When Generosity Goes Wrong
How the leaders who give the most sometimes end up with the least engaged teams…
There is a pattern I have noticed repeatedly in the coaching room over the last few years. Some of the most thoughtful, committed and generous leaders I work with sometimes find themselves leading teams they experience as entitled, unappreciative or disengaged. They are often bewildered by it. After everything they have invested, how have they ended up here?
One of the privileges of coaching leaders across different sectors, professions and organisational cultures is that, over time, patterns begin to emerge. The coaching room becomes a place where human behaviour reveals itself in remarkably consistent ways. The context changes - schools, engineering firms, charities, big corporates, boutique professional services companies, but many of the underlying relational dynamics remain strikingly similar. This is one of those patterns.
Why do so many capable, compassionate people arrive at exactly the same destination? Why do the leaders who give the most so often feel the least appreciated? And why do the teams they had worked so hard to support appear, over time, to become more dependent, less accountable and increasingly difficult to satisfy?
If we explore these observations through the lenses of Transactional Analysis, systems thinking and motivational psychology, the pattern makes a lot of sense. What initially looked like a story about difficult teams turns out to be something much more interesting. It turns into a story about relationships, and the way they are established over time.
Everything that is relational is co-constructed
That is both a challenging and a hopeful idea. Challenging because it asks us to consider the part we may be playing in creating the very dynamics that frustrate us (Thank you, Jerry Colonna). Hopeful because if relationships are co-constructed, we can also change them by showing up differently.
Transactional Analysis (TA), developed by psychiatrist Eric Berne, tells us that relationships are built through transactions. Every conversation, every facial expression, every hesitation, every act of support, every avoided conversation, every boundary we hold - or fail to hold - communicates something about how this relationship works.
Much of this happens below our conscious awareness.
We like to think that relationships are shaped by the big conversations: the annual appraisal, the difficult feedback meeting, the heartfelt thank you. In reality, they are shaped just as much by the hundreds of tiny moments in between: the email we answer late at night; the task we take back because it is quicker to do it ourselves; the work from home request that we approve because we want to appear kind; the conflict we smooth over to avoid discomfort. Each interaction, on its own, seems insignificant. Together, they begin to establish a pattern.
Berne also introduced the idea of strokes - units of recognition that we exchange with one another constantly. We all have a fundamental need to feel seen, acknowledged and valued, and we communicate those messages in countless subtle ways throughout the day. Over time, these repeated exchanges teach us what to expect from one another. They tell us who carries responsibility, who apologises first, who notices when someone is struggling, who absorbs the emotional labour of the team and who can always be relied upon to pick up whatever is left behind.
These expectations are rarely discussed explicitly, but they become the unwritten rules of the relationship - what organisational psychologist Denise Rousseau describes as a psychological contract: the unspoken expectations that shape how people believe a relationship should work. Every team develops a psychological contract, without realising they are writing it.
First, generosity becomes the culture
The leaders I am describing care deeply about others. They want their teams to succeed. They want to create workplaces where people feel supported and valued. They willingly stay late, answer emails on holiday, absorb additional work, protect people from difficult conversations and step in whenever they sense someone is struggling.
Indeed, they are often the very qualities that made these people successful in the first place. They have earned trust by being dependable. Taking responsibility has helped them climb the leadership ladder. Over many years, these behaviours have become woven into their identity - they see themselves as kind, caring, productive.
That is why I think it is so important to approach this pattern with compassion rather than judgement. Nobody wakes up one morning and decides they would like to become exhausted, indispensable, frustrated and resentful. More often, they are relying on a strategy that has served them brilliantly for much of their lives.
Family systems theorist Murray Bowen observed that human systems naturally seek balance. When one person consistently carries more emotional or practical responsibility, others often begin, unconsciously, to carry less. This is not because they are lazy or unmotivated (despite what we might think of our pre-teens who don’t pick up their dirty laundry!). It is because systems adapt. Human beings respond to one another continuously, adjusting their own behaviour in light of what everyone else is doing.
Every time the leader steps in, the relationship learns something. It learns where responsibility lives. It learns who ultimately carries the emotional weight of the organisation. It learns what happens when work becomes difficult or somebody begins to struggle. None of this is discussed explicitly. It is learned through repetition.
In other words, the psychological contract is being written in the ordinary, everyday transactions that define what is normal. And that is where this pattern becomes both fascinating and painful. The leader believes they are building a culture of support where the team may be experiencing a culture of dependence and loss of ownership, agency and autonomy.
Then, generosity becomes invisible
One of the most painful aspects of this pattern is that generosity does not always produce gratitude. As humans, we adapt remarkably quickly to what is repeated. What once felt like an act of kindness gradually becomes part of the expected order of things.
Most parents will recognise this dynamic. We spend years driving children to football practice, making packed lunches, washing school uniforms, helping with homework, organising birthdays and holding together the thousands of invisible tasks that make family life possible. Then they complain because dinner is ten minutes late or because we have given them the wrong kind of green vegetables!
We hear ourselves saying, "After everything I've done for you..." I know it’s not just me.
Our first interpretation is often that our children are ungrateful. Sometimes they are but more often, something else has happened: our generosity has become so normal that it is no longer experienced as generosity. It has simply become the way life works.
Back to organisations… The leader who always steps in to solve the problem becomes the leader who is expected to solve the problem. The leader who always says yes becomes the leader whose availability is assumed. The leader who consistently absorbs pressure creates a system in which others no longer notice that the pressure was ever there in the first place.
This is not a moral failing on the part of the team. It is a feature of how human beings adapt to repeated experience. It is one of the reasons I find this pattern deserving of compassion on all sides. It emerged because the psychological contract changed, one transaction at a time.
Death by a thousand cuts for the leader
If this were simply a story about teams becoming dependent, it would be relatively easy to solve. The reason it is so difficult is because of what happens to the leader.
Many of the leaders I coach have spent years, sometimes decades, building an identity around being dependable. They are the one who can always be trusted - the one who never drops the ball, the one who works hard, keeps going and puts everyone else's needs before their own.
These are qualities that organisations frequently reward. It is hardly surprising that they become deeply woven into a leader's sense of self.
Then, gradually, the strategy stops producing the outcome it once did. The appreciation becomes less visible. The requests become more frequent. The emotional load becomes heavier. The leader begins to notice that they are working harder than ever, yet feeling less valued than ever before.
This is often the moment when self-doubt begins to creep in.
"Maybe I'm not doing enough."
"Perhaps I need to support people more."
"Maybe I'm not the leader I thought I was."
The response to this inner dialogue is almost always to do more - to become more available; to solve problems more quickly; to work longer hours; to absorb more responsibility. From the outside, it looks as though the leader is doubling down on generosity.
From the inside, they are returning to the strategy that has always worked before. Most leaders over-function because they care deeply, because responsibility has become part of their identity, or because, somewhere along the way, they learned that being useful was one of the safest ways to belong. There is nothing inherently unhealthy about those qualities.
The difficulty comes when the strategy becomes so familiar that we no longer notice it. What once served us begins to constrain us. And, without realising it, we perpetuate the very conditions that leave us feeling exhausted, unseen and alone.
Re-writing the psychological contract
This is why I don't think the answer is simply better boundaries. If the psychological contract has been co-constructed, then changing it is not solely the leader's responsibility. It becomes an invitation for everyone to examine the relationship they have built together.
That starts by making the invisible visible.
What have we come to expect from one another?
What responsibilities have gradually drifted into the wrong places?
Where have we confused support with rescue?
Where have we unintentionally reduced one another's ownership or agency?
How do we want to relate to one another from this point forward?
These are hard conversations to have. They require leaders to acknowledge that some of their most generous behaviours may also have limited other people's growth. They require teams to recognise that responsibility has become unevenly distributed and that greater ownership belongs with them too.
The most powerful re-contracting conversations I witness are characterised by honesty, humility, vulnerability and a shared commitment to creating something healthier than the system everyone has gradually adapted to.
From there the new psychological contract can be rewritten, much in the same way they were originally drafted, one conversation, interaction, boundary, courageous act, decision at a time.
Kindness is not the problem
There is one final thought that feels really important.
Whenever we recognise that one of our strengths has become overplayed, there is a temptation to swing to the opposite extreme. The generous leader decides they need to become tougher. The endlessly available leader resolves to say no to everything. The person who has spent years rescuing others suddenly withdraws support altogether in the name of accountability and empowerment.
I rarely see that work. Pendulums have a habit of swinging too far before they settle somewhere in the middle.
The answer here is to lean on the real strength of kindness and become more discerning about how it is expressed.
Leadership means caring for people and holding them accountable - at the same time. People need to know they are supported without having every obstacle removed from their path. They need to feel trusted enough to wrestle with difficult problems, while knowing someone is alongside them if they genuinely need help. They need accountability without blame, challenge without shame and honesty without fear.
That is a much harder balance to strike than either rescuing people or leaving them to fend for themselves.
For many of the leaders I coach, generosity is one of their greatest strengths. It is one of the reasons people trust them and why they have been successful. The goal is not to lose that strength.
When any strength becomes our main strategy, it eventually begins to work against us. Generosity becomes rescue, responsibility becomes over-functioning, compassion becomes self-sacrifice. What once served us so well can become our Achilles' heel because we have come to rely on it in situations where we need other strengths in the mix as well.
My wish
One of the reasons I wanted to write this article is that I have sat with too many leaders who have concluded that they are failing behind the scenes, when what they are really experiencing is the predictable outcome of a relational system that has developed over many years.
Understanding that helps us replace shame with curiosity. If you recognise yourself in these pages, I hope you do so with compassion. There is nothing wrong with wanting to be kind. There is nothing wrong with wanting to be dependable, generous or deeply committed to the people around you. These are qualities the world needs more of!
The invitation is simply to hold those strengths a little more lightly. To notice when kindness has drifted into rescue at your own expense. To see where responsibility has become over-functioning. To discern where generosity has unintentionally diminished someone else's opportunity to grow or created a sense of entitlement.
Our greatest strengths become problems when we stop choosing them and start being driven by them. Every day, through hundreds of seemingly insignificant interactions, we are teaching one another how this relationship works. We are writing psychological contracts, shaping expectations and creating culture, whether we realise it or not.
My hope is that leaders become more intentional, not that they swing the pendulum the other way. My invitation is to continue to lead with kindness, while remembering that one of the kindest things we can sometimes do is trust another human being with the dignity of carrying their own responsibility.
If you are interested in exploring executive or team coaching as a way of supporting your team to make this shift, reach out for a chat. We’d love to hear from you.
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