The 3 Questions Every Business Owner Should Answer Before July

And why June is one of the most critical months for small businesses.


June is a critical month for Canadian small businesses.

For those who are looking ahead to the summer busy season, June is the first real test of the systems and training you’ve put in place.

Meanwhile, for those who experience a summer slowdown, the end of June is a useful mid-year check point. You’ve got the opportunity for a short sprint now, to put yourself in the best possible position to enjoy the summer instead of stressing about it.

For almost all of us, a great June sets up the rest of the year. The momentum you build now will carry all the way through Q3. One or two significant wins in June can have an outsized impact on your year-end results. And the business owners who sit with a few hard questions before July hits tend to have a very different September than the ones who don’t.

Here are three questions to make sure you’re protecting your focus and direction.

Question 1:
Where are you now compared to where you planned to be?

Look back (or at least, think back) to the goals you set for 2026. Maybe you had in mind a certain revenue target, a new hire, or a product launch. How’s the year looking as we approach the mid-point?

The idea here isn’t to beat yourself up if you’re off track. You know a lot more now than you did back then about what the year will hold.

This might be a good time to reset those goals – what feels realistic today? What’s giving you energy, that you want to push harder toward? Were you ambitious enough, or can you adjust your targets upwards?

Question 2:
What’s the one thing that’s slowing everything else down?

Growth is natural when you remove the constraints. So what are the bottlenecks or anchors slowing your progress? Is there one thing that, if you fixed that, would make almost everything else easier?

Maybe it’s a team issue, or a process that never got documented and trained. A difficult decision that’s on your mind, or a conversation you’ve been putting off.

Do you know what’s causing friction, but you’ve been trying to work around it or ignore it, hoping it will resolve itself?

Your best bet this month is to face it head on and tackle it now, rather than letting it catch up with you in August.

Question 3:
What does winning Q3 actually look like?

In the summer months, it’s easy to have goals that are at cross-purposes with one another.

For example, you might want to enjoy some well-earned vacation with your family… but also make real progress on your business goals while your clients are quiet.

You want to finally implement a management system and start holding one-to-ones with every member of your team… but you’re expecting to be short-staffed, with people covering each other’s responsibilities.

Taking a step back to think through, in as much specific detail as possible, what a great summer looks like allows you to focus on what’s important. Vague ambitions don’t survive contact with July and August – but clear targets, with measurable outcomes, and a realistic plan to back it up do.


This Week’s Takeaway

If you answered all three questions quickly and confidently, you’re in great shape heading into the summer.

If you’re not sure, but you’re willing to sit with them and work it through, you’ve got time this month to get there.

And no matter how you’re feeling, if you and your business would benefit from a structured approach to summer planning alongside other smart local business owners, I hope you’ll join me on June 19 for GrowthCLUB in Mississauga. It’s a full-day workshop to work through these types of questions, and you’ll walk away with an action plan for Q3 – so you’ll get the summer you deserve.

Reserve your seat here. Space is limited, and early bird pricing ends June 8.
extramilecoach.ca/growthclub


How to Make 61% More Profit in 2026
(With just a handful of tiny changes)

June 12 – Register for a free event, featuring James Vincent

Join one of the world’s top coaches, James Vincent, for his frameworks that will leave you with a clear picture of where your business is strong, where it’s leaking, and what to do about it first.

Having coached Team GB athletes to Olympic success and led ActionCOACH UK to the top of the global leaderboard for eight consecutive years, James applies elite performance principles that help leaders build winning systems.

There’s also a complimentary Business Health Check included (valued at $499) – a personalized assessment of your biggest profit opportunities.

Seats are limited and I’d love to see you there.

The Details:

Friday, June 12, 2026

9:00 AM – 12:30 PM

Toronto (venue confirmed upon registration)

Free

Save Your Spot Here


Uptime: Laura Mae Martin

Uptime offers a grounded approach to productivity that feels especially relevant in the middle of busy workdays. Drawing from her experience at Google, Laura Mae Martin focuses less on doing more and more on building systems that help you stay clear on priorities, manage your time intentionally, and avoid unnecessary burnout. It’s a practical reminder that feeling “on top of things” usually comes from a few well-designed habits rather than constant effort.

Check it out!


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