15 Things I Know Now That I Didn't Know Before I Started

When I interview job candidates, one of the questions I almost always ask them is: "If I was going to start doing your job tomorrow, tell me something that you know that would make me better at the job that you didn't know before you started?" You can learn a lot from the answers you get. With that in mind, 2014 marks the 15th year that I've been a working "professional". During that time I've worked with start-ups in e-commerce, real estate, finance, biotech and healthcare. I've been in some fast-paced and really competitive environments. And I've made a lot of mistakes and learned a lot of stuff that I didn't know before I started.

So I thought I'd put together a list of 15 key things that I've learned (one for each year) that have helped make me successful. Specifically, these are things that I didn't know or appreciate before I got into the real world. Here we go:

1. It's a grind. Work is hard and painful and complicated. If it's not a grind then you're probably not trying hard enough. Get comfortable being uncomfortable.

2. Be candid. Try to facilitate a work environment where if someone is doing well you tell them instantly and if someone is not doing well you tell them instantly. Get used to being honest and upfront about what's working and what's not. This is only hard when your culture isn't used to it. Force people to get used to being candid.

3. Assume that most people are lazy and incompetent and what you want from them isn't important to them. This definitely isn't always true, but you're better off assuming it is.

4. There's no such thing as sales. There are just two parties trying to do something good for themselves and their families. Everything is driven by self interest. Never defer to a buyer. They're not doing you a favor, they're getting something and you're getting something. You are equals. Act like it.

5. Cannibalize yourself. Too long to describe here. I wrote a post on this a while back. But in short, put yourself out of business before someone else does.

6. Always do the the right thing. Don't take credit for other people's work. Publicly recognize your peers that are doing good things. Share your ideas and insights with other people. Don't go over your boss's head. Help people. Don't one-up people. Do the right thing. Don't think about this from an ethical perspective. That might make it too blurry. Think of it practically. I'm telling you with 100 percent certainty, it might not feel like it at the time, but I promise you that doing the right thing is better for you in the long term.

7. The worst trait in a colleague or a boss is insecurity. Avoid insecure people. And avoid insecure managers like they have a contagious disease.

8. Manage yourself harder than your manager manages you. Don't even make it close. If your performance is being actively managed by your manager you are losing. Get in front of it. Innovate on how you should be measured and developed and managed. Never fall behind on this.

9. Try to find the trifecta job. Something that you're good at, something that someone will pay for, and something that you love.

10. Firing someone is almost always the best thing for the person being fired. I've worked in a lot of cut-throat environments and I've seen a lot of people get fired and I've fired a lot of people. Not once can I point to a time where it wasn't the best thing for the person and the company. Both sides always wind up in a better place. And be respectful to people that get fired. Someone that is awful at their job could easily be a top performer somewhere else and someone that is awesome at their job could easily be a bottom performer somewhere else. It's all about fit.

11. Credentials are meaningless. I've worked right alongside several Harvard Business School grads and several software engineers from Apple. There's absolutely no correlation between success at work and these credentials.

12. Hiring good people is really difficult. The traits I look for are grit, adaptability, curiosity and humility. These things are almost impossible to measure in a traditional interview.

13. Admit when you're wrong. If you're the kind of person that can't admit when you're wrong, please stop being that kind of person. Being wrong and admitting it 1,000 times is way, way better than being wrong one time and not admitting it. Embrace being wrong.

14. Be a lynchpin. Seth Godin has a book on this that you should read. But the point is that you should run as fast as you can to be a completely critical piece of your organization. If you're not that, then try harder or move on to somewhere where you can be.

15. Always think in terms of metrics. Whenever you think about an initiative or a new role or a team structure, think of what metrics it will impact. If what you do every day doesn't impact your company's key metrics then you're not a lynchpin.

Pitching Innovation: Short & Simple

I've never been a big fan of the psychology of sales. I've always felt that if you're challenging a buyer, providing insights, selling efficiently and helping them understand a problem, the psychological side will sort itself out. But the fact is there's absolutely a psychological impact that comes with your approach (hopefully a positive one).

I thought about all of this a few weeks ago while sitting on a plane reading Pitch Anything by Oren Klaff. Early on in the book he talks about the evolution of the human brain. There are three fundamental layers of the brain that have been built on top of one another as the human species has evolved. We started with the 'crocodile brain' and then added the mid-brain and then added the neocortex part of the brain.

The first and most fundamental part of our brain is the crocodile brain. This is basically the thing that keeps us alive. We use it to recognize danger and threats. It's an extremely simple part of our brain. It can't think critically and it can't reason. Its only purpose is to protect us.

When you walk into a room to pitch something this is the part of the brain that your buyer is using. The buyer's crocodile brain is on high alert. The buyer is asking themselves questions like: Is this person going to hurt me? Is this person trying to fool me?  Is buying this product going to get me fired? Should I trust this person?

In that first interaction, these are the things that the buyer cares about. That's their focus.

The problem for you as a seller is that when you're pitching, you're not using your crocodile brain. You're using your neocortex brain -- the most sophisticated part of your brain. You're thinking critically. You're giving insights. You're talking about details. You're probably showing detailed charts and graphs. You're probing, engaging and being thoughtful.

But the crocodile part of the brain doesn't understand the neocortex part of the brain. So you're completely missing the mark. You're speaking different languages. You might as well be speaking German to someone that only speaks English. Being smart, in this case, is actually hurting you.

As I said, I don't like diving into the psychology of sales, but there are some good lessons in here.

This insight is a great reminder that when you're meeting someone for the first time, talk to their crocodile brain. Keep it short, simple, concise and clear and don't try to do too much. Save the fancy charts and data tables for next time. Nobody is going to seriously engage with you until you have credibility and some level of trust. That's the goal of the first meeting: build credibility and trust. And try to get to the next step of your education process. But forget about complex models and detailed financial analysis. They won't listen to it, they won't digest it and they definitely won't believe it. Save all of that for the next meeting, after you've satisfied their crocodile brain.

Also, on the topic of keeping your presentation short, Klaff points out that in 1953 when James Watson and Francis Crick introduced the double-helix DNA structure (e.g. the secret of life), the presentation that earned them the Nobel Prize, was five minutes long. That's right, the most important scientific discovery of our time was pitched in five minutes.

Regardless of what you're selling, something tells me that in your next meeting you don't need to be pitching for the full hour.