The dos and don’ts of a successful workshop

Jackie Colburn
5 min readMar 4, 2024

Whether you’re leading a planning session, collaborative brainstorm, or facilitating another type of strategic workshop, it can sometimes feel like there’s a lot at stake. You have big aspirations for what you’ll accomplish and, ideally, you want your participants to feel like the session was a good use of time. And, above all, you probably want to see the ideas and momentum generated during your session materialize into tangible results. It’s a tall order! To make it feel more approachable, I’m sharing my facilitator-approved dos and don’ts for running a successful gathering.

The Dos and Don’ts of a Successful Strategic Workshop

Do: Start with what you know

  • What work has been done to date? Can you paint a picture of the existing landscape and capture realities of the current situation? Orienting the team around the work that has been done helps inform the work ahead, and also honors the effort and energy the team put in to date. This is a great starting point for any strategic session. Here’s a simple activity you can use to take stock.

Dont: Get bogged down

  • While it’s important to honor the past, don’t feel like you’re locked into prior ways of doing things, or get trapped by challenges that make the work hard.

Do: Use structured methods

  • Structured idea generation and decision-making methods aren’t just for design workshops. I use them in strategic planning sessions as well because they provide a huge lift in the team’s ability to clearly communicate new ideas, and make decisions democratically and efficiently. Here are a few methods to add to your toolbox.

Don’t: Overload the agenda

  • Overloading the agenda can lead to rushed discussions and a lack of depth when exploring ideas and solutions. For strategic workshops, err on the side of more time rather than less. Build ample breathing room into your agenda so you can flex into discussion and exploration accordingly (that’s the whole reason you gathered your team, right?).

Do: Include differing perspectives

  • As much as possible, include a broad range of participants representing different levels and departments within the organization. This ensures a well-rounded perspective and increases buy-in.

Don’t: Include too many people

  • To get to the heart of this meaty and robust work, there’s a sweet spot for the number of participants involved. After seven years facilitating workshops, I can confidently say that there should be no more than 10 people included on the core decision-making team. Too many voices makes it hard to focus and stay on track. If including a broader range of perspectives means your group size is getting too large, consider inviting some people in to share their POV as part of a panel or shorter discussion period to help strike a balance.

Do: Think about impact on people

  • What does your team or organization aspire to do and how does that impact people’s lives? Wherever possible, orient your work to the humans you impact and what you want that to look like in the future. Is it more aspirational than it is today? How are people currently impacted by the processes and ways of working that are in place today? Taking on this mindset will help ensure that the solutions you explore are rooted in the humans you seek to help.

Don’t: Focus on ops in isolation

  • I’ve seen teams get stuck in the weeds on operational challenges without connecting the systems they’re evaluating to the bigger picture. Ultimately, when looking at an issue in isolation you may miss the opportunities for change. I worked with an org that was losing millions of dollars in contract renewals because they didn’t have a clear and easy way to keep track of which contracts they needed to renew and which they didn’t. While the system in place for managing contracts seemed to be the culprit, we didn’t identify meaningful opportunities for improvement until we mapped the system out and connected it to the people, processes, and surrounding tools that were at play. Once we took that step, we were able to identify some big opportunities for improvement that would have been lost without considering the bigger picture. (Tip: it also, almost always, includes people.)

Do: Create a collaborative environment

  • To uncover your team’s best ideas, you’ll need to foster open communication and collaboration. Include methods that encourage participants to share their thoughts and ideas freely to create an inclusive atmosphere that values different opinions. It sounds straightforward, but it’s no small task! My recommendation is to follow a few best practices that will help people feel comfortable sharing, which you can learn about here.

Don’t: Disregard dissenting opinions

  • Dissenting opinions are a natural part of strategic workshops. Don’t dismiss ideas or alternative viewpoints as a knee-jerk reaction. When you allow space for constructive criticism you’re able to take on a more comprehensive evaluation of strategic ideas.

Do: Establish accountability

  • I can’t stress this part enough! Leave plenty of time in your session to clearly define next steps and action items, and assign responsibilities. This is key to keeping the momentum going after your team adjourns. I even wrote an entire article about wrap-up exercises because I’m so passionate about this step — check them out here to copy/paste them into your own session.

Don’t: Neglect follow-up

  • Even though you’ve already outlined roles, responsibilities, and next steps, you still need a follow-up plan to track progress on strategic initiatives. Without it, your planning work may stay stuck on a piece of paper without impact to the organization.

Using this list of dos and don’ts will give your team an advantage right out of the gate. Putting them into action may take some trial and error, but once you’ve honed these facilitation skills it will help fast-track your team and your initiatives. And if that sounds like a lot of work, you can always send me a note and pick my brain on the process.

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Jackie Colburn

Weekly resources for facilitators and leaders. Learn tips and methods to run better workshops, accelerate teams and uncover new ideas. www.jackiecolburn.com