How to Build An Annual Plan Your Team Will Rally Around in 2024

Having a vision for your Home Services company will only get you so far. With an Annual Strategic Plan, you and your team will be on the road to achieving scalable success and an unmatched business.


You know that feeling when you’ve finished a job and as you stand back to examine your work, you can feel an energy pulsing through you. Every walkway is tidy. Every stone is level. You have done a heck of a job.


Are those leaves rustling in the trees… or is nature applauding you?


It’s an invigorating sensation to elevate your trade to artistry. But once you’re running a booming business, between the grueling hours of firefighting and endless demands from staff, customers, and vendors, it’s easy to forget that feeling.


Nevertheless, you haven’t lost that ability to see what doesn’t yet exist. You still carry a vision for your company. You just need a way to communicate it to your team.


Enter the Annual Strategic Plan.


A far cry from being a long-winded manifesto, an Annual Strategic Plan is an essential tool to get your ideas out of your head and into a form that inspires and energizes your team. This article will show you how to create one - simply, effectively, and enjoyably. 


It’s time to reconnect with your creativity.


Why Annual Strategic Plans are important


You’ve heard the saying that life is about the journey, not the destination? Well, strategic planning demolishes that notion, because when it comes to your contracting business, it matters a lot where you’re going.


An Annual Strategic Plan sets your desired destination and gives you a map to get there. Beyond steering your course, the Plan also helps you:


  • Chunk dreams. Building greatness requires looking ahead five or ten years, and an Annual Strategic Plan enables you to fulfill your destiny, one year at a time.

  • Dodge mistakes. On the fly decisions can be costly, in time, money, and sanity. You don’t want to misstep on big decisions like a new CRM system or a key hire.

  • Avoid complacency. When companies plateau, leaders can find themselves simply going through the motions. A Strategic Plan can inject new life into your vision and operations.

  • Optimize resources. If you have 20 employees, and each works about 2000 hours a year, you’re at the helm of 40,000 hours. Can you really afford to mismanage that?

  • Stay intentional. An Annual Strategic Plan gives you a scorecard with criteria and metrics to grade your business against. Nothing keeps a team focused like KPIs.

  • Gain confidence. When you’re working from a carefully thought-out plan, you’re able to provide clarity to your team. Erratic leaders inevitably result in scattered crews.


“To create one’s own world takes courage.” 

-Georgia O’Keeffe


Contractor guide: annual strategic planning


Curious to dig deeper into the ‘how to’  of building an Annual Strategic Plan? Grab a coffee and watch this on-demand Guide To Annual Strategic Planning Web Class, brought to you by our pals at Breakthrough Academy.


The nuts and bolts of creating an Annual Strategic Plan


Strategic planning is certainly not a walk in the park, but it doesn’t need to be a dry exercise either. Quite the opposite, in fact. If you approach it right, it’s one of the most fun and revitalizing elements of entrepreneurship!


Every artist has their process. These steps can help you uncover yours.


Where to begin: Take time for reflection


Similar to how aerating a lawn allows nutrients to move more freely, a little prep work will help inspiration flow before your strategic planning session begins. Carve out some time to consider the following questions:


  • What went well over the past year? What didn’t? 
  • Did you hit your goals? Did you even have any? 
  • If you have any data to work from, what story is it telling you?


Explore your answers from a corporate standpoint and a personal one. You’re more than just a business owner and each side of you impacts the other. You need to take care of both.


  • Have you lived the life you wanted? 
  • What do you ultimately want to accomplish as a human in the world?


Your Plan should feed into a bigger, long-term vision. Pick up a pen and scribble it down. Don’t worry about spelling or grammar. Keep your thoughts honest and raw. 


Then, send out some instructions for how you’d like your team to prepare. This could include data you want them to reflect on, initiatives to think through, and business solutions to brainstorm. A little structure goes a long way. 


“You’re 42% more likely to achieve your dreams if you write them down.” 

- Gail Matthews.


Where to hold it: Somewhere inspiring


Boardrooms and meetings certainly have their purpose, but for your strategic planning session, get away from the office for two or three days.


Find a location that’s unique, fun, or peaceful to fuel your team’s creative spirit. Maybe it’s Vegas. Maybe it’s a remote mountain lodge. Maybe it’s a garden you admire. Wherever you go, just ensure it provides the mental space you need. Strategic planning requires deep thought.


However… when you’re not busy thinking… gamble, play, or ski away! 


Who to bring: Go solo or with a team?


Even if you’re the sole founder, consider bringing a few key team members with you. Just make sure whoever joins can leave their work for a couple of days without causing disruption to daily operations. If you don’t have anyone you can bring, never fear. This is still a worthwhile endeavor to do on your own. The important thing is that it happens at all.


How to do it: Break down your vision


Once you’ve sequestered yourself away from the world, you’re ready to embark on your strategic planning session. Time to breathe life into your vision and turn it into actionable steps. 


Chip away, getting more and more granular, until you’re left with manageable pieces. You can think of it like splitting a boulder into rocks, then blasting those into pebbles… and then holding a barbecue on the cleared rubble.


Here’s how to get it done:


The Why


Working off the reflective thought you did earlier, identify your:


  • Values >> These foundational nuggets guide your decision-making in virtually every facet of your business, whether it’s financial decisions, hiring and firing staff, managing customer and vendor relationships, or resolving internal disputes.


  • BHAG >> This is your Big, Hairy, Audacious Goal. The place you want the business to be in five years, such as having an eight-digit revenue that allows you to only work 20 hours a week (yes, it is possible).


  • Purpose >> What motivates you beyond your balance sheet? Identify the real underlying reason your business exists.


The Big Picture


In keeping with the vision you’ve outlined, think about what you need to achieve in the coming year to reach your BHAG.


  • Annual Goals  >> Outline the major goals for the year, and make them SMART (Specific, Measurable, Attainable, Relevant, and Timebound). Wild goals that are impossible to meet will just demoralize everyone, yourself included. Look to the sky, but stick to the ground.


  • Annual Initiatives  >> These are the “how’s” behind the goals, the tangible actions required to realize the goals you’ve set out.


The Q1 Kick


In this phase, your annual goals are whittled down further, focusing only on the first quarter of the year and what needs to happen to get the wheels turning on your plan. Think about the revenue you’ll need, especially if your business is seasonal, as well as any prep required for roles you intend to hire or tech you’d like to implement.


  • Quarter Goals >> Pinpoint the goals you need to hit in Q1 to keep moving towards your annual goals.
  • Quarter Rocks >> Determine the implementation items that feed into your annual initiatives.
  • Rock Breakdown >> Turn your Q1 Rocks into a list of tasks. Assign an owner to each, as well as the week when it needs to be completed.
  • Critical Path  >> Use your task list to see the full and sequential schedule of what needs to happen each week to keep your plan on track.


Tech can be a huge help with operational planning. The project management tool, Asana, is a great option for startup contractors. For scaling Home Services companies, a well-suited CRM platform provides a robust offering of tools to help run your business.


The Hooray


Imagine yourself and your team having successfully knocked out every task, accomplished every goal, and fulfilled your purpose. Now what?


🥁Celebration - Decide how you’re going to reward yourselves for your achievement. And yes, decide now. Trust us, you’ll need the dangling carrot when things get rough during the year.


Which is why you should also create a…


🥁Theme - Pick a mantra, or a drumbeat, to keep you all inspired during the year. Make it something that’s true to your values and that everyone can rally behind.


“Art is not what you see, but what you make others see.” 

- Edgar Degas


What to come out with: Your Annual Strategic Plan


Now’s the time to bring all that thinking, spitballing, and dreaming to fruition. To distill your vision for the year down to an easily digestible, understandable plan that takes up one. single. page.


Annual strategic plan


That’s right. Your annual strategic plan is a one-pager. Why? Because it forces you not to get too complex, and makes it easier to share with the rest of your staff. The point is to turn the plan into action, right?


Contractor guide: annual strategic planning


We’ve got you covered with an Annual Strategic Planning tool, available for free in this Guide To Annual Strategic Planning Web Class, brought to you by Breakthrough Academy.


What happens after: Keep the dream alive


Just like art, strategy should be approached as something that is (to paraphrase Leonardo da Vinci) never really completed, merely abandoned. At least as it applies to sharing your Annual Strategic Plan with the rest of your team. 


Here are some pointers for what happens after you depart your idyllic retreat and return to the real world:


 💡Communicating the Plan - It’s time to present your masterpiece to your team, but like any grand unveiling, it deserves some fanfare. Turn your Plan into a visual deck. Record a video. Deliver a speech you envision making in the future. Just give ‘em magic.


💡Getting buy-in - There may be some pushback from your team, but that’s okay - it shows they care. The last thing anyone wants at the end of a show is lacklustre applause. To win them over, highlight how the Plan benefits them and makes their lives easier.


💡Receiving input - This is a crucial reason why you shouldn’t sew up every detail during your planning session. You want to leave space for others to offer their ideas. You’re more likely to retain A-players when they’ve been able to put their stamp on the Plan.


“The creative process is a process of surrender, not control.” 

– Bruce Lee


How strategic planning shaped an elite Home Servicer’s business model


Dave Fraser began his career trimming hedges and quickly turned his skills into a million-dollar company, Birchwood Home Services. But despite going full-tilt, he had no clue which services were delivering the best profits. He wrote his first Annual Strategic Plan in 2020 after joining Breakthrough Academy and, suffice it to say… it was rough. 


His initial plans didn’t work out as expected, but over the years he’s become a planning expert. He now shuts down the company for two weeks over Christmas and dedicates time to creating his Annual Strategic Plan. It has led to some bold decisions, like swapping around his service ratio, from 80% installs and 20% maintenance in 2022 to 30% installs and 70% maintenance in 2023.


To hear more about how Dave formalized his strategic planning sessions to dramatically grow his business, listen to Episode 88 of the Contractor Evolution podcast.


Do’s & Don’ts of Creating an Annual Strategic Plan


Shout out to Alex Brueckmann, strategic facilitator and author of The Strategy Legacy, who supplied many of the following tips. You can hear more of his insights in Episode 85 of the Contractor Evolution podcast.




✅Go beyond numbers. Put both your heart and your mind into your Plan.

✅Leave space for others. It might be your company, but it’s not just about you.

✅Treat strategy like a dance. Sometimes you need to be the one who follows.

✅Turn phones off to keep the outside world from intruding on your planning session.

❌Confuse strategy with tactics. You need both, but they’re not the same things. 

❌Celebrate too soon. Recognize milestones, but save the big party until you’ve earned it.

❌Treat strategy work too lightly or you’ll sink your plan before it’s even in motion.

❌Fire off your Plan in an email with a subject line that says, “Please read.”


Gabriel Poblete | Premier Contracting


As you move through the year, you’ll inevitably encounter cool new ideas or projects. This is where your Annual Strategic Plan becomes your shield from being led astray. 


When you start considering whether a new idea is worth altering course for, check it against your Plan. Does it fit? Some ideas will be worth the upheaval, so don’t dismiss everything on principle. Just make your decisions carefully. That’s what the Plan is for.


It’s easy to look at an Annual Strategic Plan as a set of constraints dictating how you’ll spend your year, but it’s really more like a garden bed. The soil may only stretch so far, but there are endless options for what you can plant in it. Choose well, and it can bring joy to everyone who sees it.


Contactor Guide: Annual Strategic Planning

Download this Annual Strategic Planning tool from Breakthrough Academy now and start your journey towards a brighter, more definitive future for yourself and your business.


Ready to scale your business, pump up your profits, and extract yourself from the daily grind? Contact us at Breakthrough Academy and discover a whole new way to run your contracting company.