5 Great Leadership Lessons from Mad Men

The hit American period drama, Mad Men is coming to a close soon after a seven season run leaving behind a legacy of ‘mad’ executive skills. The award-winning drama is set in the cutthroat advertising business of the 1960s with some eye-catching fashion and a fantastic cast. The ups and downs of the employees of Sterling Cooper (Sterling Cooper Draper Pryce in season 4), most especially Don Draper and Peggy Olson make for good marketing lessons with a dash of drama and eye candy.

The evolution of the characters and of the show itself is very relevant to this era which is in a constant state of flux. Mad Men takes you through the 60s and 70s and demonstrates that what began decades ago still holds water today.

As the stars of Mad Men prepare for the final curtain call, let’s take a look at five distinctive leadership skills taught to us by Don Draper and his colleagues.

1. Be conscious of your own value 

At the beginning of Mad Men, Peggy Olson was the naïve 60s secretary to Sterling Cooper’s creative director, Don Draper. However, Peggy was insightful and climbed the corporate ladder becoming a copywriter. For those who aren’t familiar with the term, copywriters create the content that is published, which is a big task even today. Peggy said it like it was, bluntly and honestly. She didn’t shy away from demanding a nice office, raise and bonuses while dealing with workplace sexism rampant at that time. All this, while balancing romantic relationships and a pregnancy (season 2). Peggy Olson could get what she wanted because she was determined and knew when she had an advantage. She could shake down her boss, Roger Sterling for a bonus by doing a task he forgot to tell her about.

Peggy spent the early part of the series learning the workings of the advertising business and she progressed tremendously. In your professional life too, experience, knowledge and the willingness to learn gives you an edge and also helps you to achieve your goals.

You need to know yourself first and what you’re capable of, before you can study your teammates’ capabilities. Constantly assess yourself because you can gauge the strengths and weaknesses of your teammates only when you know yourself. It is important to be aware of your capabilities and find a way to improve your shortcomings. One way is to develop a close coterie of colleagues with a strong sense of team bonding. At the same time, you should be audacious enough to use your winning skills just like Peggy. If she knew somebody could give her something she wanted, she would assess her leverage and attain it. In short, you should be a go-getter.


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2. Be bold to think out of the box

Don Draper may be a stolen identity but the man that came out of it was completely different from his original identity. Don was shrewd enough to leave his résumé in Roger Sterling’s coat and even engineered chance meetings to pursue his aim. Now, while we aren’t expected to slip files into our boss’ suits, we can at least take a leaf from Don Draper’s Book of Daring. Don’s life was constantly about reinventing himself, starting from his ill-fated birth as Richard Whitman, making a name as Don Draper – advertising god and finally starting a new firm with his colleagues.

Don always found a solution to a crisis. Each time he did, he changed a part of himself and induced a change in those around him as well. He even became confidante to Sal Romano, a homosexual who remained in the closet due to the fear of the anti-homosexuality environment of the 60s. It shows that Don saw the person and not his choices.

Reinventing yourself doesn’t mean that you should lose your identity. It’s more about getting bolder and creative. There should be this constant desire to upgrade your professional skills and lead your team to hit the target. If you’re stagnant, you run the risk of a ‘lay-off’.  Make constant endeavours to be in your boss’ radar, like Don. You either make yourself indispensable (which is a tall order) or strike out on your own.

Every character in Mad Men evolved over the seven seasons. Evolving yourself is very important especially, in this dynamic age. Like our favourite creative director, you need to hone your skills and not be afraid of your creative ideas however unconventional they might be. To be a cut above the rest, don’t hesitate to put your ideas into action.


3. Workplace romances are risky affairs

Office romance? How boring! Mad Men epitomized why workplace romances are not a good thing. Relationships at Sterling Cooper blossomed, bore fruit or just withered away and died. If a workplace relationship fails, without resulting in any hostility in the office, it is alright; but you can never tell how a relationship will end, can you? Romances in Mad Men were full of infidelity, punishment, divorce and even unwanted pregnancies- enough to scare you away from office romances. If you know he/she is the one for you, that if things go south you can still be amicable, and no matter what you can work it out, then it might be worth a try. Otherwise, step back slowly….another step….and walk in the opposite direction as fast as you can.
Moreover, when you’re spending your work hours with your mate, what more could you want after office hours? Even at a romantic candle-light dinner, you’d be discussing work plans and strategies. Besides, which boss would tolerate his employees romancing at CTC. In this case, be sure to get the boot. If your strategy is to climb the corporate ladder by wooing the boss itself, you’re bound to remain a subordinate forever because; no boss would allow him/herself to be used by a subordinate as a stepping stone.
If you want tangible results from your concerted efforts, romance with your work.


4. Don’t put all your stakes on one horse

A cigarette company, Lucky Strike was Sterling Cooper’s biggest client. So when Lucky Strike withdrew its contract, the genius creative director, Don Draper executed a devious plan which not only got them more business elsewhere but also enhanced the reputation of Sterling Cooper. However, that came only at the end of the episode. The majority of the time was spent struggling to retain the big-wig client and all for naught. The episode though, was an important lesson on the perils of depending heavily on just one patron. The client-firm relationship should be such that, even if one client were to pull out, it shouldn’t be detrimental to the firm.

A notable example of this is in the Indian context. Narayan Murthy, founder of Infosys has reiterated the formation of the risk mitigation cell after Infosys lost a major client.

Look out for ways to optimize employees’ productivity and thus generate maximum revenue. Do not waste resources, that is, do not assign too many people to a single task. Assign jobs based on the employees’ capabilities and increase the number of tasks by acquiring numerous clients.

Don’t expect a win-win situation every time. Be prepared for a ‘win some-lose some’ situation. It’s bouncing back and learning from your failures that makes your loss-mitigating plan stronger. To quote John G. Whittier,

“Success is failure turned inside out…..

Stick to the fight when you’re hardest hit –

It’s when things seem worst that you must not quit”.


5. Pave your own path

In season 3, Cooper Sterling’s corporate English overlords were preparing to sell it off to a rival ad firm. Seeing that the employees of the firm were getting the short end of the stick, Don, Roger Sterling and Bert Cooper take their chief accountant, Lane Pryce’s help to be released from their contracts. Pryce fires them, instigates the parent company to fire him, thus releasing them all from contractual obligations and free to start their own agency. Don had a big hand in this, convincing Roger and Bert along with Peggy, Pete, Joan, and Harry Crane to start the new agency and once again work their way up. They even go through great lengths to retrieve the client files and art work (from their former workplace) which they needed for their new advertising firm. While stealing from your former employers is not recommended, we should build our own door instead of waiting for the idiomatic window to open.

Be assertive when you make your own path and stand out. Don’t be a part of the herd. At such times, it pays to take the path less trodden. When you chose your own path, be sure that it is exceptional. If there is competition all the more better, because competition only helps to improve the person.

The new agency was one of many advertising firms, but our stars were undeterred in starting their own firm. It’s exemplary considering that a lot of people in this age are at loss about what to do, when there are massive lay-offs. Lay-off is a bitter pill with a sugar-coating called ‘cost reduction’. As mentioned earlier, if you’re not indispensable to your employers, create your own opportunity independent of them and have faith in your competence to make it through.


Mad Men isn’t just about these 5-pointers. It is seven seasons of corporate marketing classes without homework, assignments and tests. If there is a ruthless edge to the corporate world, 60s was the beginning of it and Mad Men gives you a chic corporate lesson. Make sure you distinguish carefully between Don Draper’s marketing skills and his women-charming skills. While the former is useful, the latter might get you into hot water.  In the meantime, let’s eagerly await the final class of the Mad Men brand of marketing.

*credits to the pictures go to the rightful owners  –Caroline John

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