It dawned on me the other day that I need to work on listening more and talking less. As an introvert, this insight came as a surprise because in many contexts, I’m usually the last to speak, if at all.

Introvert to Outspoken to Active Listening  

Becoming an entrepreneur meant that I have had to perpetually build new proficiencies. Sales, public speaking, coaching and mentoring others all required cultivating an outgoing persona where I have been initiating conversations and making exciting things happen. Eventually, this process of pushing out of my comfort zone became more comfortable and I became much more opinionated and outspoken. Trig has formed an exceptional team of incredibly talented designers and leaders of innovation. It struck me the other day that I was being too quick to voice my opinion instead of encouraging others on the team to articulate their own thoughts on a given point of discussion. When a situation with your business is exciting and you're feeling motivated to get everyone on the same level of hype with you, you may not even realize that the conversation has been, well... not a conversation at all. Taking a step back to quietly observe was the exact habit I had been working so hard to evolve beyond. As you can imagine, it absolutely floored me to discover that listening would be the next route of the journey beyond skilled projection.

Ask Clarifying Questions

In Vistage and other CEO round table groups, problems are discussed following a specific discipline and format. The business owner seeking advice presents a case study to her peers with the problem she is facing. After she has finished, her peers are not allowed to jump in with advice, but need to ask clarifying questions. This discipline helps everyone to better understand the problem and build shared empathy so that more informed opinions can be given. Having both given and received advice in this format through the Small Giants Virtual Peer Groups, this discipline has helped me feel more listened to and built empathy with my peers. It is challenging for me to maintain that discipline outside of the moderated context in my daily interactions, but incredibly helpful to have it modeled for me through Paul Spiegelman’s leadership with Small Giants. Simon Sinek is a superb speaker, motivator, and author, so if you enjoy this clip you may enjoy his other works as well. He's performed TED talks, written books, also does live workshops from time to time.

The Art of the Segue

Fostering an enjoyable thriving work environment for everyone at Trig has necessitated going beyond simply ensuring communication lines are open and clear for my team to feel understood by me, but additionally supporting everyone by helping them connect genuinely with each other. Teamwork is challenging. Interpersonal connections can sometimes be complicated. Messy. Awkward. Sometimes all you need to cut through the tension is a laugh, or maybe a fun story. What I like to do is start our weekly company meeting by asking everyone individually what they did over their weekend. It seems simple enough, but asking instead of ordering matters. If it feels like a homework assignment it saps all the joy right out of the room. One of the most important elements to this exercise is the art of the segue.

Here's what you do: Rather than waiting for one person to finish their story, then saying "ok, Coworker, you're up next" you create an interesting segue that ties the previous story to the following person in the queue. If Ashley recounts all the yard work she's been doing to get her recently acquired house in order, once she's done I can transition to whoever I decide is next by giving a line like "Ethan, did you get any home projects done this weekend?" if I know that maybe he has. Again this seems so unbelievably easy, but it's trickier than it sounds.

This exercise accomplishes three major things:

• The person who's been sharing knows that you actually listened to them. Nobody wants to feel like a bore, especially when opening up a little bit about their life outside of work.
• Two people whose stories are connected will have a thing to talk about that maybe they didn't realize they had in common before. Perhaps coworkers can bond over having both traveled out of the country recently. Or how about the cool bands they saw live. Even staying up all night with a fussy newborn can bridge the gap between people who otherwise may have been hesitant to become more closely acquainted.
• These are great chances to tell really cheesy dad jokes occasionally. Don't let such opportunities pass you by, friends.

““In most cases being a good boss means hiring talented people and then getting out of their way.””

— Tina Fey, Bossypants

We like to think of journeys toward personal growth as being very linear. Start to Obstacle to Goal. Businessman to Overcoming Shyness to Leader. There are so many ways to develop leadership finesse. Introspection that ultimately leads to self improvement is more like a series of obstacles that never really end, but you come out better for having conquered each one. I know I certainly have, and hope to continue doing so. Climb a new mountain, then find a bigger mountain.

Gaining the confidence to really put myself out there in the world of competitive entrepreneurship in the product development and design industry turned out to be the first stepping stone on the path toward the person I am now as a leader. The newfound task is to conquer the urge to do precisely what I've been training myself to do. Now the goal is to become a listening leader. A leader is no leader without a team. The employees at Trig weren't selected randomly off the streets, as that would be a strange maneuver indeed. They are here because they belong here and I value their input. That means taking the time to understand their opinions and expertise. As I challenge myself to be the last one to speak in a meeting, I also challenge my peers in their influential positions to do the same. Let's see what we can learn about our colleagues and about ourselves.

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