Running engaging and productive content workshops

Running good workshops and meetings is a critical ‘soft’ skill for content people. There are points in the practice of content strategy and content design where bringing people together to explore a topic is incredibly useful. But for some reason, it’s something that most people are just expected to know how to do intuitively. I still have vivid memories of just how stressful running my first workshop was, and just how out of my depth I felt. Like most soft skills, it’s actually really hard. If you think it’s easy, you’re either:

1. A rare prodigy with a natural gift for facilitation 
2. Someone that’s put in the hard work and got to a place where you’re comfortable
3. A bit deluded and/or overconfident

So in this article, I’m sharing what I’ve learnt a decade after being chucked in at the deep end with facilitation. 

Know the purpose and question the format

Before you put a session in the diary and start stocking up on sticky notes, make sure you know the purpose and objectives, and consider if a workshop is the best approach. Some questions to ask yourself might be:

• What are we actually doing here? Do we need to generate ideas, make a decision, solve a problem, or communicate important information?
• What does a successful outcome look like?
• Is there another way that we could do this? Is a workshop or meeting the best way to get to the outcomes, as opposed to say, sending an email, sharing a document, one to one meetings, asynchronous collaboration?
• Does the cost justify the benefits? Cost isn’t just time, travel expenses, etc, it’s the cost to people’s energy and flow too.

Things workshops are good for (and not so good for)

In my experience, workshops tend to be a good option when you want to do the following things:

• Kick off new projects: At the beginning of a new project, a workshop can help align the team on goals, scope, timelines, and expectations. Getting people together can really help to make sure everyone is on the same page and to build a sense of being a team.
• Build consensus or alignment: If you need to get a group to align on a specific decision, policy, or direction – or even just get a shared understanding of how things are right now – a workshop can be a great approach.
• Solve problems: If you hit a roadblock, a focused workshop can help in problem solving. Bringing together diverse perspectives can help you to identify and choose a way forward.
• Generate ideas: Much like problem solving, if you need to come up with a lot of ideas, getting a group together to work on it can be very productive.
• Plan: If you need to come up with a plan, set timelines and assign actions to a group of people, a workshop can get you there faster.
• Transfer knowledge: When you need to share a lot of knowledge or information, something that’s pivotal, controversial, etc, or where people are likely to have a lot of questions or need clarification, a meeting can be a better option than just sending documentation.
• Feedback and evaluation: Towards the end of a project or at key milestones, workshops can be used to gather feedback, evaluate progress, and make adjustments. This collaborative review process can enhance outcomes and client satisfaction.

I’m less likely to suggest a workshop when you want to:

• Gather requirements: if it’s a small, close-knit team, a workshop can be a good way to go about understanding challenges, opportunities and needs. But in bigger, more siloed teams, one to one conversations often work best – followed by a workshop to create consensus afterwards.
• Develop strategy: it’s just too hard to try and create a strategy in a workshop. And a lot of people can’t do their best strategic thinking in this kind of setting. I think it’s better to look at small elements contributing to a strategy in a workshop setting. For example, a problem solving session to look at one of the challenges the strategy must respond to.
• Create ‘craft’ based stuff: trying to create an information architecture, design a page table, or write copy in a workshop setting is nightmarish. And the output is often poor too.

Choose your participants carefully, then welcome them in

This probably goes without saying, but just in case: participants can make or break a workshop.

Think about the topic of discussion, who has decision making power, and who will be the most affected by the decisions being made. If you have a RACI matrix (Responsible, Accountable, Consulted, Informed) that can help you work out who needs to be involved. Try and avoid inviting people who are not closely connected or involved – the more people in the room, the more work you have to do as a facilitator. Plus, there’s always a risk that people who aren’t that connected will be disengaged in the session, or will need more context to get up to speed.

You also need to make people feel welcome. Explain the purpose and objectives for the session, explain why you invited them, and ask them what they need to participate. This is important for finding out about any access and inclusion needs people have that you might not have anticipated. For example, some people might need to see the agenda and all the theoretical material in advance to feel able to contribute. Other people might need more breaks, for digital assets to be in a specific format, for example.

Online and in-person both have pros and cons

Workshops were almost always in-person (in my world at least) pre-pandemic. But that’s all changed now, and most people are comfortable with online sessions.

If you’re in a position to choose, it can help to think about the following questions:

• Accessibility: what’s going to be the most accessible option for the participants? Do people have barriers to travelling and attending in person? Are there barriers that would prevent people from participating online? (Remember whiteboarding tools like Miro, Mural etc aren’t very accessible.)
• Habit: what are people used to doing? What do they feel comfortable with?
• Behaviours: what behaviours are you dealing with? Got a group of people who struggle to pay attention on calls and often check their email at the same time? Try and get them to come in person. Got a group that communicates brilliantly but is time poor? Do it online.
• Timing: full-day online sessions (half days too, tbh) are very tough in terms of concentration. If you need a lot of time, and can’t spread it out across multiple shorter sessions, in-person is probably going to be the better option.

Fail to prepare, prepare to fail

Preparation is everything for workshops. The amount of prep and thought you put in has a distinct correlation with the results you get out. And if you’re new to facilitating workshops, I think going hard on the prep can make you feel more confident and in control.

Some things I’d think about as part of my preparation:

• The agenda and timings: It’s an obvious one, but I’ll plan my agenda in great depth and get very specific about the precise activities we’re going to do and how long they’re going to take. More often than not, things take longer than expected, so I try to leave myself some slack in the agenda.
• Breaks: I’ll plan as many breaks as possible, ideally 15 minutes every 90 minutes, plus an hour for lunch.
• Catering: For in-person sessions, make sure you have a good supply of water, tea, coffee, snacks, and lunch too, if it’s a full-day session. This helps a lot when it comes to concentration. Try and make sure the only food options aren’t beige carbs, to be kind to the people (like me) who get very sleepy in the afternoon after a carb-fest.
• Room: What room will you use? What’s the layout? Do you have breakout space for group work? Is there a screen, a whiteboard, can you stick things on the wall? Do you know how to use the tech/connect your laptop? What’s your backup option if it goes wrong?
• Online sessions: What functionality will you need? Breakout rooms? Q&A? Chat? Do you know how to use all this functionality and have the right permissions? What’s your backup option if it goes wrong?
• Seating and groups: do you need a seating plan, or to break people into groups beforehand? (This can be a good move if you’re dealing with big personalities, tricky stakeholders, or you want to connect specific people.)
• Materials: Are you going to make slides? Do you need materials like sticky notes, pens, paper? What about handouts and documentation? Would sensory objects/toys help people? (Thanks to Southdown Housing for introducing this last one to me.)

Make it structured

One of the most significant things you can do to make your workshop or meeting a good one is to structure it. By structure, I mean choosing specific exercises or formats for the different topics you want to discuss, or things you want to achieve.

It might be tempting to think you can wing it as long as you have a list of agenda points, or expect that you can rely on open discussion to get the job done. This might be okay for short and simple meetings, but it’s not enough for a long or complex workshop. As a facilitator, it’s your job to give people direction and make the most of their time by coming up with exercises, formats and methodologies. This will also make it easier for everyone to participate, as not all participants feel comfortable speaking to the whole room.

Facilitation methods to investigate

There are loads, and loads, and loads of different exercises, discussion formats, and facilitation methods that you can use. Things like the Hyper Island Toolbox, Session Lab Library, and Pip Decks Workshop Tactics cards are all great resources if you want to explore different ideas. Over time, most people pick up an informal toolkit of different facilitation methods that work for them. As I mentioned in the last section, it’s about choosing the right one for the situation, the people, and what you need to achieve.

A few that are in my regular rotation are:

• Check-ins: ask people to check in, say how they’re feeling, what they’re hoping for/expecting from the session
• Meeting contracts: drawing up a meeting contract with the group to establish a shared understanding of how we want the session to run, and what will make it successful
• Car park: a place to corral questions or topics that are out of scope or that risk derailing the session
• Breakout groups: to help cover more ground, or create smaller groups that are more conducive to free discussion
• Matrixes: using 2×2 matrix to assess ideas, e.g. impact vs effort
• Swarming and grouping: asking people to work individually on answers to specific questions, then grouping the answers to find common themes
• Canvases and templates: using structured templates and tools, like the Core Model.

You need to be ready to improvise

The improvisation element is the bit that a lot of people worry about. The good news is that if you’ve done your planning and chosen the right methods, there won’t be as much need to wing it. The bad news is that you’ll probably have to improvise a bit.

The main two reasons I find that I need to improvise are:

1. Managing people and group dynamics

People are wonderfully unpredictable. The workshop that’s been a 10 out of 10 hit with one team will fall flat with another. There will be people that talk too much, and people that don’t talk at all. You might find that you need to change your beautifully planned and structured agenda to get the best out of the group. Sometimes you need to be overt, call out that you’re sensing that people feel stuck or unengaged, and offer them a different approach. Sometimes it’s subtle: shifting your body language, standing in a different place in the room (for example, to make it easier for a quiet person to make eye contact and harder for a loud one).

There’s a lot of mitigation you can do beforehand though, by making sure you know who’s going to be in the room, what they’re like, and what they care about. Planning group exercises to neutralise or balance different personalities can help too.

2. Time management

Even with the most meticulous planning, things will overrun. If it’s productive, you can go with it and then adjust the agenda for the rest of the session. If it’s not, you need to be able to bring it gracefully to a close and keep things moving.

But again, you can mitigate time issues with meticulous planning. For example:

• Be realistic about how punctual people are: if people are always 10 minutes late to meetings, don’t expect to start on time – build in a buffer.
• Arrive early so you can get set up, test the tech, and make sure all the resources and materials are in place.
• Fully think through each exercise you do in granular phases and work out how much time each one needs. For example, rather than saying we’ll make a RACI in 15 mins, think about it as 2 minutes on explaining what a RACI is, 2 minutes explaining the exercise, 10 minutes on working out the different areas the RACI should cover, 5 minutes on listing the responsible people, 5 minutes on the accountable people, and so on.
• Think about what will be interesting or controversial or generate a lot of discussion, and leave more time for it.

Find your own style and confidence as a facilitator

A lot of people think that the best facilitators are confident extroverts, and that if you don’t fit that mould, it’s not for you. But I think there are different ways to facilitate. The reflective, self-aware qualities of more introverted people have some real advantages when it comes to holding space for others, reading the room, and facilitating a good discussion. Whether you’re more introverted or extroverted, I think you can find a way to facilitate that feels right for you.

Confidence in your ability develops with time as you facilitate more and get more experience. I found facilitating terrifying to start with. Some things that really helped me were:

• Working with a buddy: having a more confident, louder, extroverted person with me took some pressure off and helped me to build my confidence
• Taking on sections of an agenda: just doing one or two elements of an agenda while my buddy did the rest also helped
• Imagining the agenda playing out in my head, visualising how I wanted it to go, and predicting all the things that could go wrong – this was exhausting, but helped me feel ready and more prepared and therefore more confident (I don’t do it any more)
• Channelling someone else that had the qualities I wanted as a facilitator and presenter
• Box breathing (breathe in for four, hold for four, out for four, hold for four, repeat) before and in the breaks
• Talking to my doctor about medication to help with nerves

Get feedback

Finally, feedback is the biggest thing that will help you improve. Send out evaluation forms and ask your peers and colleagues for feedback and constructive criticism. It’s tough but invaluable, and you learn a lot from it.