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Delegate or die: the self-employed trap

423 points| razin | 15 years ago |sivers.org | reply

72 comments

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[+] StavrosK|15 years ago|reply
To be honest, though, you already had 98% of the delegation problem solved. The biggest hurdle isn't telling employees "here's what we stand for, I trust you to make decisions according to our philosophy". The biggest hurdle is to actually find people you can trust with it. It sounds like you already had a team of competent, skilled people whom you just micromanaged, and then realised they were competent enough to act on their own and let them.

This is trivial compared to actually finding such people (at least for me, I guess).

[+] sivers|15 years ago|reply
Actually my hiring policy was ridiculous.

Because I was "too busy to bother", I'd just ask my current employees if they had any friends that needed work.

Someone always did, so I'd say, "Tell them to start tomorrow morning. $10/hr. Show them what to do." And that was that.

To be fair, this was a mail-order CD store, so most of my employees were in the warehouse. But I even did this same approach when I needed a CTO. ("Anyone have a friend who's good with Linux? Yeah? Is he cool? OK - tell him to start tomorrow.")

But maybe that they were friends-of-friends helped with the trust part.

[+] DevX101|15 years ago|reply
I agree with the importance of delegating, but perhaps the work-at-home, not getting any questions after two months was also related to a major employee problem Derek mentioned somewhere in another post: employees began to feel as if he was too distant, they were doing all the work, etc, etc.

If I recall correctly, there was mutiny brewing among the employees and was the main reason he decided to sell the company.

This doesn't take away from what I think is great advice in this post, but maybe those employee issues were inevitable side effects from the super-delegation approach.

[+] sivers|15 years ago|reply
Yeah - different lesson, so different story.

I learned, the hard way, that over-delegation can lead to abdication.

[+] seltzered|15 years ago|reply
Derek, you've been a huge inspiration for me, but I remember hearing you say at a conference that your employees started to hate you a while after working remotely -- to the point that you shutoff the website for a few hours to realize you needed to sell the company.

Do you have any thoughts on what can be done to keep rappore up amongst employees in the office while still working remotely?

NOTE: sorry I don't remember where you said it, might've been towards the end of your lessconf presentation http://b.lesseverything.com/2010/2/3/derek-sivers-speaks-at-...

[+] sivers|15 years ago|reply
Yeah, that's a different story I'll figure out how to properly tell some day as a lesson in what NOT to do. I'm still trying to extract some lessons from that and think what should have been done differently.

But if an employee has low morale, (whether working remotely or not), I'd only suggest this:

Is there another job inside the company they'd rather be doing? If so, help them do that. If not, let them know it's time to go!

Many people will need a push out the door, for their own good, if they're in a rut. Give them clear warning, of course, in case they're in a temporary rut, let them know that this low-morale rut may cost them their job.

But if they're still in a funk after months, you've tried to help but it's not helping, and it's hurting business, then let them go.

I had to fire a few people in this situation, including my VP!, and most told me a year later that it was the best thing for them. That they really were in a rut and needed to be pushed.

[+] JayNeely|15 years ago|reply
I'm not Derek, but as a remote-working team member for a business that has many other remote-working team members, this is a similar problem I've been trying to solve by encouraging use of a private twitter-like network through Status.net (free) or Yammer (paid).

It provides that ambient awareness of what coworkers are up to / thinking about, gives you an easy way of soliciting helpful but non-essential feedback without adding to email overload, and allows for realtime information sharing. It's potentially a good substitute for in-office community when that's not an option.

[+] cookiecaper|15 years ago|reply
I learned about this at one of my old corporate employers. One of our local contractors was ostensibly doing very well, and I presume he was making a lot of money, but when he wanted to go on vacation, he couldn't leave for over eight months because of his obligations that he had to personally fulfill for clients. Seeing this and thinking about the futility of being self-employed in the name of freedom but running your business such that you are more trapped than a normal "working-for-the-man job" in almost every sense, I decided I would always delegate aggressively when I had the opportunity to do so in my own businesses.

What's the point in having millions of dollars if you have never the time to enjoy any of it? Also, a company that is overly dependent on one individual is unable to ever exceed the capacity of that individual; he becomes a bottleneck that slows (usually to a complete stop) the growth of the whole company. In a few years when he finally cracks, the whole thing goes down with him.

I'm glad Derek found this out before it all collapsed; many business owners don't.

[+] stellar678|15 years ago|reply
What did you do to keep the manual clear and organized enough to be useful? Many companies I've worked with have an internal wiki for information like this, but things seem to go south pretty quickly and it becomes hard to distinguish stale content from relevant content.
[+] sivers|15 years ago|reply
Actually, the new people learning it would clean it up.

If they found anything hard to understand, we'd apologize and ask them to make it easier to understand for the next person.

Since they had just felt the pain of it being unclear, they were in the best position to fix it.

[+] stefanobernardi|15 years ago|reply
Next time I'll have this problem I'll probably start using something like http://www.mindquilt.com/ I see so many questions getting asked each day and so much knowledge getting dispersed, tools like this could really make a company go faster imho.
[+] melvinram|15 years ago|reply
Sivers,

I'm in the process of doing this exact thing myself. I'm creating on average 5 training videos a day since my business is pretty much all web and information based.

I've already started being a lot more productive. One thing that I hadn't thought of was having them create the training themselves.

The first draft of these videos are fairly crude as it's mostly a brain dump and I'm figuring out the best way to explain what is in my head. This means sometimes I spend 15-20 mins to create a 5 minute video or 2 hrs to create a 22 min one (example from yesterday) when you take into account retakes and editing.

I could just create a crude one and just have them create the clean version after they learn it. It would save me at least an hour a day. Not too shabby. Thanks for that.

Mel

[+] johnohara|15 years ago|reply
Do you script your dialog or roll free?
[+] beagle3|15 years ago|reply
Not a lot of love on HN for Tim Ferriss, but his first book "The 4 Hour Work Week" is a great discussion of the self-employed trap.
[+] dave1619|15 years ago|reply
It seems like the author built a good system for operations that required little of his time, so he could focus on innovation. It's interesting that in order to delegate operations, he had to build a system (or manual in this case) to train people and keep standards consistent.

Derek - I'm curious how you handled innovation. Was it by yourself? Or did you have a team for that?

[+] sivers|15 years ago|reply
The innovation was really just me.

It was usually just looking at places where our operations were very un-optimized or ineffective, and figuring out a way to do it better.

That better way usually meant me programming some new aspect to the site, or our in-house intranet systems that ran everything. But sometimes it led to a whole new public-facing feature.

Examples:

http://cdbaby.org/stories/04/02/14/3035318.html

http://cdbaby.org/stories/04/12/31/3116514.html

http://cdbaby.org/stories/06/07/31/4461455.html

[+] cyrus_|15 years ago|reply
I really like the advice about asking your employees to keep a manual where answers are kept. Way better than trying to start with some sort of comprehensive statement of principles.
[+] KevBurnsJr|15 years ago|reply
This level of communication is hugely important not just to employers but employees as well.

I want to know that my boss trusts me enough to let me make these sorts of decisions.

Bad managers will not bother to rise to this level of communication - or in some cases will purposefully withhold it in order to maintain their dominance.

[+] tristanperry|15 years ago|reply
Great advise. And I too recommend The E-Myth Revisted by Michael Gerber; it's definitely a great book and can really help to establish in one's mind the right way to go about working on your business and not in it, a key distinction.
[+] markessien|15 years ago|reply
One important thing in delegation, I find is to not fix things yourselves, even when they would be easy to fix for you. Explain the theory behind it and let them fix it themselves, next time they do it better.

Also, if you over-delegate, make sure you have properly consolidated power at the top. When your employees get too independent, they start to get ideas about creating their own company or they start refusing to take instructions.

[+] eliben|15 years ago|reply
My experience is that this applies to "normal" management as well, not only self-employed. A manager of a team above some size can't possible know and control everything. Either he finds a way to delegate, or his team will be disfunctional.
[+] rokhayakebe|15 years ago|reply
This is a technical problem. In companies the same questions get answered forty times. I finally gave up and spent a weekend writing an app that fixed the problem for me.
[+] MrFlibble|15 years ago|reply
Hire smart people and let them do their job. If you can, after a few weeks break in period turn them loose and step back unless a serious problem arises.

Micromanagement = Macrofuckups

[+] mise|15 years ago|reply
How does the "micropreneur" achieve this?

Is it the cheap personal assistant?

Most things seem too technical for that, and I wouldn't want to be obliged with hiring one for so many hours each week.

[+] gord|15 years ago|reply
Dereks post are invariably excellent..

Im sure Im not the only person expecting him to publish a physical book with all these articles in one place.

Title?

[+] maheshs|15 years ago|reply
I read somewhere "If you are the candidate of work it is difficult to delegate".