“Does this Leadership Make Me look Fat”?

If you are married, dating, have friends and family . . . basically, if you are a human being living in our Western culture, the chances are you are familiar, whether as the “Asker” or the “Askee”, with the question,

“Does this outfit make me look fat?”

Yesterday I had a discovery call with a woman on her company’s “Wellness Committee”.  She had reached out to me about leading a mindfulness workshop for her organization. After asking a series of questions to learn more about their culture, their goals and their implemented programs, I learned these programs are not mandated. So then I began asking her questions about the attendance and the breakdown of managers vs. non-managers.  Her answer didn’t surprise me: only 2% of leadership had voluntarily participated in the 4 wellness programs offered to all employees in 2019.

In my idealistic mind, I always think, “Everyone strives to be better!” and then I am violently jerked out of my disillusion 20-seconds later with the reality check of scanning through my memory bank of leaders with whom I have personally worked and quickly remembering “No, no, no, nope. Not everyone strives to be better”.

So I ask the woman on the call, “Why do you think leadership doesn’t attend your wellness programs”?  Not surprisingly, she responded, “I don’t know”.  Now I could go down the motivation rabbit-hole and it would be very similar to all the studies conducted on why people DO or DON’T do things that would benefit them: quit smoking, make healthier food choices and the myriad of other practices that we all know promote wellbeing.

Which brings me back to the question of, “Does this outfit make me look fat”?  We all know this is a potential lose-lose question that often puts the “Askee” in a predicament. The obvious points here include, but are not limited to the following:

  1. The “Asker” asking the question is usually looking for a compliment or appeasement.
  2. The “Askee” has to make a choice on how to respond and that choice could potentially involve risk mitigation.

I happen to believe that the person asking the question has an inkling of the truth or they would not have asked the question in the first place and they are typically looking for a “soft pillow” of a response.  So why doesn’t the person answer the question for themselves? I think the answer lies in the fear of truly looking at reality. Revealing ourselves to ourselves is one of the most vulnerable and difficult things we can do.

Really seeing ourselves is almost if not always coupled with emotion, judgement, additional thoughts about our judgements such as defensiveness, denial or excuses.

We don’t know how to look with interest and curiosity. It’s even more difficult to reveal what we know to be true about ourselves to others, especially if we judge what is revealed as a weakness or at least, something we need to work on.

Somehow as leaders, we uphold this pretense that we’ve “arrived” and we’ve got nothing else to learn like the rest of the human beings.

Instead of taking a mindful look at how we really are, through the practice of self -awareness, many leaders seek the opinions of others with whom they work, yet really aren’t open to the honest feedback. And what’s worse is the people who are asked typically know this and tend to mitigate risk with their responses.

I think the same reason this woman’s leadership doesn’t participate in programs focused on wellbeing is the same reason people ask, “Do I look fat in this outfit”. If we can answer our own question with honesty, we can then join our workforce in the “human pool and become a better swimmer by being a part of the human being swim team.  (Regularly swimming trends toward a reduction of questioning, “Does this outfit make me look fat”).

If you are a leader, the next time you are invited to an optional workplace programs, before you delete the email, I’d like to offer you another invitation.  I invite you to take a mindful moment, here are the steps:

  1. Stop what you are doing
  2. Notice any sensations in your body (it may be your hand wanting to move to the computer to delete the email)
  3. Notice the feeling tone, unpleasant, pleasant, neutral
  4. What are the thoughts you are having?  “I’m busy and all I want to do is delete this email”, “Why am I on this distribution list”. What is the quality of your mind? Calm? Edgy?
  5. Then, ask yourself, “I value engagement with my employees. What is a pattern I want to learn how to change?

When you become aware of your patterns, you are now connecting the dots. Congrats, you just practiced self-awareness. Awareness gives you the space to make a choice on how to respond, the choice to make a change instead of reacting.

This is a highly abbreviated human case for mindfulness that I have translated into a business case to help the leaders of this organization realize that exploring mindfulness is just good business sense: becoming more self-aware in an effort to show up as a better leader for others pays.

Mindfulness saves companies money because the practice helps people be well and well people increase the likelihood of meeting desired outcomes.

People want the presence and attention of their leaders. 

A critical factor is creating and sustaining job satisfaction, productivity and a healthy bottom line is workplace engagement…Leadership is the cornerstone of engagement.

–Michael Bunting, The Mindful Leader

And by the way, my trick to answering the “Does this make me look fat?” question is;

“Hmmm, what do YOU think”?


Shelley Brown
Shelley Brown
I’m Shelley Brown, A "Type A" Meditator. I spent 25 years in corporate sales, climbing the ladder and making great money, all while stress slowly consumed me. Then, after a particularly difficult time, I decided it was enough. So I learned how to address my stress. Then, I became better at my job AND my life. Today I teach sales leaders and their teams how to mitigate stress so they can be human beings at work and win more deals. And, BONUS! I help teams cultivate a sales culture that drives continual success. I’m not your typical corporate mindfulness trainer. In fact, I’m probably a lot like you.

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  1. Shelly, what a great title to pull in the reader! And this is so profound: “Revealing ourselves to ourselves is one of the most vulnerable and difficult things we can do.” Isn’t that the truth? Thanks for a nudge toward further self-reflection today.

  2. Wonderful article, Shelley! The title made me laugh out loud! Self-discovery takes great courage for it involves being willing to see patterns about yourself that most likely cause pain and discomfort, especially if you have this view of yourself as a “good” person. The honest assessment of your behavior patterns that are not as effective as they could be can cause you to want to reach for another gluten-free pumpkin chocolate chip muffin-you know they took out the gluten and replaced with lots of sugar! Each person must burn through the pain in her heart of uncomfortable truths to find the way to freedom. Vulnerability requires courage. Thank you for this article!

    • Inspiring laughter with a story title! Yay! Gorgeous comment laced with such deep wisdom. Such a visceral feeling came over me when reading “burn through the pain in her heart”. Such an intense verbal capture of the impermanence of what we no longer have to hold on to…burn it, it’s now ashes… dust…we are here