September 28, 2017

Learn to Lead Honestly with Shay Howe, Episode #11

53 minutes

To become a leader, first get ready to do the grunt work

Shay Howe is a man of many talents and has helped build some of the best-known tech companies in the Midwest, including Groupon, Belly and Codecademy. But before he became a leader in the field, he was a kid just out of college, living in Chicago, unsure of how to build his career. But, as a group of like-minded developers started to organize a Refresh Chicago meetup, Shay volunteered to not only take part, but do the little things that organizers didn’t have time for. This meant showing up and being reliable while doing things like setting out the chairs for the audience, and ordering way too much pizza. And, as you’ll hear in this story, that dedication to the little things is what changed his entire career.

Midwestern values lead to prizing the ability to lead honestly and with integrity

Shay grew up in Ohio (no offense, Michiganders), the son of two educators who never quite took to education himself. He tells the story of how when he struggled with spelling, his mother would spray shaving cream on the kitchen table, and have him carve out the letters in the foam, to make learning fun for him. His father taught and worked a side business as an athletic trainer, which showed him how to work hard and pursue what you love. Shay credits his dad’s work ethic, and his mother’s creative teaching style that put student first, with his approach to his own career in development.

Sometimes you don’t need business school, you just need to play in a band

In high school, Shay played in a band and quickly learned that if you don’t look out for the business side of music, people will try to pay you in free drinks and snacks. He took over the management of the band, booking shows and ensuring they got paid, unwittingly providing himself his first lessons in business. But when he tweaked the design of the band’s MySpace page, and other bands noticed, his two loves merged: He was doing front-end development, and he was getting paid to do it. But it was another lesson he learned from his days in the band, that would go on to accelerate his career.

Doing the grunt work led to his first big opportunity and a major critical shift

It turned out, moving the chairs around and ordering the pizzas got Shay noticed, and he was asked to give a talk at Refresh Chicago. He prepared for at least 40 hours for that 15-minute talk, and the work paid off, getting him invited to speak at another conference, which eventually led to his first big job. Shay credits the time he invested into that talk with helping get his career on the right trajectory, but it also triggered something else in him: a desire to follow in his parents’ footsteps and teach. As he says in the interview, “So many people opened doors for me, of course I was going to open doors for a few others.”

From Codecademy to Lead Honestly, a career spent helping others

When Shay worked at Groupon, the coding boot camp Codecademy opened in their office space. Shay began spending hours there, volunteering to teach students and eventually put out a free resource for learning how to code (which was eventually turned into a book). After his time at Belly, he started the company Lead Honestly, which takes his years of experience building relationships and partners with organizations to help them connect better with their employees. The company sends five questions out to managers every week that will help them better understand and engage with their staff. This is a fascinating interview with a self-starter, a leader, and a dyed-in-the-wool educator.

Outline of This Episode