A Guide to Making Your Annual Strategy Session Interactive

Credit: Pixabay by AJS1

Every year, around this time, my team and I get together with our long-term clients to collaborate on their annual marketing strategies. Over the years, we’ve developed an approach to these strategy sessions that is productive and (if we do say so ourselves) fun, and we’ve found that it’s even more valuable for companies who are trying to conduct virtual strategy sessions. Our secret? Interactivity.

Why prioritize interactivity?

In short: buy-in. We’ve learned from countless discovery sessions, creative kickoffs, and branding workshops that it’s easier to follow through on plans when every stakeholder is invested from the beginning. So many companies are still crafting their annual marketing strategies by holding closed-door meetings with a small handful of decision makers. What these leaders don’t realize is that their plans would only benefit from the diverse perspectives of the larger group. Involving more people in the planning process — especially those who are ultimately going to execute the strategy — helps to get the entire marketing team bought in at every level, while surfacing some great ideas along the way.

The result is an annual strategy session that delivers on the expectations of those at the top while ensuring that everyone’s voice is heard in the process.

What our strategy sessions look like in practice

Here at Trekk, each client’s strategy session is tailored to their needs, but they all have a few details in common:

  • They’re designed to be collaborative and built around a series of activities engineered to get people sharing ideas across teams and functions.
  • We begin by defining the common language that the group uses to talk about their annual goals, objectives, and marketing activities.
  • Anytime we talk about goals, we always also talk about measurement. Nothing makes it into the annual strategy unless it’s measurable.
  • We build in plenty of time to relax, laugh, and connect as people.

In our experience, this results in a cohesive strategy, comprehensive budget, and tactical roadmap around which the whole team is aligned, minimizing the risk of rogue campaigns or fragmented messaging throughout the year.

Whereas some sessions take only a few hours, others stretch across weeks as large teams come together over multiple meetings. As an example, here’s how we divide the planning into components for larger clients.


  • We facilitate a half-day pre-planning session focused on the client’s company goals over the next year. We help the marketing team dissect these goals and determine marketing activities that could contribute to achieving them.
  • We conduct a content audit of the client’s current market research, marketing assets, messaging, and campaigns to determine what might be relevant for future campaigns. We complete additional market research to supplement what the client had provided us and to lend additional insight.
  • We interview key stakeholders one-on-one in order to understand their workflows, dependencies, challenges or sticking points, ideas for improvements, and wish lists. During this step, we often include sales leaders and at least a few sales reps to make sure that the marketing and sales teams are aligned.

Planning workshop

  • We lead a series of collaborative, interactive activities designed to dig further into the ideas, concerns, and questions uncovered during the stakeholder interviews and content audit.
  • We help the group document its user stories — the narratives of the people who are impacted by its marketing activities.
  • Through hands-on group work, we work backward from the company goals to shape a strategy that is aligned with the tactical activities of the various marketing groups represented. We use “games” like Start, Stop, Continue, in which the team lists every current marketing initiative on a post-it note and then works together to organize them into things they should start, things they should stop, and things they should continue.
  • We incorporate brainstorming and breakout sessions throughout the day to relieve any stress that might have resulted from the planning process and to help the team bond.


  • We conduct further research prompted by additional questions that are raised during the workshop.
  • We meet with our key stakeholders and present the outcomes of the workshop as well as recommendations going forward to both contribute our expertise as an agency and to ensure that the strategy we create collaboratively has approval at every level.
  • We consolidate the results of the workshop and our accepted recommendations into one document that includes the client’s annual marketing strategy, timeline, and budget. Everyone on the team has access to the strategy; it’s meant to be a living document that marketers can use throughout the year to stay on track and aligned.

And great news for teams who are still working from home: these workshops can easily be shifted to a virtual format, and most video conferencing software has built-in features to make it even easier. Zoom’s whiteboard feature, for example, allows participants to brainstorm together by adding their own notes to the screen simultaneously. Breakout rooms are also handy for encouraging small-group discussions or just mixing it up.

Whether you’re in charge of running your team’s annual planning this year or you, like me, are with an agency whose clients rely on you as a strategic partner, this approach will encourage interactivity whether sessions are conducted in person or remotely. From my team to yours, cheers to a great 2022.

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