Four Steps Most People Miss to Win Your Boss Over

READING TIME - 4 MINUTES

One of the most important people that has the biggest impact on your career is your boss. Yet, most people miss the mark in building the right relationships with their bosses.

Some people think that having a great relationship with your boss means being friends with them.

In my opinion, becoming friends with your boss is a byproduct of having a great relationship, not the way to build one.

Most people fail in building the right relationships with their bosses because they don’t know how, they feel their bosses are out to get them, they don’t like their bosses, or they think their bosses aren't great, so they don’t bother to build the relationship.

Having a strong relationship doesn’t mean you like or love your boss.

It means you both respect each other and understand what each one wants and needs from this relationship.

I had bosses in my career where I wasn’t my boss’s best friend, but I was their best employee.

Yes, it does help when you become close with your boss, but that’s not the point.

Regardless of where you are in the organization, here are four steps you can take to build better and more effective relationships with your boss.

Some of these steps will help you win their heart.

Let’s dig in:

Step 1: Show Up to Your 1:1 Prepared and Organized with an Agenda

This step is one of the most important steps people miss.

Your boss loves it when they feel you’ve got it under control.

Showing up prepared and organized with an agenda demonstrates that you take your job seriously and respect their time.

The agenda has to be crisp and simple, yet strategic and informative, so you can move away from just answering questions during your 1:1s.

Below, you'll see an example of an agenda I use during my 1:1s.

Also, figure out a way to save your agenda in a place where you and your boss have access to it. I use a Google Doc with running agendas week over week.

The biggest point here is to be consistent, so your boss knows you will always show up with an agenda.

See the attached image for an example of my typical 1:1 agenda.

Step 2: Keep Them Informed

No boss hates being informed, even if you over-communicate.

The worst thing you can do is surprise them.

Figure out your boss’s preferred communication method and use it. Some bosses like SMS, some prefer emails, others may prefer Slack or a quick phone call.

My preferred method is leveraging my 1:1 meetings to keep them informed and using Slack or phone calls for urgent matters.

This way, my boss knows they will get the full story during our meetings.

Step 3: Show Up with Solutions

Don’t be the person who just reports issues.

Highlight problems, suggest solutions, and take the lead in fixing them.

It’s okay to share issues, but if you only share problems without solutions, you’ll be considered a complainer.

This is the fastest way to get to your boss’s heart. Nothing excites a boss more than seeing their team proactively solving issues.

Step 4: Remember Your Boss is Human Too

Check in with your boss.

See how they are doing, ask if they need help, wish them good luck before big presentations, and send them a note if they are having a bad day.

I know you might think this is kissing up, but it’s not.

When you do the first three steps right, this one won’t come off as sycophantic. Your boss will appreciate your genuine concern.

You see, I didn’t mention KPIs in this newsletter, and that was on purpose.

Meeting your KPIs and deadlines and doing all the things you were hired to do will give you a solid performance review.

This newsletter is about how to win your boss over.

You might have several coworkers on the same team, and getting things done and meeting KPIs might be something everyone is doing.

But...

The steps I gave you are to take things up a notch - doing your job well is your responsibility; I didn’t have to remind you!

At the end of the day, getting your boss on your side is a great thing you can do for your career.

Your boss is in meetings when you’re not, and you want them to be on your side in those conversations.

They represent you behind closed doors, and you want them to be your advocate.

Building a strong relationship with your boss is like building any other relationship.

Show up, be positive, and be there for them, and they will be your best advocate.

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