Want to Lead a Team but Hate Managing? with JT Olmstead

JT Olmstead shares his journey from software engineer to land investor and business owner, revealing that he initially disliked managing people but recognized that accomplishing his business goals required building a strong team. He describes his early corporate experience where he was promoted to manager but actively resisted the role, explaining that humans are "messy" and unpredictable compared to code. This self-awareness led him to deliberately hire self-starters and self-managing individuals rather than trying to be the traditional hands-on manager.

Olmstead details his hiring process, which uses WiseHire to cast a wide net across job boards and incorporates DISC profiles for cultural fit assessment. His funnel includes written follow-up questions, multiple interview rounds, and importantly, a practical project where final candidates complete 1-2 hour tasks relevant to the actual job. He emphasizes that he compares candidates against an objective standard of what success looks like in the role, not just against other candidates. The process is designed to be 70% consistent across roles, with 30% customization based on position-specific skills.

He manages a team of six full-time employees in his land business plus two developers for his separate Land Loans software business. His team includes an acquisitions manager, dispositions manager, leads manager (who manages records rather than qualifies leads), full-stack developer, executive assistant, and transaction coordinator. Olmstead acknowledges that managing six direct reports exceeds the recommended four to five, but he's in a growth phase where hiring a mid-manager isn't yet justified. His executive assistant helps alleviate some burden.

For maintaining team performance and communication, Olmstead implements weekly one-on-one meetings with each team member, a weekly team meeting using a lightweight Level 10 format that covers highlights, quarterly rocks (goals), and KPI reviews. He measures performance through empirical data rather than subjective assessments, believing that proper metrics eliminate guesswork about individual performance. He explicitly states he doesn't consider all his employees "all-stars," arguing that true all-stars are rare and likely wouldn't work for what he can pay.

Regarding domestic versus international hiring, Olmstead makes role-based decisions: sales positions and customer-facing roles require domestic talent for cultural understanding and relationship-building, while administrative roles can be filled internationally as long as English proficiency is near-native level. He's used agencies like Scale Virtually, Upwork, and others, emphasizing the importance of not accepting the first batch of candidates an agency proposes and instead pushing back until they truly understand the ideal candidate profile.

On compensation and career development, Olmstead has candid conversations with employees about alignment between their goals and company direction, acknowledging that some team members may only fit for 2-3 years. Rather than only pursuing all-stars, he looks for people with good aptitude, core cultural values (extreme ownership, proactive communication, radical honesty), and potential to develop. He motivates growth by showing employees they could increase significantly in value and compensation if they develop their skills, but he's honest that this growth requires work on their part.

Olmstead concludes by reflecting on company culture, admitting he once viewed it as "woo-woo" but now recognizes that culture exists whether defined or not, so the choice is between intentional and unintentional culture. He defined core values and made them succinct and memorable, recognizing that establishing culture is critical before scaling to larger team sizes. He recommends "21 Irrefutable Laws of Leadership" by John Maxwell as a resource and acknowledges that while managing isn't his zone of genius, it's necessary to ensure his team gets what they need.