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I Was a Bad Boss

(But You Don't Have to Be One!)



When I was about 25 years old, the man I worked for allowed me to hire an assistant.


I don't remember being involved in the hiring process. One day, he just told me I could train a recent college grad and "gave" her to me. I felt very important.


But I had no framework for leadership. Until then, my two bosses had been dysfunctional in very different ways.


And I was still a kid. No one suggested I take leadership training. And I had no role models.


My new assistant became my buddy. We went to happy hours together and got stupidly drunk after work and on weekends. I taught her how to write ad copy but didn't really know how to redirect her when she was off strategy.


Fast forward to my next jobs. I had huge responsibilities, and my own supervisors were high-power men in financial services who barked orders at their staff and even brought people to tears. (Remember, this was the 1980s.) The women in management emulated the men, except they wore skirt suits with big shoulder pads.


"Well, if they are at the top and are strong, mean, and sometimes borderline inhuman, I guess I should act that way too!" I told myself.


Plus, I was under a huge amount of stress. Perpetually insecure about my abilities and role, I let the pressures on me "trickle down" to the people I managed.


Starting my own business was stressful in a different way. The people I hired were paid out of my own pocket. I had never run a business before, and my network of entrepreneurs and founders was very limited.


In short, I sucked as a boss a lot of the time. I didn't intend to make my team members miserable, but I'm sure I did.


So consider this a public apology for anyone who's reading this who worked for me during my "bitchy years."

One of my former employees once apologized to me. She said that she really didn't understand what "being a boss" entailed until she had a staff of her own. So maybe I wasn't as bad as I think I was.


I still have very high standards, and sometimes, my relationships with independent contractors can be strained, but I'm much more comfortable in my leadership role, and, as a solopreneur, I don't have day-to-day responsibility for managing people.


But here are my takeaways from those "bad" leadership years:


  1. Managing people is not for everyone. Although having a big team is often seen as prestigious (especially in the corporate world), it's not necessary for success.

  2. If you are a new leader, seek out professional training. And that training should never really end. Later in my career, I worked with an amazing coach who taught me great strategies and worked with my team to help me understand what I could do better as a leader.

  3. Don't simply emulate your own boss. That can be a formula for disaster. If your organization thrives on abusive or bullying behavior (and rewards those who practice it), find a new job.

  4. Hire the right people and make quick, bold moves if they aren't the right fit. Although it may seem counterintuitive, I was sometimes too nice in my leadership style, giving people second or third chances when I knew in my gut that they were a mis-hire. (This month at SOS, we'll also discuss "problem" team members and how to deal with performance or attitude failures, which can impact entire groups of people.)

  5. Leadership is not a one-size-fits-all skill. Learn how each team member (and even your colleagues) likes to communicate and learn and how to best give them feedback. You may not be able to accommodate every request, but you'll let the people around you know you're open to feedback and insights.

  6. Be friendly, but establish boundaries. Making difficult decisions can be even tougher when your employees are your close friends.

  7. Watch and learn from great leaders. We, as women, have more role models today than we did in my "formative business years" and should take full advantage of that.


I don't have a way-back machine, so I can't undo my mistakes throughout my career. However, self-reflection is a great step toward improvement.


And, if you're currently working for a "problem boss," evaluate whether the situation is fixable and have an honest conversation about ways to resolve your issues. Direct communication is always a great first step. Don't complain to peers or run to HR (if you work for a company). The best leaders are those who can accept and act on constructive feedback.


I hope you can all learn from my own missteps.


I know I did!





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