How to Talk to Your Boss

I could really shake things up at the office if I could just get the boss’s attention,” Sean complained. He was the son of a good friend and had been told to see me in the hope I could give him advice on how to put his career on a faster track. “I have a lot of great ideas but he never listens to me.”

I asked him whether his boss was that way with everyone. “No,” my young friend admitted. “There’s this one guy who really has the boss’s ear. But he’s just a major brown-noser.”

This “brown­noser”, it turned out, was about to be promoted to a position with better pay, more responsbility and better upward mobility.

“This brown-noser must be doing something right,” I said gently.

That suggestion prompted a long tirade about how he had self-respect and was trying to advance on his own merits, while the brown-nosers of the world got ahead by catering to the ego needs of their superiors.

It was obvious that Sean was full of anger about the situation. He considered himself to have more talent, better credentials, more experience and better social skills to boot. He was convinced the main problem was the boss’s pigheadedness and susceptibility to brown-nosers.

Seeing that I wasn’t going to get too far along that line, I switched tack.

“You’re right,” I said. “Let’s just fire your boss and get you a better one.”

At least that brought a sheepish grin to Sean’s face. My point had been made.

“All right, then,” I said, “let’s do the second best thing: quit and get a new job with a better boss.”

As I had expected, Sean went into a long explanation about how he had invested a lot of time and energy in the company and he didn’t think it would be so easy to find a better job.

“All right, then,” I sighed. “I guess we’ll just have to do the third best thing and figure out how you can talk some sense into this boss of yours.”

That brought another sheepish grin to Sean’s face. I judged that he was now ready to do a bit of listening himself.

“You want the long version or the short version?” I asked.

Glancing at his watch, Sean said, “The short version.”

“If you want the boss’s ear, speak his language.”

“Okay, let’s hear the long version,” he said after mulling that for a moment.

We had a long, very productive discussion which can be boiled down to the following points:

  1. Work with the boss you have, not the one you wish you had. Look at it this way — if he were the perfect philosopher king, he wouldn’t be your boss. Your boss will always be a deeply flawed human being but one with certain priorities dictated by his position. It’s up to you to focus on those things, not on the human flaws in his character, personality and behavior. Focusing on the boss’s imperfections and shortcomings is the deadest of dead ends for any ambitious young professional.

  2. Whenever possible, speak to the boss in his own words. During your workdays the boss hands down orders, guidelines and suggestions. If you hope ever to expand your role at work, start by listening closely to everything the boss says. Remember the words and phrases he chooses because they embody his priorities and the concepts dear to his heart. Make those words your workplace vocabulary. Begin every meeting with the boss by echoing his own relevant words and phrases. “You were saying the other day how important it is to…” is much more likely to win his attention than, “I came up with some great new ideas that you may not have thought of…”

  3. Talk to him about what is on his mind at the moment. If you have any sense at all, you already know that your boss is burdened by demands imposed by his boss, shareholders or clients. Would it be wise to keep accosting him to listen to blue-sky ideas or your need for a better parking space when he is deeply worried, let’s say, about your department’s inability to meet its production and budget goals? There is a time for everything, even for talking about the smallest of your personal concerns. Make sure you do so at the right time.

  4. If you want to ask for something, give something first. The give and take starts the day you are hired. Your boss starts off by giving you a promise of paychecks and the opportunity to prove that you are worth the money. If you want to talk to the boss about getting something more, start by making sure you have (A) fully repaid the boss’s original investment, and (B) given something extra above and beyond that. That extra giving may have been in the form of unpaid overtime hours on an urgent project, no absences from work or valuable contributions at meetings. If you give the boss reason to think that you see the relationship as take-and-take, he will quickly lose interest in listening to you. If you show that you are a give-and-take person, you will have not only the boss’s ear but his respect. That’s a great way to start any conversation.