Raise your hand if you’ve seen the “how it started, how it’s going” trend…yep, I thought so. These memes have been a staple of pop culture this last year, with some that were utterly hilarious, some sad, others inspiring and still others simply cute (like when Paddington Bear got in on the trend). The point was to show the difference between your starting line and your finish line, or even your progress toward said finish line. 


While the trend was fun, it got us thinking about how it relates to annual planning. So often, business planning starts out utopian, everyone with stars in their eyes about what’s to come. But, check-in six months later? The same set of people are weeping on the ground in the corner of their office, close to giving up on their goals entirely. Even if your “then and now” isn’t quite this drastic, it’s clear there’s an art and science to setting a company strategy that can actually be fulfilled. Here’s what I’ve learned over the years, as my team and I have refined this process time and again. 


Annual Planning with Quarterly Meetings 

One of the biggest mistakes I’ve seen when working with entrepreneurs and business leaders is trying to use an annual planning session to set a full year’s strategy. They may meet in December like we do, or at a different time based on their fiscal calendar year, but they work to come away with 12 months of plans mapped out. Not only does this make for an exhausting session, but it also can be ineffective. In fact, it will make you end up like that hypothetical “how it started, how it’s going” meme I mentioned earlier because here’s a secret: you have no idea what is going to happen in the next year. So, how can you possibly plan for it? 

Instead, be realistic. Putting an annual plan in place and meeting in an in-depth capacity once per year is absolutely a great idea. But don’t let that be your holy grail for the year. You must also set a schedule of quarterly meetings to check in on your progress, create new milestones and, yes, adjust your strategy. I know it might make your stomach clench to think of pivoting midway through the year, but you have to prepare for this possibility.

 Just think of 2020. How many of us incorporated “global pandemic” into our annual plans for the year ahead at the end of 2019, and yet how many of us had to adapt to it come March of 2020? All of us. This just goes to show that you can’t predict the future, and you need to plan for unpredictability. This simple tweak in how we set and adjust our company strategy has been mind-blowingly effective for us, and it can be for you too. 


Agile, Intentional & Fun

Handling your planning in this way will keep you in a mindset of agility. Your team will be invested in your plans and your goals, but not so stuck to them that they can’t be nimble when needed. It also helps you become intentional about issues that need your attention more wholly in the short term. For example, we create 90-day plans at every quarterly meeting, including milestones for the next quarter. By doing so, we keep our long-term vision as the focal point while dialing in the short-term work that will really get us there. 

Agility and intentionality are awesome, but business planning can be dry if you don’t add in one more thing: fun. Team members who are invested in your business may be eager to share their points of view during meetings, sometimes causing tensions and opinions to run high. Conflict often occurs and, if you don’t provide a counterbalance of relationship-building and good ol’ fashioned fun, it can leave your office dynamics sour.  

So, plan a happy hour after your meeting and ban business talk during it. Or, invite your team members to an activity, whether in-person or virtual. Relaxing and enjoying some time together can help everyone remember they’re on the same team and work better together overall. 

Looking to revise your annual plan process? Make sure to include marketing in there. Contact us with any questions!