Good Questions: Learning from endings 

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Asking good questions, often, can help you find value, keep things moving, gain alignment, and so much more.

Good questions create clarity, challenge assumptions, and allow teams to test the boundaries of a piece of work.  In this short series, we share our experience of how to ask the right questions and give you the confidence to be curious and provocative to get results.

A mini-series by Katie Stotter, Strategy Lead

Retrospectives. An important tool for examining where you’ve been and what you’ve done. Ideally, they should provide a perfect opportunity to learn too–not just from what didn’t go so well, but also what did. Far too often, we only spend time examining the failures, not the successes.

The reality is, whether things went well or not, a retrospective is an important tool to extract the learning of value, with a level of rigour beyond quick comments captured here and there.  And retrospectives aren’t just for xmas the end of a project, they’re a great way to reflect and learn regularly throughout.

You can work through this collection of questions individually or as a team. The questions should help you have great conversations; helping you first constructively reflect on where you’ve been, set some practical actions to take with you, and to make space to celebrate personal growth too.

Retrospective Part 1: Constructive reflection

It’s easy to be self-critical, so we’re going to do the harder thing first, and start by thinking about what went well. By reflecting on the positives first, you make sure you understand why you were successful, and the steps you took to be so. 

The positives

  1. What went well?

Take a minute to celebrate the things that went right, the smart choices, and the great results. Celebrate team members’ efforts, and celebrate your own. There’s great learning to be gained from what went well. 

  1. Why did those things go well?

Now reflect a little deeper. Why did those things go well? Sometimes circumstances and context make the biggest impact, but sometimes it’s our choices. What choices did you make that led to those things happening? How did you set yourself up for those things to go well? 

  1. Could you have made different choices?

In setting yourself up for those successes, are there different choices you could have made along the way? Did you consciously decide to do something else? Is it only now you’re seeing alternate choices? In hindsight, would any of these choices have made an even more positive impact? 

The negatives

Now it’s time to reflect on the parts that didn’t go so well. Approach this with kindness, with curiosity, and with practicality. 

  1. What didn’t go so well?

Reflect on some of the things that didn’t go as you hoped, the less good choices, and the results that missed the mark. Can you be specific about what those things were? 

  1. Why didn’t those things go so well?

Time to dig a bit deeper–what was it that caused the negative results? Sometimes there will have been unavoidable circumstances that had an outsized impact, but sometimes the choices we make can change the course. What choices did you make that led to those things happening? Was there anything in how you set yourself up that made the poor outcome more likely? 

  1. Could you have made different choices?

With hindsight, do you believe there were different choices you could have made that would have been more likely to have a positive impact? When would have been a good point to make those choices? What signs were there that things might not turn out as intended? Is there anywhere you could’ve trusted your instinct more or sought input from others? 

It’s also important to acknowledge we don’t always have the ability to make different choices. Sometimes the circumstances have an outsize impact on the outcome. Even then though, we can examine how we responded in those moments. 

Retrospective Part 2: Actions to take forward

Now it’s time to turn that learning into action, keeping and building on the things that are working for you, and taking positive action to proactively mitigate poorer outcomes.

Note, the language we’ll use here is ‘could’ not ‘should’. Change should feel like a choice or invitation, not diktat. 

  1. What could you keep doing?

Look back at the choices you made, and the outcomes you got. What served you well? What could you keep doing in the future? 

2. What could you start doing?

Look back at the different choices you could’ve made and the points where you could make them. Knowing this, what could you start doing?

Part 3: Personal reflection

Lastly, take some time to reflect on your own experience, as you will have learned valuable lessons.

  1. What did you learn? 

What is the most important thing that you’ve learned from this experience? (Try to resist the temptation to be only wry or self-deprecating here) What did this experience teach you?

2. What did you do for the first time? 

Doing things for the first time is hard. Take a moment to acknowledge where you tried something new, and were learning as you worked. 

3. What will you take with you?

What personal lesson will you take with you into future projects or ventures? 

More than ever, we are working with ambiguity, trying new skills on the fly, and moving at pace in an unpredictable world. The ability to quickly incorporate lessons learned from your successes and failures into future experiences is one of the most important skills in the workplace of the future. Leaving yourself space to reflect using questions like these should help you move forward with confidence. 

We hope this helps you. If you use these questions, we’d love to know how they worked for you, and to hear about what you learned. And if you’d like our team of experts to help you and / or your team run an insightful retrospective and create great new things, let’s talk!