The Leadership Dilemma: When There’s No Clear Right Answer

Leaders need to make hard decisions, but how do we know when we're making the right one? These moments often define who we are and what we stand for. Sometimes, the right path isn’t the most popular one, and in leadership, the courage to make difficult decisions is what separates effective leaders from the rest.

A conversation with a friend brought this to light. My friend shared a story about his daughter and her husband, who were applying for an HDB flat. For reasons that left them puzzled, their application was denied, and they didn’t qualify for a particular scheme. In their frustration, they sought help from their Member of Parliament (MP), hoping for an appeal.

As I listened to his story, I found myself grappling with two considerations. On one hand, the MP could write the letter, meeting my friend’s expectations. It would give his daughter and son-in-law a small sense of relief, perhaps even hope, regardless of the outcome. Writing the letter would show empathy and provide comfort in knowing the MP tried to help.

On the other hand, the MP could decide not to write the letter. This would avoid raising false hopes and respect the limited resources of public sector officers who may have already made a fair decision. Not writing the letter would show a commitment to managing expectations and acting with responsibility, even if it disappoints those seeking help.

These two paths seemed valid but conflicted, and I found myself wondering: What should a leader do in this situation?

In her TED Talk How to Make Hard Choices, Ruth Chang explained that decisions generally fall into three types:

1. One option is clearly better than the other.

These are straightforward decisions because the benefits of one option significantly outweigh the other.

2. One option is clearly worse than the other.

In this case, the decision is easy to make because one choice clearly leads to a worse outcome.

3. The options are equally good or bad.

When both choices seem to offer similar advantages or disadvantages, it can be tough to distinguish which is better.

Chang then introduced a fourth type of decision, which she called on par. This is where decision-making becomes truly complex. Choices that are on par don’t have an obvious "better" or "worse" outcome. They offer different benefits that are difficult to compare. For example, one option might provide financial stability, while the other offers personal growth. Neither is inherently better, but the decision depends on the individual’s priorities and values.

Chang argued that on par decisions are an opportunity for us to define our values and shape who we want to become. Leadership is often about navigating these difficult choices, where there’s no clear right answer. Leaders have to weigh multiple factors, knowing their decision may not please everyone, but it reflects their commitment to what they believe is most important.

After reflecting on Chang’s perspective, I found myself thinking again about the MP’s decision. To the disappointment of my friend, the MP decided not to write the letter. My friend expressed his frustration to me, saying in Mandarin: “Sometimes, this is all for show. I go to see the MP, he or she writes a letter to the government agency. I know there’s not much hope, but at least it satisfies me.” At the same time, this was a real-life example of making a decision that was on par—a tough leadership choice with no easy answer.

There is nothing inherently wrong with choosing to write the letter—it would have been a valid, on par decision. Writing the letter would have shown empathy and met expectations. But in this case, the MP opted to take the more difficult path. By deciding not to write the letter, the MP focused on managing expectations and respecting the limited resources of public sector officers. This choice reflected a leader’s commitment to long-term responsibility rather than providing immediate, yet possibly misleading, comfort.

Think of it like climbing a mountain. You can take the smoother, easier path that gives you a beautiful, immediate view but leaves you far from your destination. Or, you can choose the steeper, more challenging route, knowing it will take longer but lead you closer to the peak. The framework of on-par decisions reminds us that instead of trying to determine which choice is better, sometimes there isn’t a clear answer. As leaders, we must reflect on our values and priorities at a particular moment, and then make the hard decisions that guide our team members to long-term success.