Designing Workshops: How NOT to design a workshop

The question I get asked most about this blog is ‘How do I design a workshop?’

It’s a hard question to answer. Every workshop has its objectives, and workshop design can follow many different approaches. Furthermore, most of these approaches are oral traditions. I learned workshop design by being lucky enough to work with some of the best facilitators and workshop designers in the world.

That said, it feels like ‘designing workshops’ has become the ‘elephant in the room’. I’m going to start this occasional series of 'how to design' by looking at a design pattern most people would already be familiar with (and is also one to avoid) – Sequential Conversations.

I was recently asked to design a session for a small (~15 people) group who were looking to create a Team Charter. A team charter is:

…a written document created to provide the true “North Star” for a team or project

I sat down with the people planning the workshop, and we elaborated their intent into a set of objectives for the session:

Together, we will build a team charter, including:

  • Describe how we align to the strategy
  • Our overall team purpose and mission
  • Our immediate team objectives
  • How we’ll measure success
  • What risks we face, and how to mitigate them

The Sequential Conversations design approach takes those objectives and creates a workshop agenda that looks something like this:



It’s a sequence of conversations our 15-person group will have to build their charter[^1]. You’ve probably also seen this design approach used for board meetings and other ‘senior executive’ meetings.

Two concepts underlie this design approach.

The first concept is the group will work monolithically. That is, there won’t be times during the design we’re the group is divided into smaller teams. The logic is we need these 15 people to agree on each of the objectives, and thus we need everyone to be part of every conversation.

The second underlying concept is we build the output step-by-step. In the example above, we have an overarching output – the team charter. The team charter is composed of many components (e.g. team measures). The group works sequentially through each element to create the charter. Obvious, right?

The logic here is there is a ‘natural hierarchy’ within the structure of a team charter. This hierarchy means we can’t develop something lower in the hierarchy (e.g. measures) until we’ve ‘finished’ developing something else in the hierarchy (e.g. objectives).

The two questions we inevitably ask about a design like this are:

  1. What is the right sequence of conversations?
  2. How long should each conversation take?

Regarding effective collaboration, this type of design creates a few problems.

Not finishing the work

The obvious problem is what to do when we reach the end of our allotted time, but we haven’t finished the conversation?

In the example above we may spend an hour discussing ‘purpose and mission’ only to discover we went down a word-smithing rabbit hole and didn’t finish the work. We have some elements of purpose and mission, but it feels unfinished.

We now have two choices – neither of which is great.

Choice one is to keep going until we finish. The downside here is we’ll need to shave time off later topics (assuming we’re keeping our promise to end on time). We may even drop some conversations altogether; which means we won’t hit our workshop objectives.

The other choice is to honour the time commitment and move onto the next topic.

The problem with this choice is we’re now making subsequent decisions based on unfinished work. We are likely to discover things in later conversations that challenge our earlier thinking. Unfortunately, we didn’t plan for that and we now either re-open the earlier topic (effectively, Choice One) or live with our (now outdated) earlier work.

It’s hard to know at the outset how long a piece of work will take to ‘finish’. Part of the problem is the expectation we’re setting ourselves.

We need the work to be ‘finished’, but what does ‘finished’ mean? With this kind of design, it says the end of the activity needs to function as a kind of Rubicon – a point of no return. The whole group needs to be 100% aligned before a conversation is ‘finished’. If the group already mostly agrees on this topic, then crossing that Rubicon is relatively easy. However, if the subject is complicated and the group isn't aligned, there may be no natural end in sight to when the conversation will end.

We can’t find the right sequence

The other issue is finding the right order of conversations. This is about finding the 'natural hierarchy' for this particular subject.

Although there is an intellectual order to how these conversations should progress – that sequence doesn't account for the interdependence and messiness of the real world. In the idealised world, we shouldn't be thinking about measures until we know our objectives. In the real world, things are more complicated.

Understanding what we can, or might, measure can help provide clarity and tangibility to our objectives. That is, the thinking doesn't cascade down through the natural hierarchy. What we might think of as 'lower' order concepts are integral and influence across all the topics of the workshop.

The risk of trying to follow the 'natural hierarchy' is that we end up reducing the work into disconnected pieces. Although we might build the parts, we lose sight of the whole.

To overcome this risk, we need to accept that creativity isn't an orderly, hierarchical process. Building a team charter is an act of creativity. Building anything is an act of creativity. We need to adapt how we work so that it embraces the messy process of creativity.

Closing thoughts

Since the days of the Taylor and the Scientific Method, management thinking has maintained the idea that the workplace is a complicated (but not complex) machine.

The Sequential Conversations approach is an example of this type of thinking. On paper, the logic makes sense. However, it fails when it comes to real people in real situations. It unravels once the first point of serious disagreement arises.

Part of the issue with the approach is that it defers thinking about the 'what if…?' questions until you're in the room. What if the group can't agree on the team purpose? What if we identify a risk late in the process that affects our objectives?

The most common way to deal with those 'what ifs' is to find a 'strong' facilitator. Unfortunately, this often results in finding a person who will keep the group moving at all costs – thus trading off quality for speed (and also meaning we put the real issues into a 'parking lot')

Of course, there is another way! A better design approach can help you – and that is the topic of the next article in this series.

[^1]: This approach is also employed for any construct that has a natural hierarchy. For example, working from a strategy down to initiatives.

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