How to run a great remote planning meeting for the year ahead

The countdown to the New Year is upon us. And as we get ready for the ball to drop in Times Square, many of us are also doing our best not to drop the ball on planning efforts for the year ahead.

For most teams and companies, December and January are the biggest strategic months of the year. You’re probably writing your individual OKRs, creating a quarterly plan for your team, or setting the company’s focus areas right about now. Maybe deep reflection is already a part of your process here—if not, it should be.

Pausing to reflect is one of the most powerful ways your team can gear up for the year ahead.

According to research, taking the time to learn from past experiences helps us make better decisions and augment future outcomes—so much so that reflecting is actually more powerful than doing in terms of setting your team up for success in the new year.

In this post, we’ll walk through ways to build reflection into your team’s yearly planning rituals to help you drive results, come together as a team, and create a plan for the year ahead that everyone’s fired up about.

What inputs inform your team’s planning processes today?

Many teams are accustomed to using metrics and KPIs to shape the process—and while that approach isn’t wrong, it’s only looking at one piece of the puzzle. Strategic planning should take into account harder to measure inputs too—like how people feel, what gives them energy, and where they feel most connected to the work. These key emotional indicators (KEIs) let you see how your team is doing and are linked to improved outcomes. According to research, positive emotions are consistently associated with higher performance and quality of work.

Reflection is key to understanding and unpacking these KEIs during strategic planning. When we take the time to reflect on what’s working and what isn’t, we start to recognize patterns in the way things work and gain a powerful understanding that helps us make better decisions—and better plans.

Reflection: A two-part process

So how does reflection work anyway? To inform your plan for the year, you’ll want to do more than just look back at what happened.

The most powerful reflections consist of two parts:

1. Looking back: Recalling what happened and how it made you feel
2. Connecting the dots: Analyzing what happened for learnings and key themes

The questions you pose during the reflection process should map to this formula too. With an initial question that jogs the team’s memory and recall, and follow-ups that go deeper to build understanding.

Using the reflection formula outlined above, the following section is meant to help you plan and run a successful (and fun) planning meeting to kick off the year.

How to plan and structure your planning meeting

1. Get everyone involved. Successful reflection and planning should involve the whole team, so ensure your format and schedule allow everyone to participate, whether they’re remote or in the office. Assign a facilitator ahead of time who’s well-equipped to make the session feel engaging and inclusive for all.

2. Decide on your format. Some specifics to consider…

• One or multiple sessions: Will you do a full or half-day of planning and complete it all at once? Or schedule a few shorter sessions throughout the week? If your schedules can swing it, we recommend completing as much as you can in one session so people don’t have to jump back and forth context-switching.
• Async or sync: Will you do the entire planning exercise together as a group or ask people to do some prep work on their own time beforehand? Individual prep can make planning sessions more productive and inclusive. If you have a hard time getting folks to do “homework” beforehand, you can always build in some time at the beginning for heads-down individual reflection, and then come together afterwards to discuss.
• Smaller groups or one big group: Depending on the size of your team, you might consider breaking everyone apart into smaller groups so that folks feel comfortable sharing and there’s room for discussing and exploring new ideas.

3. Decide on your topics or areas of focus. The possibilities for reflection are pretty much endless, so you’ll want to go in knowing a few key topics you want to cover together. Consider the feedback you’ve collected from the team throughout the year and use your own observations too. Have you heard frustration with the way meetings are run? Did the project prioritization process feel unnecessarily stressful? Another good trick is to think about the areas your team spent the most time and energy on in the last year—your team will be able to easily reflect on them and they’re likely full of opportunities to improve.

4. Choose a few key prompts for each. Good reflection prompts help people look back on what’s happened and understand why things happened the way they did. They can help surface themes and areas for growth, and are a powerful way to get everyone thinking about how to apply learnings to future projects. We put together 150+, across a number of different themes and focus areas, to help you get started.

5. Share your agenda and prep materials. Give people a chance to think through the topics they’ll be reflecting on and consider doing self reflections beforehand too — this can be a great way for individuals to take a deep look at their own personal strengths and areas for growth, and then better understand how those impact team dynamics during the group reflection too.

Planning meeting agenda

Icebreaker: Start by going around the room to give everyone a chance to share in a quick icebreaker question. Studies show that when teammates speak at the beginning of a meeting, they’re more likely to stay engaged throughout. Here are a few ideas:

• What’s something or someone you were grateful for on this team last year?
• What was your highlight or favorite project from last year?
• Share a personal goal or some long-term goal you’re excited for outside of work in the new year.

Topic reflection: Here’s where you’ll dig into the focus areas you landed on above.

• Topic 1:
  • Looking back
    • Start by posting your “Looking back” prompts on a digital or IRL whiteboard.
    • Then, give folks 5-10 minutes to collect their thoughts and jot down their responses to the prompts on sticky notes.
    • After the time is up, have everyone drop their stickies onto the whiteboard and then spend 3-5 minutes reading what others posted and processing that information.
    • Tip: To reduce live meeting time, teams can choose to complete the “Looking back” exercise asynchronously before the meeting using a tool like FigJam.
  • Connecting the dots
    • After you’ve gone through the “Looking back” questions for your first topic, it’s time to take a step back and analyze what’s on your whiteboard for themes and learnings.
    • As a group, start by grouping related sticky notes together to help visualize themes and commonalities.
    • Then, have your facilitator pose “Connecting the dots” questions and open it up for discussion. If you’re a larger team, you may want to break apart into smaller groups for this step and then come back together to share your findings.
  • Create your plan
    • After you’ve done both parts of your reflection for the topic, it’s time to come up with some actionable next steps.
    • For each topic, we recommend coming up with 1-3 measurable actions you can take to grow together as a team. (If you follow the 1-3 rule, some reflection prompts may not have a next step—and that’s OK!) Keeping it focused on 1-3 high impact next steps makes it easier for the team to make progress towards the plan and ensures that whatever they commit to will likely be something everyone’s fired up about.
• Topics 2 and on: Repeat the steps outlined above for as many topics as you’re planning to cover.

Review of plans and commitments: Once you’ve gone through each topic, take a look at all the plans you’ve committed to for each and pose the following questions to the group.

• How do you feel about what we’ve outlined here?
• Is there anything important missing from this list?
• What are some ways we’d like to hold each other accountable to these?

Assign owners: To help with accountability, ensure each next step in your plan has one clear owner who will be responsible for driving that effort forward and reporting back to the group.

Align on a cadence for checking back in: This might happen synchronously (holding a follow-up meeting at the end of each quarter), asynchronously (owners send out monthly updates), or some combination of both.

Closing round: Here are a few ideas…

• Honest feelings check: How are you feeling about what we discussed and where we’re heading?
• What are you most excited to tackle in the year ahead?
• What’s something new you learned today?

The best plans stem from reflection — both on work and on how you're doing. With this in mind, we put together an ebook of 150+ reflection questions to help individuals, teams, and leaders plan for the year ahead and work even better together.