Managing Men: The Joy Of Picking Up The Tab

picking up the checkIt’s an age-old tradition. A man and a woman meet for some form of meal or beverage, they exchange pleasant conversation, and then the guy picks up the check. Sure, plenty of women are standing up for their right to pay for their own date, but there’s still that moment of uncertainty where most of society assumes that the guy will be pulling out his wallet. I’m talking about dating, obviously, and yet these traditions still seem to creep into business lunches with surprising regularity.

I cannot tell you the number of times that I’ve eaten with a male co-worker where they insisted on picking up the check. Some of these lunches were both going to be expensed, and yet they just had to be the traditional man of the meal. I’ve clients pay for drinks when I was the one pitching them. It’s like a battle between business and chivalry, or at least deeply routed gender norms. Men have a physical need to show that they can provide for women, no matter how you know each other.

This is why I absolutely love picking up the check for the men I work with. I enjoy seeing them struggle internally with their urge to pay the tab. I love the simple way that picking up the check, confidently and as if it was the most natural thing in the world, sends a message of power in the business relationship.

One of my former bosses joined her employees when we went out for drinks after work. We went to one of our accounts, a local martini bar, and had a couple drinks a piece. There five  men with my boss and me. As the evening got later and we all prepared to head home, she pulled out her wallet and paid everyone’s tab. She did it without making a fuss and insisting to everyone, “This is on me.” She didn’t act like it was a special treat. She just grabbed the check and threw her card inside of it.

That simple act demonstrated a type of control and power that I hadn’t considered possible. It’s quite possible that she went on to expense those drinks and the money didn’t come from her own pocket. It doesn’t matter though. Either way, she positioned herself as the powerful one in that group of people. With men who were twice her age and very often made condescending comments about their female manager, she showed that she was in charge. And I knew that it was a technique I would be borrowing from her.

We all agree that business offices shouldn’t yield to antiquated gender stereotypes. Honestly, it shouldn’t matter who picks up the tab at a business lunch. It shouldn’t be an issue for a woman to buy her male colleague’s drink. And yet, this is one gender bias that I find myself using to my advantage. If a man picks up the check, it’s a little expected. If a woman does it, she’s making a statement.

Of course the majority of your business meals or drinks will end with you each picking up your end, and that’s how it should be. But, every once in a while, a wonderful opportunity will present itself when I get to smile and place my card in the little holder without a word. I get to give a little, “Oh, you’re welcome,” as if I’m surprised that they even thanked me for it. As if my paying was just an expected outcome of the get together. And those moments are absolutely wonderful.

(Photo: Thinkstock)

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    • Lastango

      “I enjoy seeing them struggle internally with their urge to pay the tab.”

      “…And those moments are absolutely wonderful.”

      “…this is one gender bias that I find myself using to my advantage.”

      You are showing how small-minded you are.

      Should you pick up your share of the tabs? Absolutely. But if you think you can treat these moments as a victory march, and that no one will notice, you are badly mistaken. At a minimum, your companions will conclude your character is not equal to your position and that you are not suited to a future of truly senior responsibilities in which how you do your job affects many other people in important ways.

      That doesn’t mean you’re doomed. But you need to work on your own attitudes, not those of other people. And it’s worth being careful where we find our inspiration… truly serious people are not standing around high-fiving about how they rubbed someone else’s face in the mud.

      • LCT

        I disagree. There’s nothing wrong with taking pleasure in a technique you’ve found that both helps you get ahead (without damaging others) and “sticks it” to outmoded and inappropriate gender biases.

      • Lastango

        LCT, let’s be clear about what is going on here: (1) others are indeed being damaged, and (2) the mention of an outmoded gender bias is a red herring to excuse abusive conduct.

        To stop that red herring from confusing us, let’s consider negative articles about bad female bosses. Some of those have appeared on this site, and there’s no shortage of them on the web. A lot of us don’t even have to go outside our own experience; I’ve heard similar several times, from women alone and from groups of women. All the stories are similar — many women would rather report to a man, and they say so plainly. What has turned them off about women bosses centers around pettiness, competitiveness on a personal level, and the boss’s delight in humiliating other women. These bosses take pleasure in watching other people contort with discomfort.

        One key takeaway is that everyone knows what is happening. A boss who thinks she can secretly revel in these moments is kidding herself. (Notice there is no convenient way to blame that on men, or on outmoded gender biases.)

        Let’s assume for the moment that Lindsay Cross, the author of this piece, fundamentally wants others to respect her for her abilities and contributions. She can build a climate of respect by showing how she respects others, and making it clear she notices and appreciates when her associates respect and support each other. That is the mindset of a professional, and it is 180 degrees away from her current orientation. I’m not asking for perfection; we all have moments where we function below our own standards. But whenever Ms. Cross catches herself enjoying someone else’s pain, she ought to grab herself by the scruff of the neck, give a good shake, and say, “That’s wasn’t the leader I want to become.”

        Getting the tab can be tricky, even among groups of all men. Here’s a technique any woman or man can try. When heading out, say something like, “Bill and John, I really appreciate your contributions today. This one’s on me. I’m glad we have this chance to spend a bit more time together.”

        Another way: when the waiter first approaches, say warmly “I’m getting this one. (Or, It’s my turn…) Put it all on one check please.”

        Or use whatever phrasing works for you. This removes all the drama from when the check finally arrives, the waiter places it in the middle of the table, and the card is pulled out. Done with grace and style it’s a marvelous chance to position it as an expression of how we respect our associates and enjoy being together with them.

        Best of all, our senior-level-manager-to-be will have lived up to her own best understanding of what it means to lead other human beings.

    • Avodah

      I would say split it, or it really depends on who asked who.
      Ex: I am doing informational interviews, sometimes coffee meetings. I asked them, I therefore offer to pay.
      Ex: They are the client. You pay, period.
      Ex: Mutual business meeting, general networking, etc. Split.

      In every situation? Offer to pay. If they don’t accept- say “thank you”.

      Easy as pie. Wait, was there dessert?