How to Effectively Calendar Out Your Year
Around this time of year, most business owners are busy planning not only to try to meet their end of year goals, but for the upcoming year. Planning is a wonderful thing – in fact, it’s one of my favorite things – but unless those plans make it to your calendar, they probably won’t happen.
This is where many business owners lose their steam. They work through their goals and may even get them down on paper, but leave calendaring until the new year. Once the new year comes, however, there’s a whole new set of projects, clients, tasks, and other ideas that tend to take precedence.
If you’re ready to finally make your goals become reality this year, a key component is making sure your calendar is set before the new year really takes off. This process doesn’t have to be as daunting as it might seem – and with the right framework in place, it can be a lot easier than you might think.
A key to calendaring out your year is to look at the big picture. This means focusing on what is most important in your life and where you want to go with your business goals. You’ll find a lot of these in your business plan – they create the north star that help you focus your attention on moving forward.
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Calendar Your Plan
As you worked through your business planning, you probably started with a strategic plan. This gives you clarity of what you want to build, how you want to progress, and how you want to end the year.
You then likely moved into tactical planning. This type of planning will break down your high level goals so that you know, quarter by quarter, what you’ll need to accomplish in order to reach your goals by the end of the year.
Within each quarter, you can then break down your tasks even further, deciding what tasks need to be completed and who you can delegate them to in order to reach the interim results you’re looking for.
The most important part of the process – and the one that many business owners miss – is to get these things on the calendar. It’s been said that a goal is just a dream unless it’s on your calendar, and I’ve found this to be very true.
When you do this, it’s also important to not just write it down on your own calendar or add it to an Asana board, but to actually task someone with it (and give a due date) so that there’s ownership. That human may or may not forever be the “owner” of the task, but at least it will be placed with someone who can spearhead it and move it forward.
If this person isn’t able to complete the entire task or project, they can bring this to your attention. They may understand more about the logistics and details of it – whether someone else needs to be brought in or hired as well as who else some of the work can be assigned to rather than just letting it stay in an empty task.
It’s also vital to have interim milestones and ultimate deadlines to keep projects moving forward. I know from personal experience that it’s easy to push a task out or not hold people accountable because they’re busy with other things, but in order for the process to work well, there does need to be accountability. Someone needs to be asking those questions and helping to fill in any missing pieces. This is where a department coordinator can be very beneficial – they can be the interim person asking these questions and keeping you updated.
Don’t Forget Your CEO Duties
Too often, I see CEOs getting caught up in projects or day-to-day tasks. This is a tempting thing for a business owner to do, but it’s rarely conducive to moving your business forward as a whole. It might seem like these will “just take a moment,” but they prevent you from taking care of the higher level planning and protections for the business.
These higher level tasks that should go on your calendar may include things like meeting with your business attorney, your intellectual property attorney, and your employment attorney. (Failing to do so can land you in unanticipated trouble.) They might also include tasks like meeting monthly with a benefits coordinator to understand what you can offer, like health insurance or other benefits, even if you need to do so down the road. If you don’t calendar in these meetings, you can’t adequately plan for growth.
It’s also important that, as the owner, you have quarterly meetings with your departments to identify and address various needs. A quarterly sales meeting will allow you to take time to analyze the statistics and identify trends or changes so you can decide which additional changes you want to make.
The same goes for marketing. A quarterly meeting will allow you to look back at the past quarter, but also to the next few quarters so your team knows what’s coming up and can get to work.
Your day-to-day operations and administrative teams also need a quarterly checkup so you can stay on top of what needs to be purchased or acquired, as well as to plan for hiring needs that may be coming up.
As your business grows parts of this may come off your plate, but to some extent, you as the CEO need to be aware of quarterly team reviews and annual reviews. You may have various team members who aren’t in every meeting, so these reviews will offer a chance for valuable feedback for both the team member and for you. This process gives us a chance to analyze what’s working and what’s not so we can keep our team aligned with our mission.
Equip Your Team to Help You Calendar and Scale!
You have big plans…but if they’re not on the calendar, they’re not likely to become reality. This task doesn’t have to fall to you, though – with the proper training and resources, your team can handle a lot of it for you!
Marketing Planning and Calendaring
Planning out your marketing is one of the most vital ways to ensure a steady flow of leads coming in the door. While many business owners say they want to do this, not as many take the time to do it – and often, it doesn’t get done because it’s not on the calendar.
I find that it’s helpful to break out marketing meetings into big picture planning sessions, routine weekly sessions, and specific campaign sessions. Creating a good routine and rhythm can go a long way toward helping a team work effectively and efficiently. This will allow you ample planning time; creating last minute content is generally not a good idea, as it can waste valuable time. With effective planning, you can batch content creation weeks in advance.
While some business owners are great at calendaring out their year, many find that they need an effective framework and one-on-one coaching to make it a reality. The biggest take away for CEOs is to understand your needs, your learning style, and to get the support you need as you learn and hone these skills.
A well planned out year can make all the difference in the world for your business and your ability to thrive. If my team and I can support you, please reach out!

