Ep. 38: How to Delegate When It Feels Faster to Do It Yourself

Episode Highlights

• Upcoming Feature Episode Teaser: Hosts Cathy Maday and Ivan Konermann preview an upcoming episode featuring a client named Steve. Steve leads a high-stakes $160 million customer migration project operating under tight timelines and strict federal oversight.
• The Value of Strategic Advisory Meetings: Rather than opting out due to time constraints, Steve committed to weekly advisory sessions. This consistent engagement helped him analyze team dynamics faster, speed up decision-making, advance long-term and short-term goals, and expand his influence across the organization.
• Leadership is a Skill, Not a Trait: The hosts debunk the myth of the “born leader,” emphasizing that leadership is a set of practical skills that can be learned and developed through effort, role models, and strategic guidance.
• Transitioning from Individual Contributor to Leader: Top-performing technical contributors often struggle after getting promoted into management. They frequently default to doing the work themselves due to habits, lack of awareness, or fear of workload, loss of quality, and relationship strain.
• Reframing “Handing Off” as Role Alignment: Leaders are advised to adjust their language and mindset. Instead of viewing delegation as “handing off” tasks, leaders should recognize that those duties naturally belong to their direct reports’ roles, and continuing to do them constitutes overstepping.
• Handling Crises vs. Daily Operations: When stepping into a task during an acute crisis, leaders should explicitly communicate to their team why they are temporarily stepping in and establish a plan to step back out once the issue is resolved.
• Asking “Advancing Questions”: Rather than spoon-feeding answers or taking over tasks, effective leaders ask questions like, “How are you currently thinking about this?”. This technique allows leaders to evaluate their team’s critical thinking, target their guidance effectively, and build long-term bench depth.
• Identifying Root Fears: The key to overcoming the hesitation to delegate is asking: “What specifically am I afraid of happening?”. Pinpointing the exact fear enables leaders to address the underlying problem clearly.