The Art of Delegating: Why It's Worth Mastering and How To Do It

You’re working around the clock, drowning in emails and tasks that need to get done, but aren’t necessarily high value. You know you need to focus on higher-level thinking, but can’t seem to find the time. How will you get ahead?

In a word: delegate.

As simple as it is, it’s a tough concept to master. Most high performers (like you!) have gotten where they are by putting their head down and doing great work. What no one ever told you was there’s a shift you need to make in the middle of your career to keep getting ahead, and learning to delegate is a huge component.

I hear complaints all the time from clients that they just don’t have talented people below them to delegate or millennials just don’t have the work ethic they expect from junior employees. Quite frankly, I don’t buy it. At some point, we all had to be trained and coached to meet the expectations of our managers and mentors and those generally “ahead” of us. The time has come for you to do the same for those “below” you – especially if you want to get ahead. Here are some tips to get you started:

Identify delegatable work

Yes, I know. “Delegatable” is not a word, but you’re all smart and I think you get what it means. It may sound obvious, but it’s a step that many people don’t take deliberately. The first step to good delegation is having a clear understanding of what can and can’t be delegated.

If you’re still doing tasks you were doing two or more years ago, pass them on. They could also be tasks you don’t enjoy doing, but think you could train someone on – what a great way to free up some time and take a step toward enjoying your work more!

Doing this requires really knowing how you spend your time. If you aren’t sure where the time goes, you need to start a work journal.

Set clear expectations

With the work you can delegate identified, it’s time to clarify your expectations for that work. What does success for the person you delegate that work to look like? What are the rules you want them to follow when performing that work? How will they know they have performed well?

Setting clear expectations for knowledge workers (which most of us are) is a challenge. If you haven’t learned to do it for yourself, that’s the first step (and a huge step toward more satisfaction at work). If you can’t articulate to others how to perform work, what standards to follow and what success looks like, you will likely be frustrated by their product. Set the expectations up front so you (and they) have a clear measure of whether they performed well.

It might help to think of your work in an academic context. How would you determine your grade on your work? Use that same criteria to set expectations for those you delegate to, and you’ll be on the right track toward getting the quality of work you need from them.

Coach and Train

The truth is – and where most people get hung up on delegation – that delegating work to others takes some upfront investment of time. You need to start a little heavy handed – after you’ve delegated the work and communicated expectations, check in in a day or two to confirm they’re on track and no new questions have come up. Make yourself available for when those questions do come up (because they will!) and spend extra time explaining concepts and coaching.

Though it does require an upfront investment, that won’t last forever. I hear many people say it takes just as much time – or longer – to delegate than it does to just do the work. In the beginning, it should take more time to delegate than it would for you to do the work. But that time will fade into the abyss the better you get at delegating. Think of it as an investment.

A case study

Because it’s not lost on me that many people will still think this process is simply impossible for their work, a case study for you – from my own personal archives.

In my final role as an attorney, I was hired because the company needed a commercial attorney – someone to draft, negotiate and review contracts. I knew when I was hired that they really needed more, but they didn’t know what they needed and I was eager to find out and create my role.

The contracts that were most pressing to them were utterly boring to me. They were quite simple (after a few months of getting up to speed) and I generally hated the nature of them because my clients would get hung up on one sales agreement, when I knew I could be doing more impactful risk-management work for the company.

I pitched to my team the idea of finding outside counsel that could do those contracts and eventually hiring a contracts administrator (not even an attorney) to perform the bulk of the work. My clients were not convinced a non-lawyer could do the work, but I was. I took a risk by saying someone paid way less than me could probably do the work I had spent much of my time on for the past year, but I felt confident that I had higher value work to focus on for the organization.

So – I created a rule book. I looked at the work I was doing on those contracts and created boundaries about what another person (outside counsel or not) could do without my input and when I needed to step in. I also created rules around certain elements that were important to us as a company and when I needed to know that we didn’t get what we wanted.

It took me a long time. Full days, which, as an attorney, is very hard to give. As I was creating the rules and the process, I knew others thought I was wasting time on work that didn’t obviously impact the business, but I had my eye on the prize of getting most of this work that was below my skill set off my plate so I could pursue work that was more interesting to me and more beneficial to my company.

It worked. After creating my rulebook, I outsourced the work to outside counsel, who we paid a small fraction of what my hourly rate would have been, and I hardly had to touch those contracts I hated. It took about 6 months to get them up to speed, but by the time I left my organization, those contracts were far in the rear view mirror and I was able to do more interesting and impactful work.

Summing it up

I tell you that story to show it can be done. It does take an up front investment, but like any investment, if you’re deliberate up front, it will pay off in the end.

As you train staff and others to do work that is past your level, you’ll get better at delegating. Delegating – like any other skill – takes deliberate practice. The more you do it the better you’ll get. The better you get, the less time you’ll have to spend on work that’s just keeping you busy, but not fulfilling your duties or helping you grow as a professional. Not to mention, when others start to see how well you delegate and lead others, you’ll naturally be considered for leadership roles because of those skills. And the nice part? You’ll have a team of people that you’ve trained to work with you ready to step in when you do need to build a team.

The only way to get good at training up people beneath you to build a strong team is to start doing it now! Delegate away and you’ll take responsibility off your plate NOW while building crucial skills to lead to your success in the future.


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