Article: Plan Your Strongest Season Yet with an Annual Review

This article was originally published in the Feb/March issue of ISAO's Ontario Arborist magazine.

As we head into the slower months, it’s easy for anxiety to rise, especially if you don’t have a plan for the next season. As Benjamin Franklin said, “If you fail to plan, you are planning to fail.” While your business may grow from year to year on its own, growth without a clear strategy is luck and won’t last. Taking time during the slower season to reflect on the past year, clarify your WHY, address pinch points, and create a strategic plan for the next season will set you up for success and help you and your team reach your goals much faster.

START WITH THE BIG PICTURE

Before diving into financial ratios or equipment lists, step back and revisit the foundation of your company. Review your mission, vision, values, purpose, and goals. Include your team to ensure these statements still reflect who you are and where you’re headed. When your team agrees on what the company stands for, every decision becomes easier: who you hire, which clients you prioritize, and how you deliver your services.

It also helps to paint a picture of what a successful upcoming season looks like. Describe how your ideal year runs, from morning shop prep to client follow-up. When your team understands the vision, they are more invested in making it a reality.

REFLECT ON THE PAST SEASON

Back when we owned a tree service, my husband and I would book a couple of nights away every winter to focus on our business. We always chose a different city or town within a couple of hours of home. We probably looked a little strange walking into the hotel with flip charts, a printer, and our laptops, then disappearing for hours into our room. It wasn’t all work, though. Evenings were for exploring the area and enjoying a nice meal.

Those focused hours of reflection and planning set our business up for success year after year. It kept us aligned, intentional, and moving toward the same goals, which is especially important as a husband-and-wife team. If your business partner is not your life partner, and an overnight stay might feel a bit awkward, book a meeting room at your local library or community centre. The key is to get away from the office, so you aren’t distracted.

WHAT WORKED AND WHAT DID NOT

Start by talking with your crews about what ran smoothly, what caused stress or delays, what you are proud of, and where you saw missed opportunities. These questions uncover recurring patterns that translate into lost revenue, reduced company culture, and clients who don’t return. You can gather this information through an anonymous survey or a group discussion. It depends on your team and the level of trust you have. Take time to celebrate wins, discuss favourite projects, and highlight clients you enjoyed working with. This information will guide the next stages of your planning process.

PEOPLE AND CULTURE

Employees often spot operational blind spots long before management does, and their insights lead to stronger systems and a healthier culture. Ask how supported they felt, whether communication was clear, what equipment helped or held them back, and what changes they’d like to see. Review your team members and identify any strategic hires needed for the upcoming season. Hold one-on-one meetings to review skill development goals and set new ones for the next year.

OPERATIONAL PERFORMANCE

The systems you have in place determine whether your business runs efficiently or constantly feels overwhelming. Review client and team complaints to identify where the hiccups are. Assess workflows, truck organization, and whether crews are leaving and returning to the shop on time. Create or update your standard operating procedures to ensure your team is clear on what to do, how to do it, and what the expectations are.

Small operational issues add up to major time losses over a full season. A clear operational review helps eliminate friction and strengthens productivity and safety.

FINANCIAL REVIEW

A strong financial review looks deeper than the numbers at the top and bottom of your profit and loss statement. Study your financials line by line to identify where you can be more efficient and trim unnecessary expenses. Review your projects and determine which services were truly profitable. Look at revenue per job, productivity rate, revenue-to-employee cost ratio.

Evaluate whether reconciliations, payments, and remittances were done on time. Review how well accounts receivable were managed and whether overdue accounts affected cash flow. These insights help you price correctly and allocate resources strategically for next year. Identify opportunities to improve. Can you reduce the time it takes to send a quote or follow up with answers to questions? Any small improvement in your systems will make you more efficient and keep more money in your bank account. Don’t forget to set your budget for the next year based on increased rates, new purchases, or additional wages.

SALES AND CLIENT EXPERIENCE

Analyze where your leads came from, which clients were most valuable, and how your sales process performed. Consider whether your service area still makes sense or if expanding or narrowing it would improve efficiency. Evaluate client communication and whether you anticipated their questions and concerns before they asked them. Review ratings and feedback to identify strengths and areas for improvement. Look at your client experience journey from first contact to post-project follow-up. Are there any speed bumps that need to be ironed out? When you dial in this process, clients will not only enjoy working with you but will also tell their friends.

MARKETING REVIEW

Review your marketing strategy. Identify what generated real leads and which were a waste. Assess whether partnerships, newsletters, or networking created meaningful engagement. Consider whether your message reached the right audiences or needs refinement. Create a budget and a plan for networking, print, social media, or business-to-business referrals. Know who your ideal client is and make sure you are spending your marketing dollars in the spaces they are
engaging with.

CREATING YOUR STRATEGY FOR THE YEAR AHEAD

Once the review is complete, turn your insights into a clear action plan. Decide how many employees you need, which roles require development, and where training is needed. Create a timeline for equipment purchases, repairs, and maintenance. Be strategic. Based on what you uncovered in the previous sections, determine which services to expand, refine, or discontinue. Do you finally give up doing hedges?
Most importantly, establish measurable targets for sales, operations, financials, marketing, and team development. These goals give your business direction and keep your leadership team focused throughout the year. Be specific and set goals for no longer than 3 months at a time.

LAUNCHING THE PLAN WITH YOUR TEAM

Start the season with an orientation day that reviews lessons learned and introduces the strategy for the year ahead. Share expectations, clarify roles, and involve everyone in the plan. When the team feels included, they take greater ownership of the results.

A successful season is never an accident. It is built through reflection, clarity, and intentional planning. By taking time to review your past year and set a thoughtful direction for the next, your business becomes stronger, more resilient, and sets you up for success.

- Tracy Logan is the founder of Optimized Solutions, a coaching and consulting company that helps trades business owners, especially arborists, landscapers, and contractors, build efficient, scalable companies. With over 18 years of experience starting, scaling and selling a successful tree service business, Tracy now supports others in getting organized, streamlining operations, and building strong systems to drive sustainable growth. Find her on Instagram at @bizcoachtracy or her website at optimizedsolutions.ca.