Strategic Planning Checklist For Fleet Owners

If it’s been a minute since you sat down and created a strategic plan for growing your business, there’s no better time than right now to start! Having a goal to grow say 15% is great, but it has to be backed up by a plan or else it won’t happen. Before you can make that plan, you need information. Below is a checklist of things you need to gather to develop that killer plan to achieve your goal. Don’t forget the most important step – taking action! 

First thing is to grab your crystal ball (or a six-pack)  and make some educated guesses about how the economy is going to impact your customers, and by extension, you. Look at big things like drought (landscaping), shortage of lumber (construction), low housing stock (moving companies) and higher interest rates (money is tighter). Be aware that some “bad” things are “good” for business. For example, tow trucks have more business during bad weather and bad economies (if they do repossessions).

External – What does the future look like for your customers?

• What is the outlook for the industries you serve? Positive/negative?
• Are there any trends in technology or regulations impacting your customer’s growth plans?

Internal – What does the future look like for you?

• Are we doing better or worse than we expected this year?
• Do we have a strong pipeline of future work (3-6 months ahead)?
• How did our revenue and profitability trend over the past year? Was there a pattern?

How to find this info:

• Ask some key customers what their outlook is for the coming year. Great way to build a good relationship.
• You should look for analyst reports online for industries, say construction, and read the Executive Summary to get the general idea. No need to buy and research or reports.
• Ask Google/Bing/ChatGPT about local, regional or national trends. Take the answer with a HUGE grain of salt – as AI-generated responses often contain inaccuracies. In the search bar ask Google/Bing/ChatGPT for specific stats like: What are the projections for new housing starts in (insert your service area)? Provide links to reference material used in the analysis.

Some industry-specific insights for 2026:

• Construction trades: Jobs are out there, but growth is slow—maybe 1-4% next year. Best opportunities? Data centers, schools, hospitals, and government infrastructure work. New home building is picking back up as interest rates ease a bit. Office space and retail? Still pretty rough.
• HVAC/Plumbing/Electrical: Steady work from schools, hospitals, and infrastructure projects. Your biggest problem? Finding good people to do the work.
• Landscaping: Where you’re located matters a lot. Southern states are booming. Northern markets are tighter.
• Tow/Recovery: Business as usual—people still need help when stuff breaks down.

How Momentum can help:

Track job locations, vehicle locations, previous routes, and idling to ensure optimized routing for better customer service and reduced fuel costs.

People have choices when it comes to who they do business with. The Internet makes it very easy to find and compare businesses that offer the products and services you offer. Knowing who and what you are being compared to is really important so you can differentiate yourself from them and give people a reason to choose you!

• Who are our main competitors?
• How do we stand out from them (pricing, service quality, reliability)?
• Are our competitors expanding their fleets or adding new services?

How to find this info:

Google what you offer (Example: trailer rentals near me), check review sites like YELP, or look at Facebook groups dedicated to local towns and cities and search for your type of services (recommendations for good HVAC installation or landscapers). Look in local newspapers, publications, and see who is advertising. 

Current customers offer great insights into the type of people who like what you have and picked you instead of the competition. 

• Who are our top revenue-generating customers? What do they have in common?
• Are there opportunities to up-sell services?
• Are we relying too heavily on a few large accounts?
• Who are “lookalike” prospects we can pursue?

How Momentum can help:

Track service visits and time spent on each customer’s site to understand their value and identify high-priority clients.

Without your fleet vehicles and equipment, you are dead in the water. Keeping them up and running is job #1. Consider these:

• Are your vehicles operating at maximum efficiency?
• How much downtime are we experiencing due to breakdowns?
• Can we handle more jobs without expanding our fleet?
• Are we staying compliant with OEM guidelines to maintain warranties?

How to find this info:

Pull preventive maintenance records for your fleet. Are you up to date? Check repair records – were there a lot of unexpected repairs? Can you see how many trips/miles each vehicle has made? Make sure it is someone’s job to track preventive maintenance and make sure it happens on time. Make it part of your culture to take care of equipment.

How Momentum can help:

Real-time tracking and automated reports help you monitor usage and idle time, and reduce unnecessary mileage. Automating Fleet Maintenance tracks usage hours and sends automated reminders, helping avoid costly repairs and maximize vehicle lifespans.

Are you confident your pricing strategy is hitting the sweet spot—competitive enough to win business while still maintaining strong margins? And how do you know that every job is profitable?

• Are we pricing our services competitively while maintaining healthy margins?
• What’s our win rate on job bids?
• Which services generate the most profit?
• Were there any jobs where we lost money? Why? How can we avoid that in the future?
• Do we know exactly how much each job cost us?

How to find this info:

Track win rate/renewals for various bids – if you’re winning 70%, you’re priced too low. If you’re winning less than 35% of jobs you bid – you’re priced too high. Aim for 40-60% win rate. Make sure you account for all costs when figuring out profitability of a job. Did you take into consideration depreciation, travel time, time on the job, gas, etc. for each job or are you using a guestimate?

How Momentum can help:

Leverage job costing features in Momentum IoT to identify the exact costs down to the penny for every job. It makes it very easy to quote and to see which jobs were profitable and which jobs were not. With real-time insights, you can adjust on the fly to make sure 0% of your jobs are losing money!

Are you staying on top of how your team is performing? Talking to your crew, rewarding top players, and coaching those who need it keeps your business running smoothly—and your team motivated. It’s hard to find good employees. And it’s only getting harder.

• Are you regularly talking to your employees about their performance?
• Is there a clear path to better pay and/ or promotions?
• Are drivers adhering to safety standards? How do you know?
• Which team members are most efficient and reliable? How do you measure that?
• Do employees understand how their performance is measured?
• How do you reward top performers?
• How do you coach or retrain underperforming employees?

How to find this info:

You need some way to track performance both daily and trended over time. There is no easy way to do this manually. 

How Momentum can help:

Choose a GPS fleet Management software that offers real-time GPS tracking, Driver Scorecards, and dash cams to highlight individual performance, making it easy to reward the best and coach the rest.  With it you’ll also get real-time alerts for unsafe habits like speeding, cellphone usage and aggressive acceleration so you can quickly address issues and have proof of what’s happening in the field.

Sales and marketing make up the engine that powers growth. To bring in new customers and keep the revenue rolling, you need to know what’s working, what’s not, and where to focus your energy. Here are some key questions to guide your efforts:

Questions to ask yourself:

• Are you using customer success stories to attract new business?
• Do you ask customers if you can use them as references?
• Do you have a referral program?
• Which platforms (social media, digital ads, mailers) generate the best leads?
• How effective are your current marketing efforts? How do you measure that?
• How do you sell to new customers? Which ones get you the best results?

How to find this info:

When evaluating your marketing, track specific metrics like page visits, email clicks, and orders to identify where your efforts pay off. Don’t underestimate the power of your website—it’s the first place customers go to check you out. Make sure it’s professional, easy to navigate, and full of success stories that show off your value. Compare it to your competitors’ websites to see where you might need to improve. Place bets on different advertising channels: Google, Bing, email, direct mailers, billboards. Invest more in the tools and tactics that consistently deliver results to have a steady flow of leads to grow your business.

Once you’ve pulled together all this information, it’s time to put it to work. Use what you’ve learned to spot gaps, set clear measurable goals, and prioritize where to focus. Whether it’s adjusting your pricing, boosting fleet efficiency, or investing in new tech, a solid plan will keep your business moving forward.

It’s important to not try to do everything at once. Start by tackling one or two priorities at a time and track your progress. Spread them out into different months or quarters to ensure that what you did is working before moving on to the next thing. With a good plan, your goals aren’t just possible—they’re totally doable!

Download a streamlined checklist of the above and get started on making your plan for growth.