know it, but instead they can rationalize not being so. They actively and effectively stop you from getting things done and spend what little effort they do exert pleasing their boss or sucking up to the person with the most political power and otherwise being everybody’s friend, as opposed to getting the job done. They thwart you in what you want to do and believe is right and provide the most unsatisfying answers. It’s so demotivational. I hated this situation more than anything else, and I would say this is what most entrepreneurs hate.”
Lesson: “Being willing to stand up for your employees. If they believe strongly in something, especially the very good ones, be willing to ride with them. If you are not, sit down and explain your reasons clearly and make sure they know it is not because you are lazy. Be very careful when you tell your employees they can’t do something—you better have a damn good reason and then communicate it to them.”
Bob Metcalfe, general partner, Polaris Venture Partners: “My worst boss ever allowed personality politics to run rampant among his reports and, after giving me a raise, broke a written promise to [promote me].”
Lesson: “One of the pathologies of companies is when winning internal political battles becomes the focus of its people instead of competing to win and serve customers—when keeping your job becomes different from doing your job. The wrong people advance and the company declines. One special case of this pathology is when accountants or lawyers manage to take over technology companies. Another is when governments are taken over by demagogues. Rome fell from the inside.”
Dan Sullivan, Founder and President, Appswell: Sullivan says his worst boss ever seemed to regularly shift attention and resources to whatever new effort temporarily appealed to him, or to what Sullivan describes as, “his latest fleeting flights of fancy.” These could be anything from a new marketing plan to deciding to launch new products.
Lesson: “Focus is definitely an aspect of the lesson,” says Sullivan. There is a real difference between pursuing a flight of fancy and a true passion, he says. “Unlike other forms of business, in my opinion, entrepreneurship is ill-suited towards observing a need and positioning a product towards it, unless that need is something that you care sincerely about. If you’re not running after something you’d be chasing anyways, then the effort is just exercise, and eventually you’ll get exhausted.”
Michael Greeley, Xconomist and general partner, Flybridge Capital Partners: Greeley says he’s had several bosses who could be “mean and nasty.” But his worst boss experience came from a different type of practice Greeley found demeaning. They had offices very near each other—so that if the boss just raised his voice slightly Greeley could hear him. Similarly, says Greeley, “If he turned his head, he could see me.” But when the boss wanted Greeley, he would typically page him.
“That just seemed so humiliating,” says Greeley. The paging, he believed, took far more effort than simply calling out or just waving him over. But, Greeley felt, “he thought so little of me that he couldn’t get up to try to find me, he’d just page me.”
Lesson: “For me it was actually kind of a profound lesson. In the office environment treat everybody—junior, senior—not necessarily as peers, but as human beings. That lesson’s always stayed with me.”
Jeff Janer, co-founder and CEO, Spring Partners (creators of Springpad): “My worst boss…demanded blind loyalty and played his direct reports off each other rather than promoting teamwork.”
Lesson: “I learned two important lessons from my worst boss. One is the importance of surrounding yourself with people who are smarter than you and listening to them—rather than…surround yourself with ‘yes’ (wo)men. The second lesson is that it’s key to define reality—both good and bad—and say thank you on a regular basis, as respect accrues to the leader who is a servant to his employees—as opposed to the other way around.”
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