Tony Hawk’s office party involved a train in the desert. Yours probably doesn’t need to.

Most office holiday parties begin with a restaurant booking.

Tony Hawk’s began with gifts containing a shovel, a pickaxe, a first-aid kit, a locked briefcase and some keys. Outside was a passenger van. Then came instructions to drive into the desert.

Waiting there was a homemade train.

In a Death, Sex & Money interview featured on 99% Invisible, Hawk describes an experience created by designer N.D. Austin. There was a piano player, a bar car and a journey considerably more elaborate than dinner with colleagues.

There was also something more personal behind it. Hawk explained that some relationships among his colleagues needed attention. Part of the experience involved burying a bottle of whiskey and making a promise to return to it.

It’s an extraordinary answer to the question of what to do for the office party.

It also raises a less extravagant question: what did the people involved need from that time together?

The activity is the easy thing to ask for

A party has a date, a budget and a guest list. You can compare venues and book one.

Explaining what you hope will change between the people attending is harder.

Perhaps the team has had a difficult year. Perhaps new people have joined and barely know anyone outside their immediate work. Perhaps everyone gets on well and would simply enjoy an evening together.

Those are different starting points. They don’t necessarily need different budgets, but they deserve some thought before the booking.

That applies to other requests inside a business, too.

An owner asks for sales training. A manager wants a team away day. Someone suggests replacing the CRM.

Each could be a sensible decision. Before committing, it helps to understand what people expect it to accomplish.

Ask what would be different afterwards

Consider a fictional owner asking for sales training because the team isn’t following up consistently.

Training might help. But a closer look could reveal that enquiries go into a shared inbox, nobody assigns them and salespeople can’t see whether a colleague has already responded.

The team may need clearer ownership before it needs another workshop.

Alternatively, responsibilities might be perfectly clear, but people struggle to handle price objections or ask for a decision. Then practical training could be exactly the right work.

The original request gets the conversation started. A few specific questions help establish the job:

• What is happening now that you want to change?
• Can you show us a recent example?
• What have you already tried?
• What would people be doing differently if this worked?

The answers should influence what gets built, booked or taught.

A memorable event still needs an ordinary Monday

The train is a wonderful story. It isn’t evidence that an elaborate experience reliably repairs working relationships.

In a workplace, the causes of tension may still be waiting when everyone returns.

If people disagree about responsibilities, those responsibilities need clarifying. If one person’s behaviour is making work difficult, someone needs to address it. If a team is exhausted by an unrealistic workload, an enjoyable evening doesn’t change the amount of work.

There is room for celebration and shared experiences. They can be valuable in their own right. Asking an event to resolve an issue that needs a management decision puts too much weight on the event—and on the people attending it.

Before organising something special, make sure the everyday problem has someone taking responsibility for it.

Thoughtful doesn’t have to mean elaborate

You probably don’t need a train. You may not even need an away day.

A team that rarely overlaps might appreciate protected time to work through a problem together. New employees may benefit from introductions that explain who can help them, rather than another presentation about company values.

A straightforward dinner can be a good choice when the purpose is to enjoy each other’s company.

The care is in choosing something appropriate for the people involved. That includes considering accessibility, caring responsibilities and whether people are comfortable participating. A surprise that feels exciting to the organiser may feel very different to someone else.

Give people enough information and choice to take part willingly.

Leave room for something enjoyable

There’s a temptation to turn every gathering into an exercise with a business outcome.

Sometimes a good evening is enough. People can have dinner, laugh and go home without completing a reflection worksheet.

What makes Austin’s work interesting is the attention to the particular people involved. The train wasn’t an off-the-shelf answer. It came from an attempt to create something that would matter to that group.

A business owner can bring that same attention to a much smaller decision.

Understand the people. Be clear about what needs work. Choose something that fits.

And if you do book a restaurant, tell everyone where it is. They’ll probably appreciate knowing whether to bring a shovel.

Inspired by Anna Sale’s interview with N.D. Austin and Tony Hawk for Death, Sex & Money, featured in “Tony Hawk’s Real-Life Willy Wonka” on 99% Invisible. The workplace examples and recommendations above are Deanick’s application of the discussion.