Brian Bailey

VP of Product, Pingboard

By creating a small social network that encouraged healthy boundaries, Brian brought people together in meaningful ways, including our team members. He kept the best aspects of social media, and made Uncommon a thoughtful and intentional space where people could share who they are and what fascinates them. So it’s no wonder that his core values include empathy and trust.

Brian is also a product leader that is currently bringing his talents to Pingboard, a workplace tool that surfaces the essential information employees need to be successful.

Brian loves live music and short novels. He geeks out about process and collects writing advice. Ask him about his favorite standup comedy special.

🤓 I geek out about…

Process, specifically the way the how of the work infuences the outcome of the work. Products reflect how they’re built, meeting outcomes are tied to how they’re structured, a company’s culture can be traced to how it hires, and what kind of feedback is given is connected to the ease and expectations around feedback.

I don’t believe in complex processes with multiple checkpoints—often the best process is the simplest one. I do believe, however, in thinking deeply about your systems because the desired outcome isn’t possible when the process is in conflict with the goal.

🎒 I collect…

Writing advice. I’m enamored by the writing life and greedily consume stories about how writers approach the craft. Partly because it inspires me to write, but also because so much of the advice applies to life as much as writing.

“To partipate requires self-discipline and trust and courage, because this business of becoming conscious, of being a writer, is ultimately about asking yourself, How alive am I willing to be?” — Anne Lamott

Also, notebooks. So many notebooks.

💬 My friends ask my advice about…

Standup comedy specials. I used to memorize standup bits when I was a kid. During the pandemic, I started watching standup every Friday and it’s brought so much joy. I love the mastery of the form that creates a perfect bit—the setup, rhythm, timing, and every carefully chosen word. There’s nothing quite like one person making hundreds or thousands of people laugh for an hour by just talking into a microphone.

🧰 How my weird obsessions show up in my work…

My fascination with how systems inform outcomes means I’m immediately curious when either falls short. Since humans are continually changing, as is the context, that’s pretty often—no process guarantees the right outcome.

I have to remind myself that perfection isn’t the goal. There will always be ambiguity and things that could’ve been better, and that’s okay. I try to get better at knowing when to rethink things and when to embrace the inherent messiness of humans making things together.

🌱 What form of growth is most important for you and your company?

My goal is to continuously grow my understanding. I want to understand our customers and their unique struggles and motivations better. I want to increase my understanding of our team and how to work together effectively. And, of course, I want to have a better understanding of my own strengths, skills, and shortcomings so I can continue to improve.

💭 I wish more companies would…

Not do what everyone else is doing. There’s a remarkable amount of sameness in how businesses are run and decisions are made; formulas are followed and assumptions aren’t questioned. We need companies that are willing to be uncommon and stop relying on old blueprints.

💛 How can companies and industries take better care of people?

By seeing customers and employees as people instead of means to an end. Customers don’t exist to click the right buttons in the right order. Employees don’t exist to reach a growth target. Each is an individual with strengths and struggles. We should support, empower, and trust them—listen to and learn from them.

❓ A question I love:

Questions are one of my favorite things. A great question during a conversation can be magical.

So, if you’ll indulge me, I’ve narrowed it down to 3 :)

If you could teach a class about anything, what would be the topic and title? What’s the title of the book about your life? What do you wish people would ask you, but no one ever does?

🚶I would walk/drive/travel 500 miles to…

Spend the day talking about writing, fiction, and the writing life with Jenny Offill, Molly Young, and Robert Caro.

You can connect with Brian on Twitter.