It is a simple fact that I am terrible at delegating.

I have a very hard time giving work to someone else to complete. Even when I’m trying to think of tasks to delegate, when I am purposely trying to trim down my workload, I have trouble delegating.

But now I have a secret weapon.

Last week, on my company’s anniversary, I hired my first full-time employee. Cara doesn’t have an official job title yet, she is a jack-of-all-trades. I hired her because she is smart, flexible, likes variety, and because she is the best delegator I have ever met in my life.

Cara takes delegating to a whole new level, not because she is lazy, but because she is efficient. She is willing to do anything if it has a purpose, but if it is useless busy work, she’ll be happy to explain why. If she’s working on a project that can be outsourced to someone else who is not fully occupied with work, she’ll demonstrate how that makes sense. She is also excellent at training other people (which is a big part of delegating). Cara is a master delegator.

In the one week since Cara’s worked with me, her delegation skills have already begun to transform my business. And watching her thought-processes has given me some really good insight into why every person in every business should start delegating more today.

1. Teaching a job to someone else shows you where there are holes in your logic or where you’re taking too many steps. As I’ve begun to explain process-oriented work to Cara, she asks me questions that point out unnecessary steps or reveal a better way to do things. Today I was explaining how to check something from the admin section of a Web site. To do so involves a separate URL, login information and instructions on how to access the data. That process works, but Cara asked why we couldn’t just find the information from the public Website. Turns out we could, and that saved us about 10 unnecessary steps. Just by explaining the steps and having someone ask a question, we saved time and streamlined a lengthy process.

2. Feeling like you have to do something is a lot of pressure; it’s easier to think more creatively when you aren’t stressed with looming projects. I have a to do list that stretches for pages in my notebook. There are many items on that list that have been there for months. They are always on that list, always in the back of my mind; projects that I need to tackle but haven’t been able to get to. If there is a project that has been on your to do list for more than two months, think about delegating it. You aren’t getting it done, so at least some progress will be made if you give it to someone else.

3. Giving away something old and established makes way for something new and innovative. I have a number of repetitive projects that take up a portion of my week every week. These things are always there; kind of like during college on the weekends when I could not ever relax because I knew that there was a book to read or a paper to write. By delegating those kinds of projects, your mind has more room to be creative and to spend time on less process-oriented problems.

4. Establishing processes allows you to delegate and to increase your output in multiples. It’s fairly obvious that it is much easier to outsource something if there is a process for how it gets done. By creating processes around work, and figuring out how to get other people to help do the work, there is another benefit - the total amount of work that you can get done increases exponentially. An good example is the human powered search engine Mahalo. The site employs Guides who help to create pages that can be searched. There is a process to creating those Mahalo pages, and by making sure that everyone who works on the site knows the process, the site can grow faster as new Guides are added.

5. Freeing up extra time will allow you to write that blog post that you’ve been putting off for a week (or longer). More time for other work is the most obvious reason to delegate.

(BONUS) 6. Believing that you are the only one that can do a task isn’t helpful for you and isn’t helpful for your business. And it’s probably not true. This is the most common protest made by over-achievers and perfectionists who think that they can do the work the best or the fastest or without any help. And this notion is dangerous because trying to run a business completely alone will not work. And in most cases, it’s better to get 80% of the work done at 80% skill level than 40% of the work done at 100% skill level. On top of this, it’s usually not true that no one else could do the work.

When this article first came out, I printed it out and tacked it to my bulletin board at work because of this section:

“Moving into any new position requires that you get rid of the stuff from your old position. This means delegating. It means getting over the idea that you were indispensable on any of your old teams. You can’t do you new job well if you’re still doing your old job.

Delegating your old job should take three days. You find people who are taking a step up when they accept pieces of your old job so that they are excited. You give them an explanation of how to do it and tell them where to go when they have questions.

You are going to tell me that one day is not enough, that you have a very complicated job. But think of it this way: If you died today, your job would be delegated in a couple of days.

Delegating is not enough, though. You have to stop caring. If you are no longer on a project because you got a promotion, then you have to stop obsessing about how the project is doing.”

I try to keep that advice in mind, but I’ve already admitted that it’s a challenge for me. If you’re bad at delegating, try these seven tips to becoming a better delegator. But whatever you do, start delegating more today.

Photo by Mykl Roventine

Everyone knows at least one skimmer. Someone who doesn’t really read their email that closely, the person who reads enough to “get the point” but might miss a lot of the details.

The life of a skimmer is trecherous. They go to meetings and get asked a question “about that email that was sent yesterday” and have absolutely no idea how to answer. They never know what time the party is going to start, or who was invited, or what day it is going to be held.

Skimming causes problems. But for whatever reason, skimmers can’t stop. They might just think it’s ridiculous that people send long email messages. They might be “all about efficiency” or “impatient” or “don’t care.” The list of reasons is long.

I know some skimmers, and they are going to think this blog is about them. But it’s not. It’s about what happened to me when I became a skimmer and what I learned from the experience.

I am NOT the skimming type. I am detail-oriented, I read every word. I’m the person who explains what’s going on to the skimmers during the meetings. But with starting all these businesses, I have a lot of details going on at once. And a couple of weeks back, I forgot that my book club was meeting in a week and I still hadn’t bought a book.

My book club is a little non-traditional - it’s a history book club, we pick a different historical topic every time we meet, everyone reads a different book, and then we attempt to explain to each other what we read to try to surround the topic and get a better understanding of history. This is not because we are history buffs, but because - to put it kindly - our historical knowledge is somewhat lacking. In past book clubs, we have read about apartheid in South Africa, the time of the Cultural Revolution and Mao Zedong, and the Crusades. This book club topic was Cuba and Castro, which turned out to be very timely.

So I headed over to Amazon.com to search for a book on Cuba. I have learned my lesson in previous book clubs to not get a book that’s too long, or one that’s too intellectual - I wouldn’t be able to get through either in a week. I also know that the crowds are usually right, so I always go for a bestseller.

So I searched on “Cuba.” The first book was a travel guide, I knew to skip that. Number 2 was a book called I Was Cuba: Treasures from the Ramiro Fernandez Collection, and it was under $20, had a 4.5 star rating with 12 reviewers. I clicked to the page to find out more. The book description said this, the full text is below. But to show you what I saw, I will BOLD the parts that I read (when skimming):

“While most think of Cuba as a mythical island of rum, rumba, and revolution, period photographs reveal a more complex place. I Was Cuba is an original look at Cuban history as seen through the Ramiro Fernandez Collection arguably the world’s leading archive of Cuban photos and ephemera. I Was Cuba showcases rare, vernacular images from the nineteenth century through the revolutionary period, exploring the everyday and the eccentric. With texts from famed Cuban writer Reinaldo Arenas (Before Night Falls), this captivating volume is an intimate view into a bygone era of glamour, political upheaval, and astounding visual culture.”  

I bought the book. When it came, I found that this was not a book that I could read for book club - because there were no words. The “texts” were few and far between, and were simply short quotes. This book was a collection of (random, interesting, but not even that historical) photographs.

I bought a picture book for my book club.

And I was caught - a skimmer!

This experience helped me realize that being a skimmer is painful. But that sometimes everyone is going to skim. However, since I don’t want skimmers to skim when they are reading something that I wrote, especially an email, I need to work to combat skimming every way that I can.

So here are the five things that that you can make sure that your email messages get read by skimmers:

1) Put the point of the message in the subject line. Don’t waste the subject line with “hey” or “hello.” Put the subject of your message right in the subject line.

2) Make your point in the first sentence. Don’t take a long time to get to the point or explain background - you can do that later. Make the point in the first sentence of the first paragraph of the message.

3) Elaborate in the rest of the email - but keep your main point in the first sentence of each paragraph. Sometimes skimmers will “read” the whole email by reading the first sentence of each paragraph - so keep your main point up top.

4) If there is something that someone must read and it’s not at the top of the message, use the person’s name, in bold. And maybe underline it. This might offend a non-skimmer just a bit, but the skimmer is sure to notice their name bolded. Skimmers look for bold and bullets - they are a skimmer’s lifeline - so use them for important points in your email message. Because when she’s skimming a long email, Melissa I need you to do this, will really stand out.

5) Put a call-to-action before your signature. At the very end of the message, if there is some action that needs to be taken based on the message, remind the person at the end. “Please call me by the end of the day tomorrow.” or “I need your list of suggestions by noon.” That way the skimmer will know that they need to do something with the email, and your chances of getting a response will go way up.

And don’t follow my example and put a long personal story before the five main points in your message - the skimmers will never get that far.

There are so many good things about starting a company. The freedom. The independence. The creativity that it brings out in me. The amazing things that I’m learning. But the one thing that is so incredibly frustrating is that I have to rely on part-time contractors to get anything done.

The last job that I was at, I worked with an incredible team of people. Technically, I guess they worked for me, but each of them was so good at what they all did that I really considered us to be a team with myself at the helm, giving directions and making sure that the company, the development, the product – that everything was moving in the right direction. Quickly. Efficiently. FAST.

Now, I am a solo act. I am still working as quickly as I ever have – probably more so because I’ve upped the amount I’m working to approximately 15 hours per day (all the statistics about how much you work when you’re self-employed are right, it turns out). But no matter how quickly I work, I am always waiting for someone else to get something done.

Let me be really quick to say that I am not blaming anyone for this situation – I am still working with an amazing group of people. It’s just that they are only contracted to work some (small) number of hours per month. I mean, I work more hours PER DAY than each of them work per month. This is the way it has to be, but it really tests my patience.

According to Chris, this situation is attributable to the Good Fast Cheap theory of business. OK, I don’t think that Good Fast Cheap is technically a business theory, I think it’s more a concept that designers use when working for clients to try to help them understand how they work, but it’s a reality with my company so far. Chris’ claim (and I think he’s right) is that you can pick two of the three – Good, Fast, Cheap – but you will have to forgo the third. In my case, I have picked good and cheap, but I have to let go of FAST.

This is really too bad, because fast is one of my favorites.