Yearly Calendar Planning Tips Every New Manager Should Know

I’ll be honest I’m not the biggest fan of setting traditional resolutions. In fact, I did not set one single resolution this year. Traditional resolutions like “I need to start doing this” or “I need to stop doing this” are the types of things I try (I try…) to assess and work on regularly throughout the year.

But I do love to set goals. And I love that fresh start, clean slate feeling that comes with the new year. I love getting myself organized, looking ahead, and setting myself up for success for the year. There’s a handful of things I do that set me up for success every year and save me time in the long run.

Frontloading my calendar is just one of the ways I organize myself for the upcoming year and it gives me so much peace of mind.

As a manager, you are busy and you truly never know what the day, or your team, will bring. Because of that I strongly believe you need to put a concerted effort into organizing yourself. In whatever way works best for you!

Having an organized calendar sets a foundation and creates an environment where you are better able to handle what comes your way without dropping the ball on what need to get done.

Now, not to get too deep here, because we are talking about organizing a calendar, but I know there is a LOT of information out there about THE BEST way to organize, or time management hacks you MUST do, or ultimate ways to 10X your productivity…this is not that post.

This is what I do and have done for many years, and it works for me. I’m sharing because I love learning how others organize themselves and take from it what works for me.

Finding a system and process that works for you and the work you do takes trial and error, flexibility, and more than likely a few iterations. And if I’m going to strongly suggest you do anything, it’s that you approach organization and productivity for yourself the same way.

I do feel strongly about organization so my hope is that you do find something useful in this post and implement it in your life as a leader.

Aaand…to make things easier for you I have created a Manager’s Yearly Calendar Prep Checklist!

Click HERE to get it right to your inbox!

Start With Reoccurring Meetings, Events, And Tasks

Start by gathering and compiling a list of all your re-occurring meetings or bigger items and events that come up throughout the year. Some of these may already been in your calendar so it will just be a matter of moving it forward to include them in the current year.

This could be your scheduled uninterrupted/quiet time, one-on-one meetings, annual reviews, budget meetings, product launches or campaigns, conferences, vacation times, etc. Basically, anything you know is coming up in the year should be put in your calendar.

By having this out of your head and in your calendar (with alert and reminders obviously) you can now rest easy that you will not forget the important dates and meetings. You have already reserved and dedicated the time for them and have ensured nothing will get missed.

Pro-tip: Review last year’s calendar, emails, and notes and make note of any big items from the past year.

When Your Digital Calendar Isn’t Enough

I obviously love and use my calendar and live for a good pop reminder on my phone or laptop. But sometimes you just need a little extra help to keep you eye on the ball.

I have a very simple secret weapon when it comes to organizing my entire year. It is the simplest 3 x 4 monthly grid that I keep posted in front of me on my bulletin board at all times. This is similar to one of those full wall-mounted, whiteboard style 12-month calendar, but simplified and far more streamlined.

Yes, I still rely on my calendar for meetings, tasks, and reminders, that doesn’t always provide a high-level view of the whole year and more importantly, what’s coming around the corner. So, what I like to do is take the bigger, more time-consuming tasks or the ones that require a lot more prep and lead time, and enter them into this template:

I have included this Year by Month Template with your Manager’s Yearly Calendar Prep Checklist!

Just one click HERE will get you both of them!

Having this in front of me serves as a reminder of what is just around the corner so I can start to mentally, or literally, prepare. This is also very helpful if there is a bigger, ad hoc project that come up throughout the year. Having the bigger items already (loosely) mapped out will help you plan, or re-arrange, anything around them.

I know this seems like an extra step, but I can’t tell you how much this very effective visual has repeatedly saved me and kept me on top of what’s coming next. In fact, I even use this template in my personal life for birthdays and finances, so I’m not caught of guard.

Plan Ahead for Training

Continuous learning, growth, and upgrading skills is something that should be encouraged, both for yourself and your team. It is something that should be regularly discussed and heavily promoted. So with that in mind, it’s inevitable that you or someone on your team will request, or maybe require, to improve and/or upgrade their skills throughout the year.

This can look like a simple re-certification, training related to maintaining a designation or license, or any annual internal training that’s required from your specific company. Ensure you have all these renewal dates in your calendar and anything that needs to be booked or organized is done well in advance (another way step 2 can work in your favour).

You will also want to give some thought to any additional training or upgrading skills (think coaching, courses, or having a trainer brought in). This should be discussed between you and your team members during your one on ones and included in any goals and objectives for the year (hint: this is a great question to ask either during your last or first one on one meeting of the year).

If leadership training is in the plans for you or one of your team member this year, then click here and let’s chat. We can hop on a free 30-minute call to see if what you need is what I can help you with.

Schedule in Breaks and Vacation

I’ll admit it, I was always really bad at this one because I usually just took long weekends here and there and they were usually never planned that far in advanced. But after becoming a mum and a pretty intense bought of burnout, I now know the importance of taking proper breaks. And taking breaks was always something I encouraged my team to do (even enforced at times).

Although it can be hard for some people to plan ahead for the whole year, you can usually get a rough idea of any trips your team may have planned or any time off they’ll require throughout the year. If you are able to get this information, make sure it’s recorded in your calendar that way any additional planning or coverage can be organized well in advance.

If you or any of your team members have kiddos, then you may want to consider including spring and summer break in your calendar, as well as any other days/half days off throughout the year, as those may impact your team's availability.

And don’t forget to include your own time off and down time in there too!

You can definitely file this list under as small steps with big impact!

By me taking the time at the beginning of the year and setting up my calendar and organizing myself, I feel like a huge weight has been lifted off my shoulders. I feel like I’m less reactive to things that come up and it’s less of a mad scramble to organize my time. With an organize calendar I can be present and focus on supporting my team and everything else I need to get done.

Pre-loading my calendar has such a huge impact on me staying organized, ensuring none of the important dates and meetings are forgotten, and just clearing space in my mind so I’m not always trying to remember not to forget.

So, did I miss anything? Is there any go-to tricks you have to organize your calendar? Let me know in the comments!

Happy Leading!

Emily