David Hassell

David Hassell is a serial entrepreneur and presently Founder & CEO of 15Five, a SaaS company focused on helping individuals and organizations reach their highest potential. Hailed by Fast Company as the “15 Most Important Minutes of Your Work Week” 15Five creates an internal communication process that enables the most important information to flow seamlessly throughout an organization, to surface issues before they become problems, to celebrate wins, discover great ideas and stay tuned in to the morale of the team. David formerly served as President of the San Francisco chapter of Entrepreneurs’ Organization and was named “The Most Connected Man You Don’t Know in Silicon Valley” by Forbes.

Why does the world need a work revolution? (In other words: the way we’re working isn’t working. Why not?)
The world, and especially the US, needs a work revolution because the vast majority of people are living work lives where they’re completely uninspired and unengaged. The demands of our always-on, digital work lives keep growing, and in the US workers now work longer hours than anywhere else in the world. I’ve seen first hand the difference in the potential of a human being when they’re inspired and engaged in what they do…when they’re working on something that’s part of a larger mission, or deeply meaningful to them. Living in this old paradigm of “I’ll just work my 40 years, and THEN I’ll live the life I want to live” is not only a fallacy, but a tragedy. It’s a waste of our potential and of our creativity and joie de vivre. If we’re going to spend the vast majority of our time at work, then why not have it be a requirement, if not a commonplace standard, that the work we do be tied to something we care about, that fills us and fulfills us?

How are you or your organization reinventing work in some way (big or small)?
We’re challenging the notion that work and collaboration needs to be done at a specific time and a specific place. We all of a sudden live in a world where laptops and tablets are the norm, where we have nearly ubiquitous wifi and if not fast LTE networks where we can communicate and collaborate with anyone anywhere in the world. One of our core values is to Embrace Freedom & Flexibility. To take advantage of this as a strength, allowing us to flexibly come together in person when we need to, or travel and work and stay connected with that makes sense. It gives us the ability to simultaneously live great personal lives while doing our best work, which in turn is one of the reasons why we’re able to do our best work.

Why do you do what you do?
I do what I do because I’m committed to people achieving their highest potential in life, however each individual defines that for themselves. With 15Five, we’re working on that at the organizational level. I’ve always been curious about how individuals reach their potential, but organizationally it’s exponentially more complex because you now not only need to have every individual committed to and operating at their best, but they all need to do that together — communicating, coordinating and collaborating.

By focusing on creating candid communication practices that eliminate bureaucracy through transparency and flattening the hierarchy, and give employees an outlet to communicate so that their concerns don’t turn to negative and toxic gossip, we’re helping to create better organizations that are simultaneously much better equipped to fulfill their missions and are wonderful places to work. This in turn goes back to helping to create environments, where people are valued and have the opportunity to develop, grow, be their best and achieve their own individual potential.

What kind of art (any kind) do you like and why? Any recommendations we should know about?
I’m personally a big fan of entrepreneurship. Unlike most people, I see entrepreneurship as a creative endeavor and entrepreneurs as artists in a sense. Much like a painter or musician, an entrepreneur sees a vision of the future that does not yet exist, and utilizes his or her will, knowledge, and resources to create it in reality.

The Apple that Steve Jobs created is one of greatest entrepreneurial pieces of art of our time. He ultimately built an organization that was designed to, not only continually innovate in new markets, but that was designed to out-innovate itself time and time again, essentially running a race against it’s own best standards in many cases over what the rest of the marketplace was doing. The intention and values that went into creating that organization have been an ongoing inspiration for me.

What is one specific thing your company does that makes your culture unique and/or different?
We value oscillating between co-working collaboratively and having solo focus time. We have no fixed offices. Instead, we fluctuate between working independently on our own, collaborating at various shared spaces in and around San Francisco, or convening on another location for quarterly strategy retreats.

We also all value what we call “high-leverage productivity” so we’re always examining how we do our work to see if we can find ways to produce much greater outcomes relative to the time and energy we put into our work.

What is one discipline/industry totally different from your own that has inspired you? How does it impact your work?
I have to go back to Apple here. Their ethos around focus and simplicity have inspired me and influenced everything from the way I run my business, to the way we design our products.

I have a concept and design value that I call Elegant Simplicity, and the iPhone is a perfect example of it. I believe that simplicity lives on both sides of complexity. There’s the simple-simple, that anyone can do, and then there’s the elegantly simple, which is taking something that’s inherently complex and coming up with a new and beautifully simple solution. The iPhone did this by taking what used to be a fixed and complex device (the cell phone) and by creating a single touchscreen with one big button on the front, created a device with the possibility for hundreds of thousands of uses, including simply being used as a phone.

What’s one tangible and concrete technique other organizations should use if they want to create a more human and/or meaningful place to work?
Listen to your employees, often. Ask them for regular feedback. Every single person has their own unique perspectives and creativity, and can offer valuable insights if you’re willing to listen. Furthermore, if you demonstrate that you care about them, really care, there’s a much higher likelihood they will care about their job and the business. Everyone wins in this scenario.

What is one surprising thing we should know about you?
I was born with Tourette’s Syndrome.

What piece of technology (other than your laptop/smartphone/tablet) could you not live without and why?
My 30” Apple Cinema Display. This is one of the keys to my solo productivity, allowing me to simultaneously reference between my current work or email, and other references, side by side without having to switch back and forth.

What does your preferred work environment look like?
I love either a completely clear desk with a monitor, trackpad, keyboard, 30” monitor and headphones or an open collaborative space to work with others with plenty of whiteboard or chalkboard walls to write on — but do not like to mix them at the same time. i.e. I like to be isolated for my personal work time, and very interactive and collaborative when I’m with my team.

What do you do for fun?
On a daily basis I like to work out and meditate before starting my day, and when I have more time, I love to travel to do things like go kiteboarding or skiing.

How do you stay productive throughout your day?
I make sure to structure my time very specifically, focusing on the most important things first thing in my work day, using timers to do uninterrupted focused work sessions of anywhere between 50-100 minutes at a stretch, and taking downtime breaks in between sessions.

Where in the world are you?
San Francisco, CA

How can people connect with you?

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