• Cloudway Partners

A Better Boss


Many books have been written about what makes a good boss, and how to be a good boss. There are plenty of lists that circulate LinkedIn and the internet addressing the subject (be a good listener, do as you say, be transparent, be authentic, etc.) . Don’t confuse being a good boss with being a good leader. They sound alike, but there are differences to being a boss vs. a leader. These lists sound obvious, but they also rely to an individual’s own style. As we progress through our careers, we gain various bits of knowledge by observing other bosses. Oftentimes, I learned the most from the worst bosses – key examples of what NOT to do when I got to a position of management. A boss’ true colors come out when things go sideways. Just as no sailor ever learned anything on a clam, clear day, no boss ever learned anything when everything was running smoothly. What matters is how you set your own foundational underpinnings – your own center of gravity. They will guide you through good times and bad times.


I have found that being a parent helps me be a better boss. That doesn’t mean I treat my people like children. It also doesn’t mean being a great or perfect boss. Let’s look at the fundamental precepts of being a good parent:


  1. You want your children to be successful. Above all, I want them to get good grades and be successful. I want them to be better and have more than I did, and to enjoy greater success, no matter their chosen profession or path. Apply this to your employees: You want them to be successful. You want them to do better than you ever did. Who wouldn’t love a boss like that? I take great pride when a former employee becomes a CIO or prominent leader. Of all the bosses I’ve had, one once told me something that has stuck in my head: “My job is to protect you politically, so you can be effective and make us all successful.” There it is, in its rawest, most succinct form: the definition of a good boss.

  2. I want and expect my kids to get a decent education. That means college and some kind of graduate school. I’m a big believer in education. The better educated you are, the more options you have. Education sets you free. In the professional world, that means supporting your people with all forms of better education. That could be as simple as paying for a one-hour online course, or as complicated and expensive as supporting them through an MBA. Investing in education yields dividends for everybody: the employee, the company, and you. I remember vividly a boss I had almost 30 years ago. He encouraged me to get an MBA. I was only a year out of college and had no real desire to go back. I also remember one of his peers, who like to make fun at my expense. After one particularly nasty comment, I thought to myself, “If I get an MBA I won’t have to put up with guys like this the rest of my career.” So, the combination of good boss & bad boss led me to graduate school.

  3. I have my kids’ backs. Yes, they make mistakes. Yes, they occasionally get into trouble. But I still have their backs. Always. It doesn't mean we won’t have a loud conversation at home, behind closed doors. But out there, at school, or wherever, I have their backs and protect them. That’s my job as a parent. Apply this to your employees. Have their backs. Even if it means exposing yours. The best boss I ever had always had my back, even if that meant taking a hit himself. I, in turn, always had my employees’ backs (or tried to, at least), even if that meant getting an earful from my own boss. It’s not always easy. Sometimes there is enormous temptation to throw someone under the bus, especially if you are caught between an employee who screwed up and your own boss who believes in punishment. Of course, if this happens too often, it might be time to have a serious conversation with your employee. A boss I had told me a story about when he was managing a development team. One of his developers had made a coding error, causing a major system failure. It took time to correct. Meanwhile, the CIO was getting lots of heat from the rest of the company and customers. He wanted the developer’s head. My boss told him that the ultimate responsibility rested with him. He would deal with the developer, and if the CIO felt he needed to punish someone, it should be him. The CIO backed down. It took a lot of bravery and conviction to stand up to a person in much higher authority, especially under those circumstances. I’ll never forget that.

  4. I make sure to keep my kids well-fed and well-rested. There’s a lot of “go to bed,” “eat your lunch,” etc. The corporate analogy is to make sure you employees have enough time to get decent rest, have enough time for lunch, etc. An overworked, under-fed, tired and stressed-out employee is less effective than one who is not. I can’t always control the amount of homework the kids bring home, but I can help them. Time management is a key skill – one that kids should be learning in high school. But many adults still struggle with time management. It doesn't help when the boss overwhelms them with work. Sometimes that can’t be helped, but do your best to even out the workloads, offer to take on things yourself, and be attuned to their moods.


My “list” on how to be a better boss is short – only 4 items. But all other lists can be derived from these four elements:

  • Help your people be successful

  • Encourage and facilitate education

  • Have everyone’s backs

  • Pace the workload

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