What level of experience do you look for when evaluating candidates for leadership positions in software? Which previous roles or responsibilities would you need to see before you sign off on a potential new hire?

I appreciate hiring smart people from nontraditional backgrounds who have interests beyond software engineering. I look for out-of-the-box thinkers who can bring fresh ideas to problem-solving. For any leadership position, I also value strong speaking and writing skills.

The stage of the company is an important consideration when hiring. Some people thrive in large corporations with established processes, while others excel in startups where there's more flexibility. It's crucial to find someone whose experience aligns with the company's current stage and future direction.

Different roles require different skill sets. For example, we once had a management role where we needed a technical leader because the team was relatively junior and needed guidance in making good architectural decisions and establishing coding standards.

In another case, we had a team of experienced engineers who needed a manager with strong communication and relationship management skills. The manager we hired was less experienced technically, but he excelled at managing relationships and changed the team's dynamic with their product development counterparts and stakeholders.

We look for technical expertise in our leadership candidates. While we don't expect them to code, we do expect them to understand how AWS works and the technical landscape of our operations. My two favorite things to learn about a candidate are how they make a team operate better and how they've dealt with difficult situations that resulted in team and company growth.

When I'm hiring for leadership positions, such as managers or directors, I look for a combination of skills. I prefer candidates who have at least two to three years of experience leading people. This isn't about technology leadership, but rather about how they've worked with other team members, influenced good decisions, and driven the business forward.

I also consider how they think about the business. They may not know about our specific industry, but they should be willing to spend time learning about it. This shows they can balance their technical skills with their leadership skills while adding value to the business.

Another factor is their ability to handle politics or bureaucracies. I don't necessarily look for a specific number of years of experience in this area, but I do look for evidence of these skills in their past roles or projects.

Basically, I look for a balance of technical skills, business understanding, people leadership, and problem-solving abilities.