I'm currently reading The Engineering Leader by Cate Hudson¹, and so far, I'm really loving it. I'll share more details in an upcoming post. Still, today, I want to zoom in on one of the concepts she refers to on multiple occasions across the book: the importance of understanding the difference between being nice and being kind.

As tech leaders, we often prioritize promoting a positive work environment. We strive to be approachable, supportive, and well-liked by our teams. But in our quest to be "good" leaders, we might fall into a common trap: confusing being nice with being kind.

While these concepts might seem interchangeable at first glance, they can lead to drastically different outcomes in leadership.

Today, let's explore this somewhat unintuitive distinction and how it impacts leadership effectiveness.

What does it even mean to be nice?

nice (adjective): giving pleasure or satisfaction; pleasant or attractive.²

Being nice is usually about being pleasant, agreeable, and avoiding conflict. It's the path of least resistance, one that confuses comfort with well-being. Nice leaders are often well-liked, at least superficially. They rarely annoy, always have a smile ready, and are quick with a compliment. They don't get in the way, which earns them a reputation for being easy to work with.

The problem with prioritizing nice is that it often comes at the expense of real progress. You are painting the walls of a falling building with new shiny colors. It looks good on the outside but rotting on the inside.

Nice leaders tend to:

• Avoid giving necessary critical feedback.

• Hesitate to make tough decisions that might upset team members.

• Struggle to address performance issues directly.

• Prioritize short-term comfort over long-term impact.

In essence, being nice is often a form of conflict avoidance, which tends to have a short runway.

What about kindness?

kind (adjective): having or showing a friendly, generous, and considerate nature.³

Kindness is about genuine care and a commitment to the well-being and growth of others. Kind leaders are willing to have difficult conversations, make unpopular decisions, and challenge their team members—all in service of their development and the team's success. They understand that facing those painful experiences is part of their job—part of what they're paid for.

Kind leadership usually requires:

• Providing honest and timely feedback, especially when it's uncomfortable.

• Making decisions based on what's best for the company and the team. Personal popularity is not a goal.

• Addressing issues head-on, with compassion, and without sugar-coating.

• Investing time and effort into the long-term development of team members, even when if that development will continue outside of your team.

Kindness requires courage. It's rarely easy and might not always make you the most popular person in the room. Done consistently, though, it will make you a trusted and respectable person.

Leadership is a relationship game, and relationship games are long-term games.

I often use the more expressive term tough love to refer to the manifestation of kindness in the context of leadership. I'll use them mainly as synonyms in the rest of this article.

A Personal Lesson in Kind Leadership

Humans love stories. Besides, there is nothing worse than someone preaching concepts without direct experience. You wouldn't trust a tech entrepreneur's advice on how to run a government unless they had experience in public administration, would you?

But I'm digressing here, back on topic.

I will tell you how kindness paid off in the long term in a situation that was not easy to begin with.

I will do my best to avoid relating any information that could help identify the persons involved with the story, though I believe they might recognize themselves if they read it.

I was the CTO at a company, and through some organizational changes, a small team of engineers started reporting directly to me. They were operating outside the standard squad setup for reasons I'll not get into right now, as they're irrelevant. There were signals of the team being dysfunctional, and I wanted to spend part of my time figuring out what was going wrong there.

There were some superficial issues with roles and mandates, but that was only the tip of the iceberg.

After further investigations — through direct observation and collecting feedback from various sources — it turned out that there was a serious issue going on with the team: the most senior engineer, extremely talented on the technical side, was behaving in a way that could be defined with the brilliant jerk⁴ label: stubborn, speaking down and intimidating more junior members of the team all the while getting annoyed and frustrated because “they didn't get it”.

The rest of the team felt this engineer was pushing them to build something overly complex that didn't match the organization's needs. Yet, they felt unable to have a constructive conversation on the topic.

Once aware of the situation, I could have taken the nice approach: not intervene, manage my relationship with each individual in 1-to-1 sessions, maybe slipping in some sugar-coated comments here and here.

I could have allowed the frustrated members to complain with me, shown empathy for their emotions, recognized that life was hard, and then moved on to the following conversation.

Instead, I took the tough-love approach and set off to do it respectfully.

This was a fully remote team, but luckily, we had an opportunity to meet in person shortly after I got a sense of what was going on. And that's when I had one of my career's most impactful one-to-one conversations.

Now, you can't just get in a room with someone and tell them, “Dude, you're a jerk,” and expect this to lead to anything positive.

First and foremost, people are not jerks but can behave like one in certain situations. This is the essence of growth vs. a fixed mindset.

Second, because that's not how you get someone to be open to listening to you, they will get all defensive and escalate the fight.

The conversation we went through followed roughly this schema:

1. Priming: I told the person this was not going to be a pleasant conversation for both of us;

2. Recognition: I emphasized recognizing and valuing this person's technical skills. We were not going to talk about architectural decisions in this meeting;

3. Impact: I described what impact their behaviors were having on the team and why that mattered to me;

4. Expectations: I made it clear what kind of behaviors I'd expect from anyone in the team, and even more so from more senior engineers who are supposed to be role models;

We then went into a long conversation, which happened to be way easier than I had anticipated.

The person reacted exceptionally well to the feedback, as they valued my willingness to take the time and help them see what stood between them and success. I came across as nonjudgmental yet firm. I gave them a choice of what to do with the information I was surfacing through the conversation.

We covered a lot of ground in a single conversation, as I took the opportunity to mentor them on some fundamentals: I shared with them the importance of vulnerability in building trust, how to foster a culture of psychological safety in a team, and practical tips to use in daily life to build better habits.

That conversation had two major wins:

1. They realized for the first time that there was a way out from something they thought was just “their nature”;

2. They started trusting me and my intentions profoundly, as I was probably the first person to take the time to invest in helping them change rather than defaulting to ridding myself of the problem.

I believe in people's ability to change, but every story is different.

Trajectories are unique, and the speed of change can vary significantly across people and contexts.

Ultimately, I had to remove the person from the organization and terminate our collaboration a few months after that conversation.

They had made some improvements, but the team's frustration was still high, and we faced the severe risk of having them leave. I was feeling the bitter taste of failure when I delivered the news, though I was partly comforted by how they took it: “I don't like this decision, but I understand why you're doing it; I would probably do the same if I were in your shoes.”

It sucked, but I knew I had done the right thing both for the team and for the individual.

But the best part comes now, as the story doesn't end here.

I stayed in touch with the person I had to lay off as we both moved on with our professional lives. I've seen them keep growing their self-awareness and improving in all the areas holding them back from realizing their full potential. The brilliant jerk behaviors are now just a memory from the past.

A few months ago, they expressed an interest in working with me directly, and today, they're one of my coaching clients.

By prioritizing kindness over niceness, years after the first seed was planted, we keep reaping the fruits of that relationship:

• They continue growing in a trajectory that still impresses me. They have managed to change and improve so much that I often wonder what the limit is if they keep going.

• I have earned their trust and respect to the point they wanted me - the person who fired them! - to be their coach and mentor. I don't have any reason to believe they're masochist, so I'll rule out that explanation.

We can't A/B test people and lives, but I am confident that the results would have been significantly different today if I had chosen the nice path.

That could have taken many forms, from ignoring the underlying problem and dealing with the consequences later to firing the person by telling them, “You're not a good fit here; you'll be better elsewhere.”

This would be just another way of sweeping the problem under the rug instead of facing it directly.

Implementing Kind Leadership

So, how can you start practicing the art of tough love? Here are some strategies:

1. Prioritize clarity over comfort: Be clear in your expectations and feedback. It might be uncomfortable in the short term, but it pays off in the long run. Sometimes, the positive consequences will exceed your original expectations.

2. Be courageous: Don't shy away from difficult conversations or decisions. Remember, you're doing it for the benefit of your team. It's your job, and if you're unwilling to do it, sooner or later, you will have a bigger problem.

3. Practice compassion: Kindness doesn't mean being harsh or rude. Approach challenging situations with compassion and understanding, but do not turn that into an emotional wildcard for keeping things as they are.

4. Think long-term: Consider the long-term impacts of your actions and decisions, not just the immediate reactions. As said earlier, leadership is a relationship game, and relationships are a long-term game.

Finally, don't forget that trust and respect will often win over popularity.

When you consistently show people that you're willing to endure pain and discomfort to help them grow into better people and professionals, they'll be willing to support you should you need it one day.

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