What to think about (and clarify) before you embark on planning for the future.

In our Dear Reboot series, Reboot coaches aim to provide guidance on common leadership dilemmas. If you’d like to submit a question to be considered for our Dear Reboot column, email us here.

Dear Reboot,

I have a vision for the new year for the company that I’m excited about. How do I get my team on board, involved, and strategically planning for this? I’m worried that they will think this is a high-falutin idea and will shoot it down or won’t jump at it. …

Moving + learning + reflection will get you across your own finish line.

I was tired, defeated, and upset. My legs had nothing left. I watched as the ultra-marathoners passed me by on their way to the finish line. I cringed to see them swiftly and steadily outrun me, even though their course was 35 miles — three times the length of my own race’s distance.

I’m an executive coach and, intellectually, I know that success is not measured by productive outcomes, but rather the material impact productivity has on the individual’s experience. …

Disentangling Fact From Fiction

“Becoming a leader is synonymous with becoming yourself. It is precisely that simple and also that difficult.” — Warren Bennis

What does it mean to become yourself? The answer does not always appear quickly and in high definition. It requires effort and time and happens within our heads and hearts, not while reading the most current blog post or article. Becoming ourselves requires understanding ourselves. Understanding that who we are now is influenced by what happened to us in the past and the myths we create about why it happened.

When we use a word like…

An exercise for reflecting on all that has happened over the past twelve months.

This time of year, it’s common for us to reflect on all that has happened over the past twelve months. It’s a natural time to look back over our shoulders, to see what has shaped us and supported us to be who we are today and to be with the richness of the life we are living. It’s also a wonderful time for us to look back and take the opportunity to express our gratitude and appreciation for all that has mattered to us.

By expressing…

Even when floating through the air of uncertainty, you can still find the ground.

One of the hardest and best periods of my life took place in the spring of 2014. My wife and I were pregnant with our first daughter, Emme, I had just been part of shutting down a startup I had poured everything into over the prior 3 years, and I had absolutely, positively, no idea where or what I’d do next. It was terrifying. It was energizing. It full of scary outcomes, and endless possibilities.

Closing the company down had been like letting go of the…

How to find resilience during challenging times.

“Stressed people are creatures of habit who lack the capacity to choose a different response. They keep doing what they’ve always done, moving deeper into lostness without any means to recognize where they are. If we are to reawaken our brains and our precious human capacities, we have to create the conditions that support thinking and reflection. We have to actively cultivate insight through practice.”

— Margaret J. Wheatley, So Far From Home

If anything, 2020 has taught us much about stress and how we handle it. There are only so many feelings…

What would happen in your start-up if you and your co-founders committed to open, vulnerable conversation?

The list of daily challenges for a co-founder is just about as long as her to-dos. If you are wired to start a company, design a product, create solutions for the world’s biggest problems, or raise millions of dollars to fund an idea conjured up over a couple of microbrews, then you are also adept at managing those challenges, one by one, day by day.

That ninja skill makes you good, even great, at what you do. It is probably a big part of…

Time is just one unit of measurement for our learning.

We often measure progress by time — 14 days until launch, six years since I took the leap, 27 iterations later, employee #771. But true development, of both systems and individuals, is not actually contingent on time at all. Progress is contingent on learning.

So why do we rely on the measurement of time, and what exactly is time’s role?

Most of us get trapped into thinking that time is linear, one thing after another, on a great line back into history and forward into the future. …