The Zen of Delegation (or “How to avoid the ‘bus’ issue”)

My old friend Fred has an amazing, must-read post on his blog about “the bus issue” that every startup CEO, and their investors, must deal with.

Fred really got me thinking about why some people build their businesses to last, while others build them to collapse if they leave.

One of the most important things you build into any business is redundancy.

You don’t rely on one web server if you’re running an Internet business, and when you drill down and look at each of your web servers (if you know what you’re doing) you’ll find that they don’t rely on just one hard drive, power supply, or Internet connection.

Without this redundancy no one in the IT department would ever be able to sleep at night.

However, some CEOs build into their businesses dramaticeven direconsequences if they leave the business. They keep their investors, partners, clients, and employees on pins and needles. Is it just ego gratification? In some cases I’m sure it is, however it’s deeper then that.

Also, this isn’t just limited to the Martha Stewart’s of the world. Nope, this goes beyond the people whose personalities are synonymous with their brands. In fact this effect can be seen equallyor more oftenwith CTO/CIOs and Directors of Sales.

Those positions carry with them the keys to the castle. In some cases it’s the client relationships, and in others it’s the singular knowledge of how something wildly complex was technologically achieved. You loose a director of sales you miss two quarters, and if you loose a tech lead you can loose an entire development cycle. It can sink an entire business.

My perspective on the “bus” issue is that it parallels the delegation issue. Some people can delegate brilliantly, while others either don’t even try or even worse they sabotage the whole process.

Watching these people operate reminds me of adults who struggle with relationships later in life because a parent left them at a young age. They’re so wary of being hurt that they are self-defeating.

In my first serious business, Silicon Alley Reporter, I probably sucked at delegation and moved up to being OK at it. There were some people I felt I could give a whole project to (Gordon, Xeni, Joanna, Jamie, Karol, etc.), and others I felt like I had to keep a constant eye on (let’s forget about linking to those folks! :-).

It was a lack of experience on my part combined with some bad hiring decisions. Sometime your 100% correct in not delegating to someone, however if this is the case then you’re guilty of not hiring the right person!

Running Weblogs, Inc. has been so much easier. I’ve pulled together a six-person management team who I don’t tell what to do, and we’ve got almost 50 bloggers who we don’t even edit!

When I start working with someone I make it clear that the reason we’re choosing to work together is because I implicitly trust their judgment. Sure, I know they will makes tons of mistakes because that is what people who make great things dothey fail fast as Esther would say. However, I tell them that we’re also choosing to work together because they are the type of people who identify and rectify the problem in an ego-free fashion.

Heck, I’ve made a half dozen *major* errors in the first year of Weblogs, Inc.

Error one: Most writers want to get a revenue split. WRONG! Most writers want a steady pay check.

Error two: One domain name (i.e. with sub-domain names (i.e. is better then multiple unique domain names (like,, or WRONG! Stand-alone domains do better.

Error three: One common design for all blogs is more appealing to advertisers and users because it builds trust and familiarity. WRONG! People love a unique look and feel above the benefits of a standard design.

I wasted hundreds and hundreds of hours of our time, money, and other resources on those three mistakes alone. However, the team learned hundreds of details of WHY those decisions were wrong and why other ideas were better.

Now, what’s really great about taking yourself out of the day-to-day, minute-by-minute decision making process is that you can focus on the big picture. You can do deep, deep analysis of the actual results of your business instead of second guessing your team members approach. In fact debating which way to goNorth or Southtakes longer then just going North for a day then turning around and going back South. In fact, all you’ve done is educate yourself as to what’s up North and why the South is better.

I’ve let the sales folks go off and give it their best shot. Then I spend my time obsessing in an Excel spreadsheet with the results of their hard work and creativity. We look at the results together, come up ideas to do make things work better and everyone feel great about the process. Most importantly, everyone learns the secrets of the business in this processthus building even more redundancy!

Of course, after doing a round of this, I just do it again. Every time you figure out something newlike playing basketball or chess.

The other great thing, is that when you free up your time you can survey the whole landscape of your business and look for the team members who are struggling. You can just swoop in, give them 100% of your focus, and help them solve their problem (or fire them if you have too!). If you do this right you’ve a) helped *them* solve *their* problem, b) built up their confidence, and c) strengthened the trust between both parties. They know you’re only there to help, and you know that they are mature enough to identify (and admit) problems. Solving problems is easy, identifying them and figuring out why they happened? That’s the hard part!

The “metaskill” in all of this, which I’m currently trying to refine, is in empowering your management team to think this way. If the leader on one of our blogs notices that one of the other bloggers on the team is constantly making the same spelling error do they just fix the error and move on, or do they take 10x more time to help the other blogger understand and avoid the error in the future?

I keep telling my team that when no matter how much stuff you delegate, there is always more to do. Working your way out of your job is the goalthat’s how you build a big, sustainable business.

You can spend six months climbing to the mountain top, only to see another taller, more challenging mountain that wasn’t even visible from the previous valley.

That’s what it’s all about getting to the next mountain top.

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