In 2023, I resolve to be less cautious

Here are some fails my team shared recently:

“I went to market with no branding”

“I caused an F1 car to burrow into the floor of a wind tunnel, causing $$$$$’s of damage.”

“I accidentally shared a document with a customer that was about why they were such a pain in the neck.”

After too many mince pies, the right amount of carol-ing and insufficient board games (because it’s not possible for me to play too many board games), I am looking back on 2022 and asking myself what I learned.

Last year, one idea that dominated my thoughts was how failures can make us better. This led me to borrow the idea of a ‘failboat’ and start running one internally at Skiller Whale.

Let me explain…

Psychological safety is not just a nice to have

You may already be familiar with Google’s study on how psychological safety is the strongest predictor of a team’s success. I see a lot of conversation focused on establishing why a psychologically safe work environment is important, but very little on how to create it.

2022 has seen our industry take leaps and bounds in humanising tech roles, with some important changes emerging in productivity metrics (i.e. Nicole Forsgren’s SPACE framework). There is still a lot more work to be done, but I’d like 2023 to see us moving even further in the human-centric discussion and talking about actions we can implement to create psychologically safe work environments.

Part of the solution: failing publicly

My co-founder recently shared an experience of a ‘doh!’ moment where she realised she’d made a huge mistake continually for the past 12 months. Talking about it led to me sharing some of my biggest fails and we both felt like we learned something from the others’ experience, but also enjoyed how safe it felt to own our mistakes.

At Skiller Whale, our first company value is openness, so it didn’t take long for us to float the idea of sharing these fails with the rest of the team.

There used to be a London meetup community called ‘failboat’ where founders shared stories about why their start-ups had failed, and we decided to co-opt that name, (since it’s appropriately aquatic and we have an insatiable love of sea puns), and create a #Failboat Slack channel in Skiller Whale with the following description: ‘a place for us to safely share our failures and learn from one another’s mistakes…

Format: short Loom video

Opener: “I’m [Name] and this is a story about how I failed’

The first video came from my co-founder, and was subsequently followed by a slew of guilt-less admissions from the rest of the senior leadership team about failures that had occurred in either current or previous roles. Our team responded really positively to the stories we told, and appreciated the openness with which they had been delivered.

I think part of that appreciation came from the fact that hearing your manager say ‘it’s okay to fail’ doesn’t always make the team feel like it’s actually okay, but directly addressing your failures as a leader does. People notice and follow actions more than words — if your manager says it’s okay to be open and vulnerable, but they don’t live that value, you’re going to follow what they do, not what they say.

Further to that, hearing about other people’s mistakes really accelerates your own learning. I ran a dinner club for CTOs for 3 years and honestly, that was the main value for me. I heard the same problems come up again and again, but in different ways and with different right answers because context matters. (something that hit home so hard it became the name of my podcast — , The Pod Presents: Primarily Context-Based).

Reflection on failure is an excellent way to gain wisdom and improve your future decision-making, and part of your job as a leader is to make sure that wisdom is shared.

It’s also worth pointing out that making it safe to fail within your team can actually prevent the big, catastrophic fails from taking place. Because, in the wise words of our advisor Meri Williams, “it’s okay to crash the car, but not to let it fall off a cliff”. Being open about mistakes and creating a level of safety around failure is not equal to saying people don’t have to do their job, or that the net is infinite. Rather, openness helps to frame failure — as something to learn from but also something to own.