Gauge Commitment to Strategy: Homework as a Leadership Test
This is one of our most popular blogs of the past couple of years, so we thought we would re-share it, but this time put it into context with the new trade realities.
Is Your Team Really Behind Your New-Market Strategy? Give Them Homework
Canadian business owners are rethinking where their next dollar of revenue comes from. Trade routes that felt reliable now feel uncertain at best, and new markets in Europe, Asia, and beyond are suddenly on the near horizon. In conversations with growth-oriented mid-market executives, we've heard that many have already announced a strategy to diversify.
So, if that’s you, how do you know your leadership team is really committed to your new strategy?
Here's a simple yet powerful method: give them homework! Yes, seriously. Assigning relevant and appropriate tasks to your team members can be a surprisingly effective way to gauge their engagement and support.
Here are three ways you can put this into action.
1. Define Success (Their Version)
Ask each member of your leadership team for two to three specific success objectives for their area, and how they'd measure them.
Say your strategy is to enter a new export market. Ask your CFO what a successful entry looks like from the finance side. Is it a specific percentage of revenue from the new market within 24 months? A margin floor after tariffs, freight, and compliance costs? Ask your head of operations what success means when your supply chain suddenly spans another continent and another time zone. Ask your sales leader what "traction" means in a market where nobody has heard of you yet.
This is a strategic exercise, not busywork. Someone who fully supports the strategy can do it relatively quickly and clearly. Look for clarity and truly measurable targets.
2. Get on Their Agenda
Ask each direct report to put you on the agenda of one of their regular team meetings. Your goal is to ask their people what they're doing, in their role, to make the new-market strategy real. Willingness is a good sign; repeated scheduling conflicts are worth a conversation.
This one is revealing for three reasons. First, you'll hear whether the strategy has travelled beyond the executive table. Second, you'll see how your leader responds to the request. And third, you'll learn whether they've understood the strategic direction at their level.
This is also a good way to get off the bridge of your ship and get back into the engine room and hear what people really think.
3. Role Play
Try this: "I want to make sure we're all on the same page. Let me pretend to be one of your employees and ask a few questions about our expansion plans. I want to hear how you'd answer."
Then ask the questions your people are actually asking:
"Why are we going after this market instead of defending the one we know?"
"Will this change my job?"
"What happens if it doesn't work?"
"Are we still committed to our current customers?"
One fairness check: this only works if you've already shared the key messages about your strategy. If you haven't, don't run the exercise. That's not a test of their commitment, it's a test of your communication, and you'll fail it on their behalf.
If you have shared them, listen closely. Do they explain the strategy the way you would? Do they sound convinced, or like they're reading a script they didn't write?
The Homework Effect
Homework isn't foolproof. A leader can do the assignment well and still struggle later, and another can fumble the first try and become your strongest advocate. But as an early signal, it's hard to beat. Strong, prompt, thoughtful work is a good sign of real engagement. Delay, vagueness, or creative avoidance is your cue to dig deeper into what's behind their reservations.
But just a word to the wise, delay, vagueness, or creative avoidance is your cue to dig deeper. Those reservations may point to a legitimate obstacle you haven't fully understood, and it's far better to find out now.
Entering new markets means more uncertainty, more moving parts, and less time to correct course than staying put, which is why alignment matters from day one. A fully unified team with clarity of purpose and direction is hard to knock off course.
Go ahead and assign the homework. It could give your new-market strategy the strongest possible start.