So you want to facilitate a workshop for a team? Maybe you’re external to the team and have been asked to help by facilitating. Awesome, it’ll be fun. Just show up at the time and place annnnnnnd you’ve already lost.

You better think (think)
Think about what you’re trying to do
— Aretha Franklin

Ask The Right Question

The workshop should be answering a question. That gives all of the participants a clear vision of what they’re trying to achieve. “What is preventing the team from moving faster?” is a very different workshop than “How do we improve our deployment process?” which is very different from “How do we fully automate our deployment process?”

Getting everyone aligned on outcomes is key to success.

Get to Know Your Stakeholders

If one person felt strongly enough about this to block off time on the team’s calendar, they are the First Stakeholder. Start with them. You need to understand what they want out of this workshop. What outcomes will make them call this a success? Help them understand their role in the workshop: getting the right people in the room, taking a step back, and letting the team be awesome. If there is no such person, that’s fine too.

Hopefully the First Stakeholder has conveyed their vision of success to the team. Validate that assumption. Talk to the rest of the team. Understand what they want to get out of the workshop. It’s better to discover any differences ahead of time rather than in the workshop itself.

Use these conversations with the team members to learn their perspectives, their pains, their goals for the workshop. Is it scheduled at the same time as their kid’s play at school but they’re forced to attend? That’s good to know. Find out who on the team is quiet, who interrupts, who isn’t afraid to speak their mind. Find out who on the team likes the status quo and doesn’t feel change is necessary.

If what you’re learning isn’t making sense, or there are incompatible goals, if some constraints can’t possibly be met, etc. then have a second sit-down with the First Stakeholder or with the team as a whole. Help them understand what you’ve learned. The workshop simply won’t be successful as framed – the direction needs to change. Be supportive and advocate for the team and the individuals you’ve talked to.

Learn the Team’s Communication Style

Ask if the team has established any norms (especially around communication styles) or shared vocabulary. You as facilitator need to be aware of these and use them in the workshop. If they don’t, be prepared to suggest some at the workshop. A good baseline could include:

Of course, just because the team says they have some established or agreed-upon norms doesn’t mean they’ll be executed perfectly. The usual facilitator responsibility still applies. Having talked about it, though, helps hold the team accountable to what they said.

Pick the Right Time of Day

It matters. If you have a team of night-owls, don’t expect a lot of dazzling creativity at 8am. If the team gets into the office before 8am, don’t plan the meeting for the late afternoon. If the workshop is early, provide breakfast. If it’s around lunchtime, provide lunch.

Daniel Pink wrote a book called “When” which goes into more depth on the topic of chronobiology. If you can, plan activities to occur at the appropriate time of day to correspond with type of thinking involved. Here’s a quick summary if you want to learn more.

Of course, sometimes the time is out of our control. Don’t sweat what you don’t control, just move on and make the best of it.

Planning the Workshop Activities

Kick It Off

The first part of any workshop should be to remind the team why they’re here. The goal of the kick off is to inspire the group. Consider having the First Stakeholder do this part. They must provide a vision of success. This sets the tone for the rest of the workshop and is foundational. It’s also a good time to talk about team norms around communication. Suggest some basic ones if needed. Use that as the foundation to set expectations with the team.

Pick the Right Activities

If I tried to talk about specific activities, this article would turn into a book. Luckily for us, Esther Derby and Diana Larsen already wrote the book: Agile Retrospectives: Making Good Teams Great. Think of it as a cookbook with recipes for activities. The activities are broadly broken up into three categories: gathering data, generating insights, and deciding what to do. There’s a description of each activity and a quick note about what the team should expect to get out of it.

Every activity should get the team closer one step closer to accomplishing its goal.

Vary the Types of Activities

There are three types of activities in most workshops:

Emotional or Creative – creative work like brainstorming or how does something make you feel? Example: “What pains have you felt when using the system?” or “What would the ideal system look like?”
Mechanical or Administrative – the most straightforward. Example: “Draw a diagram of the system as it is today.”
Intellectual or Analytical – sometimes requires focused attention. Problem solving. Example: “What steps do we need to take to mitigate the problems in the system?”

In general, I would start the workshop with an emotional activity. Bonding or trust building helps to get people comfortable speaking with each other. On the other hand, if the team needs to wake up (say, they’re night owls at a morning workshop), I suggest starting with a mechanical activity to warm up.

The majority of presentations are purely analytical. They offer information but no human connection. The goal is to mix analytical content with emotional content, which creates contrast and therefore creates interest.
— Nancy Duarte

She is talking about presentations, but her advice applies here too: vary up the types of activities to keep people interested.

Know Your Audience

As the facilitator, your audience is the team you’ll be working with in the workshop. Use what you learned from talking to people before the workshop to shape your approach and the activities.

For example, if there are team members who are naturally quiet or aren’t comfortable speaking up, most activities can be adjusted to help them out. A typical brainstorming activity could start with 5 minutes of silent brainstorming. That same change would help out team members who aren’t comfortable thinking out loud or extemporaneously.

Mitigate Common Stressors

We find that the percentage of favorable rulings drops gradually from ≈65% to nearly zero within each decision session and returns abruptly to ≈65% after a break. Our findings suggest that judicial rulings can be swayed by extraneous variables that should have no bearing on legal decisions.
— Extraneous factors in judicial decisions

Don’t let easily controllable extraneous factors cause distraction or reduce the effectiveness of the team. If they fail, it should be on their own lack of merit (I kid, I kid!). If the workshop intrudes on a mealtime, provide food. Regardless, provide snacks and drinks. Being hangry is a real thing!

Likewise, plan to take breaks about every hour. Each activity should either be done within an hour or be able to be paused for a few minutes at the one hour mark. Read the room and go longer or shorter as appropriate.

Pace Yourself

Estimate time for each activity (range, not single point). Know what you want to do if the workshop is running fast, or what can be cut or shortened if the workshop is going slow.

End With Action Items

Set the team up to succeed:

Recap where you ended up with the original goals. Were they all met? What remains undiscussed?
End with concrete action items.
Action items should have deadlines or target dates when possible.
Each action item should be assigned to one person. If everyone is responsible for an item, no one is responsible for it.

After the Workshop

How involved you are in the ‘after’ phase varies. In my experience, the best results come from the team committing and the facilitator offering to be available for advice, suggestions, and help. You’re the chicken, not the pig.

Key Takeaways

You know your context better than I do. To butcher something said by the famous George Orwell, break any of these rules before doing something that doesn’t make sense.

You should still consider everything I mentioned here. Be deliberate. That doesn’t mean you need to invest time trying to account for every possible outcome – be agile and lean and pragmatic. Spend more or less time preparing based on the importance of the meeting and the expected return of that prep time.

Plans are worthless, but planning is everything.
— Dwight D. Eisenhower

Improvise, adapt, and overcome.

It’s going to be fun.

Facilitation: Don’t Lose Before You Start