Learning To Lead By Letting Go

Delegation is a challenge for leaders at all levels. Trusting your employees and being able to hand off tasks and projects to them is crucial to any leader’s or entrepreneur’s growth. So why do so many people struggle with letting go of the day-to-day minutiae and creating space for their best work? Turns out, it’s a pretty complex set of reasons.

Emily Morgan, founder of Delegate Solutions and author of the recently released Let it Go! How to (Finally) Master Delegation & Scale Freedom Across Your Organization, shared her leadership lessons on delegation. She has spent 15 years helping thousands of busy entrepreneurs to master delegation and finally reclaim their time. Here are some main takeaways for those who struggle with mastering this vital management and leadership skillset.

Why leaders often struggle with delegation

Becoming a better delegator first requires a mindset shift. Entrepreneurs, due to their experience building something from the ground up, often experience a sense of guilt when it comes to delegating, like they haven’t earned a “freedom” from that responsibility yet, says Morgan. “To me, delegation is freedom, and freedom over your time,” she says. “Self-limiting beliefs that make us feel guilty or that others can’t do things as well as we can continue to feed into themselves and hold us back.”

And while we can often trick ourselves by saying it’s easier to do a task by ourselves—which is often true—this thinking has us lose sight of the key thing delegation is meant to give us back: time. Time is finite, Morgan reminds us. If we say yes and keep taking on all the work ourselves, we aren’t getting to the more impactful things we could be doing in our role as leaders.

Keeping your eyes on the prize

Every company needs a visionary to guide from the top. So even if leaders genuinely enjoy doing the work they should be delegating, if they’re comfortable being the person that “gets things done,” spending their time doing these smaller tasks leaves a void at the place where a visionary should be guiding others in the organization.

“These everyday tasks can be hard to let go of because our self-worth is so closely tied to them. We’re really good at these things—but in most cases, so are a lot of other people,” Morgan says. “If you’re doing an activity over and over, it’s probably something someone else can, and should, do instead of you.”

Figuring out what to let go

The first step in figuring out what to delegate is to determine what you want to spend your time on. Once those items are identified, it becomes clear what other projects and duties are eating up time in the day without contributing to those core things.

This also contributes directly to getting past the mindset roadblock mentioned above. For many, the question becomes “If I’m not doing this work, what am I going to be doing?” That question can be scary for many leaders—the possibility that they might not be as good at the strategic direction and visionary responsibilities can keep them in the weeds and sticking to the things they know, rather than what they should be focusing on.

“As the top leaders of our companies, our ideas are what our contributions are,” Morgan points out. Anything that isn’t pushing you to develop more ideas is something that should be delegated.

What makes for successful delegation

Effective delegation, as Morgan says, isn’t about simply handing off tasks. If you don’t go about it with a thoughtful and systematic process, you’ll find your plate filling up again very quickly. By gaining clarity on where we as leaders can make our most impactful contributions, we know what needs to be delegated, now it’s all about developing a system to effectively delegate. Luckily, Morgan has a five-step process to speed leaders through that process; you’ll note that we’re actually a few steps into it already:

1. Focus on what your contribution needs to be (and therefore what can be taken off your shoulders)

2. Reflect on how you spend your time and what can be learned from these patterns

3. Outline a strategy for delegation that is tied to goals and priorities; what will get delegated, to whom, and via what method

4. Hand off the projects using the criteria developed in step 3

5. Gather feedback from involved parties, having a frank and healthy conversation around what worked, what didn’t, and what can be learned for next time

Common delegation mistakes

Of course, there are many common pitfalls leaders will find themselves in when it comes to delegation. Morgan shared some mistakes she often sees others make when delegating.

“Drive-by delegation” is a common mistake—delegating without being clear on what is expected or what success would look like when the employee has their hands on a project can cause significant problems.

“We are living in ideation and our team is living in execution,” she explains. “Friction can develop on teams where the leaders aren’t disciplined in how they share ideas or what their expectations are.” And this can also inadvertently lead to the “only I can do it right” mentality that holds many leaders back from properly delegating. Simply telling employees to get something done without setting success parameters will often lead to the work getting done less than satisfactorily and reinforce the idea that the leader needed to do it all themselves, when in reality, they simply should have done a better job in the handoff part of the delegation.

Finally, Morgan sees far too many leaders not having a weekly meeting or regular check-in with their teams to monitor the progress of delegated projects and build in further accountability. She uses such meetings with her clients all the time, to great effect. “Weekly, we talk about what’s coming up, what happened last week, and are reflecting on the overall delegation strategy to make sure that we are actually moving things forward that we wanted to.”

These meetings are also an excellent place to receive the feedback mentioned in step 5 of the delegation process. With that insight, leaders can iterate and strengthen their delegation skills for the future.

As with any skill, mastering delegation takes practice. When things don’t go as planned, don’t give up – learn from it and just keep trying. Once you can truly let go and have others support you, you will then be free to do your highest and best work, allowing you to scale your leadership, your team, and your organization.