Illustration of a gravestone with “R.I.P. All Your Plans” and sticky notes on it.

Pragmatic, not Dogmatic: Tips for Better Workshops

Goodmaker Team
May 13 · 6 min read

Written by Laurel Hechanova and Patrick DiMichele

Over the past few years we’ve facilitated a lot of workshops.

For clients, for coworkers, and even for each other. Each of them has been planned and structured very carefully and thoroughly. And each of them has ended up taking a slightly different form than we’ve planned.

Either because we’ve uncovered an unexpected opportunity, encountered an unknown constraint or simply miscalculated the amount of time it’d take to cover one (or more) of our topics. Whatever the catalyst, at some point in pretty much every session, our highly choreographed plan morphs into something a little more ad hoc and ad-libbed.

All of these sessions and iterations and adjustments have helped us identify effective ways to entice participation, generate clarity, and build momentum while (mostly) avoiding confusion and conflict. Although the purpose of every workshop is unique, and the specific activities vary, we think there are a handful of near universal tactics to be used to make them successful.

1. Provide a sneak peek.

Nobody likes mystery meetings. If you’re asking colleagues or coworkers to show-up for half an hour or half a day, share a bit of background information in advance. An agenda at the least, a briefing doc at the most.

Anything that provides a view into what you’re convening to accomplish and (if appropriate) gets them thinking a bit about the problem space.

2. Start with something.

It’s hard to get a group to create anything from scratch.

Blank whiteboards are intimidating, and it’s often difficult — especially if your group is new to working with each other or working in this format — to get people comfortable enough to get moving.

But it’s easy to get that same group to fill in gaps, poke holes, correct errors and add information to a (very) rough starting point. So try to start with something that prompts the group to action.

For example, if you’re asking a group to articulate goals, share a couple generic ones. If you’re convening to share customer or user understanding, draft a proto-persona. Building a journey map? Add your best guess at the stages of that journey to the whiteboard.

The benefit here isn’t that your draft is right, it’s that your draft is almost certainly wrong. Lead with that caveat up front, find the wrongest aspect of what you’ve drafted, and then engage the group in making it better.

As long as everyone knows it’s alright —actually, essential— to edit, erase and reconfigure the initial starting point you’ll be off and running.

3. Visualize constraints.

Constraints come in a variety of forms, and it’s helpful to have visible reminders to keep you on track. For example, most of the time, we’re not tackling every aspect of a particular problem or opportunity in a single session. And so, whenever possible, we make it clear where we’re focused. The easiest way to begin doing that is to write your problem statement or ‘how might we’ question on the wall or whiteboard. Once it’s up there you can quickly point back to it as evaluative criteria throughout your workshop.

We’ve also found it useful to explicitly call out — if they’ve been identified — the customer or user group(s) we’re targeting, the channel(s) we’re prioritizing, and/or the stage(s) of a journey we want to isolate.

You won’t often have constraints in all these areas but you’ll usually have them in one or two. Share them. It’s way better to thoroughly explore the right space than to waste time chasing ideas in areas that are off-limits.

And then there’s the biggest constraint of them all… time.

Do everything you can to keep participants aware of the time constraints they’re working under. A visible ticking clock helps prevent long-winded debate and an active (human) timekeeper helps things run on schedule.

Side note:
Time Timer is the best physical clock we’ve used for visualizing time constraints, but we’re working on a digital alternative we think is going to be a lot better. Want to be part of the beta test program? Hit us up.

4. Connect the dots.

Since we’ve done a bunch of workshops, we tend to know what comes next and next and next. Participants, however, often struggle to understand how the process works overall and where they are within that process. As such, we try to do whatever we can to highlight connections: between what we’ve just done and what comes next, between that thing we did earlier today and what we’re doing right now.

If you have an agenda, write a giant version of it somewhere in the room and check things off as you go, or print a copy for everyone in the room. Walk through it and explain the purpose of the sequence you’ve chosen.

If you decide to adjust it ad hoc during the workshop, let your participants know and say what the benefit of doing so is. Providing context helps participants understand how and why the process works.

(We’ve also found that actually instilling participant trust is way more effective than repeating “trust the process” over and over and over. 😉)

5. Aim for alignment.

Alignment is better than agreement. If you aim for agreement, you’ll be stuck in an endless loop of opinions and debate that’ll eventually morph into inertia and frustration. If you aim for alignment, everyone simply needs to understand what’s been decided and why. Even if they don’t entirely agree.

By aiming for alignment your job is as facilitator is much easier than if you’re trying to get 10 people to agree. Plus your participants will be energized instead of demoralized, which leads to better ideas and participation.

That said, you’ll still have moments where it’s not clear what to do. In these moments, simply:

  1. Summarize the critical considerations of each decision.
  2. Highlight the relevant pros and cons of each option.
  3. Ask the decider to make the call and share their thinking.
  4. Move forward.

6. Be pragmatic, not dogmatic.

There are tons of books and articles and frameworks out there that get really prescriptive about exactly how to run a particular exercise or activity. That’s cool and all, but we’ve found it best to anchor to the goal of the exercise and adapt the steps to the situation at hand.

We’ve made a few adjustments to the “standard” way of running lots of activities. And we often make a few more adjustments to that approach when while planning or during a workshop.

Take the “Sketch” portion of a typical design sprint (see the 2 p.m. section of this sprint agenda). The goal of the sketching phase is to distill ideas from the previous part of the sprint, get them out of participants’ heads, and translate them into visuals the whole group can start to align on. Sometimes, we’ll jump straight into Crazy 8’s. Sometimes we’ll do a couple rounds of that. Sometimes we’ll do a show and tell, and sometimes there isn’t time. It all depends on what’s possible with the time we have and what’s best for that particular group.

At the very least, be flexible enough with your group to allow minor adjustments to the timing and sequence of things if things are moving faster, slower or in a different direction than you expected.

Which is a long way of saying: go in with a plan, inform your team, and adapt as needed.

That’s pretty good advice in general.

Don’t let the fun stop here!

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Goodmaker Team

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We design workshops, trainings and tools that help teams work better together. Visit us at

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