5 Ways DIY Workshops Go Wrong (and How to Avoid Them)
Workshops are powerful moments for alignment, creativity, and decision-making. But when they’re ineffectively designed or facilitated, they often do more harm than good. I’ve seen teams walk into collaborative sessions full of energy and excitement only to leave more frustrated, unclear, or divided than before.
As a pro facilitator of nearly two decades, I’m here to say: It doesn't have to be this way!
If you’re thinking about leading a workshop yourself, learn about the five most common roadblocks that stall progress, along with a few of my facilitator-approved tips for getting ahead of the spiral.
1. No Shared “Why”
If your team can’t articulate why they’re there or what outcome they’re working toward when you gather, the session will quickly drift into side conversations, tangents, or circular debates.
What to watch for:
People asking, “Why are we even doing this?”
No clear way to connect today’s discussion to a long-term goal.
Why it matters: Without alignment on the “why,” the “what” and the “how” don’t stick.
What you can do: Rally your team around a clear sense of purpose. Here’s a straightforward exercise you can try on your own to find alignment.
2. Your Attendee/Participant List is Off
Workshops work best when the right decision-makers and subject-matter experts are present. If the group is missing key voices or is packed with people who don’t need to be there, you’ll stall out, create more follow-up work, or get stuck volleying too many differing opinions.
What to watch for:
Big decisions being deferred because the right stakeholder isn’t in the room.
People contributing but not actually empowered to act.
Too many people on the guest list by default.
Why it matters: You can’t make meaningful progress if the people with the right expertise or veto/approval power aren’t involved.
What you can do: As you build your meeting agenda, list all the participants that need to be in the room to keep things moving forward—both stakeholders and content experts—then make sure each person knows the role they’ll play by clarifying in advance. But challenge yourself to keep the list concise. Minimizing the number of attendees for focused and collaborative workshops safeguards against distracting behavior (that’s why the recommended number of seats for a Design Sprint is only 5–7; more than that is counterproductive).
3. No Plan Beyond “Let’s Brainstorm”
Calling a meeting is not the same as facilitating one. Too often, teams show up without a clear structure: no defined activities or roles, no expected outputs, no agenda. This can lead to more churn and confusion for a team, and can simply be a waste of time.
What to watch for:
Unclear facilitation (everyone assuming “someone” else will guide).
Lack of time-boxing or activity flow.
No clarity on what’s being produced: ideas, priorities, decisions?
Why it matters: A good workshop has choreography. Sometimes multiple facilitators lead different sections, but those roles need to be defined and communicated ahead of time. As a leader, you may not even be running the session, but you still need to delegate the work to the right people.
What you can do: Need help figuring out who on your team might be a good candidate to run your next workshop, or at least a portion of it? Here’s a list of 5 skills a good facilitator needs in order to be effective. If you don’t see yourself or anyone on your team in this list, that’s a clear sign that hiring a neutral third-party is the best way forward.
4. Politics and Dysfunction Take Over
If your team culture leans toward complaining, finger-pointing, or turf wars, those behaviors will creep into the session without the right methods to diffuse power dynamics. Instead of solving problems, the workshop becomes another arena for dysfunction.
What to watch for:
Negative energy (“this will never work”).
People shutting down and disengaging or, conversely, dominating the conversation.
Cynicism replacing creativity.
Why it matters: Psychological safety is a prerequisite for meaningful collaboration. Without it, the room gets stuck.
What you can do: Whether you’re leading a 60-minute meeting or a multi-day workshop, keeping people engaged and incentivized to contribute often boils down to one fundamental thing: comfort. Check out these 6 tips to help people feel more comfortable when you gather.
5. Lots of Talking, No Decision Making
Many times, collaborative sessions are filled with productive conversation where great ideas surface and energy builds, yet the group never lands decisions or next steps. Without a mechanism to close discussions, prioritize, or clarify action items, the momentum dies when the meeting ends.
What to watch for:
Conversations that loop without resolution.
No recap at the end of sessions (with clear actions and assignments).
A growing list of “parking lot” items with no closure.
Why it matters: Workshops are meant to accelerate progress, not delay it. Without making decisions, momentum stalls and meetings become a waste of time.
What you can do: Designating ample time for wrap-up exercises at the end of your session is key because it translates the team’s discussions, decisions, and ideas into distinct priorities and tangible next steps. And this direction will set the team up to move forward with clarity and confidence. Here’s a list of my favorite wrap-up activities: the ones that outline a path forward to ensure your team maintains momentum.
Leading ≠ Facilitating
At the end of the day, many of these pitfalls have nothing to do with your skills as a leader and everything to do with the fact that facilitating a workshop requires a different mindset than leading a team day-to-day.
You’re used to setting direction, driving outcomes, and weighing in with your perspective, and I’m guessing you’re great at it.
Facilitation, by contrast, requires holding space, staying neutral, and guiding the group through a structured process. Often, internal team members who try to lead the work are too close to it, too entrenched in team dynamics, or too stretched on time to play that role effectively. That’s why bringing in a neutral, experienced facilitator can unlock the clarity, momentum, and alignment that’s harder to achieve when you’re wearing all the hats at once.
If you’re considering a workshop and want to avoid these traps, I’d love to help make it a productive, energizing experience for your team. Send me a note and we’ll chat!