How leaders can move past hurdles to delegate better

How leaders can move past hurdles to delegate better

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Banks Benitez is the founder of Smart Workweek, helping businesses transition to the 4-day workweek. He was previously the co-founder and CEO of Uncharted, an entrepreneurial accelerator.

As a leader, delegation is far more challenging than we hope it would be. Leaders struggle to delegate well when there isn’t clarity around:

  • What’s a priority and what isn’t
  • The consequences of thinking everything is a priority
  • The existing workload and deadlines of their employees
  • The time and effort required to complete a task or project

Strengthen the dynamic between you and your team

Successful delegation stems from a healthy dynamic between a leader and employee, which can lead to honest conversations, mutual feedback, and confidence. The more employees understand their work and believe their voice matters, the more effective delegation will be. Here are two ways I’ve strengthened my dynamic with employees:

  • Flatten hierarchical power dynamics: As a leader, you can neutralize power differentials by creating an interpersonal dynamic where you model coachability, curiosity, and honesty with your employees. As CEO of Uncharted, opening up about my leadership struggles and asking for honest feedback from our employees helped us tap into a new level of connection and truth-telling. Use one-on-one time with your employee to ask for feedback and get input on upcoming decisions. Kat Cole, President of Athletic Greens, used the same question to get feedback from her employees for years: “What is one thing I can do differently to be more effective for you?”
  • Normalize mutual feedback: One of the most important things a leader can do is to create the psychological safety needed for employees to feel confident to manage up, provide their leader with feedback, and push back as appropriate. I’ve found success in allowing time for mutual feedback during each of my one-on-one meetings with employees—many times, it led to valuable feedback that shaped major upcoming decisions and helped me refine my approach to leadership. By sharing feedback regularly, we normalize it and reduce the fear often associated with telling someone else what they could do better or differently.

4 steps to effective delegation

Once leaders and their employees build a solid interpersonal foundation, they can push into delegation more effectively.

  1. Review existing workloads: Ask employees to share details, timing, and deadlines for their existing work. Often these conversations will center around what they will have to deprioritize to complete the work you’re asking them to do.
  2. Ask your employee about the timelines and deadlines for their existing work: What timelines or expectations will they have to adjust to absorb the tasks you are delegating?
  3. Define what success looks like: Define the outcomes and expectations of the work. How will they know when it’s complete? How will we measure success? By when?
  4. Establish roles for the project: As their leader, what role will you play in supporting the employee to accomplish this work? What will (and won’t they) be responsible for?

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