Supportive — I studied and performed improv comedy for 5 years. During those years, our team developed a ritual before we went on stage where each teammate told every other teammate “I’ve got your back.” I quickly learned that the leaders of the team were not the funniest performers — they were the leaders who were most supportive. Before the show, during the show, and after the show, they had your back.

We are living in the Renaissance of Work. Just like great artists know that an empty canvas can become anything, great leaders know that an entire organization — and the people inside it — can become anything, too. Master Artists and Mastering the Art of Leadership draw from the same source: creation. In this series, we’ll meet masters who are creating the future of work and painting a portrait of lasting leadership. As part of this series, we had the pleasure of interviewing Jason Lavender.

Jason Lavender is the co-founder and CEO of Electives. He spent 12+ years in HR consulting and health tech before graduating with his MBA from MIT Sloan and starting Electives with Krikor Dzeronian. Jason is passionate about changing who we get to learn from at work.

Thank you for joining us. Our readers would enjoy discovering something interesting about you. What are you in the middle of right now that you’re excited about personally or professionally?

This is very new for me, but through a series of random events, I have become very interested in exploring various Japanese traditions, cultural norms and terms. The urge likely began last year as two friends from Japan talked about planning a group trip to tour their country. The interest has grown ever since.

Earlier in the year, I explored “Ikigai” — the Japanese concept of finding purpose in life. Ikigai happens at the intersection of what you love, what you are good at, what the world needs, and what you can be paid for. Working at Electives and bringing the world’s experts into people’s lives provides me with exactly that feeling.

When I was watching the World Cup this fall, I admired and respected the tradition of “atarimae” — leaving a place cleaner than you left. Japanese soccer fans cleaned the stands and the players cleaned their locker rooms. If we all left places a little better than how we entered them, imagine the impact.

Most recently, while I was trying to catch up on all my unread books on my bookshelf, I learned about the practice of tsundoku, which is the phenomenon of acquiring reading materials but letting them pile up in one’s home without reading them. The important reminder, as you are surrounded by unread books, is that there is “so much you still don’t know.” I think that is a phenomenal reminder and a motivator to always be learning.

I’m curious to continue to explore traditions and more importantly, apply the ones that stand out to me in my everyday life.

We all get by with a little help from our friends. Who is the leader that has influenced you the most, and how?

One of my best mentors is a boss of mine from Willis Towers Watson. Her name is Julie, and I would describe her as the ultimate enabler. She always found ways to enable me to become a better version of myself. I would often do things that I never thought I could do, but with her support, encouragement, and confidence in me, they felt doable. In the 2–3 years I worked directly with Julie, my career took a jump in all the right directions, including the encouragement to pursue my MBA from MIT Sloan, which was life changing.

Sometimes our biggest mistakes lead to our biggest discoveries. What’s the biggest mistake you’ve made as a leader, and what did you discover as a result?

A few years ago, I shied away from constructive feedback. I’d offer it in small doses, but not consistently enough and not meaningful enough. The obvious mistake was I was putting my own comfort over the growth of others.

Now, I view feedback as a gift. One of our Electives instructors, Rachel Pacheco, teaches a class on feedback and she has this great line, “every great feedback conversation should end in motivation.” I am now excited about the opportunity to see something where I can hopefully share a perspective and be helpful, as well as motivating.

How has your definition of leadership changed or evolved over time? What does it mean to be a leader now?

Early in my career, I saw leaders at our company as people who made the important decisions — what’s the strategy for this year, where are we investing, what’s the hiring plan, etc. The leaders were solving the tough problems.

Now, I see leaders as people who enable others to make important decisions. Great leaders build great teams and great teams solve tough problems.

Success is as often as much about what we stop as what we start. What is one legacy leadership behavior you stopped because you discovered it was no longer valuable or relevant?

I needed to stop letting everything feel so personal. As an entrepreneur, we all know there are many ups and downs. There was a professor at MIT, Bill Aulet, who taught a class called Disciplined Entrepreneurship, and the term he used to describe founders was “anti-fragile.” It could not be more true. There are so many “Nos” and challenges and setbacks, in general, that you can’t take things personally and you can’t be fragile. You will crumble.

What is one lasting leadership behavior you started or are cultivating because you believe it is valuable or relevant?

I am working on two things pretty regularly — active listening and radical candor.

On the active listening side, I have to fight the urge to solution when someone presents challenges to me. Luckily, as a first step, I am aware of it — thanks to great mentors and feedback — so it’s not easy, but I am always trying to be more present, ask more questions and truly just listen.

On the radical candor side, I too often try to find the “right time” to share feedback. In a virtual world, it may not be best delivered over Slack, but finding time to connect live can be challenging and then you lose the impact of immediate feedback, which is not ideal. So I’m actively working to connect immediately — by phone or Zoom when I can… or Slack when necessary. The key is to not let my feedback slide, as that results in lost opportunity.

What advice would you offer to other leaders who are stuck in past playbooks and patterns and may be having a hard time letting go of what made them successful in the past?

Too much has changed in the last 5 years to rely on things that worked in the past. Whether it’s remote work, expectations of empathetic leadership, a change from being an individual contributor to a team leader, or even the people you now manage, everything is new.

Adaptability is a key leadership behavior to ensure you are shifting priorities and processes to keep up with the change.

Many of our readers can relate to the challenge of leading people for the first time. What advice would you offer to new and emerging leaders?

Two things. First, always invest more time than you think at the beginning of the relationship. Make time to understand the people on your team — what drives them, what’s important to them, what types of problems do they want to solve? The more you know, the more you can support and bring the right growth opportunities to them.

Second, I am a big fan of managing “skill vs. will” at the task level, not the person level. Someone you manage may be an excited rookie on one task and a bored veteran on another task. How you coach, motivate, and support at the task level should vary by task — you cannot manage the same person on every task the same way.

Based on your experience or research, what are the top five traits effective leaders exemplify now? Please share a story or an example for each.

  1. Dependability — one of our Electives instructors, Joan Ryan, is the author of the book Intangibles. It’s all about team chemistry and she explores what makes great teammates. One of her chapters is on Barry Bonds, the star outfielder for the San Francisco Giants. Most people seem to assume Bonds was a terrible teammate — because of his attitude, how he handled himself with reporters, the fact that he wasn’t friends with a lot of teammates. However, when Joan interviewed his teammates, they all said he was the best teammate and the primary reason was, “We could always count on him to execute.” Now, I’m not endorsing Bond’s attitude or other characteristics, but when you can fully depend on someone to be there for you and the team — to complete what they say and do it on time — the entire team is stronger.
  2. Respect — I was fortunate to live with my grandfather, a World War II veteran, when I was in high school and college. “Papa,” as we referred to him, showed everyone respect and didn’t tolerate anyone being disrespectful to anyone else. One of his favorite expressions was “I have two ears and one mouth” so he always tried to maintain that ratio and listen two times as much as he spoke. By living with him, I often saw him interact with people he may not have agreed with (politically or values wise), but he always respected their opinions and listened.
  3. Empowerment — when I was in my late 20s, I was promoted to a role at a consulting firm that at the time, I did not think I was ready for. I was unsure of myself, especially being in a position where I needed to influence people who were significantly more experienced than me. However, my boss at the time, Julie, was so empowering. She had a subtle way of asking me questions, helping me understand my own super powers and then letting me “fly.” I grew more working with Julie than I could have imagined and it’s thanks to her ability to empower others.
  4. Data-Driven Decision Making — sound decision making, in general, is critical among leaders, but leaders who consistently make data-driven decisions are highly effective. My co-founder, Krikor Dzeronian, who I also consider one of my leadership mentors, always sees the opportunities (or challenges) in analytical reports or asks the team the right questions that drive us in the right direction. More importantly, he builds systems from the beginning that are always data centric. Because of that, our team has started asking important questions, like “What problem are we trying to solve? How do we know if we are successful? What data can we collect now and after the experiment?”
  5. Supportive — I studied and performed improv comedy for 5 years. During those years, our team developed a ritual before we went on stage where each teammate told every other teammate “I’ve got your back.” I quickly learned that the leaders of the team were not the funniest performers — they were the leaders who were most supportive. Before the show, during the show, and after the show, they had your back.

American Basketball Coach John Wooden said, “Make each day your masterpiece.” How do you embody that quote? We welcome a story or example.

Each day when you wake up you have a new chance to create a masterpiece for that day. When you think of each day as an opportunity, it opens your mind to what can happen and gives you space to create and innovate.

Tactically, I’ve recently started conducting “calendar audits” — what meetings give me energy or drain my energy and what meetings can I make the most impact — on my own development, on the team’s growth or for the company.

What is the legacy you aspire to leave as a leader?

For me, the most important thing is seeing other people grow. The mission of Electives is to help people grow and connect (through live learning). Both personally and professionally, if I can somehow have a positive growth impact on someone, that’s a legacy I will be proud of.

How can our readers connect with you to continue the conversation?

Email at [email protected] or LinkedIn at Jason Lavender

Thank you for a meaningful conversation. We wish you continued success with your mission.