How Falling Into the Gap Taught Me to Be a Better Boss

Posted on Apr 25, 2013 | 4 comments

“Tell me about your best boss and your worst boss. What was so great or horrible about working for them?”

It’s one of my go-to interview questions. It tells me a lot about a person’s general outlook, whether they are able to distinguish between a good and a bad boss, and what it is they’re looking for in a leader.

On a recent interview, as a candidate went on and on about a bad boss in way too much detail, my mind began to drift to my own answer. (Note to future candidates: I can only listen to a whiney bullshit victim story for so long.)

I wondered, who WAS my best boss? What WAS the best company I ever worked for?

I had to stifle a smile when the answer came to me—my management team at the Gap. I was a little shocked that my answer took me all the way back to a part-time college job. It was kind of disheartening that I couldn’t think of one boss in my corporate career who stood out as “the best.” It just seemed like that should be the “right” answer.

I started worrying what my answer said about me. And here’s what I realized…

My bosses at Gap had “drunk the Kool-Aid,” as they say. They BELIEVED in the mission of the company. Our shifts started off with one-minute-meetings to bring us up to speed on the company’s focus for the day, often with additional explanation of how our daily goals tied into the week’s, month’s and even the year’s goals.

Every Gap employee started his or her day with a clear intention that tied their contributions back to the company’s vision.

So when I was “perfect-folding” (that’s Gap-speak, by the way), re-sizing and replenishing a wall of 1,500+ pairs of jeans, I was crystal clear on how that tedious task tied into the company’s vision. I wasn’t just folding a bajillion pairs of jeans, I was creating an optimal shopping experience for my customers. Yes, I too drank the Kool-Aid at Gap, Inc. And it was good.

But why DID I love working at the Gap so much? What made that management team rise to the surface as my “best” bosses of all time?

The answer is simple. They were crystal clear in how my efforts contributed to the Company’s vision. They told me in very precise terms at the beginning of EVERY freaking shift!

I’ve rarely seen such clarity, leadership or teamwork since.

The Gap really got it. Their vision leapt off the pages of their internal communications and became a living, breathing force within the company.

If your Company’s vision is just some statement you trot out once a year for new hires or annual meetings, consider the making the following changes to breath new life into your people:

  • Connect the dots – tell employees how routine (even unpleasant) tasks, changes in procedure, or new corporate initiatives relate to the Company’s vision.
  • Pour it on thick – your vision should permeate your internal communications. Consistently bring your peoples’ attention back to the Company’s reason for being.
  • Shake things up – don’t have time to meet regularly with employees? BULLSHIT! I just told you about a one-minute meeting that shaped the best work experience I ever had. Stop thinking of meetings as hour-long death sentences. Check in more frequently with your people (and yourself too for that matter).


  1. Great column Jack! I have the words “Connect the dots” written everywhere in my office. It’s so crucial and so often overlooked. I LOVE the idea of a one-minute meeting. Thanks for some great thoughts.

    • Thanks Karen! Connecting the dots is SO overlooked. I’m glad you’re mindful of it. Employees really need to know how your requests connect them to the bigger picture. By the way, I’m reading “Death by Meeting” now and getting some great ideas for a future blog about meetings! Still, the one-minute meeting appeals to me the most.

  2. Hi Jack – another great post. Loved the recommendation to reshape staff meetings from one hour-long death sentences to one minute check ins! I’ve been reading the fascinating book, “Drive: The Surprising Truth about What Motivates Us”; I think you’d find it another resource for your leadership/boss arsenal.

    • Thanks Alysa! I wish all meetings could be so short! Alas, I think the rule is to not follow the rules! Just because staff meetings have always been an hour long doesn’t mean they have to stay that way. “Drive” is on my radar as a must-read. It’s a Daniel Pink book, right? Maybe I should post my reading list soon. It’s a long one, but full of some great reads for business owners and managers. Thanks for the idea!

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