The Delegation Dilemma: How Leaders Can Learn to Let Go

A vital leadership skill that can feel daunting for both new and experienced leaders. Discover strategies to master the art of delegation, boost your confidence, and build trust with your team.


Two people before a computer demonstrating listening and delegation. Pexels | Photo by Mizuno K

Delegating is an area of leadership where leaders often struggle. Delegating tasks may be seen as an uncomfortable, intimidating, or painful experience, no matter how long you’re a leader. It is particularly challenging for new leaders still finding their leadership style, philosophy, and confidence.

Delegating is an essential leadership skill that can be–or feel like–it’s one of the most challenging skills to master. Some leaders may find their way easily, while many others struggle and become burned out trying to lead and manage with limited help from their team. This article will explore pain points and look at some strategies to make it easier.

A primary reason why delegating is so painful for leaders is because they feel like they are not in control. Delegating tasks can make them feel as if they are giving up their authority and power, which can be difficult. They may fear missing vital information or that information deemed inconsequential to the person responsible for the task may actually be critical. Unlike the leader, the team member may be without a complete understanding of other connection points that make up the task, which results in a lack of knowledge of other essential elements or other opportunities to complete tasks. 

Leaders may worry that their team members cannot or will not be able to handle tasks, or they may have preferences or “particular” ways they like things to be performed and the person appointed to complete the task will not be able to do them “as well as they would.” Funny, you rarely hear “better than I would” as a fear, but it is also there. 

For many leaders, the delegation dilemma is fear of the unknown can make it difficult to relinquish control of important tasks and trust others to complete them. For new leaders, inexperience is another factor that can lead to the pain of delegating. New leaders may not have much experience delegating tasks, so they may not know the best way to do it and need time to learn. They may be unsure of when or how to assign tasks, how to communicate expectations, or how to follow up.

By not understanding the delegation process, having a clear plan, and having strong communication skills, new leaders may feel overwhelmed and frustrated when delegating tasks. Rather than delegating and asking themselves if the task is critical enough that they must do it themselves, they may skip over this self-observation to overburden themselves by keeping tasks and juggling them with their other responsibilities, which may result in delays or errors. Fortunately, there are strategies leaders can use to make delegating easier.

First, it is important to understand the role and strengths of each team member to identify who has the best skills and resources.

Second, start by delegating small tasks that do not require too much attention or oversight. This can help build confidence in delegating and give the experience needed to get comfortable sharing responsibilities and understanding the team’s strengths.

Third, provide clear expectations and instructions. Be sure to communicate in detail what is needed so team members know exactly what they should be doing.

Fourth, communicate in the style the person(s) being delegated to need to receive and understand information. Allow time for clarifying questions and expectations during the initial ask. Make sure to take the time to determine understanding.

Finally, make sure to establish check-in times with the team member(s) and provide feedback throughout the process, but also give them the space to take accountability and ownership of the tasks they have been assigned. This is just the beginning of closing the gap in the delegation dilemma.

Delegating tasks can be a complex and intimidating experience for new and established leaders. However, developing the right strategies can help leaders become more comfortable delegating tasks and build trust with their team. When leaders’ confidence in themselves grows, so too do their teams, and delegating becomes the most effective tool to lead their team effectively, meet deliverables, and create a sense of unity and purpose that connects the team.

How comfortable are you with delegating?

DEBORAH BLAKE DEMPSEY, MS is the CEO & Founder of Human Being Human, LLC. Deborah is a Life Strategist & Transformational Coach, Writer, and Speaker. She is the author of The Hoppernots, an uplifting, can-do story about forest dwellers coming together to defeat a common enemy and is told within a diverse ecosystem teeming with life and purpose. Her mission is to help people transform their lives and develop personal mastery. She supports healthcare and corporate leaders at all levels to fulfill their greatness in their professional and personal lives by helping them understand their motivational drivers, define their purpose, find their voice, and develop their potential. She brings to her coaching more than 28 years of experience as a healthcare leader, having held strategic, financial, and operational leadership roles in physician practices, academic hospitals, and for-profit healthcare settings. Deborah is particularly interested in working with people struggling with self-confidence, personal and professional identities, and facing burnout.

She holds an MS in Psychology from Southern New Hampshire University.