When Compassion Costs Honesty
21 July 2026 | 5 minute read
Compassion and accountability are about to collide.
One of the hardest leadership decisions in the next five years won't be about technology or strategy. It will be accepting that not everyone will make the transition. And when that moment arrives, when it becomes clear that someone won't move with the organisation, the conversation you may want to avoid is exactly the conversation you need to have.
I know that sounds harsh. Most leaders don't want to think that way. We want to believe that with enough support, enough coaching, enough communication and enough patience, everyone can adapt.
And most of the time they can. But not always.
Over twenty years, I've worked with leaders and their teams through restructures, new technologies, operating model shifts, cultural transformations. The pattern is remarkably consistent: people eventually find their footing when things change. Some thrive. Some struggle for a while and then adjust. But there's also a small group who never quite make the leap. And we often wrongly assume it's because they're no longer capable. Sometimes the demands of a role outgrow the person performing it, for sure. But there's another side to this that barely anyone talks about. Sometimes the change creates a future that no longer aligns with who they are, how they work, or what they want from work. Kind of a square peg, round hole situation.
The leadership challenge isn't deciding whether that happens. It's deciding what to do when it does.
#1: We need to stop pretending everyone starts from the same place
One of the biggest mistakes organisations make during transformation is assuming everyone has the same capacity to adapt. They don't.
Some people are energised by uncertainty. Others find it exhausting. Some learn through experimentation. Others prefer stability and mastery. Neither is wrong. But pretending everyone begins from the same starting line doesn't help anyone. Particularly the people who are struggling.
Try this: think about your team. Who is leaning into change? Who is cautiously adapting? Who appears increasingly disconnected? What are you noticing?
Insight: people experience the same change very differently.
#2: Support matters. But support isn't infinite
Good leaders want to help. It's often why they became leaders in the first place. So when someone struggles, the instinct is usually to provide more support, more coaching, more training, more encouragement, more time. And often that's exactly what's needed.
But there comes a point where leaders need to ask a difficult question: Is this person still learning, or are we simply delaying an inevitable conversation? That's not a comfortable question. It's also not an unkind one.
Try this: consider someone you're investing significant energy into supporting. Are they making progress? Or are you measuring effort instead of movement?
Insight: you can be compassionate but still face difficult realities through candid, respectful conversation.
#3: The cost of avoiding the conversation is rarely neutral
I've seen leaders hold onto people for years because they hoped things would improve. Sometimes they do, sometimes they don't.
But delayed decisions don't only affect the individual. They affect the team. The workload gets redistributed. Expectations become unclear. Others start compensating. Eventually people begin asking questions in the corridor or coffee line, that they won’t say directly in the room with the right people. And that sucks for everyone, not least the person struggling. The longer uncertainty remains, the heavier it becomes.
Try this: what difficult conversation have you been postponing because you don't want to hurt someone? What is the cost of waiting?
Insight: delayed accountability often creates more pain than timely honesty.
#4: Sometimes people choose not to come with you
This is the part hardly anyone talks about. Not every transition failure is an organisational failure. Sometimes people look at where the organisation is heading and decide: nope, that's not for me. And that's okay.
A career isn't a never ending loyalty test. People and organisations both change. Sometimes those paths diverge. The most respectful thing a leader can do isn't force alignment, it's help people make informed choices.
Try this: have you created enough psychological safety for someone to tell you they may no longer want what the organisation is offering?
Insight: retention isn't always the measure of good leadership.
#5: Leadership isn't choosing between compassion and accountability
The false choice many leaders make is believing they must pick one. Be compassionate. Or be accountable. In reality, strong leaders do both. They support people and invest in their development. They create opportunities to learn. And when the evidence tells them a transition isn't working, they address it honestly. Not abruptly. Not coldly. Not punitively. Honestly. Because avoiding reality isn't compassion. Don’t mistake you avoiding discomfort as kindness.
Try this: where might compassion and accountability need to exist together in your leadership right now?
Insight: great leadership isn't being soft or hard. It's being clear.
A question to sit with…if one of the hardest leadership decisions of the next decade is accepting that not everyone will make the transition, how prepared are you to lead that conversation?
Key Takeaways
People don't fail transformation. Transformation fails when it assumes everyone has the same starting capacity.
The instinct to support struggling team members is leadership at its best, until you mistake kindness for avoidance.
When you delay a difficult conversation, you don't protect the individual. You redistribute their struggle across the entire team.
Not every person who doesn't make the transition has failed. Sometimes they've simply chosen a different path, and that's okay.
The strongest leadership isn't soft or hard. It's the willingness to be both at once: genuinely supportive and unflinchingly honest.
Frequently Asked Questions
Isn't it unkind to have these conversations? Won't it damage trust?
The opposite. Avoiding a conversation tells someone "I don't think you can handle honesty" and leaves them guessing what's wrong. Clarity about where things stand, delivered with respect, builds trust. The damage to trust comes from delay, ambiguity, and the person hearing about the decision from someone else.
What if I'm wrong and they actually turn it around?
Then you'll have named the issue clearly enough that they understood what needed to change. That clarity is what makes turnarounds possible in the first place. A vague conversation buys nobody time; it just defers the deadline.
Isn't my job to get everyone across the line?
Your job is to be clear about where the line is, offer genuine support to those genuinely trying to get there, and make room for people to choose whether this is their transition to make. Some of the best outcomes come from people finding roles where they can thrive, not from forcing fit where there isn't any.
How do I know when it's time to have this conversation?
When you've shifted from "How can I help this person move forward?" to "How long can we keep waiting?" When your support has shifted from development to damage control. When the person is no longer learning but you're no longer expecting them to. That's when.
Additional Resources
About Louise
Louise Zawada is an executive coach, change strategist and leadership mentor based in Perth, Western Australia.
She works with senior leaders and executive teams navigating complex organisational change, helping them close the gap between strategy and execution by strengthening executive judgement, reducing leadership friction and improving the quality of conversations that drive performance.
Her work spans mining and resources, government, infrastructure and corporate organisations, where she coaches leaders to make better decisions under pressure, build trust through uncertainty and lead change with greater confidence and clarity.
Louise is the creator of the Leadership Friction framework and writes regularly on executive judgement, organisational legibility and the behavioural evidence that determines whether strategy becomes action.
If you're leading significant change and need a trusted thinking partner, connect with Louise or book a conversation.