works for you and your successor
  • ✓ Preserved access to the Lifetime Capital Gains Exemption where your facts support it
  • ✓ A documented, defensible structure that can withstand CRA review
  • ✓ Reduced risk of disputes among family members or co-owners over value and timing
  • ✓ The ability to bring in outside capital or co-investors without losing the plan's tax efficiency
  • ✓ Peace of mind knowing the business you built passes on the way you intended

Most succession plans realize more than one of these benefits from a single, well-timed structure.

How We Help You Keep More Money From the CRA — and Pass It to the People You Choose

Every dollar your corporation has built up in value only has two possible destinations when you step back: your family and successors, or the CRA. Which one gets the larger share depends almost entirely on how — and in what order — the transfer is structured.

1

Preserving Capital Gains Treatment

We test every transfer against the rules that can recharacterize proceeds as a dividend, and structure the transaction — pricing, share classes, and the corporate entities involved — to keep capital gains treatment available wherever your facts support it, rather than defaulting to the higher personal tax rate on dividends.

2

Protecting Your Capital Gains Exemption

Where your shares qualify as Qualified Small Business Corporation shares, we structure the timing and mechanics of the transfer to preserve that exemption for you — and, where the structure allows, for other family members who hold shares — rather than letting an avoidable step disqualify it.

3

Managing the Corporate Tax Layer

We look at what's sitting inside the company — retained earnings, passive investments, tangible property — and structure the transaction so that extracting or transferring that value doesn't trigger an avoidable extra layer of corporate or personal tax on top of the transfer itself.

4

Building a Structure That Holds Up to Scrutiny

A transfer to a related party draws more attention from the CRA than a sale to a stranger. We document every step — the valuation basis, the elections filed, the corporate resolutions — so the structure is defensible if it's ever reviewed, not just efficient on paper.

The goal isn't just minimizing tax on paper — it's making sure the plan still works the way you intended if the CRA ever looks at it.

Who Succession Planning Is For

  • Business owners planning to transfer ownership to children or other family members
  • Owners planning a sale to a key employee or management team
  • Owners bringing in a successor who needs outside co-investors to fund the purchase
  • Multi-generational family businesses without a current, documented succession structure
  • Owners whose shares have appreciated substantially since incorporation
  • Anyone who wants to begin transferring control gradually rather than all at once

If any of these describe your situation, it's worth a conversation before the next handshake — not after.

Quarterly Review → Succession Planning

Why Succession Planning Is the Logical Next Step After Your Quarterly Review

Your Quarterly Review Identified

  • Share value that has grown substantially
  • No current succession or ownership transition plan
  • A successor in the business, in the family, or waiting in the wings
  • An opportunity to plan proactively, on your terms

A Succession Plan Delivers

  • A structure engineered to preserve capital gains treatment
  • Protection against dividend recharacterization and PUC grinds
  • A clear, phased path to transferring control
  • More of what you built staying with your family or chosen successor

Your quarterly review flags the opportunity.
Succession planning is how you capture it.

Flat Fee — $30,000

Understanding the Investment

A fixed, one-time engagement — not an open-ended bill.

The Investment

  • A flat $30,000 fee — no hourly surprises
  • Full diagnostic, structure design, and figures appendix
  • ITA-cited plan memo and lawyer instruction letter
  • Execution support through to implementation

The Return

  • Preserved capital gains treatment instead of dividend recharacterization
  • More of your business's value passing to your family or chosen successor
  • A clear, documented structure your successor and lawyer can follow
  • Peace of mind that the transition is built to last

Your preliminary succession plan includes a full cost-benefit analysis — your projected tax savings measured directly against the $30,000 investment — so you know the payback before you commit.

The Cost of Not Planning Your Succession

Without a coordinated structure in place, business owners transferring ownership often face:

  • Proceeds taxed as a dividend instead of a capital gain
  • Loss of access to the Lifetime Capital Gains Exemption
  • An unexpected deemed dividend when shares are redeemed to fund the transition
  • Extended CRA reassessment exposure on a poorly documented transfer
  • A forced sale of assets just to cover an avoidable tax bill
  • Disputes among family members or co-owners over value and timing
  • A smaller business passing to your successor than what you actually built
  • A structure reacting to problems instead of preventing them

These costs compound quickly, and many can't be undone once the transaction has closed. Succession planning stops them while there's still time to structure the deal correctly.

Why Clients Choose Us

Clients choose our succession planning service because we provide:

A Generic Share Transfer A Kilpatrick CPA Succession Plan
A handshake and a stock transfer
A coordinated tax and corporate structure plan
Guesswork on which method applies
A structure tested against the freeze, intergenerational transfer, and buyout methods to find the right fit
Tax issues discovered after closing
A plan built and reviewed before the transaction happens
A vague savings estimate
A detailed cost-benefit analysis against your investment
A structure your successor doesn't understand
A plan explained to you and your successor, before you need it

This is not a simple share transfer you can do with a stock certificate and a handshake.
This is a tax-minimization structure engineered for your succession.

Your Next Step

Ready to Transfer Your Business Without Handing a Third of It to the CRA?

Tell us about your corporate structure and your successors, and we'll put together your preliminary succession plan — including the cost-benefit analysis:

Start Your Succession Plan →