The Problems Get Squishier, with Luke Hutscal

Key takeaways

Leadership involves navigating complex, ambiguous problems where clear-cut answers are rare.
Surrounding yourself with intimidating individuals can provide valuable growth opportunities through mentorship.
Understanding the trade-offs in architectural decisions is crucial; both monolithic and microservice architectures can be valid depending on the context.
Active engagement in hiring processes, building relationships with recruiters, and developing a proactive outreach strategy are vital for attracting talent.
Opting for mature, well-established technologies can often provide better long-term stability than pursuing every new trend.

Summary

Learning and Growing in Leadership

In this episode, Luke Hutskul discusses the challenges faced by emerging leaders, particularly around performance management and team dynamics. He emphasizes the importance of reaching out for help during difficult situations and building a supportive community. Luke reflects on how leadership often requires navigating 'squishier' problems where the right answer is not always clear, discussing the necessity of learning through conversations and experience, rather than relying solely on reading.

The Value of Mentorship and Intimidation

Hutskul suggests surrounding oneself with people who intimidate you as a strategy for growth. He shares experiences from his career in which he sought out mentors who had more experience and knowledge. He explains how having a 'coaching village' of directors to rely on shaped his managerial skills, enabling him to draw from a wealth of experience and guidance. This theme highlights the importance of being open to learning and vulnerability in the journey of leadership.

Architectural Decisions and Trade-offs

The discussion shifts to the technical side, with Luke advocating for understanding the costs associated with architectural decisions—monolithic versus microservices, for instance. He highlights the need for engineering leaders to educate their teams about these trade-offs rather than adhering rigidly to one architectural philosophy. Hutskul stresses that everything can work, but the focus should be on whether the team can pay the costs associated with their choices.

Hiring and Recruitment Strategy

Luke reflects on the time-consuming and challenging nature of hiring. He emphasizes the need to invest time in building relationships with recruiters and developing a personal reach-out strategy to attract potential candidates. Luke shares experiences that underline the effectiveness of proactive engagement, noting that hiring managers' outreach generally has a higher response rate than recruiters due to the personal connection. He stresses the importance of leadership in actively participating in recruitment and being present for teams.

Choosing Boring Technology and its Implications

The episode touches on the concept of 'choosing boring technology', with Hutskul arguing that often it is more beneficial to opt for mature, well-understood platforms over novel, exciting options that might not hold up under pressure. He discusses how innovation tokens are limited in organizations, and the need for clarity in deciding where and how to innovate while maintaining operational stability.

Show notes

Luke Hutscal, Principal Engineer at Clio – formerly of Shopify and Testflight – joins to talk about finding ways to learn rapidly, the downsides of a mercenary mindset, spending time with people who intimidate you, building a coaching village, making wrong things look wrong, choosing boring technology, resume-driven development, and putting in the reps to get great at hiring.<ul> <li><a href="http://lukehutscal.com/">Luke Hutscal</a></li> <li><a href="https://mcfunley.com/choose-boring-technology">Choose boring technology</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Powerplant.