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One of the most important parts of management, perhaps the most important, is setting proper expectations. This sounds like something you've heard before, I know. It's funny how little most people pay attention to this, though. A deadline slips and they just kind of accept it.
When you delegate something to an employee, make an agreement, and make it written by sending email about it. Later on, if there's a screw up, you can point to the email. Instead of you being the "badguy" and "making them feel bad" by pointing out the problem, instead the agreement becomes the badguy. You're pointing out to them their own promises.
Here's a tip on milestones. Most people break a project up into reasonbly-sized chunks and call those milestones. I would urge you not to do this. Instead, make one milestone every 1 or 2 weeks. That way, you have a regular way to check up and see how your employee is doing and whether the project is slipping.
That's why banks ask you to pay back a loan monthly. In reality, they'd love it if you waited and waited to pay back the loan, so that more interest would accrue. But by making you pay monthly, they are getting monthly reassurance that you have not fled the country.
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