Kind Leadership: The Shepherd or the Wolf?

Kind Leaders share six characteristics. Beginning with a commitment to leave everyone and everything better. Kind Leaders are Self-Aware. They know that the organisations they lead are living systems; networks of relationships, ecosystems of collaboration. Personally, they are more interested in character than reputation. They are life-long learners determined to be high-calibre. Finally, they know that consistent practice builds habits. Read on to learn more about these characteristics, see if you are a shepherd or a wolf, and why you should ‘Be More Tree’.


Once upon a time a wolf had been prowling around a flock of sheep for a while. The shepherd was wary because he knew that wolves were wicked and would carry off a lamb as soon as his back was turned. But night after night the wolf was there and nothing happened. So the shepherd became used to the wolf being there and was troubled no more. 

One day he had to run an errand and left his flock in the care of the wolf. After all, this wolf would see off others intent on eating his flock.

When the shepherd returned he was distraught to see that most of his flock had been killed and carried off by the wolf. The sheep that were left were badly maimed and traumatised.

The moral of this fable by Aesop?

Never trust a wolf. 

Once a sheep killer, always a sheep killer. It’s who they are. 

Some leaders are wolves and some are shepherds.

Driven, strong, fearless, tireless, the lone wolf — many a leader has modelled their leadership style on these attributes. And they’ve been celebrated for it. From Henry Ford to Elon Musk, the idea of the charismatic leader runs deep through business thinking and popular culture. 

The idea of the shepherd appears consistently in all religious and spiritual thought, and for good reasons:

  • The relationship between a shepherd and sheep is built on trust
  • Sheep know that the shepherd will look after their well-being and safety
  • The shepherd ensures that the sheep are in the best environment for them to thrive
  • The shepherd has a job to do but at the core is kind-hearted

What kind of leader do you want to be, or work with?

The sheep-killing wolf or the kind-hearted shepherd?

Kind Leaders are shepherds, not wolves.

So, let’s look now at the six characteristics of Kind Leads.


Kind Leadership is Committing to Leave Everyone and Everything Better

Too many of us are stuck in ways of working that no longer work. Command and control, hierarchies, the idea of work as a machine that can be measured, optimised and tinkered with. Easy when you see your employees as: headcount, staff, roles, FTEs and any way of describing actual real living people that seeks to dehumanise. But these old ways simply don’t cut it with a workforce who are more aware, more conscious, and want more meaning out of their work.

Let’s be clear folks, there’s no “going back” pre-COVID or “levelling up” from where we were. Work is fundamentally changing and we need to become more fully aware of the impact of the way we work and how it is impacting ourselves, the people we work with, the communities in which we live, work and serve, and the only planet we get to call home. Leaders take note — more and more people are becoming aware of their impact and the impact (or not) of the organisations they work for. And, just because you can’t see it happening, doesn’t mean it isn’t.

We need to redefine work. 

Now and for the next 100 years.

As leaders go about the business of creating a new working model (again), wishing and hoping won’t work. To make a great comeback, leaders need to be dedicated to thriving. They have to shift their mindset and view work differently than they did before — acknowledging that work is a human thing. Focusing on whether people work physically, remotely or hybridly is secondary to how they work. 

  • How we work is what shapes our human experience when we’re working. 
  • How people work and work together are the ultimate predictors of organisational success, stability and growth.
  • How organisations take their work into the world determines how well their brand will thrive today and into the future.

A popular definition of insanity (usually attributed to Einstein) is: “Doing the same thing and expecting different results.” 

For people and organisations to thrive we need to work in different ways, and we need different results.

So, let’s reimagine work. Now and for the next 100 years.

Let’s look at a meaningful new way to meet the world and measure success.


Very simply, kindness makes people better and when we are better (happier, healthier physically and mentally, more satisfied) we show up authentically. We build trust. We collaborate more fluidly and effectively. When we are better, everything about work, including the outcomes we create, gets better too. 

Kindness is an ambiguous word and one that has a different meaning for nearly every person you ask. It’s also a word that’s never historically been associated with work. We don’t understand it. Maybe that explains why, historically, kindness has lacked meaning and relevance in the context of work. 

While we’re reinventing work, why not redefine kindness too? What does it mean for you? If you’re unclear or coming up short, why not consider this definition:

Kindness is a commitment in thought, word and action to leave everyone and everything better.

How can we go wrong if we start right there? By adding intention to guide our actions and decisions, as we break and disrupt, we will build a human-centric future for work that will have far reaching positive impacts. On this launchpad, we will need to support our efforts and mindset with continual attention (care and feeding). This will make the changes real and make them last.

And that is why Kind Leaders share this definition of work to leave everyone and everything better.

This definition of kindness is as simple as it is binary.

Anything (yes anything) you do at work can be viewed through this lens of kindness. 

Your next Town Hall — how is it going to go deep and talk to the concerns and hopes that people have? Giving them the opportunity to speak up, be heard, and make a meaningful contribution.

You’re doing a deal — how can both of you walk away from the table satisfied? 

You need to re-org and a significant number of people are going to lose their jobs. However, they will have to stay on over the next six months while they work out their notice, and the business needs them to keep delivering the numbers. How do you make those six months one of the most positive experiences in their career? This, by the way, is a real example of how we are supporting an organisation and the people they work there in off-boarding, a much better way to look at it than ‘firing’, making ‘redundant’ or ‘laying-off’.

Kind Leaders at all levels are redefining work right now. Are you one of them and, if not, are you going to join them?


Kind Leaders Are Self-Aware

Back in 2014 three-time Nobel Peace Prize nominee Dr. Scilla Elworthy shared that when the 75 members of Stanford Graduate School of Business’s Advisory Council were asked to recommend the most important capability for leaders to develop, their answer was nearly unanimous: Self Awareness.

A study of over 5,000 people led researcher Tasha Eurich to the conclusion that we can think of self-awareness in two ways: internal and external. Internal self-awareness is about knowing yourself, being present, and not making stuff up about what’s going on or might happen. External self-awareness is all about empathy — about truly understanding how others see us.

Leading a human-centric organisation starts with self-awareness; being present with what is in one’s body, feelings, mind, and in the world. 

I was once in an Alpha, hormonally-charged meeting (something that is actually all too familiar for too many folks) and things were going pear-shaped. The conversation was getting more heated and it looked like the meeting was going to fall apart in blame and recriminations. So, I stood up, held out my arms, palms pointing forward and quietly said “Stop”.

To a man (yep, no women in this BIG meeting) the Alpha Tech Bros all looked at me like I was insane.

I pressed on. 

“Do we seriously think we are all going to get to a better place by bringing our egos even more firmly into this room?”

Confused looks. After all, wasn’t it their ego that helped get them into the room for the BIG meeting?

But I persisted. Standing there with palms open — my invitation for them to put their ego to one side and become more self aware. I asked them to close their eyes, slow their breathing and focus on their in and out-breath.

And, like dominoes, they fell. Closing their eyes, slowing their breathing. Until everyone was. After a few minutes we returned to our discussion. Tempers cooled, minds opened.

That day we left everyone and everything better when we walked out of the meeting. It was a Kind Meeting. Just like every meeting can be.


Kind Leaders Know They Work in Living Systems

We need to Be More Tree.

“In the past the man has been first; in the future the system must be first.”  

Frederick Winslow Taylor, The Principles of Scientific Management, 1909

Don’t be fooled by the fact that Taylor wrote this well over a century ago — this view of organisations as machines has dominated management thinking ever since. Machines perform best when they are optimised and it is the job of managers to optimise and run an efficient and productive machine. So we need hierarchies, business units, silos, metrics, blah, blah, blah.

Wrong. Wrong. Wrong.

We need to stop thinking of companies as machines.

And start thinking of where we work as living systems; networks of relationships, ecosystems of collaboration.

Trees share minerals and nutrients through a network of Mycelium (fungi) which has been called the ‘Woodwide Web’. Not only do trees share resources, trees that are being attacked by bugs will send signals through this network, enabling well-established ‘mother trees’ to send them the nutrients they need to help protect themselves. Trees live for hundreds and thousands of years. The average lifespan of a company is now just 15 years.

Our company cultures need to focus on thriveability. When we do this as company leaders we stop worrying about the latest gloomy headlines. We shift our thinking away from traditional commercial and qualitative metrics to a human and planet centred approach that considers complexity, corporate responsibility and untapped potential.

We need to Be More Tree.


Being a Kind Leader is About Character, Not Reputation

Ask yourself this: How important are Likes, Fans, Followers, Shares, and Retweets to the people who have or have had the most influence in your life?

That school teacher who ‘got you’ and helped where others didn’t, couldn’t or wouldn’t?
Alfie Knott, Roan School for Boys, Blackheath, London

The person who wrote the book, lecture you attended, or programme you watched that had you on the edge of your seat, perhaps shouting in anger at the injustice of it all, resolving to do something about it.
David Attenborough, “Climate Change – The Facts’

The person who regularly inspires you?
@Alasdair Field

The sons or daughters who teach you as much as you teach them?
@Alice Wood @Olivia Wood

Influence isn’t about the social constructs created by megalithic technology companies who call us ‘Users’.

Influence isn’t about people who are being paid by brands to make us want things we don’t really need.

Back in the day before smartphones and social media, the people who had most influence on us were the people we knew; either personally or through their ideas, their insights, their personality, their words, their songs, their stories…everything they did that we valued because it made the world a better place somehow.

The people who influence us most, who make the world a better place, are people of good character.

Character that is positive, well-intentioned, consistent…a whole bundle of mental and moral characteristics that add, rather than take away.

These people — leaders at all levels — commit to the personal development work to develop and strengthen their character. Their character is built over time, as is their influence.

Contrast this with people chasing fame, fans and followers. People who obsess over what people think of them, how many people are thinking of them, and how many more people could be thinking of them. 

In the movie ‘The King’s Man’, Orlando, the Duke of Oxford’s son, shows his father the white feather one of the villagers has given him as a badge of cowardice because he hasn’t enlisted for The Great War. Orlando is desperate to enlist but his father has forbidden him. Consoling his son, the Duke replies:

“Reputation is what people think of you. Character is what you are.”

Kind Leaders know this.

Kind Leaders know that, if they want to be a positive influence, they need to do the work on their character. Day after day after day.


Kind Leaders Are Life-Long Learners Determined to Be High-Calibre 


When left alone, everything decays. 

Without work, everything that is ordered goes into disorder.

Joints become stiffer.

Weeds overtake gardens.

Relationships fall apart.

This natural order of things to fall apart is known as the Second Law of Thermodynamics. It is a foundational concept of science and a fundamental law of the universe.

So, let’s cheer ourselves up with the First Law of Thermodynamics, another fundamental law, that states energy can neither be created nor destroyed, but it can be changed from one form to another.

My thoughts you are reading here now are a form of energy. It’s a transfer of energy between you and me.

A clear message that I hope you will heed:

Unless you commit to life-long learning in the areas of life that are important to you, they will decay and fall apart. It’s as true for your work as it is for your relationships, as it is for your health, and anything else that matters.

Kind Leaders aren’t always the smartest person in the room. But they certainly make sure that they get themselves in the smartest rooms.

Kind Leaders learn just like they commit to developing their character: day after day, never ceasing, always taking in ideas, information, insights, experiences…anything that enriches their capabilities as leaders.

Capabilities lead to calibre. The more capable you are as a leader, the higher calibre you are.

And to get capable — learn. Prevent entropy and transfer that energy from others who have gone before you and apply it to your life and work. By doing so, you will not only lead better, you will be an example to others who will learn from you.

Most of us don’t work in life-or-death situations. General James Mattis commanded forces in the Persian Gulf War, the War in Afghanistan, and the Iraq War. He’s not a man who has any truck with entropy:

“If you haven’t read hundreds of books, you are functionally illiterate, and you will be incompetent, because your personal experiences alone aren’t broad enough to sustain you.”

Functionally illiterate. Nobody wants to be that.


Kind Leaders Commit to Consistent Practice That Builds Habits

Showing up every day.


Kind Leaders show up Kind every day. 

Kind Leaders commit in thought, word and action to leave everyone and everything better.

So, that’s what they do. In every conversation, meeting, decision and more they are consistent in thinking win-win and wanting to leave everyone and everything better.

Every day Kind Leaders get to see the impacts of kindness and this positive reinforcement of kindness encourages them to build it as a habit — something they do without thinking because they instinctively know that it works.

The consistent practice of kindness ‘hard wires’ us to build the habit of kindness, so that showing up kind every day becomes who we are, not just what we do.

During the COVID pandemic in the UK and expression captures the hearts of the UK population:

“In a world where you can be anything, be kind.”

Be a Kind Leader.


Lessons on Kind Leadership From Philosophers, Academics and Spiderman

The Kindness Corporation’s view on what makes leaders human, visionary and inspiring was created in the ‘crucible of corporate life’. We have decades of corporate, as well as startup, experience. We’ve worked with some of the best and the very worst leaders. And we’ve learnt to become leaders the hard way — through trial and error, getting things wrong, then learning from our mistakes. We’re human and far from perfect. That said, we have a very clear view of what great leadership looks like.

We’re not alone in this; for centuries people have thought, researched, debated and written about leadership. We looked to the ancient philosophers, most notably the Stoics, who considered virtues of great leaders such as: courage, temperance, dignity and humility. A core insight is that great leaders focus on what is in their control and don’t bother with what isn’t. That includes every day things like: how we respond to situations, the emotions we choose to dwell on, the judgements we make consciously or subconsciously; our creativity, decisions, determination, and our actions. 

We are yogis and our definition of kindness — to leave everyone and everything better — started life as the first and foremost of the five yamas (restraints) described in the Yoga Sutra; which asks us to live in such a way that we cause no harm in thought, speech, or action to any living being, including ourselves.

Reading Steven Covey’s classic ‘7 Habits of Highly Successful People’ back in the day taught us that life is a cooperative arena, not a competitive one. ‘Think Win-Win’ is his fourth successful habit; which also contributed to our definition of kindness.

When we dug into the research to consider what makes a leader truly great, the natural place to start was ‘Good to Great’ by Jim Collins. Over a 5-year research period Jim and his teams examined the performance of 1,435 companies and whittled them down to 11 they determined were truly ‘Great’. These companies shared many things in common, not least of which, the nature of their leaders, whom Jim describes as ‘Level 5 Leaders’ — the peak of leadership:

“Level 5 leaders display a powerful mixture of personal humility and indomitable will. They’re incredibly ambitious, but their ambition is first and foremost for the cause, for the organisation and its purpose, not themselves.”

We looked at the work of Fred Khiel in his deep research into what makes a successful leader, ‘Return on Character’, which showed that companies who have CEOs with a good character outperform “self-focused CEOs” by FIVE TIMES. Fred talks about leaders having four moral principles: integrity, responsibility, forgiveness, and compassion. How many leaders do you know who lead this way? In his findings Fred goes on to share the worst practices of leaders: treating people as objects, putting up barriers, and spinning the truth. 

The work of John Mackey, CEO of Whole Foods, also inspired us:

“It’s important to remember that in business, everything we accomplish is ultimately done with and through other people. That is what Conscious Leaders do — we inspire, motivate, develop, and lead others.”

‘Regenerative Leadership’ by Giles Hutchins & Laura Storm is full of lessons for leaders who are focused on the thriveability of the people and the organisations they lead:

“Regenerative Business enriches life. It enriches ourselves, our customers, and the wider stakeholder ecosystem. Regenerative Business transforms our role and purpose, from a “what’s-in-it-for-me” approach to a mindset of collaboration, co-creativity and contribution. Regenerative Leaders bring vitality and wellbeing to all our living systems…In-so-doing, we wake up to what it really means to be fully human.”

Being fully human. 

That’s who we want to be at work. Our authentic, imperfect, human selves.

Not bits of who we are, with our human parts censored because we’re worried about what people might think of us in a work environment.

When people hold back, their work is held back.

Ultimately, leadership is about responsibility, not power. Peter Parker (AKA Superman) knew this when he said:

“With great power comes great responsibility.”

This sense of responsibility for people, for decisions, actions and outcomes was known only too well by President Harry S Truman, who had on his desk a sign that read “The buck stops here.” A lesson which a more orange recent President would have done well to heed.


This is our moment for us all to redefine work, the experience we have, and to create what we want work to be like now and for the next 100 years. What will you choose to be?

Shepherd or wolf?

Will you choose to be a Kind Leader?