Difficult People in Your Workshop (featuring The Office)

In hundreds of workshops, I’ve seen them all. From the Stanleys to the Pams, there are personalities that shape the culture of the team and the outcome of the project. And even if you’ve rewatched tons of times (guilty), you’ll still never quite know what to expect.
Difficult People in Your Workshop (featuring The Office)

Art imitates life. There are character archetypes we all know and love who happen to show up in nearly every situation. Maybe that’s why we resonated with them so well on our 1st (and 50th) rewatch of workplace mockumentary The Office.

In hundreds of workshops, I’ve seen them all. From the Stanleys to the Pams, there are personalities that shape the culture of the team and the outcome of the project. And even if you’ve rewatched tons of times (guilty), you’ll still never quite know what to expect.

I’m not superstitious, but I’m a little stitious. The truth is, a facilitator can’t know the dynamics of a group until a few minutes into the workshop. We don’t have the history of the project. We might not even know how many times the group has already been down tis path. Our best hope is to get the right people—or characters—in the room, and then (give me strength) manage the others.

Here’s my overview of the common patterns and behaviours you’ll come up against, and how to motivate, nudge and inspire them while maintaining trust and welcoming vulnerability. 

The Jan

Jan doesn’t like to get her hands dirty. She also has no patience for ambiguity and indecision. This is fine as Jan tends to leave before the team starts to slay dragons. Once she’s gone you’ll feel a collective sigh of relief as the group will instantly gain more confidence to contribute.

Jan wants you to be efficient with time, and doesn’t care for details—they may make her ‘collapse in on herself like a dying star.” Jan wants results and trusts you to drive the group to meet their objective (and not to email pictures of her to the entire company).

How to manage Jan: 

Jan performs best when she contributes early, as she’s far more likely to buy into the conversation. If Jan’s onside, she’ll be the strongest advocate for success. 

But be warned, Jan can become impatient if the conversation strays into the unknown. Their propensity for play is quite low, and you and the group can become puppets in their hands! This can be particularly tricky when motivating people to think differently. Your goal as a facilitator is to use their expectations as ‘guidelines’ and push the group while considering the level of risk you push the group towards in terms of their decision making.

The Jim

Having Jim in the group is fun. Having a Jim in the group means you’re in for a good time. They’re instantly likeable, but beware their tendency for mischief; they can turn rogue very quickly. Typically they have been told to attend, but they’ll pretend it is their decision.

They have serious FOMO and don’t want to miss a few hours to cause some mischief or alleviate the mundane of the day-to-day. This is an opportunity for them to understand what happens before the project gets passed to them. 

How to manage Jim: You want Jim to be bought in from the start. You want him to feel like this is an opportunity to have more influence over decisions. Be warned though, Jim has the potential to be a serious disruptor. 

Jim doesn't really want change, as it means that it could push him out of his comfort zone. He’s also worn down and suspicious of new ideas and people as they have contributed to similar past processes without any or ineffective results!

The Michael

Oh, Michael. He can either fall into the camp of humble and helpful or arrogant and disruptive. He will believe his ideas are the best (but, as we learned with Scott’s Tots, they’re not). Michael wants (needs?) more attention than others. Data and evidence takes the back seat to a "good gut feel." They will likely talk over other people and take the lead to speak when sharing information back to the larger group. They even take control of your Spotify playlist – DO NOT ALLOW THIS!

Michael sees your workshop as an opportunity to remind people of his talent. He is here as to take the lead or have a more substantial contribution to an outcome.

How to manage Michael: It is your role to keep Michael onside. He has a serious influence on the group as he’s so vocal, he can change the entire mood of the room. You need to harness their influence for good. Don’t be afraid to meet them where they are at and assert authority on behalf of the team.

Be warned, they will tend to ignore timings, especially for breaks. Plus expect them to disengage at every opportunity to gaze at their mobile device or distract the group!

The Angela

Angela thrives off of structure. Seeing an agenda gives her confidence. She is the most prepared: reading all of the materials and responding to the pre-workshop survey. She may even bring her own vegan lunch and disappear between activities to update timesheets (or check in on her cats via webcam).

Angela is super eager to improve things. Anything. She sees the workshop as an opportunity to be across new information, to classify and organise this new information neatly, as well as to ensure it meets organisational standards.

How to manage Angela: It is important to help her understand and empathise with the group. She will find the ambiguity of creativity and ideation a stressful experience (she does not enjoy being titillated). Guide her through this as you want to help her wield her powers for the good of the team. Bonus: Angela is a solid communicator and you can use her to help with follow ups after each session.

Be careful: Sometimes Angela presents very well though may lack knowledge or expertise. When pushed they don't understand the detail or the impacts of decisions or their suggestions. Encourage the group to work alongside them to help build out ideas and scenarios.

The Pam

Pam is the secret weapon. She can be introverted and inconspicuous at the start of a gathering, but Pams tend to be the people closest to the focus area, dealing with customers, working with requests, managing the flow of information. They are crucial to the dynamics of the group as they are the truth tellers. They have respect from management as they understand the business and have a deep knowledge of the people impacted.

Pam knows that it is important she participate as decisions will likely impact her the most. But she may not realize she is also the gatekeeper of information and has significant influence on decision making.

How to manage Pam: Your goal is to identify Pams as quickly as possible. Put them with the Jims and Michaels (even though they may dislike it at first). Something magical will happen where they will influence others' mindset, and the other group will be able to build on and sometimes take credit for Pam's recently learnt insight. 

Keep a keen eye for body language. You want Pam to keep contributing and stay engaged. They can be extremely fragile and will disengage if they feel like they aren’t being heard or valued. Find a balance to encourage them to contribute to the group without them feeling threatened. 

The Stanley

Stanley is here, but doesn't want to be. He’s doing a crossword in the back, but he’ll be mad if you change anything without checking with him first. The ‘big picture’ is something they are happy to leave to other people. Stanley is so ingrained in the fabric of the company that he is considered part of the furniture.

For Stanley, it is important to be part of the conversation as it is another thing to add to their endless list of things to do. Plus, Stanley loves an opportunity to tell people the way it is. 

How to Manage Stanley: Your goal is to capture his attention, to emphasise his contribution and influence, and to impress upon him a better world. A world where they don’t feel compelled to go to bed and wake up to the silent hum of their office phone! A world where their team can share responsibility and they can lead instead of manage.

Watch as they will become impatient quickly and shoot down others ideas. They will likely clash with creative thinkers. You need to ensure you help them unpack the issue to understand how they can help problem solve to be part of the ideation process.

BONUS: How to know (quickly) who’s who

To quickly find out what the dynamics of the group you are about to take on a journey consider a quick ice break activity. Here's one of my favourites: Superheroes.


This activity is designed to allow you and the group to quickly learn all the players in the room in a fun and creative way. It also enables you to get people to participate as quickly as possible to break down any barriers from contributing. 


  1. Hand out the attached worksheet with Sharpies.
  1. 1 min – Instruct people to look at the person they are facing/ opposite and draw their portrait on the right hand side of the worksheet. 
  2. 2 mins –  Tell people to swap back their worksheet with their subject so they have their portrait. Then to complete the remainder of the info.
  3. 1 min per person – Invite each person to present their responses and portraits to the group.

Pro-tip – Hand out name labels during each person’s intro. People hate wearing labels. We’ve found during their intros they are far more likely to follow the pack and wear their label.