We all have a boss.

Directors have CEOs. CEOs have board members. Board members have shareholders.

And managing your boss is a form of art.

I’m not going to bore you with the basics of showing up on time, asking for feedback or avoiding surprises. Those things are fundamental.

This article is going to cover four things you won't normally hear. Tactical things that have helped me. 

Because if you can manage upward, you can gain more responsibility, have a bigger impact, and earn more money. It will accelerate your career.

But many people get this wrong and think it’s about ingratiating behaviour and favouritism.

It's not that. It’s about making life easier for your manager, so your life gets easier too.

How do you tactically do that? Here is the playbook that has worked for me.

1. No problem should come without a solution

In 2015, I got my first job in technology as Chief of Staff.

Coming from banking, I had a bunch of skills, but not a lot about the nitty-gritty details of actually running a business. I had a lot to learn.

Every Monday, 8 a.m. sharp, I’d meet with the CEO.

I was an eager newbie at first. I had a list of problems, then each Monday I’d hit him with all the things.

'Account conversion rates are down. What do you think we should do?'

He was patient. He even took the time to brainstorm solutions with me. But it consumed his energy and focus, which he should have directed at problems only he could solve.

I had just moved to San Francisco, and without much to do in the evenings, I was reading a ton of books.

One of them was Jack Welch's 'Straight from the Gut.'

If you don’t know Jack, he was the CEO of GE. In 20 years, he grew its market cap 30x to $450 billion, making it the most valuable company in the world at the time.

There are a ton of lessons in this book. One of them covers his mantra: 'Don't Walter Cronkite Me!'.

I had no idea who Walter Cronkite was (an American broadcast journalist) but the lesson stuck…

Don't tell me bad news without telling me how you are going to fix it.

I realised that when I came to the CEO each week with problems, I needed to bring solutions.

This was hard at first. I was out of my depth. But it forced me to put in the extra work to find solutions to the problems I was bringing up.

My goal was to hit him with the problem, evaluation, and suggested path, so that all he had to do was say 'yes' or 'no.' This allowed me to learn and require less of his energy.

You should train your team to do the same.

When they come to you with a problem, flip it back on them. “What’s your plan to fix it?”

It saves you from being the bottleneck and teaches them to think like problem solvers.

This approach will show your boss that you’re proactive and reliable. This builds trust and earns you more decision-making power.

2. Make Your Boss Look Good

I once worked under a visionary manager.

He was very good, but his organisational skills? Not so much.

He could lay out a big-picture strategy, but the day-to-day execution was messy. The team needed order and discipline.

I started writing his internal updates and announcements. I also made polished presentations for his managers.

This is stuff that comes naturally to me. It allowed him to not just look good, but more importantly, focus on what he did best.

Work quality across the company also improved. As a leader, people look to them as the example and standard.

The stronger he was, the stronger the organisation was.

It wasn’t long before I became his go-to for anything operational. That earned me more opportunities than any amount of self-promotion could.

But you can't do this with everything. 

You need to be highly selective about picking up more responsibilities…

3. Take the right balls out of their box

Another CEO I worked with would send out monthly investor updates.

Simple enough. Just crunch some numbers from our internal reporting, write a few paragraphs. Send.

I knew eventually that I wanted to start my own business, so I asked him.

“Can I handle those updates?”

“They usually take me just a couple of hours", he answered skeptically.

But I was persistent and unaware just how much I was asking for.

A framework from the Effective Manager I’ve since learned is to think of everyone's work capacity as a box. The box contains a mix of balls.

Big balls are big responsibilities, like executive goal planning. Small balls are small responsibilities, like sending out the investor updates.

Balls are generated at the top of the company and then passed down through the organisation via goal-setting and alignment.

If you understand that analogy, you should grasp this: an organisation's output is limited by how many balls people can handle in their box.

Your goal is to take the balls out of your manager's box, so they can work on more impactful stuff that only they can do.

But here is the catch, their small balls are big balls in your box. Because you don’t know how to do it. 

Only as you get better at the craft do those big balls become small balls over time.

The first time I did those investor updates, they took me three times longer than it did for him. It was a big ball for me.

The second time, a little less. By the third month, I had it down and could do it almost as well as him.

With the ball out of his box, he could focus on bigger things. I got to learn how to communicate with investors.

The lesson is that you want to find the small, recurring tasks that drain your boss’s time, and offer to take them on.

It’s hard at first. It’s easier as you improve your craft.

4. Keep the Receipts

You might be thinking, “Andy, I’ve done all this—where’s my raise?”

I get it. You want to make yourself easy to promote. Once you have been clear on your future job description and what you want (which is not covered here), the best way to add weight to that is to keep the receipts.

For every major achievement, document it in your 'swipe file.' This includes project wins, initiatives you led, awesome feedback from your peers, and things that helped your boss shine or organisation grow.

A Google Doc is fine. Name it something like  'Wins & Achievements'.

Every time you complete a major task, contribute to a key initiative, or help your boss succeed, screenshot it and add it to the file.

You don’t need to wait until performance review season. This is a living document.

And then when it’s actually time for your performance review, you’re not scrambling to remember all the good stuff you’ve done—you have got it all in one place.

It’s hard to deny someone a raise or promotion when they can back it up with evidence.

Wrap Up

Managing your boss is about making their life easier.

You do that by:

1. Bringing solutions
2. Making them look good
3. Taking the right balls out of their box
4. Keeping the receipts

Pretty soon, you won't just be managing up - you’ll be moving up.