River Island, Tech Connect ’23 : How to job.

12 min readOct 20, 2023

I spoke at River Island’s Tech Connect this week about ways of working. What I said will still be relevant next year so it’s worth writing down here.

The short version

Every failure is an attempt at goal: go kick the ball. I don’t remember exactly what I said, but it went something like this.

The long version

I want you to think if you’ve held your tongue at some point this year. Obviously you have. We all have.

Park that thought while I explain that I don’t want to talk about ‘ways of working’ as they relate to processes and governance artefacts that float around in Confluence Spaces, Miro boards and <spit> ‘SharePoint’ </spit>. Get rid of all the necessarily prescriptive ‘how to do your job’ artefacts and what do you have?

People

Yes, under everything is people. It’s easy to forget how much of our lives today remain dependent upon people working together, and when you think about it, when you think about how many people dislike so many other people the fact that for millennia we’ve worked together and now are even creating things like the device you’re reading this on… it’s incredible. We’re all damaged in different ways. We’re all blessed in different ways. Me with my looks and charm, you with your fabulous device there. Some of us really annoy each other, sometimes just by breathing. I for example noticed recently — due to a train strike — I’m more excited by a dinner date being cancelled than I am of the dinner invitation.

We’re different

Identical twins have different ideas at different times, choose different numbers, marry different people. We all have differences of opinion every day, and every day good debate is had and settled by good people trying to do good, because fundamentally humans are a good bunch all trying to get through the day.

We each bring our own aptitudes, preferences, abilities and knowledge to the table, and around that table we can be greater than the sum of our parts. Look around any public space. If a bunch of randoms had a shared task to achieve, would they get the best from each person within arms reach… or would that be left to chance?

I would say that it entirely depends upon whether or not a good facilitator is among them. It takes a certain type of person to get the best from others, to be a multiplier of people. Are you that person? Do you get the best from everyone… in every meeting? Or can you think of a meeting in which there were passengers that got nothing from it, or people were talking who provided no value?

In a previous life I ran an F1 competition for Pirelli. I was told over a business dinner about someone’s experience with a certain vendor who would host business lunches, but during which a hierarchy stifled the kind of conversation we were ourselves enjoying. At those lunches only the highest paid people around the table were heard. He recalled a dinner where the discussion was of how to market a sports car to people in their twenties, but not a single one of the twenty something people at that table spoke, because by the time the higher paid people were done dessert had been finished. This was a time when social media was beginning, but the twenty somethings at the table, on social media themselves no doubt had no voice…

I’m not saying that 18 year old me could say and do more useful things than 40 year old me but just as Oasis brought more to the table with their debut album ‘Definitely Maybe’ than they do today, there are departments in some companies where critically fresh insights are stifled by hierarchy.

My point: getting ‘people’ right is difficult, and nobody gets it right all the time. Not even 100 year old business. Having everyone in a spontaneously formed group of people all add value to the point that they’re greater than their individual parts can’t be left to chance. It’s difficult. It takes effort. It requires facilitation. It requires leadership.

At this point I had everyone in the room play the Spaghetti game.

The founding members of the SAS demonstrated in WW2 that who dares wins. Sometimes — and it’s more often than not — the situation calls for action rather than discussion. Obviously if you’re designing a nuclear rocket don’t do that, but when the consequences allow for failure don’t be afraid of failure, understand that you should go into ‘failure mode’. Almost everyone that ever succeeded at anything have proven time and again that the faster you iterate, the faster you fail and therefore, the faster you reach the final state of ‘success’.

There’s a Terry Pratchett quote which applies to anyone doing anything for the first time — which is where software developers often find themselves — and the quote is “The first draft is just you telling yourself the story”. The point is: get your first idea done on time, and get all notions of perfection out of your mind because it’s better to aim to fail than to be perfect; you’ll iterate without hesitation or fear.

In 2016 Google looked at what made their best performing teams work so much better than their worst performing teams. They proved what a 1999 paper first documented: the best teams log the most mistakes. Why?

The best teams admit their failings. They treat failures as attempts at goal. The more attempts at goal, the more goals. Not making attempts at goal? Not failing? You’re not trying hard enough and you’ll score fewer goals. If the fastest way to success is to fail 10 times, then fail 10 times as fast as you can. Hence the phrase ‘fail fast’.
The people in the team feel psychologically safe enough to admit and share their mistakes, so others in the team learn from them and themselves get better faster than where mistakes are punished, mocked and therefore discouraged.

I want us to consciously now encourage psychological safety everywhere. If you see someone punish failure, don’t hold your tongue. At the very least, post a spaghetti meme.

I should have at this point asked for a volunteer and waited for a nervous hand to raise. At which point I should have awarded them an SAS ‘Who Dares Wins’ badge. I certainly had them in my pocket. But I failed, so I forgot to do this at this point. Had I remembered to then I would have gone on to say:

“Congratulations for being the first — the only — of 150 people to be brave. What held 149 people back from volunteering…?”

Being more worried about a potential loss than a potential gain is not ‘how to succeed’. We must be more vocal. We must step forward with less hesitation. We must not be afraid of negative consequences. We’re not going to be as effective in any of our interactions if we hold our tongues.

Who dares wins.

For the sake of the next point I want to make, please pretend with me that there are only two types of team:

Stable teams made of people that stay together for a long time
Temporary teams made of people that come together for a short time

Additionally, please also pretend that there are two types of people:

People that like change
People that don’t like change

I really want to talk about temporary teams, but let’s quickly cover off stable teams first:

A stable team often requires a balance of personalities for it to continuously succeed. Within the people making up any stable team you need a multi faceted balance of personality traits. You need a leader, a learner, a teacher, a rule breaker and a rule enforcer, etc. You need a balance between people that like change and people that don’t, you need action orientated people and details orientated people. There are so many nuanced ways to look at and understand and nurture stable teams. One of those people needs to bring the heart to the team and remember birthdays. Everyone needs to feel different levels of growth, mastery, purpose, autonomy, and feel appreciated. Everyone needs to be resilient. Or famously “not an asshole”.

People can be rough around the edges in stable teams and smoothen out over time because there’s time and space within a stable team to find your place, so long as the balance is maintained. In this respect stable teams are hard work to maintain.

Harder still however, is creating a temporary team. Or rather creating its culture because you can’t create culture. Culture is just what you do, and if what you do is be an asshole you can’t form a successful temporary team. You can be rough around the edges in a stable team, the stable, existing culture of that team will smoothen you out, with time. There’s no such safety net when ‘teaming’.

‘Teaming’ is what happens when people come together to form a temporary team to solve a temporary problem. A real world River Island example of this happens around Development Principals who themselves don’t sit in any one team, they each drift around, going to where they’re needed, teaming on things most days. They drift around like the Littlest hobo. They don’t go around, glory hunting, like the A-Team. They don’t want their names associated to successes, they’re satisfaction comes from success not notoriety and kudos.

As far as I’m concerned they’re development steroids. They’re effective because they do teaming well. Why do they do it so well? First off, they’re the type of person that likes changing things, but more importantly they’re not concerned with status. They’ll say something that could harm their status as quickly as they’ll say something that could elevate their status.

How do we get more people to be less aware of their status? Less aware of their brand? How can we make people feel like they belong enough for them to risk looking silly with their questions or failed attempts at goal. We can all create this ‘safe space’. We’re all in meetings, we’ve all been in chats where we see people get shut down for asking a question. We’ve all held our tongues. Humans have a deep tribal need to feel like they ‘belong’. Let’s help people feel like they belong by being more fallible, more vulnerable around each other, faster to fail in front of one another.

Let’s make psychological safety, and not ego — part of our culture.

In 2018, a soccer team of 12 boys and their assistant coach became trapped in a cave in Thailand when heavy rainfall flooded the system, and their exit.

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On July 8, 2018, a rescue team made up of 13 international cave divers and 5 Thai Navy SEALs made their way to the group to help them get out of the cave. All in all though over 1,000 people were involved by the time two British divers first discovered them, 2.5 miles into the cave system.

All 12 boys and their coach were eventually rescued, with Stanton saying that “It was miraculous that all these things happened sequentially. It was a collaboration between thousands of people, it was exceptional planning. It was miraculous that everything happened.”

Thousands of people, several cultures and languages. Most of those on site had never met before. How did they achieve their goal? How did they all do ‘teaming’ so well?

Before the soccer team was the Chilean Mining disaster. Same thing happened: thousands of people did do ‘teaming’. How did so many people come together and succeed?

There was a clear north star
There was a deep desire to win
Although there was a single leader in both situations, status was left at the door. The leader was a servant leader
Humility and curiosity reigned supreme. All ideas were explored
Disrespectful people that could not ‘team’ were identified as drag, and thrown out early
Musk famously was thrown out of the cave mission in Thailand, and told to shove his torpedo into a painful place before retaliating by calling the first diver to find the boys ‘pedo guy’. Disrespectful people are anti-teamers, and I’ll go on record as saying that anti-teamers are not people that are going to put the team first

Think about it yourself. Who would you like to set the example and take lead in a local zombie apocalypse scenario?

Someone with all the answers or someone that admits they don’t have all the answers?
Someone that never admits their mistakes or someone willing to admit and apologise for their mistakes? By admitting our own mistakes we show our vulnerability and open the floor up for others to share their mistakes… and we all learn faster.

Failure is not an option

‘Failure is not an option’ is a much misused quote from a Nasa mission controller. A space shuttle, many years ago lost its primary oxygen tank. The controller said “Failure is not an option” because being surrounded by extremely smart people among whom he felt the possibility of failure was not possible made him supremely confident the answer was in the room. His job was to have people feel safe enough to throw all the ideas out as fast as possible because he knew the right one would be uttered eventually.

It was an aspirational attitude, a supportive and encouraging attitude, not a threatening one.

Things will go wrong in software development. Our work is complex and creative. Our communications are complex and across lines. Failure isn’t just an option it’s a desired inevitability that we fail as often and as quickly as possible, so that we can learn and succeed as quickly as possible. We will fail. The best teams will admit it, and they will admit it loudly and proudly. And by sharing their failures they’re sharing lessons that we can all learn from.

There are three types of failure:

Basic failure. You’re on mute.
Intelligent failure. You choose a vendor that says they do X, and their documentation backs up the fact that they send X through the API, but after building the system and plugging it in, the API sends Y. You do all the right things, but you still fail.
Complex failure is the one we want to avoid. This is when a series of basic and/or intelligent failures all happen together and nobody raises their hand and makes the right noises in time to save it. That happened too, when a pilot was fired from every pilot job he ever had until one day he crashed and killed everyone on board.

This has happened in River Island many times? Who will be brave enough to be the first to admit when they think the next one is unfolding?

How to prevent complex failure

Having a north star — a vision — reduces the rate of complex failure by an order of magnitude because within one company culture —there are many, many micro cultures. We are not Borg. We are an armada of Federation ships on which several teams operate across each of those ships’ floors.

Among those cultures we can at least share a singular mission.

Those that work with the CEO experience one culture, those that work with the CIO experience another. The CIO will influence their report and therefore will influence the culture they cultivate, but there’s no hive level control over all the micro cultures that branch off from each report. Each micro culture is determined largely by everyone in any team, and everyone they interact with, only mildly influenced by what their line managers encourage and discourage. That’s entirely as it should be.

We all have the ability to influence everyone around us. We all therefore need to encourage psychological safety. We all need to show each other respect, humility and vulnerability.

When we fail, and our failure impacts someone else we must apologise. All the other person needs is our acknowledgement that we failed. Empathy matters. Accountability matters. The ability to genuinely care about the other side matters. Giving an accurate account of the mistake and drawing a line under it matters. Berating that person beyond that point is a fresh failing that will have an impact on the person that apologised. Where does it end?!!?

When not to fail fast

I’ve only scratched the surface of these topics. I’d like to conclude this article by adding a caveat.

When someone does fail, be that by dumping a database, closing a port, meeting all but one of the acceptance criteria, uploading the wrong photos to prod, sharing a private key to the public or ironically makes a bad decision… when you find yourself having to respond or solve a problem caused by a failure, that is where you do not often want to practice failing fast. That is a culture building moment. That is your growing moment.

Do not press buttons. Do not make decisions. You’re in failure mode. The lightbulb in your mind is red. While you wait more data will surface, and the risk of regretting your next move reduces. Your lightbulb returns to white. Recognise your attitude.

We’re all bozos on a bus, separated from apes by less than 2% of our DNA, and that’s only on our best days. On our worst days: take a break, use a friend as a soundboard, think about all the bullshit I’ve talked about here, and do things the right way.

Because ultimately, it’s nice to be nice.