Futurespectives: learning from failures that haven’t happened yet

This post describes a workshop format I’ve used a few times: help a team think through risks and possible disasters that might affect a piece of work, before the work starts and while there’s still time to do something to avoid all those bad outcomes.

What’s a futurespective?

Teams often do “retrospectives”: Looking back, reflecting, and trying to improve based on what they’ve learned. A “futurespective” looks the other way:

• consider a possible future,
• discuss how likely that future scenario seems,
• agree what you’d like to do about it (ideas to make good futures more likely to happen, or ways to avoid bad ones).

One focus I like: disastrously bad futures. When getting a new team together or kicking off some new piece of work, there can be a lot of positivity and exploring the great things you can achieve. That’s good, and needed! But it can leave the “risk management” section as a bit of a tick-box exercise. Bringing the “bad stuff” to life a little can help everyone be aware of pitfalls, and creatively work on increasing the chances of success.

A session to look back on a failure is sometimes called a “post-mortem” – as in, examining at a dead body to determine the cause of death – so looking forward like this can be called a “pre-mortem”. That’s a bit of an unpleasant metaphor, but to look for more ideas on this topic both “futurespective” and “pre-mortem” are good terms to search for.

One way to run a futurespective

I’ve been on some coaching skills courses and they’re full of good approaches for helping people pull out ideas and work through them, with just simple prompts from the coach. In one class, we did a kind of guided storytelling: the coach read out various prompts, leaving space for people to write their answers. Everyone quietly thinking and writing about the same topic at once was interesting – you can see reactions and get other cues that we’re all working together, but maybe writing very different answers. I thought this would be a great format to try out for a futurespective.

Start by explaining the plan to your group:

• You’re going to read a series of prompts about an imagined future for this piece of work, and they’ve to fill in the blanks by writing whatever comes to mind.
• Keep your notes in order (can write responses on post-its, index cards, or whatever virtual equivalent you like).
• We won’t discuss things as we go – there might be chuckles, groans or other hints on how people are feeling, but we’re looking for quiet reflection and writing for this part.
• At the end we’ll collect and compare answers, to see what we all came up with – and agree what we want to do with this.

Prompting stories

For the prompts: You can ask any questions really – but open ones, slightly surprising ones, or repeating the same ones again asking for a different answer can help get some really good responses and insights you can use.

My script for one run of this:

“It’s after the end of this piece of work, and it was a disaster. I’m still too upset to talk about it. Could you just write it for me?”

• “What was the end result? How bad was it?”
• “And what happened to cause that?”
• “But that wasn’t the only thing that went wrong. What else was a huge problem?”
• “And what did we try right away to fix that?”
• “It didn’t work. How did our panic fix only make things worse?”
• “What was a problem from early on, that we tried to ignore?”
• “What always goes wrong – and hit us here too?”
• “Someone left – got a promotion, took a sabbatical, or something – and it really affected us. Who was it?”
• “And what did we lose? What skills/knowledge/support?”
• “And what huge problem did that lead to?”
• “Who was expecting something this project was just never going to give them?”
• “And what was it they were expecting?”
• “What did we assume would be fine, and it really really wasn’t?”
• “And on top of all that, what else went wrong?”

Comparing stories

At this point, everyone might be feeling very down: if that story’s how things are likely to go, should we even start? This is a good time to remind them that thinking and talking through all the bad things now is our best route to making sure none of them come true. Let’s see what we wrote and agree what we’d like to do about it.

Write each prompt on a board or wall, and give everyone space to put their responses, read other people’s, and start clustering similar ones. Some things that might come out of this:

Surprise similarities: for one team, “who left, and what did we lose” had piles of responses naming the same engineer on the team. It hadn’t been discussed much before, but there was a wide range of things that only they knew how to do. The good news: they’re not going anywhere yet, let’s make a plan to share knowledge and responsibilities around – that both reduces the impact if they do leave, and puts less pressure on them to do all the things in busy times.

Easy fixes: for “who was expecting something”, you might find a range of stakeholders and groups that really could throw in late-breaking problems to your work. For some of these, someone else on the team might say “good point, but that one’s OK – I’ve been talking to them”. For others, “really good point, I hadn’t thought of them!”

Unspoken common worries: this might bring out fears that have been on people’s minds already, or things they hadn’t consciously thought about until prompted to look in that direction. It can take courage to bring up an issue, especially if you’re not sure how much of a risk it is – will you be seen as too negative, or foolish? Framing this as a “what if” game, where any answer is fine, can encourage sharing – and sometimes you’ll find multiple people wrote the same thing and agree it’s worth considering.

A vast array of dangers: some prompts bring a variety of pitfalls, all of which sound plausible. You don’t need to enumerate every one and monitor throughout this piece of work – making some specific plans for the most likely / most damaging ones is more useful. You can decide what to do with the rest: just keep in mind that all kinds of pitfalls are possible, and keep alert as you go? File this stack away, and review it in a month or so to decide if any of it needs a plan now the work’s underway?

Laughs: you will get some spectacularly implausible disaster scenarios. For every response up on the board, you as a team get to decide what to do with it – including thanking people for bringing some humour and not worrying too much more about it.

Retelling stories

With all workshops: it’s easy to feel like you’re finding all the issues and fixing the world while the session’s going on, and then to forget all about it when you leave the room. Help make sure there’s a lasting impact!

When you agree actions, or on things to revisit, do follow up together later to see how many were done (taking away far too many is common), and what impact you feel it’s had (”oh we should knowledge share” sounds good – but are others on the team now confident they can do those things?)

This format in particular lends itself well to getting back together once the work’s further along, to remember the disaster future you painted.

• Do we feel like any actions or awareness we took from that session actually helped head off problems?
• Was there anything we predicted, but still failed to prevent happening?
• What would make a similar futurespective work better next time?

If you try this out, I’d love to hear how it went. In the comments below, on LinkedIn, or on Mastodon. Thanks!