Through my work coaching executives, I’ve learned there are four reasons why delegation can be one of the most difficult leadership skills to master. 

First, our view of the world is limited by our own perspective and sense of self. As a result, it’s hard to imagine that anyone else might do the work we’ve asked them to do as well as we might. This is a logical extension of our misimpression that our view of the world is the only accurate view of reality. We might be forgiven for harboring this illusion, since many of us in leadership roles are surrounded by others who spend much of their time nodding in agreement with whatever we say. 

Second, assigning work to someone else to do means giving up some degree of autonomy, a sense of being in control of things. When we feel we’re losing control over events around us – including the quality of work done by those we manage – we feel socially threatened and at risk. Doing the work ourselves helps us feel more secure, even when we suspect that the work might be done better by someone else. 

Third, immersing ourselves in the details of work that might be handled better by others helps us avoid the responsibility of dealing with more strategic concerns, which as leaders is the very work we’re being paid to do. These strategic concerns almost always involve making high-stakes decisions that are central to the future success of our organizations. Focusing our attention on less consequential matters helps us avoid – or at least put off – the risk inherent in making these decisions, the outcomes of which are always uncertain.

Finally, and most important of all, delegation is difficult because it involves asking for help, which is anathema for many leaders. Asking for help forces us to acknowledge that there are certain tasks we can’t do, either because we don’t have the time, knowledge, or skill to do them. Asking for help is one of the most difficult challenges leaders face, because when we ask for help, we reveal that we are not the omnipotent beings we like others to believe we are – much as the “man behind the curtain” revealed the truth of his being to Dorothy in The Wizard of Oz.  

The poet David Whye, in a recent podcast interview with the neuroscientist Sam Harris, tells Harris that he reminds the corporate leadership teams he counsels that “we’re all desperate to be recognized for what we have to offer…and everyone around you is looking for some invitation [to be recognized]. The greatest invitation is for you to say [to those around you] that they have gifts you do not have, and that therefore you need their help. That is the most powerful leadership invitation you can make.”

Ironically, it requires a certain degree of self-confidence to ask someone else for help. When we do, as Whyte points out, we benefit those we ask as well as ourselves. When we ask for help by delegating work to others, we recognize the value they can contribute to our organizations through the help they provide – which is a powerful way of creating loyalty between leaders and those they lead.