October 10, 2026 By The Corporate Janitor Subscribe
The Garbage In Our CareersThe career advice nobody says out loud
Essay 2

The One That Matters Most

You must have guessed it. The one that matters is your immediate manager. This is your customer. You have to help this customer succeed. And once your customer succeeds, you succeed. Not always a given but true most of the time.

I can’t help but start with Robert Greene, the first chapter in the 48 Laws of Power, Never Outshine Your Master. I won’t belabor how you will destroy your life by leaving your master in the dust except to say don’t you ever dare do it even if your manager is a utter idiot. Beyond that, think of your relationship with your manager in terms of stages of growth:

Stage 1: The most basic form of relationship is in which the manager gives you a few tasks, you do those tasks and you go home. You are transactional. Your manager is transactional.

Stage 2: You manage you work independently but with complete oversight and approval of your manager. You identify new opportunity areas for your team, get buy-in from your manager and get stuff done. You are on your path of becoming a star

Stage 3: You are your manager’s primary advisor. Whenever a new problem emerges or even your manager is not sure, you are the go-to counselor, you brainstorm together, discuss options, lock the path ahead and your truly delivers it with perfection

Stage 4: All of the above but your manager is invested in your journey, cares about you, will bang their fist of the table on promotion day and is a safe space for you to voice your reasonable concerns, reasonable being the operative word

Level 4 is not easy to achieve. I think I truly achieved it once. I deeply cared about my manager and it was so the other way round. I delivered enough impact in 7 months that she gave me a performance bonus; later, when things took a turn for the south due to department re-org which was completely out our control, I counseled her to leave.

She took my advice, applied for the role I identified and got promoted to a higher position and is on track for Vice President. If she had stayed, she would have lost her job. I didn’t know that for sure then but I do know. Yes, I did shoot myself in the foot but I cultivated a relationship for life. Relationships are like flower, fertilize them. And when I need her, she still shows up.

Admittedly, while you may be Michael Phelping at it work, it is possible you are stuck on Level 1 or 2. Progressing further may also depend on the temperament of the manager and how your energies match. Find your sweet spot. For me, as a man, it was working with female managers, and in particular Asian female managers. That is my experience, not a rule. Once I found that fit, I almost sought it out and pushed the relationship as far as I could.

I concede that there have been times when things have not worked well. Temporary fissures. Remember, the answer is never to go to your manager’s manager (“skip level”) or fill an anonymous survey (aside-never ever trust anonymous surveys). That is the nuclear option which make sense only in the case of harassment or bullying.

For all else, try to work it out with your manger. Remember, the folks sitting in HR are not your friends. Don’t you ever trust them. Your skip level probably doesn’t even know who you are. When it is your words against your manager, overwhelming majority of the time, your manager will win. Because they have superior agency and you may have none at all. They have a track record of achievement that is higher than your and it will take more effort to replace them than it will take to replace you.

And why play a game you are designed to lose? For example, your argument might be, “the manager is too direct and his conduct is not in line with the culture of the company”. If your manager’s response to the independent third party is, “my subordinate’s work is garbage and was a hiring mistake of my predecessor”, this is the end of the conversations and the start of the managing out plan. We don’t want that.

If nothing works, bide your time and leave. Patience is a very powerful characteristic. Only exceptions are cases of sexual harassment. I would encourage a good fight. This is not when you let go or keep silent or stay patient.

Finally, remember that how people in the company think of you, especially those that you are not in the room with, may never interact with and yet will have a say in your promotion, may depend on how your manager speaks of you. Your manager is your portal to the entire company.

If your relationship with your manager is healthy, you work life will be healthy and since work cascades to personal life, your personal life will be healthy. Which is why I must emphasize, do whatever you have to do to make your manager love you. Well, not literally.

The book so far
  1. Prologue
  2. Essay 1: The Fundamentals of Success
  3. Essay 2: The One That Matters Most

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