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The ultimate annual strategic planning playbook: How to set visionary priorities and make the most of your time every year.

May 9, 2023//by Hutch
The ultimate annual strategic planning playbook: How to set visionary priorities and make the most of your time every year.

When you’re a small business owner, making time for intentional growth and scaling is a real challenge. It’s easy to get caught in an endless cycle of putting out fires or responding to unexpected opportunities. When this happens, longer-term planning often falls by the wayside. It can feel impossible to plan for the future when more immediate needs are eating up all your time. 

But proactive planning is actually one of the best ways you can get time back

Annual strategy planning is just one part of the strategy planning framework we teach at Hutch, but it’s a key way that our entrepreneurs get out of the daily grind and make real forward progress. By making time for this kind of vision casting early on, you can set yourself up to see the growth needed to successfully scale. 

Looking for more time-saving tips? Check out our Time Management for CEOs Playbook. And for help focusing on what matters, read our Prioritization Playbook.

The annual strategic planning playbook

Our annual planning framework is designed to help you develop short-term goals to achieve your long-term outcomes. By connecting your day-to-day actions to your overarching vision, you’ll be able to grow intentionally in the ways you need to.


You’ll also be able to say no to those tempting distractions that threaten to derail you from your objectives. As Steve Jobs put it, “People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully.”

Illustration of a well blocked off calendar.
Illustration of an annual strategic planning roadmap.

Through the following plays, we’ll help you learn to say no by crafting a yearly roadmap that includes your priorities, goals, and strategies. Our annual strategic planning process will prompt you to identify the things that are essential and which will pull your focus away from your goals. It’ll also help you figure out how to balance all of this with your personal life.

Ready to get started?

The benefits of setting effective annual priorities. 

  • Improved return on time, giving you a laser focus on the things that will have the greatest impact on your business.
  • Better discipline and focus, enabling you to say no to anything that doesn’t align with your strategy.
  • Elimination of high-effort, low-impact tasks, allowing you to get out of the daily grind.
  • A more aligned and focused team, making delegating tasks easier and allowing you to shift from the primary doer to the visionary leader of your company. 

Play 1: Kick off your annual strategic planning by brainstorming all the things you might want to prioritize this year.

There are a million things you could focus on each year as a business. You might be looking to grow your team and scale your internal operations. Or you may feel like you need to work on systematizing your business development process. Revenue is a big priority, so you might need to focus on winning a few prime contracts in a key sector.


At this point, everything is fair game. Jot down anything you think you might need to prioritize this year to survive and thrive as a business. Don’t say “no” to anything yet. Just focus on generating as comprehensive a list of potential priorities as possible at this stage of the annual strategic planning process.

Illustration of an annual strategic planning brainstorming session.

Things to think about as you generate your priority list.

  • Are there specific customers you need to make ins with? 
  • Is there an industry you need to break into? 
  • Are there revenue targets you need to hit? 
  • Is there a capability you need to develop?
  • Are there shifts you’ll need to make to address changes in your customers’ behaviors?
  • Is there a weakness or threat you’ve identified as part of a SWOT analysis that you could eliminate? 
  • Do you have the internal processes in place to grow the way you need to? 
  • Is anything preventing you from delegating tasks, and if so, how might you remove those blockers? 
  • Do you need to expand your internal team to get where you need to go?

Play 2: Pick three priorities to focus on for the next 12 months.

At this point in your annual strategic planning, you’ll need to start whittling down the list you generated in the previous step. But first, take a minute to reflect on why you’re setting these priorities in the first place. 

Annual priorities allow you and your business to focus on the initiatives that will be most important for your forward movement. That’s why it’s so important to pick a limited number to focus on. It’s easy to be overly ambitious at this stage in the annual strategic planning process, which is why you should pick just three priorities for the year.


To help narrow down your list of priorities, we recommend hosting a sticky note session (either physically or virtually using a tool like Miro). You can do this on your own, but it’s useful to have partners — whether they’re peers, mentors, or business partners — to give you a fresh perspective. Then together, you can start combining and consolidating ideas.

Illustration of an annual strategic planning sticky note session.

Start by jotting your priorities down on sticky notes, then see if you can group them. Could any be combined? Are any redundant? When you’ve finished grouping your priorities, you can start to rank them. 

Use the following questions to help you test priorities and pick the three best ones.

  • Why is this priority critical? 
  • Will this priority enable you to take your business to the next level? 
  • Would achieving this priority put you closer to realizing your business’ vision? 

Once you’ve settled on your top priorities, write a brief description of them, along with an explanation of why they’re critical for your annual strategic planning.

Play 3: Pressure test your priorities (and revise as needed). 

Picking the right priorities is hard. It’s much easier to just choose a few that feel “good enough” and call it a day. But this can defeat the entire purpose of an annual planning framework. After all, priorities are only useful if they’re actually used. And this means you need very intentional and strategic priorities, as they’ll guide everything you do. 

So, how do you tell if you’ve picked the right priorities or if they still need some tweaking? You pressure test them.


It’s very hard to see the gaps in your own work, so it’ll be important to bring in fresh perspectives. This is even more important if you’ve been working on your own up until this point. If you have a peer, mentor, business partner, or even just a friend who’s willing to support you in your annual strategic planning process, ask them to help you evaluate your priorities.

Illustration of two people testing ideas with each other.

Put each of your priorities to the test by asking yourself the following questions. 

  • Is your priority clearly defined? You want each priority to be described so clearly that a stranger could read it and understand exactly what needs to be accomplished. 
  • Is the size of your priority appropriate for an annual goal? While there will always be problems that need to be addressed right away, your priorities should be bigger picture goals that can help your business take large steps forward. 
  • Does everything that you plan to focus on this year fit into these priorities? Your priorities are the north star of the annual strategic planning process, and they should influence everything you work on for the next 12 months. Because of that, you’ll want to make sure there aren’t any big tasks you plan to work on that don’t align with them. 

If you answered “no” to any of the questions above, don’t worry. Your priorities will almost never be perfect the first time around! Make some tweaks and repeat this step as needed until you’re a “yes” on all of the above prompts. 

Play 4: Set 2–3 goals for each priority.

At this stage in the annual strategic planning process, your priorities should be pretty solid. But how do you start to turn them into action? And how do you measure your progress towards them throughout the year? To start, you’ll need some goals. 

Aim to create 2–3 goals for each of your priorities. Your goals should be good proxies for the priority, and they should be easy to measure and time bound. 


For example, if your priority was to generate enough revenue to sustain your growth, one of your goals might be to book a certain dollar amount in revenue in the next calendar year. You might have another goal around the number of your existing contracts that are coming to a close this year that get renewed or extended.

Setting goals is a key point in annual strategic planning, as it’s where your more theoretical strategies start to become tangible action.

Illustration of setting goals.

Use the following questions to test each of your goals. 

  • Is your goal related to a priority?
  • Is your goal easily measurable?
  • Is your goal realistic in the given year?
  • Is your goal specific and concrete?

When deciding on your goals, make sure they’re broad enough in scope and that it’ll be easy to tell if you’ve accomplished them. Your goals should be big proxies you can track over time, like a certain number of contracts won or a percentage of projects completed on time and on budget, rather than lower level benchmarks. Those will come in the next step.

Play 5: Tie it all together into an operational plan. 

Now that you have your goals, you can start mapping out how you’ll achieve them. During this stage of the annual strategic planning process, you’ll start to get into the weeds of what exactly you’ll do and when. 

Taking one goal at a time, think through all the steps you’d need to take to achieve it. Then start attaching dates to each step. If you want to secure work with three new health agencies by the end of the year, for example, you might spend the first quarter doing business development research to find out which agencies most need your services. After coming up with a list of target agencies, you could start planning around their procurement schedules. After this, you may want to spend some time building strategic relationships before prepping for the proposals themselves.


No matter what your goals are, try to be as thorough as possible at this point. Good annual strategic planning requires both high-level visioning and in-the-weeds tactics for how you’ll get where you want to go. Your operational plans are how you bridge this gap, connecting your everyday actions to your long-term goals.

Illustration of an annual operational plan.

Questions to ask yourself to help develop your operational plan. 

  • What are all the actions you’ll need to take to meet each of your goals? 
  • What sequence would all of these actions have to happen in? 
  • What are the benchmarks and milestones that you’ll need to hit (and when) to ensure you’re on track? 

Once you’ve answered these questions, it can help to get an outside perspective. If you have a peer, mentor, or business partner you can ask for support, pressure test your plan with them to see if there are any gaps that need to be filled or revisions that need to be made.

Play 6: Add your personal life to your plan. 

At this point in the annual strategic planning process, you should have a solid understanding of your priorities, goals, actions, and benchmarks. But this is an ideal plan, and it assumes that you’re working on your business in a vacuum, with nothing else competing for your time. 

Unfortunately, that’s not how life works. 

Entrepreneurs are people first, and they have families and communities. Many work another job, on top of building their own business. If you don’t account for these realities, you’ll either try to do everything (and burn out fast) or some of your priorities will get sacrificed. 

That’s why the final step in the annual strategic planning process is adding in the rest of your life.


If you’ve got a big project due in February at your day job, you probably shouldn’t try to do a big business development push at the same time in your own business. Or if you’ve got a family vacation booked in June, you might want to make that a lighter work month all around. Whatever the reason, if you anticipate there being any constraints on your time, make sure you include it in your annual strategic planning and adjust your deadlines accordingly.

Illustration of a couple with a baby.

Things to think about as you generate your work + life plan. 

  • What does your capacity usually look like? If you tally up all the things you need to do outside of working on your business (including work on anything else, spending time with your family and friends, chores, errands, taking time for yourself, etc), how much time is left each week? It’s important to be realistic at this point; don’t try to fill every hour of every day. Instead, try to calculate the time you could put towards work while still balancing your other needs. That should be your baseline capacity. 
  • Are there periods where you know you’re going to have reduced capacity? While your baseline capacity is the normal state, there will be times when your capacity will be significantly reduced. As you’re working on this step of your annual strategic planning, try to account for periods when that might be the case as much as possible ahead of time. 

Once you have a sense of what kind of capacity you have to work on your business and when, you’ll be able to use this information to set more realistic goals and deadlines in your operational plan. 

If you do strategy planning right, you can achieve anything.


It can feel hard to make time to build out a planning framework, but it’s a critical tool in any entrepreneur’s toolkit. By working towards a set number of strategic priorities every year, you can hone your focus, cut the unnecessary, and free up your time. 

But learning how to do effective annual strategic planning can be deceptively challenging. After all, anyone can take a stab at following the above plays to create a plan. The hard part is figuring out if you’ve created the right plan.

Illustration of an entrepreneurial community of support.  

That’s why, at Hutch, we have dedicated strategic planning sessions. During them, our cohort companies create, workshop, and improve on various elements of their plans with advice from experts and from other entrepreneurs. With this built-in group of peers and mentors, our entrepreneurs can bounce ideas off each other and get advice from people with expertise in their specific problem areas.

 By getting early feedback from others as they craft their plans, our members are able to pressure test and hone their ideas early on in the process. And this can save them from issues and rework later on, allowing them to identify (and sidestep) any potential pitfalls before they start running. 

Want to learn more about annual strategic planning

Do you have questions about how to plan out your yearly strategy? Sign up for our weekly newsletter. We are sharing tips and education from our cohort classes, and subscribers get first access to free webinars.

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