Sterling’s Gold: 7 Lessons for Success from Mad Men

John Slattery as Roger Sterling
(Photo credit: srqpix)

Roger Sterling: fictional ad man, chronic drinker and serial womanizer. An inspiration to wiseasses everywhere, he says the things we wish we could say in the workplace — only funnier.

But his collected quips, lovingly catalogued here, represent more than a cautionary tale about the dangers of cynicism and debauchery. A few precious gems stand out, offering honest-to-goodness wisdom to work and live by.

So here is the best of Sterling’s Gold, and what it has to teach us about business success.

1. “I don’t know if anybody’s ever told you that half the time, this business comes down to ‘I don’t like that guy.'”

The importance of being likable should never be underestimated. Whether you’re interviewing for a job, pitching business to a potential client or trying to close a sale, the fact is, people like to work with people they like. All other things being equal — skills, experience, service — they will pick the person they can reasonably envision spending 8 hours a day, 5 days a week with.

2. “Baked beans and the Rolling Stones: a client’s idea if I ever heard one.”

If you don’t have clients, just substitute “customer” or “boss.” They’re the people who want what they want, no matter how impractical it is. They’re Homer Simpson, designing the $82,000 car of his dreams, complete with tailfins, shag carpeting and three horns. They’re the advertiser looking for a spokesperson who’s a combination of Stephen Colbert, Clint Eastwood and Jon Hamm. (True story.) There may be no bad ideas in brainstorms, but most of them, like Roger’s own unfortunate memoir, don’t deserve to see the light of day.

3. “The day you sign a client is the day you start losing them.”

Pessimistic, yes, but there’s a grain of truth here. A relationship — any relationship — is hard to sustain. It can grow and strengthen, sure, but it can also very easily dissolve, molecule by molecule, with every little misunderstanding and miscommunication. Minor disappointments build into resentment, until one day the work itself is not enough to sustain the relationship. And to be sure, not every relationship is worth sustaining.

4. “Maybe every generation thinks the next one is the end of it all. Bet there are people in the Bible walking around, complaining about kids today.”

If your goal is to sound old and out of touch, few things beat complaining about “the kids these days.” Honestly, if I have to read one more article about how to handle millennials in the workplace (here are 474, 000 — dig in!), I’m going to throw up. The workplace is changing and people’s expectations are evolving — that’s been going on since the end of the feudal era. Don’t gripe about it; manage it.

5. “Nobody knows what I’m doing. It’s good for mystique.”

Every office has one of these types. Usually it’s a senior-level person who drifts in and out of meetings, occasionally contributing a thought or two but delivering little discernable value. Unfortunately, it’s not mystique they’re emanating — it’s contempt. And it’s not just about your Roger Sterlings and Bert Coopers — if you’re starting out, get in the habit of doing your own personal PR. Be sure the right people understand the value you bring.

6. “You know, I used to jump off mountains, and it never occurred to me that I had this invisible parachute.” 

Whether you were born with a (sterling) spoon in your mouth or you clawed  your way up the ladder, you had help. Put another way, you didn’t build that. Don’t forget it. Be grateful, share credit and give a helping hand to those on the rungs below.

7. Never take yourself too seriously.

Okay, this one’s not a quote, but Roger lives this sentiment every day — to an extreme, of course. But he’s the one guy in the room you can count on to puncture the air of self-regard that consumes everyone else, reminding them all that it’s not life and death … it is, after all, just business.