Mid-year check-in: Do you know where you stand?

Most leadership teams start the year with a clear plan: well-defined priorities, solid forecasts, and a strong sense of where the business is headed. But even the best-laid plans can go awry. Markets shift. Expectations evolve. Talent challenges persist. And new technologies show up with big promises they can’t always follow through on. 

The organizations that adapt well don’t wait until year-end to figure this out. They pause at the halfway mark, assess what’s working and what isn’t, and make changes while there’s still time. 

As we head into the second half of the year, our experts weigh in on 10 questions every leadership team should be asking right now. 

Financial readiness 

Rebecca Adrian, Senior Manager, and Rayna Laiken-Baker, Associate Director, in our National Tax office, offer guidance on what leadership teams should be thinking through as they prepare for the second half of the year. 

1. Do you have clear visibility into your cash flow over the next six months? 

A quarterly check-in can be particularly valuable at mid-year. Start with a simple question: how much have you withdrawn from the business so far this year? Withdrawals can affect your overall tax position, so planning ahead is important. You should also confirm that tax payments, including corporate tax instalments, remain on track. Falling behind can result in interest charges, and catching up late in the year can strain cash flow at exactly the wrong time. 

From there, take the analysis one step further and assess your resilience. Are your receivables aging more slowly or more quickly than they were six months ago and are collection terms starting to slip? If revenue dropped by 15% to 20% tomorrow, how many months of runway would you have, and what would you reduce first? How concentrated is your revenue, and how exposed would you be if one or two major customers left? You may never need to rely on these answers but having them can improve the confidence behind every other decision you make this year. 

Big year-end surprises are usually avoidable; they simply require a check-in before options become limited. A brief discussion with your advisor can help identify issues early and preserve flexibility. 

2. Have you refreshed any forecasts or budget assumptions? 

January's plan was based on the information available at the time. Federal and provincial budgets, policy changes, interest rates, and market conditions can all materially affect your corporate or personal tax position by mid-year. Your income projections matter as well. If an expected transaction has not materialized, or if an unexpected opportunity has emerged, your projected taxable income may have changed, which means your planning should be revisited. 

A useful stress test is to ask where you would stand at year-end if the second half of the year unfolds much like the first. If that answer is not where you want to be, it is time to reassess. Consider which of your original assumptions have changed, and make sure your forecast reflects them, rather than relying on a stale plan. Waiting until the fourth quarter to recalibrate leaves far less room to act. 

3. Are you investing in the right areas, and can you actually afford to? 

Budgets have inertia. By mid-year, it is worth asking whether your spending still reflects where you expected growth to come from, or whether you are continuing to fund commitments made in a different environment. Review costs that may have increased without much scrutiny, such as software subscriptions, insurance, and contractor spend, and ask which of them you would not approve if they were presented today. Consider what you have deferred, and be candid about whether that reflects discipline or avoidance. Sometimes the most useful question is what you should stop doing entirely to free up capital and attention. 

When you commit to a major initiative or purchase, confirm that you have the cash flow to support it. How a purchase is structured, including who makes it, how it is financed, and when it closes, can affect the tax treatment and overall outcome, particularly for acquisitions completed near year-end. Have that conversation with your advisors before you sign. It is far better to plan ahead than to address issues after the fact. 

Market & client positioning 

Nisha Soundararajan, our Director of Digital Solutions and AI, shares her thoughts on where customers and markets are headed and what it all means in terms of strategy. 

4. Do you know how your customers are approaching AI right now? 

 According to our digital/AI expert, customers are splitting into two camps this year based on industry maturity. In tech-forward industries where companies have historically adopted new tools, customers are asking strategic questions: What does this mean for us? How do we adopt responsibly? They're planning ahead. 

In legacy heavy industries like construction, where the same systems have worked for years, customers tend toward reactive behaviour. They see the shifts happening, but they're watching and waiting rather than moving. 

Understanding which camp your customers fall into and whether they're asking strategic questions or watching from the sidelines should shape what you prioritize in Q3 and Q4. 

 5. Has your competitive landscape changed more than you might realize? 

The competitive landscape has most definitely fractured recently. Businesses are not just facing traditional competitors anymore. Thanks to technology, tech-native players are now entering markets they previously couldn’t access, because technology now enables them to compete without deep industry expertise.  

 They're building platforms that become competitors, even though they came from outside the industry. If you don’t know what your competitors are doing in the automation and AI space, or why, that's a significant gap and that’s worth a conversation. 

6. Are you leveraging technology strategically or simply reacting to it? 

“Strategic adoption is about being intentional, whereas reactive is about being defensive,” Nisha explains. Strategic adoption starts with focusing on a specific problem and finding the right technology to solve it, whereas reactive adoption is more, “everyone’s using this tool, let’s implement it and see how it goes.” The difference shows up in whether the technology actually gets implemented properly, used responsibly, measured, and built upon – or quietly abandoned. The overlooked question: is "what will the team have to stop doing"? If organizations don't answer that, adoption fails and ROI disappears. 

7. Can you explain your digital strategy in one sentence? 

Clarity here is usually what separates businesses that pursue the right opportunities from those that simply chase the most visible ones. If you can articulate your digital strategy in one or two sentences, you’re in good shape and very well positioned to do the adoption right. 

Leadership & talent 

Tracy Mohn, our National Director of People & Culture, chimes in on the questions that matter most for leadership and talent heading into year-end. 

8. Do you have the talent required to execute your strategy? 

Start by taking a look at who you already have. But don’t just look at the skills they have right now – look at their potential moving forward. Where do your people want to grow? Does it align with where the business is going? How can you help them, and the company, get there? Clearly communicating your strategy and helping your people see their role in it matters just as much as any hiring plan. 

9. Are your leaders sustainable? 

Leadership sustainability is really two questions in one. The first is about succession and pipeline: do your senior leaders have people below them who are developing, growing, and invested in a future with the firm? The second is more immediate: can your leaders realistically continue doing what they’re doing today? If the answer to either is no, give some thought to what needs to stop, not just what needs to be changed. 

10. Is your business investing in the people it needs for tomorrow? 

It’s easy to forget that the next generation of leaders haven’t had the same opportunities to learn, connect, and be mentored as today’s leaders have. The cost isn’t just a development gap – it’s retention, pipeline, and even the ability to attract people at all. The fix doesn’t require a formal program. One of the simplest approaches: bring someone along to every client meeting, every important conversation. Not for the billable hours, but as an investment in their development. 

And there you have it. 10 questions every leadership team should be asking right now. But as our experts know, the point isn’t to score a perfect 10. It’s to treat any shortcomings as a jumping off point for what to do next. 

If any of these questions gave you pause, that’s worth a conversation. Reach out to your Baker Tilly advisor to talk through where you stand — and what to do about it before the year ends.