An interview with Colin Hostert, CIO of music streaming service Grooveshark.
The Enterprisers Project (TEP): How do you develop future leaders at the same time you are growing a company and community?
Hostert: It starts with hiring being our number-one priority. Our core mission is to fundamentally change how audio content is discovered, virally marketed, and monetized, so we hire people who understand and believe in that mission. We find people who are passionate about using their technical skills to achieve big things, and many of those people go on to become the next generation of technical leaders at Grooveshark.
TEP: What qualities do you look for in a technology leader?
Hostert: I'm not sure there is a one-size-fits-all description of what makes a good tech leader. I would say it's a combination of technical proficiency, communications skills, and the ability to quickly learn new ways of doing things. We help build on technical proficiency by providing mentorship and training materials, and promoting a culture where knowledge transfer is encouraged.
Most of the growth we see here comes through experience more than anything else. When you work with a cross-functional team and constantly practice your skills in an ever-changing environment, it's natural for you to grow and mature your leadership abilities along the way.
TEP: What special skills are required in a technology startup such as Grooveshark?
Hostert: There are two key essential skills we try and develop: First, we never want to say no when it comes to implementing a feature that could help us create an amazing experience for content creators, curators, or music fans. To do this we are often required to push the limits of (or completely abandon) the well-defined, widely-deployed, and comfortable ways of doing things. Instead of saying no, we have a culture in which we teach our team how to evaluate and prioritize when making decisions, such as when to use an existing solution vs. building out a brand-new system or service.
Second, we try and teach how to work well in an environment where things change rapidly. In enterprise environments, things tend to move in longer and more well-defined cycles. In the start-up world, not only do requirements change rapidly, but iterations are measured in days instead of weeks or months. Through example and practice, we have developed a culture where the default way of approaching a problem is to build the simplest version of a solution, then test it and solicit feedback.
TEP: Are there things aspiring leaders need to learn not to do in the world of Web 2.0?
Hostert: You can't rely on what has worked for you in the past if you want to solve all the problems you will encounter in the future. At Grooveshark, we have had to constantly innovate to stay competitive. Some needed innovation will be impossible to accomplish with a safe bet, so it's crucial to be able to communicate why you want to take a risk on a new technology to other stakeholders in your company.
Learning how to fail is also important. No one is going to bat a thousand. You should always have a plan for what to do when failures happen: how to communicate what went wrong, and how you will prevent a similar failure from happening in the future.
TEP: Is there a single personality trait that effective leaders need?
Hostert: Communication skills, and the ability to learn new things quickly can be challenging both to teach and to measure in a quantitatively way. Because of this, we tend to look for a trait which is usually highly correlated with both good communication and the ability to pick up new skills quickly: Curiosity. We want the person who when asked to change a spark plug takes apart the entire engine to find out how it works. We think this kind of person has the best shot at eventually mastering the skills needed to become a strong technical leader.
