Handshakes Don’t Age Well: Why Your Business Needs an People + Culture Audit
Every small business has a handshake deal somewhere in its history. A promise made in good faith. A shared understanding about “how things will work.” A quick agreement that kept the wheels turning when formal paperwork felt unnecessary.
The problem? Handshakes don’t age well. They feel rock solid in the moment, but a few years later they often turn into confusion, resentment, or even legal messes. Just ask any employment lawyer about termination pay after 20 years of “understood” service and you’ll see what I mean.
The Handshake Problem in Real Life
I’ve watched it play out more times than I can count.
Case 1: A founder told two early employees, “If you stick around, there’s a piece of the company for you.” Everyone left that conversation feeling good. Ten years later, the business is thriving, the founder is ready to sell, and suddenly those two employees are waving around emails and memories of what they thought they heard. Cue the lawyers.
Case 2: A manager makes a side agreement with a high performer: “Don’t worry about the pay band; we’ll make it right.” HR never hears about it, and their pay never actually catches up. Years later, when that employee compares salaries, they feel cheated, and when word spreads, the rest of the team feels betrayed, too.
Case 3: A family business runs for decades on nothing but trust. No contracts. No policies. “We’re all family here.” Then one sibling wants out, another wants control, and the “family handshake” isn’t worth much in a courtroom.
It’s not usually about dishonesty or ill intent. It’s about assumptions. People assume they heard the same thing. They assume goodwill will carry the business forward. They assume they’ll feel the same way in five years. But businesses evolve. People evolve. And the handshakes that once felt generous can start to feel unfair when the stakes shift.
The “Big Four” Handshake Traps
In small businesses, I see handshake risks crop up in four main places:
Compensation Promises
“We’ll bump your pay once the business can afford it.” Sounds fine until “afford it” means different things to different people. Without documentation and a fair process, you risk pay inequities, resentment, or even human rights complaints if it looks like certain employees got better deals.Ownership and Succession
Future shares. A verbal agreement about buying out a partner. A “don't worry, this business will be yours one day.” These are the most dangerous handshakes because they collide with people’s life savings, retirements, and family legacies. In provinces like Ontario and BC, succession disputes can grind a business to a halt.Policies and Practices
“We don’t need rules; everyone knows what’s fair.” Until one person doesn’t, or until “fair” looks different depending on where you’re sitting. A verbal understanding about vacation carryover, work from home, or overtime pay might feel small, but once someone leaves, you’re dealing with the Employment Standards Act, not just memories. Plus provincial rules vary. What’s legal in Alberta isn’t necessarily okay in BC.Performance and Promotion
Promises of titles, opportunities, or “next in line” status. Without clarity, you end up with multiple employees who believe they’re being groomed for the same role. Nobody wins.
Why a People + Culture Audit Fixes This
One of the services that we offer at Reimagine Work is a comprehensive People + Culture audit. It’s designed to shine a light on hidden risks and vulnerabilities, and show you how to strengthen your policies, procedures, systems and safeguards.
An Audit isn’t about doing a dusty, performative compliance check or pointing fingers over what’s missing. It’s about surfacing these handshake deals and asking the hard question:
Will this hold up when things get messy?
Here’s what you actually walk away with:
Clarity - No more “understood” deals. Everyone knows what was promised, and it’s documented.
Protection - Your agreements line up with provincial employment standards so you’re not blindsided by legal surprises later.
Alignment - Your people strategy matches your actual business strategy. If you plan to grow or sell, the promises you’ve made won’t derail it.
A Roadmap - Not just problems flagged, but step-by-step recommendations on how to clean them up.
Think of it as future-proofing your business. Instead of running on good intentions and crossed fingers, you create agreements that work today, and still make sense five years from now. Agreements that protect relationships, money, and your reputation.
Self Check: Where Are Your Handshakes?
Ask yourself:
Do I have a compensation promise that never made it into a contract?
Do I have a partnership agreement that’s still just “understood”?
Do I have a succession plan that only lives in my head?
Do I have policies that everyone thinks they know, but nobody’s written down?
Pausing on even one of these is a clear sign to take a closer look.
Turning Handshakes into Strategy
The good news is that cleaning this up isn’t about becoming more corporate or killing your trust-based culture. It’s about being fair, clear, and ready for the future. When we do an audit, we don’t hand you a PDF of generic policies you’ll never use. We give you a tailored roadmap built for your business.
The outcome is peace of mind. No more lying awake wondering if that promise you made five years ago will come back to bite you. No more hoping that “we’ll figure it out when we get there” will actually work.
Clear, documented, sustainable agreements that help your business grow without the weight of old promises holding you back.
So here’s something to think about: which handshake deals might still be floating around in your business?
Those handshakes are really what an audit is for, taking well intentioned promises and shaping them into something clear, fair, and built to last.
If you’d like to explore whether now is the right time for that step, I’d be glad to walk you through what the process looks like.
Let’s connect! You can always email me at jocelin@reimaginework.ca to get the conversation started.