How can I change my boss's time-wasting ways?
August 27, 2010 12:25 PM   Subscribe

How can I help my procrastinating, disorganized boss improve his workflow?

I recently started working as a personal-assistant/project manager. My boss is a very creative one-man studio who's amazing with people: he can schmooze any client, get a job, and then typically hires other developers/editors to finish the grunt work.
I was brought in (mostly telecommuting) to organize the projects, help control workflow and help organize him. So far, this has consisted of transferring the projects to an online project management tool, and using it to schedule his tasks, milestones, and meetings. He told me, very clearly: "It'd be great if you could give me a list of major tasks to do for that day, in addition to whatever meetings I have."
A few weeks in: opening our PM homepage reveals that he has 10 late tasks; I can reschedule some, but not all, because of previously arranged deadlines. Because his business is "his baby" and he's been doing it solo for so long, he's not used to delegating, and feels uncomfortable giving me some of the tasks. I had to fight to get him to contract an editor and another designer to keep up with the deadlines: he's capable of doing all of these things, but would rather spend the time than the money.
He spends most of his time emailing and doing "urgent but not important" tasks. He realizes that it's inefficient, but also says that all the time he spends sending silly emails helps him build relationships with clients; he's also social, and a natural collaborator, and the chatter seems to be his way of avoiding the hermit-freelancer thing.

He has a video to edit that he won't let anyone else do. The production company that wanted it weeks ago never gave him a drop-deadline, so I gave him a deadline in early September. I've scheduled it for him for two hours each morning, before he opens his email—I'm fairly organized and use a mix of ideas from GTD and the Four-Hour Workweek—but he hasn't done it once.

I realize that being someone's mostly virtual, part-time employee isn't quite the best position to motivate him, but does anyone have any tips? We get along really well on a personal level, he's an amazing source of contacts, and I'm learning a ton of great things. But I'm starting to realize that his work is ultimately affecting my opportunities at this position; and since it's only part-time, I'm not sure how motivated I am to help him over working on my own projects. Also, since he's not getting more efficient, I feel like I'm not doing what I was brought on to do. I know it's up to him at the end of the day, but maybe I can do more to nudge him.
posted by blazingunicorn to Human Relations (3 answers total) 4 users marked this as a favorite
Can you get in an intern to do some of the more routine stuff you're doing now, and then you take over more of the interesting/pressing projects? An on-site intern? Or can you be onsite more?

If you can present a plan to him so that he can easily see (don't tell, show, esp. if he's a visually-oriented person) how much more work can get done and how much more money can be made if you're used to your best advantage.

Flow chart, storyboard, whatever works.

Since he's a connector guy, having him work before emails is probably going to seem like punishment, I think.
posted by Ideefixe at 12:51 PM on August 27, 2010

I have a friend who only has the job she has because her boss can't be organized. If he learned to be organized, she'd be out of a job.

You're likely going to have to let him fail, on the stuff that's outside of your control. The trick may be in having him recognize it as his failure and not yours.
posted by vitabellosi at 2:29 PM on August 27, 2010

I'm in this situation, but i'm in your boss' shoes. It takes time to develop trust for delegation. Ask him to give you a shot at running one of the smaller projects 100% your way (pick some low-hanging fruit) and make it more about your opportunity for growth than correcting his ways. schedule a post-project review, trumpet your successes, and go for something slightly bigger the next time. Criticizing the way he does it is only going to breed distrust and resentment.
posted by Señor Pantalones at 2:48 PM on August 27, 2010 [1 favorite]

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