How an Enterprise Founder Improves his Leadership With Good Habits

Peter, our CEO, and Co-founder, once said: “I can’t imagine how much impact the small features of Habitify can have on people’s lives.”

He said it after reading the story about Christopher Villar, Founder, and Chairman of a 13-year enterprise Frontpoint. I couldn’t express my excitement when Chris, with his tight schedule, agreed to share his stories with us. And like Peter, I was taken aback by how much impact Habitify has had on his personal and professional life. 

Let’s welcome Chris!

Hi Chris, do you mind sharing your current habit mechanism?

I actively add & remove habits based on behaviors that I’m working on, usually related to self-growth.  Some of my current habits include daily meditation, daily journaling, and a morning review of my current goals for the quarter along with priorities for the week.  

Why did you decide to use an app to track your habits?

I use Things as my todo list app to manage my projects and actions and have long used David Allen’s Getting Things Done workflow.  I used to put habits and todos in the same app, but have found that separating my daily habits helps me keep extra attention on the behaviors I’m working on - so they don’t get lost in my todo list.  While I like the concept of pen & paper, I always come back to using an app -- it’s always with me, can give me reminders, and I find it more actionable.

You mentioned “actionable” so I guess you must have made a lot of implementations towards a better self. Have you ever stopped and reflected on how much you have actually improved?

I think of habits as the things that eventually become part of my daily & weekly routines.  In a busy world with lots of distractions and a heavy workload, it’s easy to let self-growth and inner-work go by the wayside.  Over time, habits -- and the act of treating habits separately from my overall todo list -- have helped me improve my health, increase mindfulness, and ultimately become a happier person.  I think that’s also translated into being a more self-assured leader.

I use Apple Health to measure mindfulness minutes -- take a few minutes to stop & breathe throughout the day and doing meditation in Headspace.  I also use an app called Moodnotes, which tracks “happiness” and is a nice app for keeping track of both your positive & negative thoughts.  It’s based on the Cognitive Behavioral Therapy framework.  However, beyond the tracking, the real impact is on how all of this makes you feel and how it improves your life.  Through these practices, I’ve learned to slow down, enjoy the present moment, find joy in simple things, and lighten up a bit… all of which makes me feel more connected to friends & family. 

Career-wise, I think it has helped me be more productive, but also more in touch with the human side of leadership. Since I use habits mostly for self-growth and inner-work, the benefit professionally is constantly making progress to being what I hope is a better leader & colleague.  It’s helped me be more collaborative, less intense (while still being goal-directed and action-driven), more humble, more patient, and more present.  Those are all leadership qualities that I admire and are all ones that I’ve used habits to help grow over time.

Along your journey, what was the most memorable experience? 

I used to try and take on too much at once.  As a result, certain things would remain on my list of goals for months or even years.  I think the biggest thing I’ve learned is the focus.  I’m a big fan of John Doeer’s Objectives & Key Results framework.  We use that framework to set quarterly goals at work and I use it to set personal goals every quarter for myself.  At least one of those goals is always self-growth related and I use my habit app to hold myself accountable for making daily progress.  I still set goals & worked on self-growth. But, the structure & cadence of OKR's has helped make that process easier and more routine. I also force myself to never have more than 4-5 objectives in a quarter… and never have more than 3-4 key results per goal.  By having the discipline to focus on what’s most important and “say no” to things that aren’t aligned with my top priorities, I find that I actually accomplish a lot more progress toward my ultimate goals, both professionally and personally.

Could you share some productivity tips you’ve learned for yourself?

I’m a big fan of having (and writing down) a clear vision for the future and often focus on a 1-2 year time horizon in doing so.  I revisit that a few times a year to make any tweaks.  From there, I think the most effective tool for productivity is using that vision to drive clear goals and to have a system to break those goals down into the actions that are needed on a daily and weekly basis to make progress.  

It’s fine to have lofty visions and big annual goals.  But it’s the day-to-day and week-to-week work that actually drives great execution.  One of my long-standing habits is reviewing my quarterly work & personal goals for the quarter each morning as well as the priorities I have for the week in order to make progress toward those goals.  It’s usually the first thing I do each morning because it sets the tone for the day -- what I need to do, how it connects to my larger goals, and why those goals are important (i.e. how they connect to my bigger vision).

‍