7 Tips For An Impactful Quarterly Planning Meeting

You’re in the last month of Q2, and everyone is heads-down trying to finish strong as the year’s halfway point draws near. Summer has begun, kids are out of school, and getting out of town for vacation is on the minds of most, especially coming out of the lockdowns of the pandemic. Your team finished most of their projects for the quarter, sales numbers are ticking back up, and you’re happy with the progress that was made. 

Then you realize that you don’t have anything on the calendar for Q3 planning. At best, you’re scrambling to align calendars around vacations for at least a full day with your leadership team to set the next quarter’s priorities. At worst, and this is very common, your team decides to skip planning this quarter because “there’s no time.” Before you know it, you’re over a month into the next quarter, and the train has already left the station. Sales numbers are behind, productivity is down, and team morale is taking a hit. 

As a management consultant, it’s always surprising to see how many companies aren’t doing any planning whatsoever as one quarter ends and another begins. Perhaps there are annual sales targets in place that the CEO prescribed in the hope of year-over-year growth, but beyond that, there’s no formal process for reporting out on progress, reviewing what needs fixing, and deciding on the most important projects to tackle, or topics for professional growth. 

Below are 7 Tips for Quarterly Planning that will keep your H1 momentum going as you head into the summer months. 

Step 1: Schedule Ahead of Time... Way Ahead of Time

If you don’t, they will sneak up on you! A best practice is to schedule quarterly planning meetings a year out when you’re doing your annual planning. Teams get busy, especially sales teams at quarter-end when everyone is pushing to drag every last deal across the finish line in an effort to make their number. If you can schedule them out a year ahead of time and get them on everyone’s calendars, that gives your leadership team and anyone involved in the meeting enough time to plan accordingly. 

From past experience, the best time for having a quarterly planning meeting is the third week of the last month of the quarter or the first week of the new quarter. This will avoid the squeaky wheels on the sales team saying, “I’m too busy trying to hit my number to make time for planning.” A wise man once said, “Failing to plan is planning to fail.” So true.

Step 2: Send Out Pre-Work 2 Weeks in Advance

A big part of quarterly planning should be hearing from the team regarding what’s working (so you can do more of it) and what’s not working (so you can pivot accordingly). As part of pre-work for the meeting, I always ask for these two pieces of feedback from the entire team, especially the frontline employees. This is also a great time to collect employee satisfaction feedback, which every company should be collecting quarterly and using for management team bonuses (but that’s for another topic at another time). 

Additionally, as part of the pre-work, I ask the team to ensure that all of the pending projects for their department are listed on the future project's roadmap and scored by priority and size. This will be used to prioritize and load balance the next quarter’s projects during the meeting. 

I also include a learning topic (which we’ll discuss in a minute) that usually requires a little bit of homework on their end (reading an article, listening to a podcast, etc.) 

Ask that the team completes the feedback portion within a week so that you have time to distill and organize the information. And two weeks is enough heads-up on the homework assignment to allow them to work it into their schedule. 

Step 3: Kickoff with a Retrospective

It’s important to look at the past performance to inform the future. I try to spend no more than 90 minutes on a retrospective of the prior quarter that includes a review of financial performance (high-level budget-to-actuals & year-over-year), sales performance (quota attainment, meaningful wins/losses), churn, departmental projects completed, and employee feedback that was collected from the pre-work. 

Reviewing the prior quarter’s performance achieves a couple of things: first, it lets them know that the work they’re doing matters and someone is watching. Aside from driving accountability, this gives their work meaning and is also a great opportunity to give recognition in front of their peers for a job well done. Second, this provides transparency into work being performed in other departments. Silos pop up quickly, and sharing progress (and challenges) at quarterly planning meetings is a great way to drive alignment. 

Lastly, sharing the company feedback in public is by far the most interesting part of the retrospective, and it’s a great way to cap off a session that can be viewed as a slog, which is another reason to get it out of the way early in your planning meeting. Every person wants to have their voice heard, and it’s often reassuring when they hear that they’re not the only one noticing some things that could be improved. 

Step 4: Decide on the Next Quarter's Projects

If you walk away with nothing else from your quarterly planning, walk away with the workload assigned for each team member. This will require having some processes and tools in place prior to the meeting such as keeping a running list of projects. If you’re operating correctly, your departments and leadership team are meeting weekly throughout the year to solve issues. This should result in a healthy list of project work that needs to be tackled at some point. 

My favorite tool for this is Asana. I use this to track current-quarter projects on a separate board so we can check in weekly on their status and % complete. I keep a separate board in Asana for tracking future projects where they’re weighted by priority (high, med, low) and size (large, med, small). We also have a column for “projected quarter” which notates when we think we’ll get to this project. Lastly, I assign points to each project to assist in load balancing everyone’s work. I assign 3 points to large projects, 2 points to medium projects, and 1 point to small projects with guidelines that nobody can take on more than 12 points in a single quarter. This may vary slightly from company to company based on the types of projects you’re doing, but you get the idea - you can’t do it all. 

Step 5: Solve Some Issues 

If your team is meeting weekly and doing a good job of adding issues to your issues list, then there should be a list of issues that need to be solved. A best practice I’ve adopted is to prune the list when it gets to 30. I do this by asking: Are they still issues? Can they be solved in a smaller setting? Can a decision or finding a solution be delegated to someone? Try to keep only the most relevant issues on the list that require input from multiple parties. If you’re doing this, then there should still be some large issues sitting there that need to be solved. 

Even if you’re keeping your issues list pruned, there’s likely a large issue sitting out there that’s been punted because you haven’t had enough time during your weekly meetings to solve it, or you haven’t had everyone whose input you needed in the room. Quarterly planning is your chance to solve 1 to 2 of these larger issues. It’s best to decide what those issues are prior to the meeting and to give everyone a heads-up. If you plan far enough ahead for the meeting you could even include a prompt in the pre-work to come prepared with ideas to help solve a specific issue. 

It’s typical to block up to 2 hours for solving 1 to 2 large issues as a group. Whether it’s a brainstorming session or breakout group, be sure to come up with a framework for solving these issues. You have a room full of your best talent, so some preparation will be required to lead them through this session. 

Step 6: Learn Something Together 

According to Tony Robbins, one of the six core human needs is GROWTH. Keep this in mind as you curate your employee experience roadmap, but especially when it comes to your leadership team. Quarterly planning is an excellent opportunity to bond with your leadership team and shape the type of leaders that you’d like to see in your organization. I block an hour at each quarterly planning session to cover a learning topic. The topic varies based on what’s going on in the business. I keep a running list in Asana of potential learning topics comprised of books, articles, videos, and podcasts. Harvard Business Review puts out a ton of great content, but there’s no shortage of useful content out there. Topics related to how you work together (communication, productivity, as a team can have a lasting impact, remove friction from the organization, and teach your team something new in the process that meets their core need for growth. 

Step 7: Fill Their Gas Tank! 

Quarterly planning is a full day (and sometimes two full days depending on the size of the organization) of pure focus. Asking your teams to come well-rested and ready to participate won’t be enough. It’s important to carefully curate the schedule in order to keep everyone engaged for the entire meeting. 

This includes thinking through the order and duration of each session, when to do bio breaks, and when to have food and snacks delivered. I like to use Trello to map out each session and label them either “gas” or “brakes.” “Gas” sessions are the ones that fill their gas tanks (e.g. bio breaks, food, snacks, and fun sessions that require some movement). “Brakes” sessions tend to be more grueling and require focus and critical thinking (e.g. retrospectives, solving issues, project planning). Make sure you don’t schedule back-to-back “brakes” sessions so as not to nuke everyone’s gas tanks. 

Anything you can do to gamify a session and hand out rewards (e.g. gift cards, gift certificates, cash!) will certainly catch their attention and keep them engaged. Happy hour or dinner is also a great way to cap off a long day of critical thinking, problem-solving, and planning. 

Your team is coming focused and ready to help bring your vision to life, so do everything you can to pamper and spoil them while they’re giving you their undivided attention.