Replace Yourself – A Guide to Delegating Your Workload

For most entrepreneurs, ambition far exceeds even a superhuman workday. No matter how you slice and dice it, one person can only do so much. To do more, requires something more than working really, really hard. It requires delegation.

There may only be one of you in the world, but there are plenty of other people. So to overcome the speed bump of your own personal capacities, you’re going to need to get other people to do your work. This can be quite a daunting prospect, after all how do you find people? How can you trust them to do a good job? How do you pay them? What if they don’t work out?

In fact taking this step is so formidable that in many instances it can appear easier just to continue doing the work yourself. Personally I often disguise my worries with excuses that sound very legitimate, like “only I have the extra, special, super skills to do this task” or “by the time I teach someone else how to do it, I may as well have done it myself!”

But what I have found is that if you want to grow and expand and get to do all the things you want to do, you’re going to need to let go. And in fact there IS someone else who can do one or many of the tasks you do, sometimes they’ll even do them better. Yes, it takes some training and uptake time, but for almost every task there will be repeats or similar work and then you’ll reap the rewards.

Over the years I’ve gotten some practice hiring new staff, taking on regular contractors and commissioning one-off freelancers. So I’ve put together some thoughts on how to go about replacing yourself.

1. Recognize your core skills and try to delegate everything else (first)

For most entrepreneurs, the course of a workday involves a wide variety of tasks, some of which play to your strengths and some of which you do because, well, you have no choice. Make a list of all the different types of things you do, then prioritize them according to what you’re actually good at. Think to yourself: if I was going to hire someone to do this job, would I pick me out of a set of candidates? Chances are you’re doing a lot of things that someone else could do a lot better.

It’s important when doing this exercise not to focus on any particular knowledge of your own business you may have. That’s a trap. Yes, you might be the only person who has been there since the first day of your business and only you know what’s inside your head, but forget about all that. Just think in terms of actual suitability. What tasks suit you? What do you enjoy?

The things which you are most suited to you should try to delegate last. The rest you can now try to group into similar job types. Sometimes it takes a bit of mental agility to group jobs together, especially if they aren’t a natural job role. I’ve found that in the early days of our startup I needed much more general, smart people who could just help out with a variety of things. Often these people were my cofounders who were willing to do everything from manning support and moderating forums, to setting up bank accounts and putting together financial reports. Over time as our budget and needs have warranted, we’ve been able to bring in more specialized people for these roles.

For example recently I’ve noticed the number of jobs which have a legal component to them have been mounting. Whether it’s reading through agreements, dealing with our law firm for trademarking, deciding what sorts of usage terms we should specify, or simply giving a quick opinion on a copyright question. Right now a lot of this work is done by myself, or other management staff. While we don’t have enough work for an actual general counsel (thank goodness, because they are expensive!) we do have enough for a part-time person with a legal background. And importantly such a person would undoubtedly do a better, quicker and more effective job!

2. Beware of false economies

One common reason for not delegating is simply that you can’t afford to pay someone else. Often startups and small businesses are on tight resources, so of course the obvious thing to do is to do everything yourself. In general I applaud this strategy, and it’s certainly something that I have done throughout my business. But you must remember that doing things yourself holds its own pitfalls.

My favorite television show is an English one called Property Ladder where they follow would-be property developers on a big development project. Oftentimes these are people just starting out and with correspondingly limited budgets. One of the ways they often decide to save money is to take on project managing the development themselves. But in half the cases they in fact end up losing money because they don’t actually know what they are doing. Even with the best intentions and hard work sometimes it simply means things take longer, or they accidentally do things in the wrong order. When the recap rolls at the end of the show you realize that they would have been better off just hiring a professional.

Another false economy can arise from the misuse of your own time. Ask yourself: What could I achieve if I freed up some hours? What tasks are there that I would be most effective at? At many stages of Envato’s growth I’ve found myself doing jobs that I could find someone else to do, and in the meantime leaving tasks that no-one else could do languishing on the side. This is a bit like using a tank to ferry soldiers around the battlefield instead of what it’s actually good at – blowing stuff up on the front lines!

The key is to make the most effective use of all your resources, including both time AND money. Sometimes that will mean doing things yourself, but in quite a few cases it will mean delegating.

3. Get a replace-yourself mentality

When you’re up to your ears in work it is extremely difficult to be thinking about finding and bringing in someone else. This is doubly difficult when you have accumulated a lot of experience with your particular set of circumstances that you’d need to train someone else in. To get past this you need a replace-yourself mentality.

To begin with, don’t let yourself be attached to specific jobs. It sounds crazy, but many people want to be *the* person to do the job. President Harry S. Truman once said “It is amazing what you can accomplish if you do not care who gets the credit”. Letting go of important and fun jobs can be hard, but ultimately will help you to do more overall.

Secondly it’s important to prepare yourself for the extra workload the delegating brings in the initial stages. Finding and training people can be very time consuming, but it’s only for a short while. Then afterward, all of a sudden you’ll have more time as the workload suddenly drops off your shoulders. You just have to be prepared for the short burst of work and hunker down until it’s past.

4. Find people … anywhere!

I’ve been asked a number of times where we find the great people who work at Envato. The answer is pretty much anywhere and everywhere. Here are the four main sources:

• Freelance Sites – Many of the times that I have delegated work, it has been to freelancers and contractors. There are lots of sites where you can post job ads for a freelancer, but the best is FreelanceSwitch’s Job Board where you can post for free – and which coincidentally happens to be run by Envato. I’m very proud to say that a large number of our freelancers have been found there! Of course you can also try sites like Elance and oDesk.
• From your userbase – This might not suit every start-up or business, but for Envato we find tons of people out of our own community. Many of the Tuts+ editors were readers and/or writers for the sites, all of our marketplace reviewers are sellers first, similarly with moderators, site managers, and plenty of other positions. In fact being a user of our sites is a huge plus whenever we hire because it means the person doesn’t need to learn the culture, product and company from scratch.
• Job Sites – Lately we’ve been hiring quite a few full-time local staff for our Melbourne office. For that we post job ads on Seek, which here in Australia is the largest job site. Every country will have their own job sites, and it’s important to advertise where your market looks. We once advertised for a programmer on the 37Signals job board and got absolutely no candidates. It turns out Australian developers don’t pay that much attention to that particular job board.
• People you know – All through Envato’s life we’ve been hiring people we know. On many occasions it’s been friends or family, and as we’ve grown it’s started including people who worked with our employees at previous jobs. Knowing someone or having a personal recommendation can go a long way to establishing how well a person might fit in. But always keep in mind that you should be choosing the right person for the job, not just whoever happens to be available.

At the end of the day you can find people from pretty much anywhere. Just keep your eyes open, and make sure people know you are looking – whether that’s by posting job ads or telling friends.

5. Briefing and training are crucial

Unfortunately just hiring someone is not enough. Your contractor, employee or partner must be fully briefed or trained on what they need to do. This is a crucial step that it’s very easy to skimp out on, running instead on the vain hope that they’ll just ‘figure it out’.

While it’s not a bad idea to throw people into sink-or-swim situations, you do need to make sure they have what they need to get the job done. This will mean a time cost while you properly brief or train the person. But the perils of trying to save on that cost are high and in general it never works out very well. On a number of occasions I’ve sent over half-briefs or not fully trained someone about a job and one way or the other I have always paid the price.

Whether briefing or training make sure you take a very detailed approach. Imagine yourself in their situation but with zero knowledge of the job. Think through every piece of information they are going to need and make sure you document it all. A thorough, specific and well documented brief will save buckets of time later on, will empower your freelancer or employee to get the job done and will make for a smooth transition as you delegate the work out.

6. Don’t micromanage!

You should not in any circumstances be micromanaging every detail of another person’s work. It is very disempowering for the other person and highly redundant because you have two people effectively doing the work.

There are two reasons you may find yourself micromanaging a person. First you can’t let go of the work, so you’ve decided to check in all the time, give direction and oversee it all. There is only one solution to this scenario – let go. There are no two ways about it, you absolutely, must let go of the job. Give yourself periodic check ins at sufficiently long intervals for the person to actually do the work and produce results.This means you will still have some oversight, but it will be at a measured distance. When you do check in, look solely at the results, not the manner in which they have done the job. If the results are there, then you can relax. If they aren’t there, then that brings me to the second scenario …

You’ve got the wrong person. Sometimes you will have simply botched the hiring or contracting and brought in someone incapable of effectively doing the job that needs doing. You know it, and you’ve started micromanaging to try to compensate. Sorry, it won’t work. You have to bite the bullet, get rid of the person and start again. The good news is the process is so painful that next time you’ll be more careful about choosing people!

But remember there is no good situation that involves micromanaging. If you are going to delegate your workload, you need to do so and then stand back so you can reap the benefits. If you don’t want to delegate, that’s completely understandable, just don’t pretend to delegate and then micromanage as it will simply cost you money and not save you any time.

7. You must set expectations, demand accountability and provide feedback

Whether it is a freelancer you have hired or an employee, it’s critical that you set parameters for the job and then hold the recruit to those parameters. This encompasses the briefing and training I mentioned earlier and also includes specifying how you will judge performance, what is a good result, what is a bad result and how often you will give feedback. It also means that you need to follow up and evaluate how the person is doing.

Without expectations and feedback, you are leaving things to chance. Nobody likes working in a vacuum and for good reason. Without expectations and feedback, your contractors and employees won’t be able to tell what they are meant to do, whether they are doing it, and whether they are performing well.

I hope these 7 tips will help in your own quest to delegate and offload some of your workload. Even after all the people I’ve hired, I’m still learning about the process. Luckily it’s pretty fun and when you look back and see what is getting accomplished without you actually doing the work, it’s a really, really awesome feeling.

After writing this long article on how and why you should replace yourself, I will finish with a cautionary tale. In her book ‘The Stories of Facebook, YouTube and MySpace’, author Sarah Lacy recounts the story of Jay Adelson who founded the company Equinix during the dot-com boom. As Lacy writes:

“Like so many first-time entrepreneurs in the bubble, Jay made the mistake of losing control. By 2000, he was still one of the largest stockholders in Equinix, but he had given up his board seat to make room for the company’s new “grown-up” chief executive, Peter Van Camp. Although Jay retained his titles of co-founder and chief technology officer, his influence had waned considerably – he didn’t even report directly to Van Camp.”

Later when things went pear shaped Adelson found himself unable to influence direction and was increasingly shut out from the company he started. While the company still exists today and is worth some $2 billion, Adelson through a series of events outside his control, lost everything.

So while it’s important to delegate and offload, you also don’t want to delegate yourself right out of your own startup! Still the story has a happy ending because it was while at Equinix that Adelson was to meet a young, enthusiastic tech reporter named Kevin Rose. Rose and Adelson were to go on to become fast friends and co-founders of a little site called Digg. Yay!