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30 September 2025

In this Issue

đŸŠș    Working on the Business
đŸ—“ïž    18 Month Planning
📈    Fear the Peak
Coach Taylor, in Friday Night Lights, said, “I expect you boys to execute.” It’s in the work you win. | NBC

đŸŠș  Working on the Business

“Working on the business versus working in the business” is one of the most misunderstood clichĂ©s, especially for small business owners.

Working on the business isn’t about the business owner. It’s about the business.

Consider your company like it is an entity. It has a personality, skills, wants, and needs. Now ask: What does that entity need right now? Where does it need you to focus your attention to help it evolve and grow?

Working on the business is not about what the owner doesn’t have to do anymore, like sales or accounting. And it’s not about them carving out sacred time to ruminate on the future of their company.

Working on the business is often the most direct and mundane tasks of all: developing systems, solving capacity constraints, and getting things done.

When I work with leadership teams in companies between $100 million and $1 billion, there isn’t an attitude of “I don’t do that.” The leaders are operators.

They drive business growth by operating the business. If the business needs them to swoop in and manage a department because the manager just quit, they do that. If the business needs them to clean up a sales process because no one else on the team has the skill or time to do it, they do that.

The ego of “working on the business” disappears as a business grows, and the recognition is working on the business means being an effective operator.

One Stat to Watch

45%

45% of businesses fail due to a lack of management control, according to Statistics Canada. The report states, “Management’s deficiencies in adaptability, flexibility, communication, and initiative were cited as causes of failure.”

đŸ—“ïžÂ  18 Month Planning

Strategic planning cycles are getting shorter. The idea of a 10 year vision or a 3 year plan seems almost fanciful.

With once in a generation events happening every other year, it’s hard to build an enduring, detailed strategy for the next three, five, or ten years.

In our strategic planning with clients, we recommend 18 month strategic plans. Mid-term planning leads to better strategy because it is more focused and more action oriented.

An 18 month plan has 6 quarters or blocks of work. This cadence enables you to make key policy decisions, validate assumptions, and make clear investments in people, processes, and infrastructure.

The shorter horizon also makes it easier to make commitments. Projects or initiatives that won’t advance the strategy in the next 18 months are put aside to revisit later.

Evaluate your progress against the strategy every 6 months. This enables you to adjust course quickly, and you can extend priorities or initiatives as required.

As you approach your 2026 strategic plans, try a shorter horizon. Build your plan for the next 18 months, and see if that leads to a clearer, more achievable growth strategy.

📈  Fear the Peak

Every week I meet companies that are still digging out of bad COVID investments. They’re not alone:

  • Business bankruptcy filings rose 22.1% in 2024, according to the United States Courts.
  • 41% of firms in 2024 were denied all or some of the financing they applied for because they already had too much debt, according to the 2024 Small Business Credit Survey.

What can we learn from this era? How did the banks, investors, and businesses get it so wrong?

For me, the key lesson is don’t jump on bandwagons and be paranoid when things get so busy.

I advise sales teams that the most important time to prospect is when you’re busiest. Too often salespeople stop prospecting when they are crushing it, because they are too busy serving demand and working active opportunities.

The challenge is when you stop prospecting you will find the inevitable “trough” of slow sales a few months later. It’s a viscous cycle of a lumpy sales funnel.

The same can be said from the COVID era. Businesses and banks needed a healthier skepticism to prospect and sell more as things got so overheated. This wasn’t a moment to buy more stuff: buildings, equipment, and businesses. It was a time to sell ahead of the curve.

đŸ€”Â  Thoughts on Today’s Issue?

We’d love to hear your feedback. Message with any thoughts, comments, or ideas for future issues.

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