How To Talk To Your Boss
I remember Sello. He’s not around Here anymore. but He’s still kind of famous for the way he mishandled Rob. Rob’s the boss, see, and he must be handled right.

March 5, 2012

I remember Sello. He’s not around Here anymore. but He’s still kind of famous for the way he mishandled Rob. Rob’s the boss, see, and he must be handled right.

Anybody who knows Rob, who has taken the time to sort out his Robitude, knows that there are certain things Rob likes and certain things he detests. For instance, Rob likes people who call him Rob. He likes people who are brief and don’t schmooze. He hates peo- ple who call him names like Mr R, the Robster, and Boss. So here comes Sello, a director of one of our divisions. Early on, he starts calling Rob “Big Cheese”, as in, “Hey, Big Cheese, how’s it going?” The first time I heard
Sello say this, I knew he was doomed. One day I met up with Sello in the men’s room. “I was just in with the Big Cheese,” he told me. “He was a bit short with me. You think he’s in a bad mood?” “No, Sello,” I replied. In my mind, I said goodbye to Sello. Sure enough, a month later he was gone. Very few gaffes in the workplace are fatal ones. You can dress like a chop and still succeed. (Bill Gates, anyone?) You can be rude to subordinates. You can be late to meetings or be a lazy schmuck and still thrive. But you can’t fail at Boss Communication. Fortunately, there are many ways to effectively talk to the Big Cheese. (Oops.) Let’s look at the top six.

Boss-talk rule 1

Have a message
Bosses hate blab, unless it’s their blab. Every one of your communications has to have a point. What’s the purpose of your talk? How long should it last? Should it happen at all? Understand this: you are the master of the discussion. The boss may have called the con- fab, but it is you who sets the tone, establishes the content and organises a clear structure. Do not waste the man’s time. Even if all he does between conversations is look out the window, this is a person who believes his time is more valuable than yours. So spend that potentially overvalued time wisely. Be short. And punchy. And when you are through with all you have to say, blow out of that room with gusto, because you’re a busy guy. Of course, if Rob wants to sit and shoot the breeze, awesome. But be hyper-aware of the shifting sands of Rob’s attention span. You’re in the middle of a vast desert of inattention and anxiety that is the executive mind. Treasure your access, and remember to always depart with something concrete – an order, an action plan, a laugh. Whatever. This has been a formal transaction. That’s why they call it Business.

Boss-talkrule 2

Play your meetings like a violin
Naturally, there is no replacing the meeting as a prime means of talking to the boss. I am referring not to hobnobbing and jawboning but to an organised gathering with an agenda. At a decent meeting, outside the stated purpose (which is often not particularly important), you may do certain very important things with Rob, including but not limited to…
1. Impressing. Don’t be a show-off – just know your stuff and show it when you can.
2. Humiliating adversaries and competitors. Others may need to be prodded a bit.
3. Mild and appropriate flattery. Don’t think it’s not an important part of the job.
4. Ascertaining future pitfalls. Many an insight was gained by keen observers. 5. Eliciting laughs. People are generally so bored in meetings that even a mild attempt at humour, if sanctioned by Rob, may succeed in leavening the atmosphere. Great meetings are short and focused and make everybody feel good about themselves. And keep in mind that the genuine task of all meetings, no matter what the ostensible sub- ject, is to come out of them just a little bit more powerful than you were when you went in.

Boss-talkrule 3

Be smarter than your phone
Your phone is now the ultimate tool by which true communication is both accomplished and avoided. We use our smartphones to talk to people and to ignore them while they are talking to us. The phone enables us to be every- where and nowhere at the same time. It’s a news
aggregator, a game machine, an asset and a liability. Ever try to have a conversation with Rob while he’s looking up stocks on his iPhone? “I’m going to purchase a new Range Rover with my department funds,” I said to my boss once as he was looking up our ticker symbol on Market- Watch. “Uh-huh,” he said. “We’re up a quarter!” The phone is great, however, as a way to let Rob know that you’re on task every moment of the waking day. “Rob, remind me to tell you about the Harbert outcome. It’s good,” is an ideal SMS to pop into Rob’s brain at 9.30pm at night. And when you’re on the road, dispatch little bulletins to keep him aware that you’re reading, thinking, meeting. Not too many, though – just enough to tell him you love him… in a business-like fashion, of course.

Boss-talk rule 4

Send only two kinds of email
People generally overuse electronic communi- cations, particularly with their bosses. There is no substitute for face time in serious matters. A cup of coffee in the morning is the golden thread from which entire careers have been spun. That said, email has two hugely valuable functions: (a) to impart regular news and (b) to ask for a decision on something focused and relatively quick. See, a lot of news happens during an average working day. The informa- tional email should be short and pithy. “Met with Barfinger. Went well. Let me know if you need more.” That’s perfect. Here’s one that isn’t: “Rob: the meeting with Mr Barfinger of Barfinger, Barfinger & Bean took place in the 40th floor conference room at 10am today. The possible upgrade of the pugmill in Postmas- burg was blah blah blah.” See what I mean?
As for the second function, executives are called upon to “make decisions” every moment of the day. I put that in quotes because 98% of the time they are not decisions per se, but sim- ply permissions. In corporate-speak, we call that “clearance”. When you ask Rob if it’s okay for you to go to Pretoria for that thing, you are not seeking a decision. You are asking for his clearance. All Rob wants to do is say yes or no. The perfect medium for this function is email. What you should never do is give Rob a piece of stinking garbage by email. That is the coward’s way out, and the gutless never prosper…

Boss-talkrule 5

Be a bad-news bearer
The great boss-talkers know how to pick up and package a pile of dung without getting it all over themselves. But there are those who avoid giving noxious news to Rob. In addition to being cowards, they are failing to think straight or strategically. Telling Rob things that may disappoint or anger him (even if you are the partial cause) lets him know you are courageous and not terminally afraid of him. Yes, managers may yell, scream and punish the bearer of bad tidings. But shooting the
messenger is a recognised no-no among bosses who consider themselves good. That doesn’t mean it sometimes doesn’t happen, of course. But you’d be amazed at how many wounded messengers later receive an apology for such miscreancy. These admissions of wrongdoing are pure gold for the intelligent employee.

Boss-talkrule 6

Open your ears more than your mouth
In the end, the Boss thinks the guys who listen to him best are the most communicative. So sit. Listen. Offer more questions than answers. In the end, Rob will be mystified at how much fun he has when you’re around soaking in his wisdom, his foolishness, his big old self. And who knows? At some point, you may just move silently and imperceptibly into that zone that lies just beyond business in the borderlands of that undiscovered country known as friend- ship. That’s where people have a lot more fun, believe me. Not to mention money.