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.

Invisible ordinary day

We are so accustomed to ordinary days that we fail to see how special they are.

Friday felt meh. I woke up, had breakfast, went to work, talked with the boys, attended First Friday Mass, took Ingrid out to dinner at Apero, and met a large orange cat at the Corinthian Hills clubhouse.

Nothing extraordinary happened.

What struck me later was that this day would have been unimaginable to a younger version of myself. There was a time when I wanted meaningful work, financial stability, and someone to share dinner with. Somehow, after years of effort and a fair amount of good fortune, many of those hopes became ordinary.

That may be the problem. Once a blessing becomes familiar, we stop seeing it as a blessing and start treating it as a baseline.

Psalm 118:24 says, “This is the day the Lord has made; let us rejoice and be glad in it.” It does not say to rejoice on exciting days, successful days, or memorable days. It simply says, “this day.” This means, that in all circumstances, we need to be grateful.

Most days are not dramatic. They are made up of work, meals, conversations, errands, and routines. We keep waiting for something noteworthy to happen, while missing the fact that an uneventful day is often a sign that many things are already going right.

That Friday was not exciting.

It was simply a good day.

Education is knowing. Application is learning.

Iuri had just returned from a month-long training camp overseas. The next day, he played against someone he had never beaten before — a player who can smell annoyance and use lobs, awkward pace, and irritation to exacerbate the annoyance. That is tennis, it is not cheating.

The match was tight. It went to a tiebreak.

On all four match points, the ball bounced badly in favor of his opponent. Four times. Iuri lost the tiebreak not because he lacked the strokes, but because frustration got to him first.

Competitive tennis is a mental game. At that level, everyone can play. Matches are often decided by how quickly a player recovers from a bad point. One bad bounce can hijack the mind. Players begin rushing. Errors multiply. By then the player has dug their own hole.

That is what makes tennis difficult. Not only the rallies, but the accumulation of emotion over the points. Professionals play matches lasting two, sometimes five hours. By then, the legs are tired, but so is the mind.

After losing the tiebreak came a short tantrum like an 8 year old child whos candy was snatched.

When he had settled down, I told him I never expected him to win every match after camp. Tennis is not boxing where opponents can be chosen carefully. In tennis, losses are unavoidable. I also told him that if he pressures himself, he will only get frustrated more.

Training teaches technique. Application teaches reality.

The camp improved his serve and forehand and all other techniques. You could see it in the match. He stayed in points longer. He competed better. But the mental side of the game cannot be downloaded in a month overseas. That only comes from experience — from accepting the misfortunes of the game like bad bounces, difficult opponents, heat, nerves, and losses that stay with you for a while.

The court does not adjust itself for one player. The bad bounce that hurts you today may save you tomorrow.

Mental toughness doesn’t not only come from physical strength, and from speed of mental recovery but also from accepting that not everything can go your way, that there are circumstances beyond your control. Only then you can focus back on your strategy. No, it is not denying the existence of emotions but knowing that it has to take on the sideline.

If only maturity could be accelerated for young athletes. But growth has its own pace. First comes knowing. Then applying. Then learning.

He remained quiet after the loss, but I noticed something had changed. Before, a defeat like this would ruin his whole day. This time, it only lasted an hour.

We had lunch in Goodah after.

By then, everything was already good-ah.

That afternoon he played again, he was tired but pushed himself. The day after, he played again and pushed himself despite being tired and carrying the mental effect of loss from yesterday