How to be a boss

Your very own personal leadership development plan

Congratulations!! You just were placed in a position of leadership and are now the boss. You can now kick back and relax on the golf course while all of your people do all of the work. Everyone will be back at the office, but this is going to be you.

Well, not exactly. That’s mistake number one as a boss.

I’ve found that people tend to criticize their boss constantly for not doing “actual work.”

However, once they become the boss, they’re overwhelmed by how difficult it is. Their hours get longer as a boss. They feel like they’re still failing, so they work even more. Then, they start driving their teams harder because they feel like they’re failing as a boss.

Suddenly, they’ve turned into the boss they loved to criticize and hate.

Fear not! Let’s put together your very own personal leadership development plan. The goal here is to highlight four mistakes new bosses make and how to avoid them best.

The plan here writes out four fundamental errors that many new bosses make. After describing the mistake, we provide a “tips” section that has a couple of strategies for how you avoid this mistake. It’s up to you to pick out which approach makes the most sense to you.

Why am I writing this? Because, as regular readers know, I started my entrepreneurial career freelancing while working for other people. I worked for some shitty bosses. Here’s what they did wrong, and what I do try to do right when managing my own people.

How to become a good boss 

Watch out #1: Beware the dinosaur’s tail

Remember back in middle school when someone was asked to go to the principal’s office? Everyone would immediately start with “OOOOHHHHH, you’re in trouble!”

That poor kid would have to walk to the principal’s office, expecting the worst. Once they got there, it typically was something minor. Their parent had come to pick them up for a Doctor’s appointment or something.

But that’s the power of the dinosaur’s tail.

Here’s what I mean. A principal is a dinosaur. They’re big and scary, with a huge tail. Even if the dinosaur doesn’t mean any harm, they turn around, and their tail accidentally knocks down a tree. Something as simple as asking to see someone can put the fear of God in them.

That’s you as a boss.

If you ask to see someone on a Friday afternoon, they’re going to be freaking out until then. You could want to congratulate them on a job well done, but they’ll assume they’re being fired.

If you cancel a meeting, recognize the impact that will have on the other attendees. They probably were working hard to prepare materials to impress you. After all, you are the boss. By canceling, you’re also communicating that their preparations mean little to you.

Tips to beware the dinosaur’s tail

  • Always consider how your employees might receive a message, such as asking to meet on a Friday afternoon
  • If you do need to ask to meet someone on a Friday afternoon, always qualify it. “Hey John, can you swing by my office this afternoon? It’s nothing bad at all, I just want to congratulate you on a job well done this month!”
  • Say thank you! The more you acknowledge that people were putting in work to prepare for a meeting with you, the more they will appreciate you as a leader.

Watch out #2: Make sure your team feels valued

As a leader, you’ll need to understand what each member of your team cares about. If you don’t, you’ll fail as a leader.

The reason why is your team members need to feel valued. Harvard Business Review frequently mentions how feeling valued is the most important thing to do at work.

In other words: if your team doesn’t feel valued, they won’t be able to perform.

So it’s your job to get to know each member of your team. As you do, you’ll learn what your team cares about and what they’re good at. You need to know that Stacey loves Powerpoint and thinks she makes great slides, while Doug loves Excel work.

Otherwise, you might accidentally tell Doug to do the powerpoint and Stacey to do the Excel.

It’s a small point, but vitally important. If you accidentally make this mistake, but Stacey and Doug won’t feel valued because they aren’t able to use their skills.

Tips to learn about your team are:

  • Hold meetings with each team member to get to know more about them. If you’re nervous to do so, check out our article about how to have conversations with Uber drivers.
  • Say hello to everyone each day. Ask them “What are you excited about?” rather than the generic “How are you?”. You’ll learn the type of work that your employees get excited about
  • Be the accessible boss: keep that office door open

Watch out #3: Acknowledge your team will know more detail than you

It’s an ego thing that all bosses need to get over, but the reality is true: your team will be better informed with you.

Think about it as breadth vs. depth.

From a breadth perspective, no one knows more than the boss. You know what everyone is working on and you can see the whole picture. For example, you know that Jim is working on selling more paper.

However, each individual knows more depth than the boss. For example, Jim knows more detail about the specific contracts with customers than the boss does.

In this circumstance, it’s easy for a boss to forget their teams know more detail than they do. When this happens, it can lead to a lack of productivity.


Watch out #4: Set a vision and make sure everyone knows it

As we talked about before, you have breadth! You understand how everything fits together. It’s up to you, with input from your team, to set the vision.

Think of the vision as: “what does good look like six months from now?”

Every single person on your team should give the same answer to that question. With everyone working together for the same goal, amazing things can happen.

My first time as a manager, I thought it was pretty clear what the team’s goal was. I had said it at the kickoff meeting.

However, once we failed to miss the goal, I went back and debriefed with the team. It turns out that everyone was confused as to what the goal was.

So next time, I doubled down. I over-corrected and said the goal more ten times a day. Everyone knew the goal and was working for it. Even better, the team ended up exceeding the goal by a wide margin.

The trick is the famous Rule of 7. It essentially says you need to repeat a message a minimum of seven times, or people won’t remember it. Use that to your advantage as a boss and continuously repeat it.

Tips to set a vision and make sure your team knows it:

  • Solicit input from the team when deciding on the vision. Remember, you probably have the best breadth of knowledge
  • Repeat the vision constantly (7+ times) so everyone knows what good will look like six months from now

Being a boss is hard, but we hope this plan will help your transition to leading a team

It’s difficult to be a boss. There’s no doubt about it. It’s okay to be unsure and worried about it. It’s okay to struggle. I did as well when my first team missed our goal.

But that’s okay.

What matters is to have a plan that will help you improve as a leader. We hope that the tips here will help you avoid some of the common pitfalls you might see.

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