Don Draper's Four Rules of Selling

by Chris Young


Mad Men's Don Draper is a "get its, get it".  Thanks to Oren Klaff's brilliant book, Pitch Anything, I am now a fan. If you have yet to read Pitch Anything, I HIGHLY recommend you do so.

The traits that make Don Draper successful include:Don_Drapers_rules_of_selling

  • An insatiable desire to win.
  • Solid business acumen.
  • Ability to take action.
  • A rare ability to see what others will never see.  

I have met many "Don Drapers" in my career. Companies with ten to twenty salespeople are lucky if they have one on their sales team.   

The good news is you can hire salespeople who are "wired" like Don Draper if you use the only sales personality and aptitude test with validity backed by brain research.  If you hire more salespeople like Don Draper and follow his selling approach, you will make a LOT more money and solve more Customer problems than you currently do.  

Whether you are in marketing or sales, I highly recommend watching Mad Men.  The early seasons are the best. In Mad Men, Don Draper has learned what works and what does not work.  As a result, his sales strategy is extremely effective.  

  • Only Sell To Believers
  • Want It All
  • Never Be Needy 
  • Nothing Is Free

Tweet: Everything you need to know, Don Draper can teach. #sales @therainmakerEverything you need to know, Don Draper can teach. 

All problems start at the head.

You set the tone. You shape the mindset of your sales team by everything you do or do not do.

As an executive or sales manager, it is critical that you are crystal clear about to whom you sell and to whom you do not. You set the tone in your sales team.  The code of conduct your sales team operates from will accelerate or slow you down from achieving your objectives.  

This article is written to be shared with your sales team.  Take a few minutes to read it fully, watch the attached clips, and align your culture accordingly.  It will be well worth your time.  

Only Sell To Believers 

If you watched this clip and thought to yourself, "Don Draper is an idiot...  He should have tried to convince the prospect..." then stop reading right here.  You are wasting your time.  If there are salespeople on your team who do not get the ramifications of what Don did in this clip - help your competitor get them hired away.  

How many times have you chased a sales opportunity only to come to the bitter end realizing you never really had a shot anyways?  And worse yet, you realize you wasted all of those hours schmoozing and writing the proposal.  It all could have been avoided if you had just saw the warning signs.

Yes.  I have been there too.  I have flown cross country to meet with those who did not have the capacity to "get" - to understand the value proposition I offered.  Too many times I have boarded a plane thinking, "I will convince them...  All I need to do is a little time and show them the data..."  Then I arrived, rolled out my presentation, and heard them say, "Our recruiting budget is $200 per sales hire..."  

Price is what you pay and value is what you get.Tweet: Price is what you pay and value is what you get. #sales @therainmaker

Trying to sell to a non-believer is an exercise in extreme futility.  Get rid of your flat forehead.  When you smell that you are selling to a potential non-believer, you must hit the "eject button" - disengage - stop - bail out.  Stop wasting your brand and time on people who will never get you.

Don Draper did the right thing in this scene.  He cut the meeting short and left because he knew they would never believe.  Was it rude?  Perhaps.  But it sent a powerful message to the rest of the sales team to cut your loses early.  

At The Rainmaker Group...  As soon as we identify that we are engaging with a non-believer, we exit the dialogue.  Immediately.  We refuse to engage valuable time with non-believers.  

Want It All

Don Draper is laser-focused.  He knows what he wants.  

What kind of mindset is necessary to be true to who you are and be completely fine if others do not agree with you?  

The "law of attraction" absolutely applies to sales.Tweet: The  If you expect great things and you have real potential, you will make great things happen.  You just have to want it badly enough.  

If you play "not to lose," your sales team will do the same.  If you do not want it all, nor will your sales team.  


The best dialogue is near the end of the clip.  Don Draper and Roger Sterling received push back from Dow. The company is fat and happy...  The Client states, "But it doesn't change the fact that we are happy with our agency..."

Don's reply is priceless...  This is one of those "throw down the gauntlet" scenes and he does just that.  

"Are you?  You are happy with 50 percent.  You're on top and you do not have enough.  You're happy because you are successful.  For now.  But what is happiness?  It's a moment before you need more happiness.  I won't settle for 50 percent of anything.  I want a 100 percent.  You're happy with your agency?  You're not happy with anything.  You don't want most of it, you want all of it.  And I won't stop until you get all of it."  

Watch the clip again and look at the faces of those watching him.  

Do your Prospects and Clients look at you this way?

I expecially love the words...  "And I won't stop until you get all of it."
Do you carefully hire Don Drapers?

Never Be Needy

I love the beginning of this scene...  "Can I put my feet on this?" asks the Client.
Roger Sterling replies, "Pretend like it's your livingroom..." 




Clearly this was a mismatch.  Sterling, Cooper, Draper, Pryce is not for them and the Prospect should never be their Client. 

Have you ever been so needy that you sacrificed who you were to get the deal?Tweet: Have you sacrificed who you are to get the deal? #sales @therainmaker  Yep, I have too.  Never again.    

The best part of this scene is when Roger catches Don as he leaves saying, "Control yourself...  Cool off... And hopefully Campbell can talk them into hearing a few more ideas in a week or so..."

Roger's statement sends Don into immediate action.  Don does not want a second chance.  He wants the Prospects out of his office.  Now.

Have you ever kicked an unworthy Client out of your office? 

Nothing Is Free



Conrad Hilton wanted Don Draper to look at an ad mockup and asked, "What do you think?"

"I think you wouldn't be in the presidential suite if you worked for free," replied Don.  

"Don, this is friendly."

"Connie this is my profession, what do you want me to do?" replied Don.

"I want you to give me one for free..." 

In the end, Don Draper provided his expertise but made sure it was limited.  

Most companies give away something to earn trust, to build the bridge to the deal.  The problem is the freebies are often given away far more often than they should be.  Freebies need to have a "quid pro quo"Tweet: Freebies need to have a - I-share-something-and-you-share-something.  

Most important...  Freebies must be shared with at least an implied understanding that there is a very finite limit to what will be given away.  


Right now you may be thinking, "It is easy for a fictitious character like Don Draper to say and do those things...  To be bold...  To be decisive....  To be committed."  

It is if you say it is.  

I have met and profiled many "Don Drapers" using our Sales Personality Aptitude Test.  They are rare yet more common than one can imagine.  

The decision is yours to make.  

  • You can hire people like Don Draper if you decide to.  
  • You can shape the kind of sales culture that gets results if your decide to.

We made the decision in 2013.  In 2013, we refocused The Rainmaker Group - to only work with "get its" - those that have real potential to get what we do here -identifying and hiring the best salespeople possible - to hire salespeople like Don Draper.    

It was frightening to let "what worked" go.  For over a decade, we were a "management consultancy".  We did a lot of things.  There was a time we would have washed your car if we thought it would help close a sale.  The problem with our strategy is we rarely took a stand.  When you are everything, you stand for nothing.  When you are everything to everyone there is confusion.  I was confused.  My team was confused.  Our Prospects were confused.  And some of our Clients were confused.

We do not have that problem any longer.   Today, we are all crystal clear about who we are and who we will serve.  We are crystal clear about who we will not serve.  

Today, we help "get it" Clients hire the kind of salespeople that emulate Don Draper's best traits.   

Have you made dramatic changes to the focus of your business model?  If so - please share your experiences in the comments below.  

Sales Personality Aptitude Test Sample Assessment