How Talking To Your Boss Like An Equal Proves You're Ready To Be A Manager

by Christian Bonilla

Early in my career, I learned a valuable lesson about communicating effectively with my managers. This is all thanks to two faux pas I would never have knowingly committed.

Six weeks into my first job after college, I was working at my desk one day when an email popped up on my screen. It was from someone whose name I didn't recognize. In the body of the email was a single line of text that read, “Pls send me what you have been working on for [my manager].” That was it. The lack of salutation, the commanding tone and the absence of a “thank you” seemed a bit curt to me.

I didn't care for the abbreviated "please," either. In lieu of her name, she signed off with her first initial. A bit put off, I sent back a terse reply of my own, along with the document she wanted.

Two years later, I was interviewing at a software startup. I had to present some of my work to the management team. At one point in my presentation, someone in the audience asked me a question that I didn't think was relevant.

I may have been overcompensating for wearing a tie to an interview with a startup. So, I casually dismissed the question by saying something like, “I guess you could do that, but it's kind of beside the point.” I kept moving right along.

As it happened, the woman whose terse email I replied to was a managing director at the firm, as well as my boss's boss's boss. I doubt she got many terse emails from 21-year-olds who were still figuring out how to book conference rooms.

What about the man in the audience for my interview presentation? He was on the company's board of directors, as well as one of the country's most widely published academic economists. I would have never answered either of them so flippantly had I known who they were at the time. Yet, in both cases, what followed was the exact opposite of what one would have expected.

The managing director had one of her lieutenants talk to me about joining her team, and the board member recommended that the CEO hire me. What was the common thread? In both cases, I communicated with my superiors like they were my peers, and they responded by making me a peer (or at least closer to being one). When I was blissfully ignorant, I didn't think twice about how I approached them. I didn't second-guess myself, and I wasn't afraid to stand behind my ideas.

Sometimes, I think we all need to remember what we can learn our younger, more fearless selves. One of the themes I revisit often at Smart Like How is the importance of thinking like a manager from the onset of your career. The reason is simple: A significant portion of your career advancement will be determined by whether or not you make your managers comfortable with trusting you with more responsibility.

You build trust by showing your managers you are focused on the same outcomes they are. You prove that in any given situation, you would make not just the right decisions, but the same decisions they would.

Communicating with your superiors as though they are your peers is an extension of thinking like a manager. By engaging your managers on their level, you encourage them to treat you like a peer (rather than a newbie whose experience and judgment pales in comparison to their own). You want to encourage their communication “muscle memory” to take over, so they don't remember any of that.

The first step is to stop communicating in a way that emphasizes how junior you are. Remember you can be respectful without being deferential.

1. Don't thank people when you give them something.

I spend a lot of time crafting emails, as well as reading between the lines of the ones I receive. Maybe I even spend too much time doing this.

One of the things I've noticed through looking for the emotional tells in other people's emails is that new hires have the tendency to give people something, and then say, “Thanks.” It's a weird habit, but it's not uncommon for a manager to get an email like this:

Hey Christian, I worked all weekend on this report and won't sleep until I can get the updated numbers after the opening bell in Tokyo. On Page 65 of my report, you'll see a placeholder for the data. Please take a look when you have a moment. Thanks, Jimmy Overachiever

At best, that unnecessary “thanks” makes the sender seem like a sycophantic droid, which is the opposite of a peer. You shouldn't thank someone for reading your email and graciously accepting your hard work.

At worst, this email can come off as passive-aggressive, which is also blech. If you want to sound more like one of the adults, thanking people only when you mean it is a good place to start.

2. Don't be a pushover.

Young or inexperienced people are frequently too timid when it comes to defending their ideas after they have been challenged. Rather than explain their thinking, they too often abandon their ideas at the first whiff of a challenge.

In her 2003 Harvard Business Review article, "How To Pitch A Brilliant Idea," Kimberly Elsach called these people “the pushovers.” She noted,

[They] would rather unload an idea than defend it. One venture capitalist I spoke with offered the example of an entrepreneur who was seeking funding for a computer networking startup. When the VCs raised concerns about an aspect of the device, the pitcher simply offered to remove it from the design, leading the investors to suspect that the pitcher didn't really care about his idea.

Remember that sometimes, people just want to test your thinking. You often have probably considered things your audience hasn't, especially when you're presenting your own work.

Don't be belligerent in the face of fair criticism. But, a peer wouldn't bow out at the first sign of a challenge. So, neither should you.

3. Don't be overly formal.

Manners are important, but excessive formality makes you seem like a child. If you treat the person you're interacting with like a head of state, you subtly encourage him or her to treat you like a serf.

You can be polite and respectful without being submissive. If all you need to do is convey some information to someone who needs it, you don't need pomp and circumstance. Much like constantly thanking people, being too formal all the time gets tiresome. It cheapens the real thing when you really mean it.

4. Use as few words as possible.

The origin of this quote is dubious, but for the sake of argument here, let Einstein be your guide. Make your communication as simple as possible, but no simpler.

I worked for years under an executive who was one of the most poly-talented people I have ever met. He would wax philosophies on any topic you could name. But, he was adamant his direct reports explained things in the simplest language they possibly could.

He would claim to not understand an email from me. He would ask me to rewrite a slide, even if he perfectly understood what I meant.

That manager taught me the simpler you can explain something, the better you yourself understand it. Explaining things simply helps people organize their thoughts, and it makes them more likely to trust you. What's more is, you also give your ideas their best chance to shine when you don't hide them amidst superfluous text.

If you stand up for your ideas and drop the deferential posture, you might find yourself in some more gruff debates with your superiors from time to time. Don't take this the wrong way.

As the stakes of what you're working on go up, pleasantries are much more likely fall by the wayside. If your managers trust you enough for you to take the kid gloves off, it's a sign you're making real progress in your career.

This article was originally published on the author's personal blog.