From Start-Up to Grown-Up - Grow Your Leadership to Grow Your Business

If you haven’t done some self-reflection, you hire yourself over and over again without realizing it. Your company becomes a mirror of yourself, with all the good and all the bad. (View Highlight)

I look at my triggers. I think a great leader understands their personality type. For example, I don’t like the victim mentality because that is just taking you down a road where you’re losing your motivation. I’m not saying that people don’t have good justification to feel victimized, they do, there’s lots of situations where that’s true. But then the question is, how do you try to solve for that?

Before we get into how to build yourself as a CEO, a foundational question you should ask yourself is whether you really want to be CEO. Many people think that founders make the best CEOs because they have the vision and the drive necessary to inspire employees and investors and keep them marching in the same direction. But you, you the founder, should reflect on whether you want to keep doing the job of CEO as your company grows. You’ll be required to stretch yourself, to learn rapidly, and to recover from the many mistakes you’ll inevitably make. All the while you’ll be moving further away from your area of expertise (say, product, design, or engineering) and closer to the amorphous, frustrating role of leading people. It’s not for everybody. (View Highlight)

The problem is that when you don’t go to the trouble of getting to know who you are, what your triggers are, what your blind spots are, and what motivates you, you’ll unavoidably do things you’ll regret. If you avoid addressing conflict, you’ll explode in frustration at someone because you’ve let small issues build up. Do you keep your thoughts close to your chest? (View Highlight)

Every founder/CEO needs to inspire her team with a vision of what the company can be—to make sure the music in her head plays the same as the music in their heads. But those people are all different from each other and that means they need something different from you, depending on

How do you express yourself to people? Do you ask them questions, listen to the responses, and supportively explore solutions together? Or do you tell them what to do and hold them accountable for the result? (View Highlight)

How do you deal with conflict? Do you lean into conflict to try to eliminate it, or do you avoid it and hope that people work it out for themselves? (View Highlight)

What’s your natural swing on giving feedback and having difficult conversations? Do you tend to wait to address issues or weigh in bluntly whenever you see a problem? (View Highlight)

How much do you want to control the process? Do you watch over every step in the process or wait for the end result? Do you tend to assume you should handle most things or do you instinctively ask yourself who else could do a certain task? How much personal participation do you prefer and how much can you give up? Do you make decisions by yourself and let people know or do you gather opinions and get consensus from the team? (View Highlight)

How do you respond to stress? Do you check out or shut down? Do you lash out? Do you work harder? (View Highlight)

How do you make decisions? (View Highlight)

Now consider your responses. Did any of your answers surprise you? Were you even maybe surprised that those were the right questions? (View Highlight)

‘This is the CEO megaphone effect. Whenever you say something, it’s taken in by others as if you are standing on the table, looking down at them from twelve feet. You need to have that awareness.’” Most CEOs have to learn this the hard way. (View Highlight)

To become a great CEO, Tony has to learn how to encourage ideas to come to light by praising the team and drawing them out with questions rather than issuing directives. (View Highlight)

Many people have only two speeds when it comes to conflict: silence or violence. Either they avoid it completely or they blow up, and sometimes one after the other. (View Highlight)

Meanwhile, some CEOs think as they talk, leaving people confused, trying to figure out what they are supposed to act on and what is just brainstorming. This leads to a reputation of “crazy-making,” since you seem like you’re constantly shifting what you want, reprioritizing—“moving the goalposts before I even understand the game,” as one frustrated executive once told me. (View Highlight)