Antifragile leadership in 2022: Checklists for Leaders & for HR

Show of hands: how many of you have a list of dream goals or experiences or achievements that you crave in your life? Maybe it’s an actual list, maybe it’s the stuff of your daydreaming and procrastination at your desk. Finding true love? Lying on a beach in the Seychelles? Making a million? Don’t get me wrong, I love a bucket list. But the danger comes when you are forever envisioning these items – like a carrot on a stick – as the things that will make you happy.

I watched a video the other day by Tal Ben-Shahar, a Harvard lecturer and writer in the field of positive psychology and leadership. His advice? Don’t chase happiness. Become anti-fragile instead.

As Tal says, there are only two types of people who don’t experience negative emotions – the first kind are psychopaths, and the second kind are dead. He explains that there is a false understanding and expectation that a happy life means being happy all the time. In fact, an important part of leading a happy life is learning to accept and embrace negative emotions.

Some of my biggest learnings have come from negative emotions and messing up. I’m sure the same is true for you. Painful at the time, sure, but essential to our self-development and developing our resilience too. 

Antifragility is resilience 2.0.

There’s an old Japanese proverb that says, “Fall seven times, stand up eight.”

Life seems to be full of what was once thought impossible or unimaginable, and there’s a distinct lack of practical guidance about how to cope and move forward proactively in the face of ever-growing and constant uncertainty

Ben-Shahar talks about a very important concept introduced by Nassim Taleb: antifragility.

If resilience 1.0 is putting pressure on a system, with that system going back to its original form once that pressure is lifted, then resilience 2.0 is when that system grows bigger and stronger because of the pressure. Physically, that’s our muscular system, for example, when we lift weights. On a psychological level, that is post-traumatic growth. 

Post-traumatic growth is not a quality, but a mindset. One to be continuously stretched and built – in order to make the most of future crises. And if there was ever a time to embrace this idea, I feel like it’s now. 

One silver lining to the last couple of years has been that a lot of us reached a point where we started to really focus on taking better care of and developing ourselves and adopting active listening in our own heads. Now, we know it’s okay to not be okay, and to struggle and to want different, or more, or less. 

We need to understand how to develop more of these soft skills in the workplace. Skills such as flexibility, agility, vulnerability, versatility, emotional intelligence, agile learning, listening, navigating through change, and managing uncertainty, to name a few. We need to be able to make some sense of the chaos and become more intuitive. Transforming our businesses into sustainable workforces and brands of the future requires us to strategically transform ourselves on the individual level.

What does antifragility look like in the workplace?

Research by Iris Moss and others found that paradoxically, people who pursue happiness end up being less happy, and are more likely to experience depression. Valuing happiness as a good thing may be problematic, but Ben-Shahar proposes that breaking it down into its elements can lead us to enjoy the indirect pursuit of happiness. Staring directly at the sun is painful, for example, but who doesn’t feel positive when admiring a rainbow? 

Happiness is more than pleasure. It is whole being. This is how we need to think when creating workplace cultures. We need to enjoy the ride, enjoy failures and small wins. An antifragile culture is a culture of innovation – to build and sustain it, we need to adopt a new mindset. One of humility, growth, curiosity, experimentation, and open-mindedness. 

Have you ever worked with a leader who made you feel dumb or out of line for asking questions and being curious? Or shamed you in front of the whole office over a failing? Ben-Shahar sites research proving that people who are curious and ask questions are not just happier, but they also live longer. 

However, it’s more than just asking questions – it’s about leaders and their employees all deeply engaging with material. So, this new culture needs to be a psychologically safe space where that mindset can flourish. Where there’s no fear of failure or the consequences attached. Only creativity and learning and a thirst for answers, driving the success of people and the businesses they comprise. 

Ben-Shahar also introduces the S.P.I.R.E model as a way to trigger the AFG system (our spiritual, physical, intellectual, relational, and emotional wellbeing). When we embrace our spirituality and find a sense of meaning and purpose in life, at work and at home, we are more likely to overcome barriers. Relationalwellbeing is also very important when it comes to increasing the likelihood of AFG and growing through hardship. The number 1 predictor of happiness is spending time with people we love and who love us. And when we are focusing on gratitude and our emotional wellbeing, we receive more of what we’re appreciating.

Like happiness, leadership development resides on a continuum


Ben-Shahar’s ideas tie in beautifully with the way I approach leadership development. Self-development (for everyone, not just for leaders) is an ongoing, lifelong process and when we understand that, we can have realistic expectations about what’s possible, and we can learn to make the best of negative things that happen. We can stimulate our post-traumatic growth.

For a leader to develop antifragility, they must first understand what is important, so they can provide focus and motivation to themselves and their teams. That focus needs to be grounded in an accurate view of the surrounding environment. I do a lot of work around cognitive bias, so I know that this is easier said than done, but this is where that self-awareness, self-knowledge and opening yourself up more to the outside world so you can anticipate and respond to new needs comes in – these are the essential leadership skills to achieve a broader reach and thrive through radical organisational transformation. 

These are the leadership skills that will build sustainable workforces. Putting antifragility at the heart of your organisation and your leadership development strategy – investing in values and culture – is the only way to ensure that your organisation and people are ready for the next disruption. 

Developing antifragile leadership: a checklist for leaders

  • Open your mind – inside and outside of the business.

  • Take time every day for self-reflection, so your own self-awareness is a constantly evolving thing.

  • Make strides to develop your emotional intelligence. How can your organisation assist with this growth? Would you benefit from a leadership development program?

  • Even if ‘tried and tested’ always works – always be thinking about new ways to approach problems. Open it up to the floor too. 

  • Acknowledge your own weaknesses and failings, embrace them, and learn from them to grow your antifragile confidence. 

  • Decentralise the decision-making

  • Practise active listening and encourage two-way feedback

  • Leverage the intelligence of your teams – look for opportunities to welcome and facilitate collaboration and contribution. 

  • Look beyond the data – use your intuition and allow yourself to be vulnerable when making decisions.

  • Create a psychologically safe space where it’s okay to fail. The more the better, in fact – it means you’re thinking creatively. 

Supporting leaders and fostering an antifragile culture: a checklist for HR 

  • HR has become a fragile department and it’s why the past couple of years have been such a struggle. HR needs antifragility at its own core. So, ask the right questions – starting with the same question as these scientists of happiness: “What conditions can we put in place to increase the likelihood of growing from hardship?” “What can we add to our leadership development strategy with antifragility and PTG in mind?” “What can we do as a team to make leaders and employees feel more supported?” “How can we become more antifragile as a department?” 

  • Consider how you can encourage your leaders to discover their meaning and purpose, and who they are within your organisation. 

  • Provide opportunities for individual development. I’m certainly talking about leadership development, but I’m talking about further down the ladder too. How are you identifying and developing your high potential talent? When individuals have more opportunities and eggs in multiple baskets, they won’t be so fragile when an egg breaks every now and again. The same applies for the organisation itself. Don’t be afraid to ask for help with this from a leadership development consultant like myself.

  • Speaking of breaking eggs, don’t try to shield your leaders and workforces from negative experiences – if you develop your leaders into supporting and caring managers, then exposure to these negative experiences is an opportunity to grow, learn and reinforce your new mindset and culture. Inviting employees to be involved in finding a solution to problems will also further motivate them.

  • Don’t be so overly focused on staying positive that it becomes a mask and breeds distrust in your teams, or becomes something that instils fear of failure in your workforces. 

  • Think outside the box, go with your gut, experiment, and learn from wins and failures.

  • Understand that it’s a long journey and you can’t turn ideas into action and success overnight.


Written by Michael

Michael Mauro is the founder of a forward-thinking organisation specialising in leadership, HR and employee development. With over a decade of global experience, Michael has become a leading voice on topics such as culture, inclusion, wellbeing, and the future of leadership.

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