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Discover what planning a holiday can teach you about training design, from clear outcomes and learning journeys to pacing, reflection and flexibility.

Home TDC Blog What planning a holiday can teach us about training design

What planning a holiday can teach us about training design

October 21, 2026TDC BlogNo Commentsadmin

By Sheridan Webb

I’ve recently come back from a holiday in Portugal, and it was one of the best we’ve had. It also reminded me how much planning a holiday has in common with effective training design.

The weather helped. So did the pastries and wine! But part of what made it work so well was the way we designed it.

You perhaps won’t be surprised to hear that I plan holidays in much the same way as I design training. I want a clear idea of what we’re trying to get from the experience, a sensible structure and some things organised in advance. I also want enough freedom to respond to what happens along the way.

That balance matters in training too. People sometimes tell me they avoid detailed design because it feels restrictive. They want to respond to the group, follow an interesting discussion and make the experience relevant.

So do I. But spending time on design can make those things easier.

Effective training design involves agreeing the outcomes, planning the learning journey, choosing relevant content and preparing activities, while allowing time for reflection and flexibility during delivery.

Start by agreeing what you want from the experience

For this holiday, we wanted to explore as much as we reasonably could. Relaxing by a pool, getting a tan and reading three books is a perfectly good holiday for many, but that wasn’t the holiday we wanted.

That decision shaped everything else.

The same applies to training. Before choosing content or activities, you need to be super clear about the purpose of the training: what people need to be able to do afterwards, and why it matters. A broad topic such as “communication” is too loose a topic to be meaningful. Helping managers address a performance issue clearly and constructively gives you something much more useful.

This clarity also helps you decide whether training is the right answer in the first place. A workshop won’t fix a process that prevents people from doing what’s expected of them.

Agree the overall structure before filling in the detail

We chose two bases: three days in Porto and four in Lisbon. That gave us the overall shape of the week before we started deciding what to do each day.

In training, this means planning the learning journey before producing slides or creating handouts. Does it need one workshop, a series of shorter sessions, some independent preparation or opportunities to practise between sessions?

You don’t need every detail at this point. You do need a structure that makes sense for the outcome, the people involved and the time available. Otherwise, you can spend hours polishing a session that turns out to be in the wrong place, too long or unnecessary.

Identify the things that matter most

Our priorities included exploring Porto and Lisbon, visiting the Douro Valley wine region, and seeing Sintra and Pena Palace. Those were the experiences we definitely wanted to do, and although there were plenty of other appealing possibilities, we couldn’t fit all of them in.

Training design involves the same decisions. Which elements will make the biggest contribution to the agreed outcomes? Which are useful extras? Which are simply interesting?

Deciding what to leave out is one of the more difficult decisions in training design. This is where we often need to be quite firm with ourselves, and sometimes with stakeholders. A topic shouldn’t be included just because we know a lot about it or have a lovely exercise to go with it.

In my practical guide to designing training, I suggest ranking potential content by its relevance to the objectives. That helps you protect the essential elements and put the less important ones to one side. I explore the pressure to cram more into courses in a previous blog – The Comfort of Content.

Decide what needs agreeing when

Flights and hotels (essential for the trip to happen) and the day trips we particularly wanted to do were booked well in advance. Other decisions could wait until we were there. We always spent the evening planning the following day’s activities, agreeing where we would go and what we wanted to see. We left finer details, such as where and what time we would have lunch, until the moment.

Pretty much everything in training should be planned in advance too, apart from the specific interactions that emerge with the group. The question is how far in advance each decision needs to be made, and how much detail is useful.

The overall learning journey, key outcomes, content pillars, format and structure need to be fixed quite early on. Closer to the session, you can play with timings, refine examples and make final adjustments to activities based on what you know about the participants.

The activities themselves need proper design in advance. If you want people to practise a difficult conversation, you need suitable situations, clear instructions, enough time and useful feedback. “We’ll do a role play here” leaves a lot of work to be done the night before.

In the moment, you can choose which follow-up question to ask, explore an example someone shares or adjust how long a discussion needs. Having the design in place gives you a basis for those decisions. There’s also a useful distinction between designing the learning and preparing to deliver it, which I explore in When does prep become design?.

Plan how people will get from one part to the next

Choosing Porto and Lisbon was only part of the plan. We also needed to organise the transport between them. Two excellent destinations wouldn’t have been much use if we couldn’t get from one to the other!

In training, individual sections can be good while the overall experience feels disjointed. Having a ‘red thread’ that runs through the whole journey or session helps people to link learning and see its relevance. It also taps into the practice of repetition which we know is needed if learning is to stick.

Think about what people need before they can tackle each activity. Have they encountered the relevant ideas? Seen an example? Had a chance to ask questions? Is the connection between one section and the next clear?

Plan the practical transitions too. Moving people into groups, distributing materials and explaining a task all take time. A session plan that ignores these things will soon fall behind – and is a common mistake made by AI.

Be realistic about pace and capacity

There’s a limit to how much you can enjoy in one day, even when everything on the list looks appealing. Time to travel, wait for the bus you just missed, eat and stop for a while has to fit somewhere. You also need time to sit, watch and listen to a place, to take it in rather than simply grab a photo and move on.

It’s easy to make the same mistake with training. Too many people fill the available hours with content, then wonder why people struggle to take it all in.

Just as you need time to take in a place, learners need time to reflect on what they’ve experienced and make sense of it. Allow time for thinking, questions, practice and feedback, as well as breaks. These all need space in the design.

And consider who is taking part. A holiday itinerary needs to suit the people travelling. Training needs to reflect the group’s existing knowledge, experience and access requirements. An activity that works well for one group may need adapting for another.

Leave some wriggle room

We had other things we wanted to include, with a rough idea of where they might fit. We also left periods with nothing specific planned so we could go where our feet, and our mood, took us.

That freedom was part of the design.

You can build similar flexibility into training. Identify which elements are essential and where you have choices. Prepare an alternative way to approach an activity. Know which additional examples might be useful and which content can become a follow-up resource.

If a group needs longer to practise an important skill, you can make an informed adjustment. You know what you can move or leave out, and what needs protecting.

Flexibility works best when you understand the consequences of changing the plan.

Give yourself a plan you can actually use

A great holiday doesn’t require every minute to be scheduled. Equally, some experiences are much harder to enjoy if you haven’t done the necessary planning.

Good training design requires that same judgement. Plan the learning and prepare the activities in advance, with options ready to use as appropriate. Leave room for the specific interactions and decisions that are best made with the group in front of you.

Walking into a room with an outcome and very little else means making a lot of design decisions while you’re also trying to facilitate. You’re managing the group, listening to contributions, watching the time and working out what should happen next. That’s a lot to ask of yourself.

For me, a detailed session plan makes those decisions visible. It records what people will do, why they’re doing it, what they’ll need and how the learning will be drawn out. It gives me a basis for making changes when the group needs something different.

If designing training feels painful rather than helpful, take a look at my ebook, A Practical Guide to Designing Great Training.

I wrote it for people who want a practical way to create training that achieves something, not just to learn more about the theory of designing training. It takes you through the process, from understanding the need and deciding what to include to structuring the learning, creating materials and checking whether it has worked.

You can use it as a starting point and adapt the approach to suit your circumstances. The aim is to help you make better design decisions, with enough structure to be confident and enough wriggle room to respond.

cover of the training design book
Tags: design process, learning and development, Learning design, training design
Previous post How do you design a training workshop that makes a difference at work?

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