7 Things I Have Learned About Senior Executives and Leaders

The one thing I noticed as I went through my career is how my views have changed about leaders and people in power, specifically in the corporate world. The higher they were up the corporate chain, the more frightened I was to speak with them and the quieter I was around them.

Every email that I wrote was written with fear, and I had other people take a look at it before I sent it. They are extremely busy people, and I didn’t want to bother them. I respected them and their work, and obviously I wanted to impress them. Many times my communication with these executives failed, because I was unable to have an honest conversation with them.

To put it short, I was very uncomfortable dealing with them.

Over the last few years I have had the privilege of being able to interact with experienced entrepreneurs, CEO’s of successful companies and many partners / directors, local tech celebrities, investors, etc.

So, what’s changed about my view now? Here are some things I didn’t know 5 years ago, that I now know very well.

  1. They might not respond back to your email, but they did read it. Rest assured, they read your email. They just chose to not respond back. Why? Because there wasn’t a reason for them to do it. Want them to respond? Tell them you have playoff tickets and need an address to send it to. Magically, they will respond back to your email. The other way is to keep doing great work, and constantly stay on their radar. The more you do this, the better chance they will respond back to you.
  2. They have the same issues similar to people starting in their careers. You know that analyst position you didn’t get because some other talentless person got it instead of you? Trust me, this has happened to them too but on a much different scale.
  3. They all have bosses, even the CEO. When you’re at the bottom of the food chain, you think the CEO is the top person at that company. He / she has it good right? They report to no one! False! Unless they are a founder of a bootstrapped company, they usually report to a board, or a group of investors. And believe me, those aren’t the people you want to report to if you want to have a fun time at work.
  4. They all have weaknesses, they are just better at hiding it. You know everyone’s favorite question “what’s your biggest weakness?”. For lower level jobs, even if your weaknesses are obvious, it doesn’t have much of an impact on the business. It’s more of a “learning objective”.  At a senior level, once a Senior Exec’s weaknesses are known it could have a huge impact on their business if it’s vital for the business. At a senior level, their isn’t this “well, hey you don’t seem to be good at business development, let’s see how good you would be on the operations side” type of deal. If you aren’t good at what you do, you’re gone.  Senior level people have had time to figure this one out, and stick to it and delegate the rest.
  5. What they’ve done in the past defines them in the community – Countless times, I’ll hear other people ask me about someone else and usually the first thing they ask is “what have they done in the past?”. There is this natural tendency to put people in buckets.
  6. Just because they were successful in the past, does not mean they are “successful” now. A lot of them are still actively “trying to make it”. If you are trying to get a hold of them, you have to understand what they are trying to accomplish and how you can help the achieve that goal. It’s a lot harder than it sounds.
  7. They are like you and me, just a lot busier. They are just like everyone else, and most of them are very easy to talk to.  The only thing that separates them from the rest is how good they prioritize their job / life because of how busy it is. 9 times out of 10 you don’t fit in to their busy schedule, unless you can prove to them that they need to talk to you. Don’t blame them for not responding back to your email. It’s not their responsibility to help you just because you requested help. The real question is, how can you help them?

Of course, a blog post isn’t complete without a funny picture related to point #4.

PS: Read the only resignation letter template you’ll ever need.