January 3

What does it mean to manage up? Here’s why it’s the most important skill.


I graduated with:

  1. First class honours
  2. A board directorship at a charity with an annual turnover of £7 million
  3. Writing a book with a professor
  4. Shortlisted for Module of the Year, and Global Graduate of the Year

You may have had greater accomplishments. If so, great job!

I don’t say this to boast. I say this to show you how success in university is no evidence for success at work.

I say this too as a warning for those of us who may think that we are doing well at university. Sure, doing great at university can help us to land a great job, but it’s no guarantee that it will bring us to the next level in our job.

As a Gen Z who just entered the workplace, I thought I knew everything. I thought I didn’t need my boss. After all, I had done well at university, led my own projects, and been trained for this job. How hard could it get?

I didn’t need my boss.

Or so I thought.

Who are you to talk about this?

Two years later, after a Performance Improvement Plan, being thoroughly disliked by my colleagues, and having 60 rejected job applications, I’ve learnt my lesson (I hope!)

The most important relationship at work is with your boss. My hope is that with this article, you will learn why that’s important, and how you can manage it better.

Sure, I don’t have a PHD. But I’ve had painful work experiences that I would be loath for other people like you to go through. This article is a reflection on books I’ve found on the topic – ‘It’s Okay to Manage Your Boss’ by Bruce Tulgan, and Watkins’ ‘The First 90 Days’.

The problem

As a Gen Z, what has been frustrating for me is the current under-management epidemic that Tulgan describes.

For the last decade, Tulgan shared about how more books have advocated bosses to take a hands-off approach towards employees, giving them the space to do their best work.

As a result, staff do not have the guidance to even know where the boundaries lie. Or what great work even looks like.

Indeed, in my first job, beyond a 30-minute chat in my first day, and tons of readings to do, there was no systematic conversation about how to approach my transition. I wasn’t even clear what I had to accomplish in my first 90 days, beyond reading those things.

That’s why more than ever, I’ve realised that the most important thing is to take charge of your relationship with your boss.

It’s not about waiting for him to do something with you. It’s about you taking charge to speak to him, to guide him, to ask from him what you need, and to tell him what you don’t need.

What’s worse is that today, with many people remote working, it becomes harder to have that structured, developmental conversation about what’s necessary with your boss. Everyone is too busy to talk to you, inundated with a series of emails, messages, and electronic alerts about what’s important.

In this article, the bulk of the examples would be my personal experiences. This is not because I’m looking to be narcissistic. But it’s because I hope it presents an authentic account of the struggles I faced. Besides, putting the stories of others may misrepresent what truly happened.

Why is this important?

Make no mistake about it.

For all the myths that we have about having a boss, the boss is a crucial factor behind you succeeding and failing in your job.

But we have certain myths about submitting to a boss that makes it difficult for us to get out of our own way in truly succeeding at work.

Why do Gen Zs fail at this?

Myth 1: If you’re a high performer, you don’t need guidance from your boss

I thought I was a high-performer. After all, I had suggested new ideas. I executed on ideas. I made fancy presentations. I looked confident. I thought I knew what I was doing.

During my first appraisal, I was already asking for a pay rise!

Who needed a boss to guide me?

It was not until a big problem hit the fan that I realised…

Maybe I wasn’t that much of a high performer after all.

It was not until my Performance Improvement Plan, that my boss told me to read the job description, and to follow the job description, that I realised that what I was doing was outside my job description. That I wasn’t even addressing my basic work before trying to do extra.

It was like running before I tried to walk.

Let’s be clear. Before you think you’re a high performer, you need to get the basics right. Getting the basics right means knowing 3 things.

Bruce Tulgan talks about how you need to:

1. Make sure your work fits with the company’s overall mission

Before you come up with the next fancy idea, do you know what your company’s mission is? Do you know what they want to achieve?

manage your boss
Do you know what your company wants?

During my first job, I thought I was a high performer because I was introducing these new ideas. But little did I realise that this did not square with the company’s mission. The company’s mission wasn’t to reinvent the wheel. It was in a place where it simply wanted to continue running things reliably.

It wasn’t looking to be a trendsetter. It wanted to be providing services as was spelt out in the contract allocated. It wasn’t looking to do extra. It was looking to be doing things reliably.

My work, didn’t fit with the company’s mission.

Does your work fit with the company’s mission? I’m not telling you to kill your ideas. But I’m telling you that without knowing your company’s mission, you may be banging your head against the wall. Even if you execute a new idea to perfection, in the eyes of your organisation, you may not be valued because it did not contribute to their overall mission.

Here’s one practical way to understand your company’s mission.

Watkins’ wrote a book titled ‘The First 90 Days’, where he shares about the key transitory challenges that leaders make in their first 90 days of a new role, and what they would need to do to succeed.

He suggested 5 conversations with your boss, the first of which is the situational diagnosis conversation. This is to help you to understand what point the organisation is at, and what is needed from you at this moment.

Watkins' STARS model to diagnose what stage your organisation is currently at.
Watkins’ STARS model to diagnose what stage your organisation is currently at.

4 questions Watkins suggests you can ask your boss are:

  1. What are the elements of the STARS model you see in this current situation?
  2. How did it reach this stage?
  3. What factors (soft and hard) make this situation a challenge?
  4. What resources can you draw on?

When I started at my job, I wish I did this. I realised that the company wasn’t ready for large scale change, and that it was simply at a realignment state, where we were looking for initiatives to reenergise an ailing business. We were not looking at a startup phase, where new, wild ideas were needed.

Now you know what to do.

2. Have goals spelt out and guidelines and parameters for your tasks made clear

Do you know your goals? Do you know your Key Performance Indicators? If you don’t, you need to find out. For the first year, I was supposed to see clients. Yet I didn’t know how this factored into my final performance review. Was a great job done about meeting more clients? Or was it about meeting the outcomes they wanted? I had no idea.

Some questions that I found useful were:

  1. What are your expectations for me? What would be a great job in your eyes?
  2. What are the goals you have for me?
  3. What can I do?
  4. What can’t I do? What are absolute no-nos?

Do you know what you can and cannot do? If you’re not sure, ask. If you’re not sure about where the limits of your autonomy and power lie, ask. It’s better to be safe than sorry.

In a knowledge economy job, the degree of flex in your job and the variables that are involved are infinite. There’s no way of listing out every thing that’s a no-no. That’s why I say,

Listen to your gut.

If you feel uneasy about something, it’s better to take a step back and to ask, rather than to go forward.

Someone once told me,

You have to remember that not everything is on your shoulders. Whose head gets chopped is ultimately not yours.

It’s your boss’, especially if something goes wrong.

Making your boss look stupid is an easy way to lose credibility.

3. Know the concrete deadlines, timelines and reasonable performance benchmarks to meet

Have an expectations conversation. That’s the second conversation that Watkins suggests in his book.

Questions you can ask during the expectations conversation, adapted from Watkins
Questions you can ask during the expectations conversation, adapted from Watkins

You need to know:

  1. What to deliver (in what quality and quantity)
  2. When to deliver

Myth 2: It’s my boss’ responsibility to tell me what he needs

Forget how you were treated in university. This is the workplace. And in the workplace, what I’ve come to realise is:

No one is put on this Earth to take care of you.

Except yourself.

This quote, from Robert Glover’s ‘No More Mr Nice Guy’, is a reminder of how you need to take care of yourself. Remember how in university, everything was made clear to you? You were told how to submit, when to submit, what format to submit it in, and how you were supposed to do the assignment. You were told what to read, how to write, how to structure your essay, and how to do it well.

You’re not going to be told that at work. You need to ask.

Go down to the basics and clarify. Be humble. Say something like,

This is my first time doing this, and I would like to learn how to do this well so that we can make work easier for all of us.

You have to remember, sometimes bosses have been doing it for so many years that they forget that there was a time when they didn’t know.

They might say,

just try it. Have a go at it. Tell me how it goes.


Make a checklist for how you would approach the task, so that you can do it over and over again.

manage your boss
What’s on your list to do, and to stop doing?

For example, when I was recently recruiting another member for my team, I realised that it was hard to put down what her job responsibilities would be. I had never codified what I had done, nor reflected on the exact process that made me successful in the previous instances.

There are likely to be many different tasks you’re going to be asked to do. For each task, ask yourself if you can break down each component task so that you can replicate the success of the task.


I’ve been jobless for 3 months.

Finding a job for the past 3 months has been made harder by the reputation I had from my previous job, as someone who was not strong at teamwork.

But whenever I look back, I remember that if I had managed my boss better, I would have gotten a better experience. If I had clarified what the situation was according to the STARS model, in that I wasn’t there to try and transform things, but to run things as it was previously, then I would have had less headache and frustration.

If I had taken time to know, as Tulgan mentions in ‘It’s Okay To Manage Your Boss’,

  1. Clear and reasonable expectations, with specific guidelines and a timetable
  2. The skills, tools and resources needed to meet those expectations or an acknowledgement that you’re asked to meet these expectations without them
  3. Accurate and honest feedback about your performance and how to adjust when things go wrong
  4. The recognition and rewards in exchange for the performance

Yes, sometimes it is terrifying to think that we are being let out into the real world with little idea about how we’re supposed to deal with work.

But I realise that if you don’t take charge, then no one will.

Take the first step to managing your boss.


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