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The Delegation Experiment, Part 3: Teaching It

In the last installment of the Delegation Experiment we worked through the challenge of deciding what pieces of your business you could, in theory, hand off to someone else to do for you. Because if you plan to delegate, you need to identify what it is you plan to delegate, right? But once we’ve done that – counted the hours involved in each area, and marked certain jobs for delegation – we get into scary territory. Now we have to start thinking about actually handing those tasks off to someone else.

To do this, we need a brief overview of how this ideally plays out. I’m a freelancer right now. Most of you are too, I’m sure. You work by yourself, for yourself. And honestly, you do all of it yourself whether the task falls into your skill-set or now. So I’m going to randomly pick one of the regular tasks I have to tackle and use it as an example, but I’m sure you can just as easily find something in your own workflow that you’d love to never had to do again. Me? It’s managing invoices and payments.

Gather the Tools

First, I’ll need to write down all of the pieces required to complete the task – the tools, if you will. For me, there are two separate spreadsheets that are used in recording that information. There are the individual invoices I’ve sent out (in PDF format). And then there are payments received (either physical checks, or email receipts from credit card payments).

To prepare a specific task or chore for delegation you need to spend a good long moment contemplating the tools needed to get the job done. The types of tools will depend on the type of task. It could be computer files, access to email, your growing pile of mail beside your desk, or countless other types of tools. Whatever those pieces are, write them down. Make a list and label the list with the name of the task. If it helps, think of this in terms of writing a recipe: your tools are your ingredients, and without them you cannot make the cake.

Write the Instructions

This is the hard part. There’s a concept called The Curse of Knowledge that basically means that the more and more we know about something, the less capable we are of effectively communicating it to others. And when we start talking about those tasks we perform daily and yet hate to do, we’re talking about tasks we know intimately. And that means we need to very intentional and careful when we explain the process to others.

What I have found to be helpful is to first list the process out in basic terms, from memory, and then go back and flesh out each item as if I were explaining it to someone I just met. It’s easy to write “open the P&L spreadsheet” but forget that no one but you knows where that file is saved. Fight the Curse of Knowledge with every word you write and spell things out as clearly and precisely as you can. The more specific you can be, the less likely the delegate will make mistakes or need your help to complete the task.

Something to consider as a way of helping the delegate understand things accurately is the use of images. If your process involves specific sheets in a spreadsheet, or columns that are difficult to locate, use a simple screenshot application to grab the image and highlight the areas that need attention. If you use a Mac, apps like Skitch and Littlesnapper are great tools for making this work smoothly. They say a picture is worth a thousand words, and when it comes to writing out procedures I think images are worth a thousand questions.

Prepare the Way

The final obstacle between you and delegation isĀ  accessibility. If someone is going to read through your instructions and get access to the tools for the task, then you are going to need to remember to make all of those things available to that person. A shared Dropbox folder is a perfect solution for keeping all of those important files on your computer and yet sharing them with the delegate at the same time. If the task requires access to email, or the sending of email from your company, consider setting up a new address specifically for that person. If you are delegating out the management of leads and prospective clients, a system like Highrise would be perfect for sharing contacts and noting their status over time in a way that you can still access, view and monitor.

A Procedure Manual

Here’s the deal with this whole procedure-writing stuff: all the big businesses do it. They do it out of necessity, as a business of multiple team members and departments. And all of these instructions get gathered into their operations manual, or procedural guides, or whatever they may call the resource in their company. For these businesses, delegation is more about teaching their employees to do things the same way all the time for consistent, accurate results.

For the freelancer, though, the push for delegation is different. You’re a business of one. You have no one else with you there, on staff, in the building. So you don’t really need a binder or a guide printed up and in-house. And that’s even more true if you plan to delegate items on your list to people who live hundreds of miles away. For people like us, we need a central repository for our procedures that our delegates can access as needed.

The best tool for the job, hands down, is ProperProcess. ProperProcess is a web-based service for building your procedure manual. You can create each “recipe” like you would in any word processor, and even add files to clarify specific ideas, but all of it lives online, in the cloud. It’s organic too, so you can return to a procedure months after you drafted it and edit it. All of the steps in a procedure can be re-ordered using simple drag-and-drop. And the best part is that tasks can be scheduled.

Say you want invoices and payments recorded once a week, on Fridays. Use ProperProcess to assign the procedure to the person handling it for you, assign a schedule to it, and let the system work. It’s that simple. They will get an email Friday mornings telling them what they need to complete that day, and when they’re finished, they simply log into the site and check off the items, allowing you to review their progress.


What’s an experiment without homework, right? So you’ve read all about it. Delegation is possible. And the best way to start is to write your procedures down. So, this week your homework is to write a procedure. Remember to list out the tools needed, and write the process from the point of view of a newcomer. And as an added bonus, devise a method for making all of the required tools available to your delegate.

So, what are you waiting for? Go write that procedure!

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