David Hassell – Founder and CEO of 15Five.com

[quote style=”boxed”]Sleep. Exercise. Meditate. I admit that I don’t always do them regularly, but when I keep up with these my ability to do what needs to be done is like night and day. When I get enough sleep, take care of my body, and center my mind, I am so much more productive and creative at my desk. I produce so many better outcomes.[/quote]

David Hassell is Founder and CEO of 15Five.com, a SaaS company with a powerful and simple solution that gathers critical insights from employees in minutes each week, enabling informed management to get the visibility they need to boost engagement and drive alignment across their entire teams. Follow David on Twitter @dhassell and @15Five.

Where did the idea for 15Five come from?

The idea behind 15Five originated in the 1980s with Esprit founder Doug Tompkins, who asked all of his employees to spend 15 minutes writing a report that took their manager no more than 5 minutes to read, so that his employees would feel heard and he would have better insight into the workings of his company. Doug shared it with his friend Yvon Chouinard, founder of Patagonia, who used the practice to keep his employees engaged and to stay informed even when he was out of the office climbing and surfing for up to 6 months each year.

Later, Brad Oberwager, CEO of Sundia turned the practice into software, allowing key information to be automatically rolled up to the highest levels of an organization. Brad shared his idea with me and I decided to take it to next level, allowing reports to be turned into conversations and creating the vision that 15Five could become the communication backbone for thousands of companies, where employees could be supported in doing their best and most creative work.

What does your typical day look like and how do you make it productive?

Much of my time is spent with my 6 month old baby Connor, and my 2 year old baby 15Five. The key to my productivity is to dedicate specific chunks of time to get into flow with whatever I am doing. Whether I am preparing a presentation, meeting with investors, or answering interview question, I put all of my focus on the task at hand. Then I take several minutes to reset before becoming engrossed in the next one.

How do you bring ideas to life?

I allow ideas to flow freely, and write them down as they come without judging them. When one is really calling to me, I go build it and sell it to the team and customers to see how it is received.

From there, I define who will be involved in the project and I manage the team as it comes alive. It is critical to get clear on priorities, and decide what you are going to do and what you are not going to do. This process becomes extremely challenging if your focus is spread too thin. So clarity allows all stakeholders to retain enough individual and collective juice to get it done well.

What’s one trend that really excites you?

I am a huge fan of wearable activity tracker technology. Basis, Nike, and Fitbit all have real-time feedback devices to monitor my activity and healthy (or not so healthy) behaviors. Living into greater health and vitality is one of my most important personal values and a cornerstone of the 15Five culture.

What is one habit of yours that makes you more productive as an entrepreneur?

Ha. Reading 15Five reports every weekend. I know that it sounds self-promotional, but it’s true. The feedback that I get allows me to get an in-depth look at the company. I can manage the business priorities more efficiently across all teams, and prevent small issues before they become full-blown disasters.

What was the worst job you ever had and what did you learn from it?

Right out of college I worked as a technical analyst for a massive, DC-based consulting firm called American Managers Systems. I began working in their New Jersey office which was beige with beige cubicles. From 9am until 7pm I worked in a windowless office attached to a windowless server room at the end of the hall. Within a very short period of time I was promoted twice and my salary nearly doubled, but the job had very little meaning and was far from life affirming.

I requested to get out into the field and was relocated just south of Denver. I was consulting at a big insurance company, whose standard hours were 7am to 3:15pm. At 3:15 on the dot I found myself working all alone for the next seven hours. I was a cog among other cogs who were clearly unenthused and disengaged, showing up for their paychecks and running out the door at the bell.

I thought, ‘is this what it means to have a career? Spending 70-80 hours a week around people who just did the minimum?’ It felt more like a life sentence. Was I doomed to spend my life at my keyboard at computer #117 in cubicle-land? All my energy was going towards something where I felt no sense of service or contribution. I was trading the most active and energized time of my life to spend those few moments before and after work doing the things I really cared about.

My physical, mental and emotional health are incredibly important. I need to work in more natural, less beige environment and pursue my passions with others who desire the same. I learned that fulfillment from work is paramount, so I walked out the door and onto the entrepreneurial path.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Sleep. Exercise. Meditate. I admit that I don’t always do them regularly, but when I keep up with these my ability to do what needs to be done is like night and day. When I get enough sleep, take care of my body, and center my mind, I am so much more productive and creative at my desk. I produce so many better outcomes.

High performance comes at a cost. You can’t add more and more to your plate and think that you are just going to power through. It eventually takes its toll. Without rest and self-care we all quickly become ineffective.

What is one strategy that has helped you grow your business? Please explain how.

Ask questions. If you are open to some tough responses, along with the positive, questions can generate amazing new ideas, new answers and new possibilities.

I find that customers, employees, and colleagues are a wealth of untapped ideas and opinions just waiting to be asked. Often the most valuable information comes from negative experiences–going back and asking unhappy customers why they left or investors why they passed on the opportunity.

Asking well-crafted, intelligent questions continues to give me insight into what my customers and potential customer want, need, love, and hate. The responses help me better understand market trends and opportunities, and allow me to streamline the business structure.

Questions are the gateway to feedback that helps us improve the product to be more relevant and useful for our customers. And when those customers are delighted, they recommend the product to other businesses.

What is one failure you had as an entrepreneur, and how did you overcome it?

When I was raising our angel round of financing, I had made an assumption that one of the first investors who was talking about a really large check would follow through. They kept putting off the decision, but I was attached to my belief that it would close. When they decided to pass in the final hour, I was devastated. This was in December, and I was always told that it’s impossible to raise funding around the holidays.

My wife helped me to overcome the feeling of defeat by reminding me that other people were not going to dictate my future. Feeling empowered by that shift in perspective, I made some calls and closed the round before Christmas.

What is one business idea that you’re willing to give away to our readers?

Nice try, Ideamensch.

What software and web services do you use? What do you love about them?

From our humble beginnings we have been a globally distributed team. So we rely heavily on a variety of tools to stay in touch and collaborate. The team use Zoom for video conferencing during our ‘Daily Boost’ every morning. We can share our screens, and even record meetings and presentation. Zoom can handle 100 participants so it’s nice to know that they will grow as we do.

I also use Boomerang to manage the barrage of daily emails. The application lets me remove an email from my inbox and schedule it to return at a future date. I avoid losing important emails that are sent way in advance of my needing to take action on them.

Baydin also created Inbox Pause, which allows me to get into an uninterrupted flow of productive work. Emails are placed in a hidden folder until I am ready to receive them. Senders can even receive notifications that they are paused.

What is the one book that you recommend our community should read and why?

The Power of Full Engagement by Tony Schwartz. Being an entrepreneur means starting on a path of potential burnout, where you get engulfed in business and keep going and going. With increased demands comes the risk of running yourself down.

There are unlimited options for time management courses, and yet time doesn’t seem manageable. Schwartz offers that we should manage our energy, not our time. I have learned to be intentional with how I manage my relationships and actions within a span of time. Just as important as what and how, is understanding and managing your own energy levels. That has been instrumental in avoiding burnout.

What people have influenced your thinking and might be of interest to others?

That’s a long list. Tony Hseih, and Verne Harnish for sure. And I have a priceless group of advisors: Chip Conley, Hetin Shah, Cameron Herold, and Vishen Lakhiani of Mindvalley. Simon Sinek’s thought leadership around finding purpose has been very influential. I also recommend his book, Start With Why.


15Five on LinkedIn:
15Five on Twitter: @15Five