Unlocking Brave Curiosity: Three Questions To Uplevel Your Next 1-on-1

Another special edition of The Inner Radio Newsletter! This week with Bobby Kolba. He was the first employee at Textio, a software company helping managers hire and develop diverse teams, where he led the team that built the product from the ground up. He is a theater-kid turned tech-executive and shares his unique take on how to rally a team through storytelling, empathy, and curiosity. Enjoy!

Jennifer Altman: I loved learning that you spent your college years producing theater before pivoting to software. What connects the two?

Bobby Kolba: At the end of the day, you're going from point A to point B and building something with a rough kind of spec or idea of what you want to have happen and a really diverse group of people and skills that you have to align to make that thing happen. In theater you have a set designer, a lighting designer, a master electrician, technical director, actors, and the director. In tech, you have sales, marketing, product, engineering, design, data science etc.

In both cases, you're producing a thing to put out into the world. A bunch of skills you learn in theater end up translating to the kinds of problems that you need to solve for engineering and product development. As an example, in theater you have a punch list of things that need to be fixed on the set. Triaging a list of bugs and fixing them uses sort of the same brain pathways.

Jennifer: Storytelling is also a big part of theater. What kind of storytelling is important in engineering?

Bobby: Where I spent my energy, on this sort of production and backstage side of it, you end up needing to tell stories to explain the why behind things, how we're going to do things, why they're happening the way they are. And that's the part that I found carries over to engineering incredibly directly. Everyone has some version of goals, objectives, or KPIs. It's all kind of window dressing on the same root concept of trying to get somewhere and measuring that path. Storytelling is an incredibly important tool for explaining why those things are important and helping bring people along. If there was a thing I learned convincing people to work long hours in a theater, it was how to tell that story and how to bring them along. It was college. We weren't paying anybody. No one was getting credits for it. People want to work on things that they understand why they're important and what it means to be successful. And so, I think storytelling can be incredibly important for that. 

The other thing about stories is that they have this lingering resilience in a team or company. If you wrap something in the right language, the right story, the right metaphor, it can have legs of its own and it can carry beyond that interaction. So you don't need to be in the room, you don't need to be making the decision. You can set the stage for other folks to make the decision. I think about stories as a tool to carry context between places, share it with others, and leave it with them. That lingering aspect leaves people with the information they need to make better decisions. 

Jennifer: Effective storytelling brings people along. It also creates empathy, especially cross-functionally. How has empathy played a role in your leadership?

Bobby: Look, everyone's job is hard. Everyone has unique skills. That’s the foundation to start building on. Sharing what makes your specific job hard and appreciating what is hard about others’ jobs helps develop empathy across the board. Take sales as an example, I don’t have the skillset to even get started. I would break after like the twentieth cold call rejection and go cry in a phone booth somewhere. But listening with curiosity to my counterparts in sales explain what it takes to get a large enterprise deal across the line? I had no idea how many touches that takes, how many meetings, how many different combinations of stakeholders end up getting pulled together. So the more that can be shared, it makes it a little easier to imagine yourself in that position. And that builds empathy which ultimately makes me a better partner and leader.

Jennifer: That’s a great partnering mindset: “everyone’s job is hard.” How else can we be good partners to executive colleagues in engineering?

Bobby: Having a colleague take the time to ask questions, to check in, to show curiosity in both how I am doing and how my team is doing. At a purely human level, all these little things that trigger feelings of warmth and care just by showing up. Especially at a leadership team level where our interactions often revolve around OKRs and KPIs. Asking about the next set of things that I am looking at. How do I know that things are going well versus poorly? And why is that the set of things I care about? Practically, this is going one level deeper on understanding my day to day but showing that care can build an enormous amount of trust and empathy. 

I’m a big fan of the power of open ended questions. So I would love to be asked things like: 

“What customer-facing pieces of work is the team working on that you're most excited about or the teams most excited about?”

“What are the biggest challenges facing the team this month or quarter?”  

“Anything that you need?” 

And then when something doesn't go the way that somebody thought it should, say a feature slips out, it doesn't make it into a quarter. Or there's a big outage, the sites down, and like what you’re experiencing is lots of angry customers calling into support. 

A quick: “Hey. This seems hard. Can you help me understand what’s going on?” can go a long way.

I'm a firm believer in not just sort of spitting out assumptions but instead talking through them. 

Jennifer: Spitting out assumptions is a recipe for disaster. It reminds me of John Gottman’s “harsh startup” concept where 90%+ of the time if a conversation begins “harshly” such as with spitting out assumptions, the conversation goes nowhere and can actually damage the relationship. You’re better off not having the conversation in the first place. 

Beyond not spitting out assumptions, when you’re leading a team what else do you want them to know you value?

Bobby:  Brave curiosity is really important to me. I put those together because there's a shade of bravery that enables a different level of confidence in the face of something unknown. If you're not scared of the results. If you have a culture where people aren't gonna get reprimanded or in trouble. If you have systems that are resilient that no one person can truly break. People can be more free to take risks or free to dive into something unknown and learn. They have access to what they need. They can both get really curious about why something is the way it is or what's causing a certain issue. And they can go into it with that bravery-fueled confidence. 

Curiosity is something that I’ve always celebrated. When you open something up and you don't know what's going on and you say, “Okay, I'll figure it out”. That doesn't mean don't talk to anybody and just figure out everything alone, especially if a quick conversation with someone could unblock you. Reaching out to experts is part of exploring and learning.  But you’re not hitting a wall and saying, “Well, I don't know how this works, that's for somebody else, that's not my job.” Instead, I really value that mentality of “Let's just dive into it. Let's get curious about it.”  That has always been really important for me on teams.

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Jennifer Ouyang Altman is the CEO and Founder of Inner Radio, a leadership coaching company working with executives hungry to define their leadership style, build effective interpersonal relationships, and harness the power of team. She facilitates communication and leadership courses with Stanford’s Graduate School of Business and is a CEO coach for Berkeley Haas’ CEO program. Her work has been published in the Los Angeles Times and Washington Post. She believes in the rules of radio: clarity, simplicity, and personality. You can’t speak and listen at the same time.