Learn to Become Equals With Your Boss

Published by Ryan Healy on June 12th, 2008 in Career Development | 20 Comments

I have a problem with authority. I have since I was a kid. It's probably the reason I wasn't cut out for life in a large organization and it's why I eventually became an entrepreneur. But as much as I don't like to admit I'm working for anyone else, Penelope Trunk is our CEO and, well, she's the boss. So over the past 8 months I've learned how to work with her so that I put myself on equal footing, most of the time. Here's how I've done it.

Know what's important to get approval for in advance, and keep the rest for yourself

If your boss is any good, he is busier than you are. That's just how work works. As you move up the chain, you're responsible for more things and you have less time for details. I've seen this first hand as Brazen Careerist has moved from a 3 person start-up to a larger team with six full time employees and a whole handful of part timers.

Penelope does not have the time to check off on everything. It's been a big switch for me, but I've learned to be selective about what I present to her. In the past, I would call her to give me the green light to draft a proposal to send to our lawyer or the investors. Now I make the call on what is important enough to get the final go ahead. What I've found is there aren't too many things that are truly necessary for her to give the go ahead on before I get started.

Going around the boss is a little risky, you need to know what things must absolutely be approved before going through with, but in the end, getting the right things done, even without permission in advance will make you and your boss look good. And it will begin to turn the boss-employee relationship into a peer-to-peer relationship.

Save the details

Tiny details do not need to be shared with your boss. When you're explaining a new product, service or opportunity, talk about the big picture. If your boss is high up on the food chain the chances are that she is always thinking five steps down the road. As an entry level employee or new manager, it's your job to do the day to day work to keep the company moving in the right direction and it's your boss's job to be thinking 3 months down the line. Sharing too many details will open a big can of worms that should be avoided.

Tell your boss about the presentation, talk about the benefits and the potential risks, but don't bother going through the PowerPoint slide by slide and don't tell him how nervous you are. Then follow through, and things will work out great. You may think you're holding back information that your boss wants to know, but in reality not discussing the minutia will save time and allow your boss to concentrate on the important things.

Notice the little things that help you make good choices about communication

It's important that you learn how your boss operates in different situations. Penelope often quickly says no when I bring up a new idea, without giving it much thought. I've realized that when she is thinking about something else, she often makes snap decisions. I used to argue. We would scream at each other for a few minutes, I would be pissed the rest of the day and nothing would get done. Now, I just say OK and I walk away.

I've realized over the past few months that often she doesn't shoot my ideas down because they're bad, she's just busy with something else. So I'll approach her the next day, usually in the middle of a conversation that's going well, and I present the idea in a new way. I explain the benefits and possible risks, and almost without fail, we go ahead and give the new idea a shot.

If you want to gain some authority in your company, no matter what size, it's important that you take ownership of your role, and sometimes, do things without asking. When you're the boss, there won't be anyone to ask, so you may as well get some experience doing it now.