Why Aren’t I Better at Delegating?

All leaders—from new managers to seasoned executives—must delegate tasks to free up time and attention for the big-picture work their more-senior roles demand. This is an axiom; indeed, delegation is one of the first skills typically required of new managers. But research shows that leaders too often find themselves mired in the details of their teams’ efforts, with debilitating consequences for their organizations.

Failure to delegate well produces three bad outcomes. First, a relatively expensive employee (you) is doing work that could be done more cost effectively and probably better by a lower-paid team member who is closer to the customer or the operations. Second, your team is likely to become frustrated at micromanagement, and stagnant from the lack of real responsibility, undermining your leadership pipeline. And, finally, you stay mired in your old work, which prevents you from focusing on the critical strategic planning, cross-functional networking, people management, and self-development work your organization needs you to do to stay ahead of the competition.

According to the author, most leaders she worked with understand that they need to delegate, but they don’t always know how to distinguish between the work they should be doing and the work they should be handing off. And even when they get that determination right, they often fail to follow through.

Deciding What to Delegate.  Before you can successfully delegate, you need to learn to differentiate between the work you should keep—and, indeed, do more of—and the work that is better left to a team member. The author’s advice is simple: When considering any meeting, task, or responsibility, always ask yourself, “Am I the best and cheapest person to get this done?” If the answer is no, delegate the work and give the person you’re handing it to the context needed to succeed.  Context-setting includes explaining why the work needs to be done (following an organizational strategy, entering a new market, onboarding a client, or investing in a project, for example); the results the person or group is expected to deliver; the deadline for the work; and how people should behave (with one another, other colleagues, clients, and others) to get it done.  By contrast, activity-based work—including making decisions about what work to do to achieve the company’s or team’s goals—should be your team members’ responsibility.

Four challenges that stop even those who know how to delegate from doing it successfully and (their solutions are): A) an addiction to the dopamine hit of easy productivity (Create different types of checklists, routinize good practices, and reframe your purpose); B) a disinclination to reject requests for help (Re-explain the context, Give the work back, Teach with examples, not answers; and establish accountability and support);  C) The boss’s or client’s expectations (Start small, be accountable, Give visibility to team members, and Over time, target the more complex work); and D) a misunderstanding of what “work” should mean for a manager (recognize your limits, decide if you really want to manage, and spread the mindset).