They don't cover for him. They manage people's expectations. These are the ones who did it (and sometimes him) best.
  1. 1.
    She can't spell "Strategy," and she doesn't know what "breach of contract" means. But goddamnit, she sure can man a desk. On top of her secretarial duties (all of which she performs beautifully) the army brat, turned SC&P secretary decorates apartments, keeps you trim, and covers for you when you disappear for months. Not only is she Don's best secretary, she is also his strength.
  2. 2.
    Dawn Chambers
    Originally hired because of a prank gone wrong, Dawn proved to be a perfectly capable secretary to Don. She did this while going through the struggles of being the first black employee of the agency. Eventually pulling double duty as the agency's Office Manager, she never let that interfere with her secretarial duties. Extra points for having to deal with Lou fucking Avery.
  3. 3.
    She might have been number 1 had it not been for her inability to manage Dons personal life. In her defense, she had the unfortunate task of working for Don during his darkest days. It eventually led to a one night stand that she could not get over. Despite that, she was sparkling in her duties. Don even told her to write that in her letter of recommendation...
  4. 4.
    Joan Halloway
    She was his secretary on two occasions during season 2, and at least one time before (how about a cup of coffee? I think I remember how you take it.) She gets this ranking based purely on her status as executive secretary during the days of Sterling Cooper. She was a mentor to every woman in the office. Especially to the next woman on this list
  5. 5.
    Peggy Olson
    Introduced in the pilot after the unseen Eleanor left the agency. She had more than a few bumps along the road while being Dons secretary for about a year. She unsuccessfully flirted with him after he defended her from Pete. She panicked after learning of Dons infidelity. She panicked again when Betty and the brats visited his office. Good thing she was a GOD at writing titillating copy.
  6. 6.
    Ida Blankenship
    She was put on Dons desk by Joan as punishment for treating Allison so poorly. It's as if Miss Blankenship was aware of this, because she drove him crazy. She didn't know how to work phone lines. She had a 3 second delay in buzzing people in. Her sass was entertaining to everyone but Don. She was the secretary he deserved. May God rest her soul.
  7. 7.
    Jane Siegel
    She got everyone but Don's attention the minute she stepped foot in Sterling Cooper. She was far from terrible, but other than her looks she was incredibly forgettable. It's a good thing Roger waved his money at her because we could have been stuck with her for years.
  8. 8.
    Megan Calvet
    She only made one real mistake, but it cost the agency North American Aviation, and almost cost Don his freedom. Let's face it, if this were a list of Dons best lovers, she would be this low, too. The only reason she isn't last is because she is an excellent babysitter. I'm actually convinced she only agreed to marry him to save her job
  9. 9.
    Lois Sadler
    Stick to the switchboard, Lois. Surprisingly, this ranking doesn't even factor in the fact that she ran over someone's foot with a lawnmower, since she wasn't Don's secretary when that happened. In the beginning of this list I described the secretary's most important task. That quote was given to us while Don was firing Lois for not being able to do said task. The only secretary to actually be fired from the position due to her performance, she rightfully deserves the lowest spot on the list.