As Toronto’s skyline and commercial footprint evolve, so do the liability exposures facing small businesses. From shared spaces and subcontractors to informal pop-ups, many risks remain poorly understood - and often uninsured.
“The biggest blind spot I see is a question of who is liable,” said David Woolfrey (pictured), broker at Connex Insurance Brokers Ltd. “Businesses might assume it’s the landlord’s problem or the city’s - but the plaintiff just wants money. They’ll go after whoever is easiest.”
Toronto’s dense urban mix - multi-tenant buildings, subcontracted services, and joint-use areas - blurs the lines of accountability. When something goes wrong, the legal aftermath is rarely straightforward.
“A client might say, ‘The landlord handles snow removal’. Sure - but if someone slips, the tenant, landlord, and contractor can all be named,” Woolfrey explained. “Everyone involved shares some responsibility.”
He added that Toronto’s ever-present construction adds further complexity. Falling debris or site hazards often raise difficult questions: Who owns the site? Who dropped the tool? Who should have maintained the area? Even when a client isn’t at fault, they can get pulled into years of subrogation.
“Litigation costs are rising,” he said. “A million dollars sounds like a lot until it isn’t.”
Shared retail hubs and weekend markets have become staples of Toronto’s business scene. But they often introduce unaccounted-for exposures.
“You might have one business leasing a storefront and another operating there every weekend,” Woolfrey said. “It’s a material change in risk - one that brokers need to recognize and evaluate. If something goes wrong, could this arrangement void coverage entirely?”
Informal arrangements can inadvertently shift liability in ways that standard commercial general liability (CGL) policies don’t always anticipate.
Converted factories and aging commercial buildings often retain rigid insurance requirements that don’t reflect how the spaces are actually used.
“Landlords hand down insurance clauses written by legal teams, not risk professionals,” Woolfrey said. “A lot of growing businesses treat insurance as a compliance box to tick - not as a tool for resilience.”
Helping clients reframe insurance as part of business continuity planning is where brokers can add real value.
“If there’s a fire, the client's first priority is getting operational again. Their customers don’t care why it happened. They still expect their photoshoot next week,” he said. “The right coverage makes that possible.”
Woolfrey believes commercial tenants and landlords should work more closely to avoid disputes and build resilience - particularly in mixed-use or repurposed properties.
“No-one benefits from a catastrophic loss,” he said. “A joint insurance model - like in condo management - could prevent conflict and reduce exposure. But we're not there yet.”
For brokers, staying engaged in their communities isn’t optional - it’s essential. Woolfrey stressed that brokers must see the changes firsthand.
“You can’t spot new exposures from behind a desk. Walk the neighbourhoods, talk to people. If something in Toronto could affect a client in Brampton, flag it,” he said.
He also pointed to the value of peer-to-peer learning. “I hear about things like new liability limits from other brokers. That kind of sharing helps protect everyone.”
His takeaway is clear: “Insurance isn’t one-size-fits-all. But with good communication, there’s always a right-fit solution.”
