When Friendship Meets Leadership

In my years of handling corporate clients, there are a few training needs that consistently come up. One of them is helping managers learn how to lead, delegate, and get their subordinates to work toward their objectives. This is not exclusive to local companies. Even multinational companies have raised the same concern.

Whenever a client requests this kind of training, there is one question I would ask:

“Are these newly promoted managers now handling people who used to be their friends?”

The answer is almost always yes.

In other words, these are employees who have been promoted and are now expected to manage the same people they used to work alongside as peers.

I ask this question because pakikisama is a big part of Filipino culture. We value relationships, getting along with others, and maintaining harmony within a group. I cannot simply dismiss these cultural realities and call these managers unprofessional because they find it difficult to manage their friends. I want to understand what makes the transition difficult.

Sometime in 2013, I conducted training for newly promoted managers and supervisors. When I asked them about their difficulties in managing their friends, many shared a similar experience. Their friends would tease them and say, “Hindi ka na ma-reach” or “Nag-iba ka na.”

Think about what happens in this situation. A person gets promoted, and with the promotion comes the responsibility to give instructions, correct mistakes, and hold people accountable. But the people they now supervise are the same people they used to joke around with, eat lunch with, and share stories with.

How do you exercise authority without making your friends feel that you have changed?

On the other hand, I have also observed companies where friendship works in favor of newly promoted managers. Their friends cooperate, accept their direction, and support them in their new roles.

This tells me that friendship itself is not necessarily the problem. The same relationship that makes it difficult for one manager to exercise authority can help another manager lead a team effectively.

The difference may lie in how the manager and the team understand their relationship now that their roles have changed.

A manager does not have to stop being a friend. But friendship cannot be the reason for avoiding a difficult conversation, tolerating poor performance, or refusing to make a decision. At some point, the responsibility of the position must take precedence over the desire to keep everyone comfortable.

This is one of the challenges of moving from being a team member to becoming a manager. The promotion changes the position, but it does not automatically change how a person relates to others.

The Difficulty of Speaking Up

Another training request that frequently comes up is helping managers learn to speak up.

Clients would often tell me that their managers are talkative during breaks, lunch, or informal gatherings but become quiet during meetings. They have ideas, but they do not share them. They may see a problem or have a suggestion, but they hesitate to bring it up.

When I ask these managers about it, I often hear that they are shy or afraid they might not be able to defend their ideas when questioned.

Again, I notice something familiar in our culture: pagkamahiyain.

There is nothing inherently wrong with being shy or reserved. Not everyone has to be outspoken, and being quiet does not mean a person has nothing valuable to contribute. But when a manager cannot express an idea because of the fear of being questioned, the organization loses an opportunity to benefit from that person’s knowledge and experience.

Part of being a manager is communicating decisions, raising concerns, sharing ideas, and sometimes disagreeing with people who may be more senior. A manager does not have to win every argument, but should be willing to explain the reasoning behind a recommendation and consider a different point of view.

The question, then, is not whether a manager is naturally shy. It is whether that person can learn to speak when the responsibility of the role requires it.

The Real Challenge of Management Development

Looking at these experiences, I see a common thread. Some managers hesitate to exercise authority because they want to maintain good relationships. Others hesitate to speak because they are afraid of being questioned or embarrassed.

In both cases, the manager’s behavior is influenced by the desire to avoid an uncomfortable situation.

Of course, this does not mean that pakikisama and pagkamahiyain are the only reasons managers struggle. Some may lack experience, communication skills, or confidence. Others may be working in organizations where questioning a superior is discouraged. These factors also matter.

But my point is that we cannot develop managers simply by teaching them techniques for delegation, communication, or leadership. We also need to help them understand why they hesitate to use those techniques in the first place.

Knowing how to delegate is different from being willing to delegate. Knowing how to give feedback is different from having the courage to correct a friend. Knowing how to present an idea is different from being willing to defend it when someone disagrees.

The gap between knowing what to do and actually doing it is where much of management development happens.

A newly promoted manager may understand the principles of leadership during training but return to the workplace and fall back into familiar habits. The first time a friend complains about being corrected, the manager may hesitate. The first time a senior executive challenges an idea, the manager may choose to remain silent.

This is why I believe that developing managers requires more than a training session.

Training can introduce concepts, challenge assumptions, and provide opportunities to practice. But the real test comes when managers apply what they have learned in actual workplace situations. They need opportunities to practice, receive feedback, make mistakes, and try again.

Management must also do its part. Companies cannot expect managers to exercise authority if they do not give them the necessary support. Nor can they expect people to speak up if the workplace makes disagreement uncomfortable or risky.

Developing managers is a shared responsibility. Managers must be willing to change their habits, while organizations must provide the environment and support that allow them to grow.

After all, promotion gives a person a new position, but it does not automatically provide the judgment, confidence, and discipline required to lead.

The real work begins when managers learn to act on what they know, even when doing so is uncomfortable.

That may mean correcting a friend, defending an idea, or making a decision that not everyone will like. These are not necessarily signs that a manager has become arrogant or difficult to approach. They may simply be signs that the person is learning to take the responsibilities of the position seriously.

The goal is not to make managers abandon pakikisama or change their personalities. It is to help them understand when to preserve harmony, when to speak up, and when their responsibilities require them to make a difficult decision.

That kind of judgment does not develop overnight. It takes practice, experience, and commitment from both the manager and the organization.

Too much empathy and too little love

There is too much empathy and too little love. I think this is one of the reasons why the world is increasingly marked by anxiety, fragility, anger, and confusion.

Empathy is valuable, but empathy by itself is not love. Empathy asks us to enter into another person’s feelings, to understand their pain and to avoid causing them distress. But if our desire to prevent someone from feeling bad comes at the expense of truth, justice, virtue, or their genuine good, then empathy can actually become uncharitable.

Consider three examples.

A child joins a competition and receives an award simply for participating, so that he will feel appreciated even though he lost.

A person is given recognition because of a personal characteristic rather than because of the work, virtue, or achievement that normally deserves recognition.

Someone described abortion as an act of mercy because it prevents a child from experiencing a difficult life.

All three can be motivated by a desire to prevent pain. They are, in that sense, deeply empathetic. But empathy asks primarily, “How do I make this person feel better?”

Love asks a deeper question:

“What is truly good for this person?”

Love is not merely a feeling. Love is a choice and an action. To love is to will the good of another.

And what is good?

A classical Christian understanding, especially developed in the thought of Augustine, is that goodness is connected with perfection: good is what perfects a thing according to what it is and what it is ordered toward.

A thing is good when it becomes more fully what it is meant to be.

A good knife cuts well because cutting belongs to what a knife is.

A good eye sees well because seeing belongs to what an eye is.

And a good human being develops and exercises what is proper to human nature.

The human person is rational and free. We possess the capacity to know truth, to deliberate, to choose, to love, to form relationships, and to develop virtue.

Therefore, qualities such as wisdom, self-discipline, courage, honesty, justice, and responsibility do not merely make us socially acceptable. They perfect us as human beings.

This is where love sometimes becomes difficult.

Sometimes love means comforting someone.

But sometimes love means telling the truth.

Sometimes love means affirming someone.

But sometimes love means correcting them.

Sometimes love means protecting someone from suffering.

But sometimes love means allowing them to experience the consequences of their choices, because suffering can be part of learning, maturity, responsibility, and growth.

Sometimes love means saying, “I understand why you feel this way, but I don’t think what you are doing is good for you.”

That is not a lack of compassion.

It may actually be compassion guided by truth.

We have become so afraid of making people uncomfortable that we sometimes deprive them of the very things that help them become stronger: correction, accountability, discipline, responsibility, resilience, and the encounter with truth.

A child who never learns how to lose does not become stronger because we protected his feelings. He may instead become less capable of dealing with failure.

A person who is never corrected does not necessarily become more confident. They may simply become less capable of recognizing their own weaknesses.

And a society that confuses affirmation with love eventually loses the ability to distinguish between what feels good and what is actually good.

Empathy says:

“I don’t want you to hurt.”

Love says:

“I don’t want you to be harmed, and therefore I want what is truly good for you—even when what is good may be difficult, painful, or uncomfortable.”

The goal of love is not merely to eliminate suffering.

The goal of love is human flourishing.

Because sometimes the most loving thing we can do is not to remove someone’s pain, but to help them become the kind of person who can face reality, endure difficulty, choose what is right, and ultimately become more fully human.

Empathy without truth can become sentimentality.
Truth without charity can become cruelty.
But truth guided by charity is love.

Building highly effective teams

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In 1999, I joined Citibank as a young employee with much to learn. I was fortunate to work under two leaders worth watching closely. My team leader was the kind of person you could approach with any technical question — patient, knowledgeable, and generous with her time even when she had none to spare. The department head taught me something different: the power of appreciation. When I hit a target for the first time, she walked over and handed me movie tickets. It was a small gesture, but what it gave me was not entertainment. It was the feeling of being seen. Of mattering. That stayed with me, and I have tried, in my own way, to pass it on ever since.

That team performed well. We passed every audit. Our metrics were consistently strong. Looking back, I believe the reason was simple: we had good leaders. That experience reshaped how I think about leadership. I used to think a leader just needed expertise and the ability to delegate. I was wrong. Building a highly effective team begins with the leader — someone who brings not only technical knowledge but sound decision-making and genuine people skills: the ability to communicate, to build relationships, and to navigate conflict. What I advocate for is a more democratic kind of leadership, one that earns authority rather than just assumes it.

Across many years and many organizations — large and small, local and foreign — I have seen this pattern hold. High-performing teams are almost always led by someone their people look up to. That regard can come from respect or from fear, and both can produce results as well as both positive and negative consequences. But a leader who relies on force extracts compliance. A leader who leads through encouragement and recognition builds something that lasts. Your style, your choice.

In a few weeks, I will be facilitating a team building program for about 60 employees of a printing company navigating a significant transition. A new generation of leaders is stepping forward, and they are asking their people to embrace three values: accountability — owning your work fully; transparency — speaking up, sharing perspective, making better decisions together; and malasakit — genuine care for the work and for one another.

These are not small asks. Leading through transition requires maturity and wisdom. There will be moments when the mission feels too large, when the road ahead is unclear. But that is precisely when leadership matters most — when a team needs someone steady enough to guide them forward.

My hope is that when this program ends, every person in that room walks away feeling what I felt in 1999: seen, appreciated, and heard. Not because of a grand gesture, but because they experienced what it means to be led well. And that when their turn comes, they will know how to pass it on.

How to start journaling?

It is truly a challenge to start a journal, let alone write in it consistently. I’ve been journaling for eight years and have managed to be fairly consistent, though not daily. There have been days, weeks, and even months that I’ve missed, but I always come back to fill the pages with my observations and emotions.

Journaling is not a juvenile activity. It’s a powerful leadership tool used by many great individuals, from Winston Churchill to Anne Frank. For Churchill, journaling helped him navigate the complexities of his role as a statesman, allowing him to better understand himself, his world, and his place in history. In the case of Anne Frank, journaling provided her with a means to cope with the horrors of the Holocaust, offering a safe space to process her emotions and preserve her thoughts for future generations.

I started journaling when I bought a Midori Traveler’s Notebook in Hong Kong. At first, I simply wrote whatever came to mind. I didn’t find it difficult. I followed tips from Julia Cameron’s The Artist’s Way, particularly the idea of “dumping” everything in my head to start. Attending a Mind Mapping seminar years ago also helped me organize my thoughts and keep the flow going.

Another key to my journaling success is reading. I always have plenty to say after reading an essay or a book. After all, they say you can’t write if you don’t read. Reading has been instrumental in shaping my journaling, and even if I can’t pick up a book or article, I make sure to read movie subtitles or anything I can.

So far, journaling has helped me clarify my thoughts. There are days when my mind feels cluttered, overwhelmed with ideas. In those moments, I sit down, grab my pen and notebook, and start reflecting on my priorities. Often, those thoughts evolve into to-do lists.

Those thoughts are just irrational fears. Writing them down helps me to view them logically, free from emotion. Fears can hijack your brain, but labeling them on paper cuts the wire, allowing you to reset yourself.

Journaling doesn’t take much time—only 10 to 20 minutes a day. I do it in the morning, right after breakfast, while sipping my coffee. This gives me time to clear my mind and start the day with a fresh perspective. If mornings are too rushed, journaling before bed works just as well. You can write anything that comes to mind, or even use daily prompts from Google.

You don’t need special tools—just a pen and notebook will do. The most important thing is to start.