Reflection from our conversation on management last week 

My style of managing has always been to set the right expectation. My team should understand that if they were to defy any rules, they would face the full brunt of the law. But if they were to make an honest mistake, I will see if there is ground for mitigation. However, it must be that they always expect that there will be no concession given. So they should keep that in mind before trying anything funny. I can be a nice person, but they don’t have to know that. One of the leadership styles I reference is Lee Kuan Yew, almost like a benevolent dictator, though he earned his way through votes still.

As an instructor, I dealt with playful youths. And before that, I was running a social enterprise dealing with youth at risk. I had my fair share of days being the ones that had to be managed. Hence I think I understand the mentality of non-conformists slightly better than most. Over my career, I have seen many leaders set their people up for failure by being nice. You come to a group of people wanting to connect with them, and you adopt a nice and soft image. Do you know what the trade-off is?

A true leader can foresee problems and resolve them, sometimes even bringing them forward. This can make the leader appear ineffective, primarily when these problems do not surface previously. A mediocre leader, on the other hand, may be known as a nice guy. Things will go well when times are good. But when shit hits the fan, all the problems will be magnified. And it will be too late. As a leader, we need to think about the people who come after us. We need to have the courage to deal with matters that may not impact us but the next one taking over. Not pretend to be a good, popular leader but push the problem to the next generation.

Lastly, how I deal with a group differs from managing an individual. When dealing with a group, I need to consider the “upper bound” and “lower bound”. I cannot set rules that only take care of the average or the upper bound because the lower bound will test my rules. To prevent it from being over stifling, we consider if these rules make sense in the first place. If it is not necessary or unenforceable, then don’t implement it in the first place. Because what happens at the end will be the good ones following and finding it ridiculous, while the bad ones flout it anyway. And the message you send is that rules can be broken. Instead, consider the essential rules, set them, and enforce them. There are times when rules are set to influence culture. Then I won’t call these rules but guidelines. And we need to make it clear that it is not a rule but guidelines.

Lastly, it is a given that, as leaders, we need to understand our men. We should not push them away with our harshness. But we need to understand the context as well. When I was in the OCS service term, I expected resistance when I chose to adopt the style I adopted. But one constraint was always at the back of my head: I only had seven weeks with the team, and I might never see them again. I also only had one week as the IC. There were many important things that I wanted to share, and I don’t know if I would get to do it. I was young once, so I know some things we can only appreciate later. What matters is that the proper perspective gets seeded. How others perceive me is secondary. Then I was told I seemed to have changed in the professional term. I haven’t. The context has changed.

Over time, people will call your bluff. So always be genuine. While I was typing this, my daughter wanted to walk around. I said no, as there were many people in the restaurant, but I was just reluctant to let her roam around. Five minutes later, I forgot what I said. She suddenly said that so many people had left. And I casually said yes, so empty now. She killed me with her last sentence: Now I can walk. You may forget what you have said if you don’t believe in it. But your people won’t. Always be consistent with your values, genuine, and have the best interest of your people at heart.

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By [email protected]

Hi, I am Benjamin. I am a Singaporean son, born and bred. I came from a modest background, just like most Singaporeans and went to mainstream schools like most middle-class Singaporeans. What makes me different is my unconventional choices and journey in life, giving me a different insight into life. I share my thoughts not because I think I am right but to be corrected if I am wrong. I am not too concerned about who is right but what is right. Drop me a PM or leave a message and I am happy to talk about anything!

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