Do Mad Men make mad mentors? When Don Draper met Peggy Olson in Mad Men, she was a timid secretary. Fast forward a few years, and she's standing toe-to-toe with the big boys in the creative department, armed with sharp wit and sharper ideas. This transformation from a secretary to a creative powerhouse is a testament, in part, to the effectiveness of Don's mentorship. How did this transformation happen?

Much of it concerned Don's complicated, messy, often borderline dysfunctional mentorship. Let's take a stroll down Madison Avenue and explore the pivotal highs, lows, and baffling middles of Don Draper's mentorship of Peggy Olson. These moments shaped their relationship and profoundly impacted Peggy's career.

Great Mentors: Look for Growth Potential

The Good: "You're More Than Just a Secretary"

Don's first significant moment of being a top-notch mentor came when Peggy impressed him with an off-hand tagline for Belle Jolie lipstick in Season 1. Peggy was an eager beaver, desperately wanting to please her boss by taking notes, answering phones, and maybe typing faster than the girl next to her. But Don saw more in her, famously saying, "You are going to need to decide what kind of person you want to be. Don't let anyone else make that decision for you."

Key Mentoring Moment: Recognizing the Diamond in the Rough

This was the moment Peggy took her first steps from "girl who fetches coffee" to "girl who creates the ads people read while drinking coffee." She realized that Don saw potential in her beyond just being a secretary. He was giving her a choice: Stay in your box, or blow the lid off it. Peggy chose the latter, and honestly, could you imagine her delivering Don's coffee forever? No. No, you cannot.

The Bad: "That's What the Money is For!"

While Don certainly believed in Peggy's talent, he wasn't always the warm and fuzzy mentor she probably could have used. One of the most iconic moments of the series (and by "iconic," we mean "Don Draper being the king of emotional inarticulacy") comes in Season 4, when Peggy confronts Don about not receiving enough recognition, including financial compensation, for her hard work. His response?

"It's your job. I give you money. You give me ideas. That's what the money is for!"

The Good: Sharing the Creative Process

Don doesn't just acknowledge Peggy's talent—he challenges her to elevate it. He knows she's capable of more than just following orders or playing it safe. By pushing her to dig deeper, Don is mentoring Peggy not only in the art of advertising but also in the art of self-confidence. It's a subtle but powerful moment where Don shows Peggy that her ideas deserve the spotlight and that she should never settle for mediocrity. Peggy walks away with a new sense of determination, realizing that Don's belief in her is genuine and that it's time for her to start believing in herself, too.

Great Mentors: Share Your Process

The Good Again: "Move Forward"

Perhaps Don's best advice to Peggy—maybe even his best advice to anyone—comes in Season 7, when he tells her, "Move forward. This never happened. It will shock you how much it never happened."

When Peggy has a terrible experience with a client, she wallows in it like the rest of us might do. But Don uses it as a teaching moment. He shows her the art of resilience, a critical lesson in an industry where rejection and frustration are constants.

A Key Mentoring Moment: How to create an idea

Don shares a simple but significant truth with Peggy. Ideas are hard to come by. So think about it deeply and let it go. It is great advice on the process of generating fresh ideas. She sees him in action and, as in this moment, learns from a more direct mentoring approach of sharing the process he uses to spark his imagination.

The Bad: The Price of Talent

This moment exposes the darker side of Don's mentorship. While he is excellent at pushing Peggy to be her best, he often fails to provide the emotional support or recognition she craves. Instead of acknowledging her feelings, Don reduces the issue to a transaction, showing that while he values talent, he can be blind to his mentees' emotional and psychological needs. This exchange is a reminder that mentorship isn't just about honing skills; it's also about understanding and valuing the whole person. This is a pivotal moment for Peggy to realize that while Don has helped her grow, she might need to step out of his shadow to truly thrive.

Great Mentors: Are Empathic and Kind

Don is often right but not always nice. Kindness and empathy are traits good Mentors (and managers) work to embrace. After all, nobody likes a bully.

A (Dysfunctional) Mentoring Moment: More Push than Pull

This is the moment you realize Don is more of a "push-you-into-the-deep-end-of-the-pool-and-hope-you-swim" kind of mentor than the "guide-you-gently-along-the-path-to-success" type. Not exactly nurturing, but in his twisted way, he was teaching Peggy the harsh reality of the industry: no one is going to baby you. He valued her, but he showed it very Draper-esque: direct, cold, and with a side of Scotch.

The Bad Again: The "I'm Sorry" That Wasn't

Don wasn't always the picture of emotional availability (shocking for a man whose favorite coping mechanism was staring pensively out of windows). One of his most exasperating mentor moments came in Season 4 when Peggy asks for recognition for her work, only for Don to lash out at her, deflecting and blaming her instead of acknowledging her contributions.

When Peggy leaves the office in tears, we see a rare moment when Don reflects on his behavior, but instead of apologizing, he brushes it under the rug. In their next interaction, he offers her a bottle of whiskey, which in Don's world is code for "I'm sorry, but I don't know how to say it with words because I'm a complicated man of the 1960s."

5 Lessons We Can Learn from Don and Peggy's Mentoring Relationship

Or how Mad Men showed us how to be an accidental mentor.

Don may be an accidental mentor. But he is often effective at it. He builds her confidence and shares insights into his creative process - helping her thrive. But as noted, he does as many things wrong as right along the way. Could you be an accidental mentor? Here's some time to help your team thrive.

1. See Potential Where Others Don't

   Don recognized Peggy's talent before she even knew it herself. Mentors should see beyond what's on the surface. (Also, try to see beyond the Scotch too.)

2. Push, Don't Coddle

   Don rarely held Peggy's hand—he shoved her into the spotlight whether she was ready or not. Mentors should push their mentees but maybe offer more emotional cushion than Don did. Throwing someone to the wolves is a questionable but time-honored method of character-building. Just be sure there's at least one hug somewhere down the line.

3. Let Them Fail (But Pick Them Up When They Do)

   When Peggy flopped, Don didn't linger on her failures. He taught her to "move forward"—failure isn't the end; it's part of the process. It's like Don knew the future would include LinkedIn posts about "failing forward"—he was just more brief about it.

4. Give Credit Where Credit is Due

   Don had a "bit" of a problem with giving credit, which nearly led Peggy to quit on more than one occasion. Lesson? Mentors should remember that acknowledgment isn't just a formality—it's the fuel that keeps the engine running.

5. Build Confidence by Trusting Their Skills

   One of Don's most remarkable things was trusting Peggy with important work. He didn't just see her as a worker bee—he believed she had what it took to rise, even if he was too emotionally stunted to tell her outright. The lesson here? Trust your mentees. Sometimes, all they need is someone who believes they can do it. Plus, it saves on whiskey.

What it Means to be a Mad Man Mentor

The mentorship between Don and Peggy was sometimes pretty. It had sharp edges, spilled drinks, and more than one instance of someone storming out of the office in frustration. But, through it all, Don Draper helped Peggy Olson transform from a wide-eyed secretary into one of the sharpest creative minds in the business.

Was he the world's most nurturing mentor? No. Was he the most emotionally available? Also no. But he gave Peggy the tools she needed to succeed in a cutthroat world, whether it was a well-timed "move forward" speech or just handing her the reins and trusting she wouldn't crash the car. So, maybe Don Draper isn't the mentorship hero we wanted, but he's the one Peggy needed—and in the end, that made all the difference.

Now, if only he could have thrown in an actual apology along with that whiskey, we'd call him perfect. Well, almost.