Context

Recently, I had the same conversation with two different people, who both said the same thing: “That is very interesting, I never thought about it like that before!” So here’s what I shared with them, as this perspective might be helpful for others too.

I was explaining that I was very privileged, as a middle manager in EDB’s Strategic Planning team from 2015-2018. The EDB SP team (together with our Corporate Planning colleagues) functioned as the secretariat for our Executive Committee (“Exco”), which comprised of our most senior management. Exco met weekly, and we supported them with secretarial work: the duty secretariat members would clarify the meeting agenda with EDB Chairman, coordinate with the EDBians tabling items to Exco, take minutes, and also capture follow-ups.

So we had a very intimate view of how EDB and our leadership operated.

The fundamental dilemma as a leader

After some time, I realised that there was a fundamental dilemma, as a leader of leaders.

I first realised this dilemma, when I observed that many senior management often put a LOT of effort into convincing their direct subordinates. This puzzled me: why would they do this? Wouldn’t it suffice to just tell their subordinates “hey, do this!”?

After thinking it through, I realized that there are two fundamental tradeoffs facing every leader:

If you tell your subordinates what to do, that sends the signal that in future, every simliar decision should go to you. This is Coaching 101, but is especially true for any leader. As a leader, you have overriden your direct subordinates, who are now no longer leaders in their own right, but are now order-takers. This reduces your managerial leverage as a leader, because your team can no longer make their own decisions. Every future decision will now go to you.
But if you don’t tell your subordinates what to do, then you have to accept that they might not do what you want them to do! Afterall, these are established leaders who rose up because of their capability, and capable women and men often have their own points-of-view that will differ from yours.

Every senior leader faces the dilemma/tradeoff that I outlined above. As a consequence, it is not always true that senior leaders have absolute power, and can simply command things to happen by diktat. So even someone like Xi Jinping or the Prime Minister of Singapore are not entirely free, to push things as they want in their respective systems.

And that was why the EDB senior management team often put a lot of effort in convincing their subordinates. It was the best balance of both.

This wasn’t just a EDB thing: I vividly remember a Fortune 500 CEO complaining that he understood the importance of digitalisation, as did his youngest staff, but “the middle layer is just concrete (i.e. his middle managers just didn’t move on his digitalisation initiatives)”… so he also struggled with convincing his direct subordinates.

How this helped me

This dilemma, together with many of the situations I sat in, made me realise that “if I was placed in the same shoes as senior management, I will end up having to make the same disagreeable decisions….” The tradeoff means there are no perfect solutions, no perfect decisions in corporate life.

This made me have a lot of compassion for senior leaders. Many of them suffer a lot, and people often lack compassion for them, as they often say “hey, they are paid enough!” Yes, they are paid a lot, but no, I don’t think they would have necessarily accepted a promotion if they knew exactly how much stress and burden they were getting bribed to handle.

And that is why I refused to get promoted, because I didn’t want the stress nor burden.

Finished on 9 Jul 25 at 2200hrs.