Executive Coaching in Singapore: Coming Into Leadership

In my work of executive coaching in Singapore, I frequently encounter individuals who find themselves in the unfamiliar shoes of leadership. The scenario typically goes like this…

You’ve worked hard to build your technical expertise, and it’s brought you to this new role—a promotion into leadership. But while your technical skills got you here, being effective in a leadership role calls for a different set of abilities. Your work is no longer about just the tasks or projects you manage; it’s about understanding and motivating people, leading through complex situations, and communicating with clarity and confidence.

This shift can feel daunting. In a fast-paced environment like Singapore, new executives and managers face high expectations. The transition from a hands-on technical role to a leadership role requires a keen understanding of how to work with people—often without the experience or guidance to navigate these changes.

It’s extremely difficult to learn these skills in a course, because most of them are caught, rather than taught. It requires practice, out there in the real-world. Hence, many organizations and individuals employ executive coaching in Singapore as a resource to cultivate confidence, improve communication, and lead with intention.

In my years of executive coaching in Singapore, I observe that leaders are frequently beset by the following 6 pain points.

6 Pain Points: Why Leaders Seek Executive Coaching in Singapore

① You want to be more assertive, but fear offending others.

② You feel you should speak up, but you keep quiet instead.

③ You overthink or people-please.

④ You struggle with your words and sentences, as well as your decisions.

⑤ You feel awkward in conversations and disengage too quickly.

⑥ You want your presence to be stronger in group interactions.

Executive coaching can help you to overcome these pain points, in a way that is super-customized and relevant for your leadership challenges.

① Building Assertiveness Without Offence

Being assertive is an essential ability for leaders, but many fear offending or hurting their team members. A skilled executive coach can help you find the balance, enabling you to stand your ground, make your ideas heard, and command respect without damaging relationships.

② Speaking Up with Confidence

New leaders often struggle with speaking up, especially in front of senior colleagues. Many worry about how their ideas will be received, and in turn, stay quiet even when they have valuable insights to offer. In the safe space provided by an executive coach, you can learn to access the confidence to express your ideas and opinions clearly, enabling you to contribute meaningfully and inspire trust in others.

③ Overthinking & People-Pleasing

Trying to please everyone can feel like the quickest way out of conflicts, but it causes you to overthink each decision or interaction. While wanting to support the team is admirable, constantly second-guessing yourself can be mentally draining and even counterproductive. Executive coaching can help you learn to break free from people-pleasing tendencies, helping you set clear boundaries, make firm decisions, and prioritize your time.

④ Effective Articulation & Decision-Making

When you were in a technical role, you might have required only a limited language pattern, as you were communicating with others who were more or less the same as you. But in a leadership position, you are now expected to speak to more diverse audiences, explain complex decisions, and obtain buy-in from stakeholders. There is no way to learn this aside from real-life practice. Just like in other countries, executive coaching in Singapore can accelerate this by making sure that what you are practicing is useful and effective.

⑤ Overcoming Awkwardness in Conversations

Feeling awkward in conversations or disengaging too soon can make it difficult to form the relational connections that are essential in leadership. One of the reasons why I do executive coaching in Singapore, in-person, is because I employ practical experiments to help you learn how to stay present and engaged in conversations. We co-create strategies to manage anxiety and connect meaningfully with people at your workplace.

⑥ Developing a Stronger Presence in Group Interactions

Projecting a strong, confident presence in group settings is crucial for any leader. If your leadership presence is diminished, what you say and do is less likely to be taken seriously. Executive coaching can help you uncover the blindspots that prevent you from commanding attention and creating impact in high-stakes conversations.

How Executive Coaching in Singapore Can Be Like… and Why I Focus Differently

I’ve seen how many coaching sessions are actually more like lectures, where the coachee is simply being told what to do. I could almost hear a flow-chart being narrated, i.e. “If Sally does that, you say this.” In some cases, I’ve seen them being given ‘magic words’ or scripts to aid them in their communication. And in worst cases, the ‘coaching’ sounds more like a talk on business administration.

As you can guess – in such environments, the coachee doesn’t develop sustainable leadership skills.

From Technical Expertise to Emotional Mastery

Your promotion reflects your ability to excel in technical roles. But as you transition into leadership, your responsibilities shift from working ‘with your hands’ to working with people. You’re now tasked with motivating, guiding, and supporting a team. This requires mastery of emotions (both yours and others), empathy and the ability to build trust. When you are tasked to take care of people, you’re actually tasked to take care of emotions.

Inspiration.
Confidence.
Influence.
Conflict.
Trust.

Do you notice how all these aspects of leadership are emotional in nature?

This is why I make sure to delve into the emotional nature of interpersonal boundaries. It’s not easy to navigate, and it can be highly uncomfortable. But emotional mastery is essential for building trust and sustainable leadership.

Jace Chen | Senior SDR

Effective Leaders Are Emotionally-Adept

I hope you can see how keeping emotions out at the workplace is a misconception that can seriously impede your leadership. Emotions are a natural and integral part of a healthy human being, and acknowledging them is the first step to improving your ability to communicate and lead effectively. You can learn to become more aware of emotions, both in yourself and in others, which is something that can be practically-achieved through ontological coaching.

If you wish to learn these skills, the privacy and safety of 1-on-1 executive coaching in Singapore can be highly beneficial.

What coaching is

Coaching is a form of super-customised learning, focused solely on your needs. It is one of the most dignified forms of professional help, because you choose the topic, direction and depth of what you wish to work on.

In fact, my clients are NOT ‘broken’ in any way. They are capable, creative and self-initiated individuals who want to live out their full potential. Many of them are high-performers at their workplace.

They just want support to help them hit their objectives more quickly and with less pain.

If taking ownership of your growth appeals to you, coaching is might be suitable for you.

WhatsApp me now, to accelerate your leadership journey.