When asked during an interview on The Breakfast Club to describe Kanye West’s approach to pushing hip hop’s boundaries, Jay Z responded by saying:

“Someone has to experiment and do it first…[Kanye’s] actually like the cowboy. You know, he runs over the hill. And…the [enemy] hits him with the arrows…he comes back, he’s like ‘Yo! There’s a lot of them over there!’ And then we go over there and conquer.”

My last boss described me as both “the most delightful” person he’s ever led, as well as “the most difficult.” Delightful, in part because I was an overzealous pioneer in the field of higher education marketing – I led a first-of-its-kind marketing team to establish our university as a national leader in online student engagement. Difficult, in part because my management style was anything but orthodox — that very same team would set their own schedule, regularly work from home, and enjoyed unlimited vacation days. Was any of this approved by human resources? Of course not. To make matters worse, I actively encouraged my team to break the rules of our institution.
As an entrepreneurially-spirited worker operating within a traditional corporate environment — an “intrapreneur,” if you will — I believed that the only way I’d get award-winning work out of my team of millennials was by creating creating conditions conducive to supporting both the way they worked, as well why they worked. And while my boss was supportive of my experiments with this results-only-work environment, my lack of subtlety and discretion regretfully put him in some difficult positions; I went from shooting first and begging for forgiveness later, to firing blind and telling the world about the unruly mess I made.
Now, could I have taken a more delicate and thoughtful approach to unlocking workplace flexibility? Absolutely. But was I patient enough for human resources to officially change its policies to keep pace with my generation’s growing expectations in a rapidly evolving workplace? Absolutely not. The responses to my recent diatribes against traditional management styles as well as my manifestos on managing the next generation have provoked some very important questions about the future of work. One criticism in particular prompted this entire piece. My friend Sharmin Kassam posited the following:

How do you employ that train of thought to workplaces so rooted to the traditional mindset? There are so many industries growing into what you mention, which is great. But there are still equally as many who dominate key industries (for example, construction), and still don’t see that change. Structure is good, micromanaging, not so much, and that’s the issue that’s hard to have a conversation around.

The question of how to unlock workplace flexibility in a more traditional organization is one that I wish I had an easy answer to. While the rebellious approach at my last job was effective, it was also chaotic and stressful. Not to mention, I started my campaign with a significant amount of permission space. And though I’m certain that inflexible organizations will fail to attract and retain top millennial talent, I’m also certain that navigating change without a sound strategy can be costly. If I had less influence & social capital but more time & tact — if I could go back and re-advocate for a flexible workplace in a more delightful rather than difficult manner — this is how I’d do it:


Before you start your campaign, the following pieces must be in play. Without them, you risk losing your job.

  • Be Good at Your Job: Be productive and indispensable. Before you can advocate for a flexible workplace, you need to be valuable to the organization. It’ll make leadership think twice before taking the easy route and letting you go, rather than bending their policies to retain you.
  • Keep Your Portfolio in Ship Shape: A place for everything, and everything in its place. Use Asana to keep your tasks in plain sight, Slack to stay in constant contact, and Google Drive to keep files organized. Create a system that allows you to work remotely and transparently.
  • Be Known For Showing Up: Develop a reputation early on for punctuality, and following through. Don’t give older generations the satisfaction of stereotypes coming to life by being tardy, or worse, lazy. Use Calendly as a way for people to know when you’re available for meetings.
  • Have Structured 1:1’s: Create a feedback loop with your boss that allows you to plant the seed for a more flexible workplace. I use WorkLife to keep a paper-trail of such conversations. Use these 1:1’s to bring up your challenges with the status quo in a constructive way.
  • Brace For Impact: It’s unlikely that people will acquiesce to these changes easily. You’ll probably have to burn through some social capital to help facilitate the transition. Therefore insulate yourself from the inevitable temporary discomfort of change by nurturing relationships in advance.

The Campaign:

Once you’ve created enough permission space for yourself, here’s how to go about making your workplace more flexible.

  • Plant The Seed: Practice “inception” on your colleagues. Keep them in the loop with regards to what you intend on doing so that it doesn’t come to them as a surprise later on. To prime them, share your learnings about flexible workplaces internally, as well as through social media.
  • Track Your Time: How long does it take you to get tasks done? How much time do meetings consume? What about your commute? Analyze your time expenditure to pinpoint where you’re losing productivity each week. I use Toggl and Rescue Time to help me visualize this.
  • Present The Data: Without data, you’re just another person with an opinion. Here’s the infographic that you need to share with your boss. Here’s the study that you need to share with your boss. Make sure you root your asks in sound research (both external, as well collected from your time-tracking above.)
  • Start Slow: Don’t start working from home every day of the week. Start with a half-day. Then a full-day. Then a few days. And if you need to go slower, then gradually expand the geographic radius from which you work. Start with the coffee shop across the street. Then across the block, and so on.
  • Make Yourself Available: Create a protocol for people to get in touch with you both synchronously and asynchronously. I’d go as far as writing out a sequence, ie. “If you need a response in a day, e-mail ; if you need a response in an hour, text ; if you need a response immediately, call.”

Follow all ten of these jabs, and you’ll have no problem landing a big right hook. Ultimately, your campaign should advocate for one or more of the following configurations to escape the 9–5 bind:

  • Compressed Work Week
  • Remote Working
  • Early Start, Early Depart
  • Results-Only Work Environment
  • Part Time

By the end of my campaign, I developed an apocryphal reputation for rarely being at my desk. The truth is, I was always hard at work. Just not in the way that critics of my campaign wanted me to be: tethered to my chair (optics), and readily available for interruptions. There was no way I was going to let my team’s work be compromised by reactivity and distractions. Otherwise, we would’ve never been able to achieve the feats that we did. In retrospect, my heresy was necessary to rile up millennials across the organization who looked to my team as a blueprint. In fact, it was only less than a month after I left the organization when a formal flexible work policy came into effect.
I was lucky that my boss championed my team’s work, trusted my intentions, and supported most of my management experiments. And while I do have some regrets about being a bull in a china shop in order to unlock complete workplace flexibility, I rest easy knowing that my campaign played a significant part in attracting and retaining top millennial talent. There was, however, a more tactful and elegant way to go about all of this. One that didn’t require running over the hill and getting shot with arrows.

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This post was originally published on LinkedIn.