Lessons Learned Are 4 Losers

business lessonsNotes for my Leadership Memoir:

Let’s take a lesson from Tom, the newly minted and inexperienced CEO. When you’re the new CEO on the block, everyone is looking at you to do great things. Some, like your employees and especially the leadership team, are a little wary and waiting to see whether you prove yourself or fail. They hold off a bit on hitching their wagon to yours—watching out for their own butts. The board brought you on to shake things up, so you’re on a short time frame to prove yourself. Generally speaking, you’re also given a lot of leeway to do whatever you want.

I took over a great organization that was a cash cow after a buyout, and the board wanted me to grow it in three years and triple the multiple. With that kind of cash being thrown off, how could I lose? The old CEO offered to spend time with me and walk me through some of the more nuanced areas of the company, but why waste the time? I didn’t plan to do anything he had done, so I didn’t want to be cluttered up with what didn’t work. I love how our US presidents leave letters for their successors with what are supposed to be inspirational and helpful lessons learned—does anyone really read those? If you’re the one in the Oval Office now, why would you even care? You have new ground to plow and great things to accomplish. They were part of yesterday, not tomorrow. (Note to self: Remember that phrase for my memoir)

The business was not complicated. First order of business was to get rid of the senior team and bring in my own. Not a big deal that it was two totally unrelated types of business—they’ll learn quickly, they always have. Business is business. Once they’re in place, they can tell me how they think we should proceed. I only kept the CFO and got rid of the overpaid, undereducated bunch of freeloaders anyway, so no loss with them.

My team went right to work, except for the COO, who had to take some personal time off between gigs, which cost us about three months. Not a problem, though, as I spent the time introducing myself to the customers and independent contractors that delivered our services. And might as well take advantage of the great city while I was here! A little R&R on the company dime is just what the doctor ordered.

OK, back to business. My team recommended we roll out three new and radical programs to jump-start growth. I love it. They were new and different and would really shake things up. We rolled them out with great fanfare (the secret is always in the marketing pitch behind any new initiative), and they were widely received as new and innovative—mostly by the staff, which I found to be very supportive. I had heard a few rumors that this had been tried before, but my comeback was, “Not like I am doing it!” The real pushback came from the field contractors. They started raising alarm bells and telling me I didn’t know what I was doing. First, I was shocked that these assholes were telling me what to do with such disrespect. Then I realized they were really just frustrated wannabe CEOs who failed and were now contractors. What did I care what they thought?

A year into our innovations, I started to hear a daily drumbeat of messages of “we’ve tried this before and it failed,” “we’re not getting support from the field,” “this is like Groundhog Day,” and “it’s déjà vu all over again.” We were not getting the results, and in fact, we had moved backward. The bottom line was shrinking before my eyes. Why didn’t they tell me all this before? The board was not happy.

I brought the leadership team together and asked them to give me a rundown of what wasn’t working. Well, the floodgates opened up and they dumped all over me that I didn’t listen to what had already been done and was ignoring the fact that all of these initiatives were not new, just retreads. I exploded at the team. How could they have let me down like this? I had asked them to vet these ideas, so of course, I thought they were new. How could I possibly have known that they had been tried before when my team let me down so badly?

Of course, I was going to have to make a lesson of these guys. One of them would have to go. I would have to make one of them a scapegoat. Unfortunately, I decided to let the COO go since she took three months to actually get here—she’s the one who missed the due diligence. It’s not my job to look backward; it was hers, and she should have presented only new and fresh ideas.

When faced with a bad plan, or a plan that has been tried before, resist the urge to go back and look at lessons learned. Remember, success only comes through trying out new things and moving as fast as possible away from failures until you hit on one that works. (Another gem for my leadership book.)


Ignoring the wealth of knowledge from our predecessors or outgoing leadership is a reckless—sometimes fatal—mistake. Sometimes it can be due to pure hubris, such as in our current political leadership. Sometimes it can be due to ignorance or even fear. Fear of failure or of doing anything the same way as it was done in the past is not an excuse to overlook the lessons of others. But both past successes and failures have invaluable lessons for every leader.

When developing leaders, you want to share examples with them of what has worked for you and what has not. Ignoring those, you’re casting them out to sea without a safety rope. They might make it, but they might not. Why take that chance? One of the great benefits of using the past as context for your decisions going forward is that you will save enormous amounts of time and resources. Why would you try something that failed in the past in exactly the same way? Learn through a debrief what didn’t go well and try something different. Time and money are things we never get back, so why would you spend the same amount on a clunker that won’t drive? You wouldn’t. Don’t waste your precious leadership capital without carefully considering the lessons from the past. (Note to self: Put that in a leadership book! Oh yeah, I am!)

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