Work Isn’t Working
Leading healthy teams isn’t a luxury anymore. It’s a necessity.
In today’s complex working environments, people don’t know how to work with each other. When I say that, I get pushback.
“What?? I work with people every day! That’s absurd.”
“Sure, it’s not perfect, but it works. What’s the alternative?”
“Oh another catastrophist. Next you’re going to tell me AI will replace me.”
If this was you’re response, you’re not paying attention.
When work is the source of most of our stress then it’s not working. When work hurts people it’s not working. When there’s declining trust between workers and leaders, work is not working. When confidence in the job market is at a 60 year low, work isn’t working. When 48 million people opt out of work because work sucks then work is not working.
Not a surprise
That our worst dysfunctions show up at work shouldn’t be surprising. We are asking people to come together in stressful environments, almost always as strangers, and solve big problems. We assemble these teams without giving them any understanding of what’s going on.
We devise onboarding plans and write elaborate employee handbooks. We spend money on free lunches and game rooms. Apparently these are going to magically help people read minds and instantly understand the multitude of personalities (with all their associated trauma and nuances).
We are asking people to work with people they hardly know for the majority of their waking hours, and just when they get to know each other we switch out entire departments, destroy morale, justify company wide layoffs, bring in new leaders and change the rules.
Please tell me again how work is not broken.
We’re not actually working
We’re hiring people to do bullshit jobs in the name of status and a paycheck. Jobs that people can’t even describe to their friends and families. Not because those jobs are complicated but because they don’t make sense to anyone. We can’t even describe our jobs to ourselves.
“If you cannot explain something in simple terms, you don’t understand it.” — Richard Feynman
We’re exhausted by the ‘work.’ Exhausted by the indecision, the disagreements, the conflict, the tone deaf work culture, the lack of empathy, and the meetings. The endless fucking meetings.
We don’t know how to make high quality decisions. We don’t know how to find agreements or overcome inevitable (and often creative) conflict. We don’t know how to create healthy team dynamics.
A lot of this can be traced back to assumptions. We’re assuming that because people have titles, skills, and a place on the org chart, they also know how to do their work. It’s a dangerous and unhealthy assumption.
High-performing teams don’t assume they know how to work with each other. Instead, they work to get connected and design clear agreements on the behaviors.
Bureaucracy and sabotage are indistinguishable
We’ve confused complexity and complicated. What’s the difference? The car engine is complicated, weather patterns are complex. Complicated can be difficult but predictable, complex is by it’s nature is unpredictable.
We believe work is only complicated and for that reason we think we can understand how to mechanize it.
Work is complex because it‘s done by complex people. People are not machines and companies are not factories .
We think we need to put reins on chaos. We’re adding policies and rules to protect from risk. We call for innovation and creativity but build processes and procedures to fill our days with laborious admin and mind-numbing meetings. We’re killing the vibe.
Squares in a round world
A world dominated by bureaucracy turns us all into little squares. Squares have no soft edges. When the tech-bro narrative of hustle and “no pain, no gain” gets more airtime than empathy, love and respect we have a problem. We’re being hard on people, and soft on ideas. We’ve got it upside down.
Hard work is good. I love working hard. It’s not that being hard or working hard is the problem, it’s that it’s become the only narrative of success. Apparently, you can’t have what you want unless you grind, hustle and sacrifice.
The problem is that people are not hard squares. We are full of delightful creative soft edges borne out of organic minds and shift and change. We can be hard working while remaining compassionate and kind. The grind is causing good people to burnout and drop out.
We need an alternative.
Traditional leadership’s legacy
As a child I was hardened by the dangerous and insensitive environment of Apartheid South Africa. By the time I was conscripted into the army my compassion for others was at a low point. Years of propaganda had me thinking it was a dog eat dog world and there could be only one winner.
Military service made it cool for me to be tough guy. As I rose to being an officer in a leadership role there was no room for complaining or questions. Being hard was lauded. Being compassionate was for “gays and chicks.”
I was modeling the tough guys around me and teaching my reports to be the same way. There was simply no other option.
I was 17 when I went in to the army. By the time I left my body was covered in a few scars and my heart was deeply calloused. An impenetrable square with no soft corners.
It wasn’t until I tried to have a meaningful relationship that I realized my calloused heart was an obstacle to connection. What had been a badge of honor was now a geiger counter warning others that I was unapproachable.
Quick to temper, low tolerance and a general lack of empathy made me a shitty boss and an questionable husband and father. Without question, me holding up the tough guy status was a contributing factor to my divorce years later. I wish I was only describing myself but the reality is that most leaders are trying very hard to be too tough, resilient and unbreakable.
Gentle leadership
The older I get the gentler I become. And I like it.
For a long time gentleness has been equated to weakness. That’s not surprising given the constant over-the-top bro culture we’re experiencing on social media and podcasts. So let’s be clear, I’m not suggesting we all fall to our knees and let ourselves be walked all over. I’m gentle but not in the way where I don’t have boundaries. I know my worth.
But softening has allowed me to have an unapologetic open heart and an open mind about all aspects of my life. It’s a softness that let’s me hold opinions lightly. A softness that let’s me treat myself and others with care.
I trust others, even though I know I might get hurt. Trusting others can feel risky. Not everyone has your best interests at heart. You might even get hurt by these people.
If they hurt you, this very small percentage of people will make it feel like you can never trust yourself or anyone else.
Don’t allow their behavior drive you to live in fear. Trust anyway. Trust your kindness and love. Lead with openness.
I’ve been hurt and deceived a few times in my life but I’m not going to let the 1% mess up the 99% of relationships. There’s way too much to gain from coming from a place of trust.
I’m gentle. While my questions are direct, they are spoken with kindness. My inquiries are hard on ideas but gentle with the people who share these ideas. I’m gentle with my own ideas. I place curiosity above being right.
This is what I call gentle leadership.
This gentle leadership shows up with clear boundaries and a growth-oriented attitude. Gentle leaders seek to find an aligned vision, mutually beneficial relationships, and honored energy.
I’m more excited to work towards a healthy capable body and a nourished soul than working late nights or trade peace for status. Gentle leadership is a response to the hustle culture. It chooses to be lighter and smaller. To tread with care.
Rough riding across corporate America
Before I allowed myself to be gentle I bought into the idea that teams needed to be pushed toward goals. There were leaders and followers. The leaders pushed or pulled the followers. If you got left behind it was your problem, not the leaders.
I gave my teams BHAGs (Big Hairy Audacious Goals) and that often meant big batches of work. Big goals suggest a bigger business. Big goals mean you are growth orientated. Who doesn’t want to be ambitious, right?
The problem with big goals is they get translated into big batches of work. It’s near impossible to talk a big game and not also shape a big project to match. The problem is that bigger projects also require bigger teams, and longer roadmaps, and lots of meetings.
Bigger goals also mean more potential for parallel work. As teams try to deal with big projects they naturally divide and conquer. They split into workgroups to tackle more reasonable pieces of the project. This is a slippery slope. Suddenly the separated teams are siloed and working in different directions. Gaps appear in communication and outcomes.
Visually this “big batch” work looks like big teams and a huge burn-down or product board with hundreds of tasks and dependencies.
It looks like big experience maps and flow charts to try keep everyone sane. But have you ever tried to visualize a big project on a screen? Doing this is near impossible.
In a remote-first work environment we can’t expect teams to all understand the massive work we’ve proposed just because we have a big virtual whiteboard. Bigger is not better when it comes to the shape of a project. It just becomes overwhelming.
Big product boards mean lots more meetings and discussions. Trade-offs become mega-battles instead of quick choices. Never ending inputs pile up and the output slows. Tetris comes to mind. I call this overfeeding of the workflow organizational constipation. It’s a awful as it sounds.
The myth of predictability
Overconfidence is a byproduct of big projects. If you have a big project with no idea how you’ll actually deliver that project you need to bluff your way through the work. Overconfidence is the result. Hubris is the beginning of the end in any endeavor.
Leaders need to reign in overconfidence by letting go of prediction and speculation. There are principles that allow teams to render prediction unnecessary. These are the principles of antifragility.
While resilience is about recovery after performance degradation, antifragility is defined as a performance gain when exposed to adversity (Taleb, 2012)
Here are Taleb’s principles of antifragility:
- Stick to simple rules
- Build in redundancy and layers (no single point of failure)
- Resist the urge to suppress randomness
- Make sure that you have your soul in the game
- Experiment and tinker — take lots of small risks
- Avoid risks that, if lost, would wipe you out completely
- Don’t get consumed by data
- Keep your options open
- Focus more on avoiding things that don’t work than trying to find out what does work
- Respect the old — look for habits and rules that have been around for a long time
Think of being a Hydra, not a rock
When I read the antifragile principles I can’t help but think of the peony flowers that bloom in my garden. A delicate and fragile flower that erupts each spring only to be destroyed by the winter snows. As the freezing cold settles in, there’s no evidence that a beautiful flower even grew on that spot. But somehow, each spring, the peonies comes back even bigger and more luminous than the year before.
The greek legend of the Hydra (according to the early Greek poet Hesiod’s Theogony), was agigantic water-snake-like monster with nine heads (the number varies), one of which was immortal. Anyone who attempted to behead the Hydra found that as soon as one head was cut off, two more heads would emerge from the fresh wound.
This is the underlying strength of the gentle and antifragile team. While it can be damaged, it grows back stronger.
These principles are the foundation of gentle leadership. Instead of the hubris of overconfident speculation, these principles ask for humility. Instead of overconfidence in launching oversized projects, the principles ask for respect and experimentation.
Assembling a team to build anything should be built on the assumption that bad things will happen. Instead of seeking resilience, seek antifragility. Let the challenges make us stronger by adopting principles and relationships that make predicting the future unnecessary.
Applying antifragile and gentle leadership to work
So how might we work better with one another and allow for a kinder set of relationships to emerge? Here are my suggestions.
- Research is not a prediction of the future. While understanding patterns is important, it should only guide us to what habits and rituals result in potential performance. Avoid predictions that if proven wrong will cause damage to your team, product or morale.
- Spend time considering the principles of you specific work context. Too few teams have ground rules for interaction. Invest time getting to know each other so you can agree on how you’ll work together.
- Experiment, and then expand on the findings. The act of experimenting is thinking by doing. Or more specifically, learning by doing. You can’t think your way to a solution, you must act. Fuck around and find out.
- Reduce risk by doing less. Small teams, small batches of work, and small time boxes are the only way progress gets made. Big is risky, overwhelming, leads to burnout and is unsustainable.
- Randomness is to be embraced. Premature convergence on ideas and direction can be fatal. Allow accidents, feedback and surprises to guide your path. Diverge for a long as is reasonable before deciding on a way forward (and even then, be willing to learn more and adapt).
Removing risk by being more like nature
Ultimately, being gentle and antifragile feels more natural. More like nature. More like the amazing organisms that have outlasted millions of years of changing environments and shifting patterns. Our most fragile species are also the ones that have been around the longest. Small and indestructible apparently is a thing.
Doing work with a gentle touch is the real flex of modern work.
I dare you. Go be gentle. Go build relationships that have gentleness built in to them. Embrace your fragility and the ability to learn from that fragility so you can become antifragile. Teach others to be gentle with caring and kind words and behaviors. Be hard on ideas and soft on people. Maybe then we can work better together and create more value and less waste. Maybe then work can start working.
