Very early on in my career, I had to run a layoff. I had only about 5 years of experience as an IC and had barely settled into a management role. Suddenly, I was standing before ten people, about to deliver news that would upend their lives.I made the rookie mistake of addressing everyone as a group. No one-on-one conversations before that; just a big room, a speech and an invitation for people to come talk to me individually after. I scripted my words, rehearsed deliberately and delivered them with shaking hands but without stumbling. And then I sat alone in an office cabin, dreading what was going to come next.
The conversations that followed were nothing like what I had expected. There was neither any anger nor confrontation. It was a relief, but I couldn’t understand what had happened until much later, when I learned that a project manager who had also been laid off had spoken to the group after I left. She told the group that the company had done this in good faith, acted as kindly as possible, and done more than most other companies would in a similar situation. And she had mentioned something I had done for her months earlier.
She had been pregnant and exhausted during a high-pressure sprint, worried she'd fall behind. I told her to take a few days off and that I’d handle things. It just felt obvious at the time.
But she remembered, and in that room, her memory of that moment shifted the atmosphere. She had brought the authenticity to my speech that I so obviously lacked. I was lucky.
That was the first time I realised how even a small act of care can travel, and how it matters that people feel seen, not just herded around.
The actual challenge in leadership is not the decision itself, but solving for the distance it creates.
As engineers, we love abstraction. When you start climbing the ladder and managing other engineers, and further down the line, other managers, abstraction is the familiar tool we reach for. You need it because, lets be real, you can’t expect to hold the weight of 200 individual realities while making high-impact decisions.
It is all in good faith, after all this is a shorthand that lets you function. But it comes with a cost that compounds quietly and you need to be mindful of that. People get reduced to headcounts and teams become nodes in an org chart. You start pulling your hair trying to curve-fit performance reviews.
Just as brain fatigue causes words to lose meaning with repetition, extended reliance on abstraction makes you forget what those concepts actually represent. A 10% reduction stops registering as colleagues with whom you weathered challenges. A product pivot ceases to feel like a decisive moment that uproots someone's well-established team or their work identity.
Abstraction doesn’t make you a bad leader, it makes you an efficient one. Efficiency applied without thought and at the wrong moments is its own kind of cruelty. And that’s where the real damage begins.
A leadership failure event that is seldom discussed is the scripted conversation that is a direct outcome of that abstraction. The same scripted conversation that I resorted to.
Picture this: you are deep into a restructuring exercise; you have had numerous back-to-back difficult conversations, you carry the weight of information you cannot share, and you aren’t sure about your personal situation either. Add the constant pressure to stay consistent and avoid saying the wrong thing. You inevitably craft a script, perhaps unwritten, a groove that you have eased yourself into. Same opening, same structure, it feels polished and sterile, clinical even.
What it signals to the real human being across the table, however, is that they are a variable interchangeable with the next person waiting to enter. It stops being a conversation with a person with a name, a home loan, a child starting school, a spouse who just switched jobs - reduced to a rehearsed performance.
The cost of this doesn’t appear on the dashboards. It quietly trickles downstream as trust is withdrawn and psychological safety erodes. This is where empathy becomes essential.
Empathy is not about being warm or sending a heart emoji at the end of a Slack chat. It is about genuinely trying to think and understand where the other person is right now, what they’re likely carrying with them. Different individuals experience the very same event in different ways. A reorg announcement lands differently for a 20-something who joined a few months ago and is building credibility than it does for a 45-year-old who turned down a job because they believed in the direction. Understand that this is your problem to solve and not theirs. Empathy is only useful if it shows up in the room.
The discipline that I’ve built over the years - imperfectly and inconsistently - is to pause and ask that question - What might this person be feeling now, knowing what you know about them? As against what you want them to feel or what they should feel. It takes a few moments, but it changes everything about how you show up.
At my level, the challenge is finding those 30 seconds to pause when you have ten such back-to-back calendar invites, two of them already emotionally charged, the awareness that you’re already running 15 minutes late and that person has been waiting for a week to find your time. When you feel the pressure to just push through, what matters is not accepting it as the norm, but designing against that schedule.
Why is that important? One thing I’ve noticed over the years is how much people remember how a conversation felt more than what was actually said. Did it feel like you were ticking some boxes or did it feel like a proper talk? Did you avoid peeking at your watch 5 times? All of those send a signal. When you rush, what the person hears is: this conversation is a task I need to complete. When you slow down, what they hear is: you are the reason I’m here.
Allow for silences, however awkward it may feel. When someone is searching for words to process tough news, or even when they are being recognised, resist the urge to fill in the gap. Let it breathe and understand that silence is respect. That’s how you make presence matter.
I also want to call out something that I hear internalised in leadership culture. There's an idea that rigour and kindness are conflicting. Being kind does not mean cushioning hard truths or lowering standards. That simply is conflict avoidance masquerading as kindness.The real kindness that should show up in your leadership is in the how of delivery, not in its absence. It is the difference between delivering the same message in a way that gives someone clarity about what needs to change, rather than leaving them curled up and defeated.
I think about this especially with performance conversations - and to be self-critical - I’ve mishandled many of them in my career. Learning from those mistakes, the feedback that I have seen land well (and I include feedback that I’ve been on the receiving end too) always had the same qualities: authentic, honest, specific and delivered by someone who clearly gives a damn about you.
And then come the hardest moments, letting someone go. They are genuinely the most awful conversation you can have. For the people losing their jobs, the loss of income, identity, routine, and often a community they built over the years. That is the primary reality of the event and should never be obscured by whatever the person delivering is feeling.
There is the emotional burden on the manager. I’m not calling it out to equate the two - there is no equivalence here - but not acknowledging it leads to worse outcomes. If you walk into a meeting in denial of that burden, it manifests as avoidance and a hollow performance of composure. Another signal that diminishes your presence, adding to the burden for the more important person in that room.
There is nothing worse than acting out prepared empathy. Always open with the objective reality of the situation. Resist padding it with fluff that obscures that reality. The message should come from you, and not an HR script read with a warm tone. That is how you protect the dignity of a person whose life is being upended.
Dignity is about providing clarity. “Your role is being eliminated” is better than 10 minutes of beating around the bush. It is about being honest. “I don’t know about that yet, but I’ll find out” is better than a promise you can’t keep. It is also about recognition of their contributions, thoughtfully delivered without patronisation.
People remember these conversations, both the ones that left them wounded and the ones that improbably left them with their sense of self intact. The difference is almost never the decision; it is about how the person on the other end showed up.
Empathy in leadership is often considered meaningful only when big, pivotal events occur. Those moments are, of course, important, but I’ve found that empathy is often missing in smaller, quieter moments. A cancelled yearly hike, or a shifting of priorities that shelved a project can look more manageable on its own than a layoff. From the inside, they can feel like a loss of progress or purpose. They rarely get the care or attention that they deserve.
There’s also the positive side, which I think people take even less care of. Promotions or recognition feel easy to give, so it's easy to assume that they always land well. But what feels like a reward can land surprisingly in opposite ways. What you think is validation can feel like relief or even unexpected pressure to the one receiving it.
There is something else worth saying. You are almost never talking to just one person. Every conversation you have with a direct report is also a signal to everyone else in the organisation. People watch how their colleagues are treated. They draw conclusions about what this company values, whether leadership actually means what it says and whether it is safe to be vulnerable, take risks or tell someone above them an uncomfortable truth.
Culture is not built in town halls, values workshops or leadership off-sites. While they do matter, they are not where culture lives. Culture lives in the difficult moments. Whether the manager who missed their targets last quarter was spoken about with respect or contempt in rooms they could not enter. Whether the engineer who raised an uncomfortable concern was heard or quietly sidelined. How the person let go in a restructure was treated on their way out.
The engineers you are not speaking to right now are learning from the conversations you are having. They are asking, "Is this a place where I will be treated as a person when things get hard?"
This is not an argument against processes and systems. The goal is not to replace process with intuition; it is about understanding standardisation where it serves people and where it fails them.
I want to be honest about something this essay might suggest implicitly: I’ll be delusional if I say I can have genuinely personal, fully present conversations with all 150 people in my organisation. That’s a mathematical impossibility.
What the job necessitates at this level is something different. I can design systems that carry the values I talked about into rooms where I’m not present. I can explicitly set expectations with my directors about how their teams should be treated and ask hard questions when those expectations aren’t met. I must model the behaviour I want to see in the conversations I do participate in and let it propagate.
All in all, at scale, it is about building a chain in which the people below you recognise, through the lens of their manager’s behaviour, something of your values. That’s easy to say but hard to build. It needs patience and perseverance - and a lot of time spent designing it. Start with hiring well, then coach deliberately and have frank, uncomfortable discussions about whether their teams feel treated as humans or as resources. Use standardisation and governance to reduce variance stemming from individual managers’ biases and moods.
Standardisation though cannot signal that the person sitting across from you is processing a recent diagnosis or is on the verge of quitting. That cannot be in a framework. Your managers need to know when they encounter them, they are not just allowed, but expected to throw the framework away. The skill is knowing when you are talking to a role in an org chart and when you are talking to a human being. The answer, if you are paying attention, is almost always the second one.
Protect your schedule around your conversations - and importantly, hold that line. If you have a calendar event for a product review right after one for a layoff conversation, it signals a lot more than a scheduling error. The conversation you just had deserves 10 minutes of processing. The next conversation deserves your presence, not the weight of the previous one.
Coach your managers on how, and not just the what. Most engineering managers reached there on the back of their technical judgement and not on their emotional skills. Ask them whether they felt present, and tell them what you would do differently. Encourage them to learn what empathy really means.
Push back on the clinical when you sense it's going awry. You will feel pressure - legitimately from HR or your management to keep difficult conversations tight and legally sanitised. Advocate hard for the humane version of it, even when the clinical is more convenient, when you realise that it does damage to the trust and culture that took you years to build.
After significant decisions, ask: how will this land for the person it lands on hardest? Not collectively, but for the specific person that has the most to lose. It is easy to design a policy that is fair in the abstract and genuinely painful for someone in particular. You will not always be able to change the decision. But you can often change the delivery, timing, support offered and follow-up. That is not nothing.
Reflect on the chain, not just the conversation. After hard stretches, the question worth asking is not only did I show up well in my conversations? Also ask did my directors? Did theirs? If the answer is uncertain, that is useful data. The humanity you invest in your own interactions is only as durable as what you build into the layer below you.
I have been leading engineering teams for long enough to have collected a fair number of regrets. Almost none of them are about decisions I got wrong, a bad technical bet, a hire that didn't work out. Those sting for a while and then fade.
The ones that stay are moments when I was not present. The ones when I was efficient and not human.
Leadership will not be remembered for your roadmap decisions or your OKR scores. The people who work for you will remember how they felt when things were hard. Whether you were willing to sit in the discomfort of someone else's difficult moment without rushing through it.
No matter how many people you lead it always comes down to the person in front of you right now.
Scale it down to one person and one conversation. That's the job.