Delivering a good pitch is more important than it is hard. People practice, hire “presentation experts”, do all kinds of things. There’s an endless amount of written materials on this topic but people still struggle. I thought I’d share my view.

My relationship with presentations started almost 17 years ago and I loved it from the get-go. This is my first lesson: there’s a significant amount of God-given talent involved in delivering a successful pitch or presentation. If you have it you’ll enjoy doing it and you don’t, you’ll struggle and often shy away. This text is aimed at those of us to whom it does not come easily. I sincerely believe 99% of us can deliver a decent pitch — under the one condition that they know what they are talking about. Meaning, if you are experienced in your field and you know your shit, but you find it hard to draw attention and convey your message, I’m talking to you.

In the past 17 years, I had various public speaking positions, I took part in the training of hundreds of people with public speaking responsibilities. During my time at “HaGal Sheli” I believe I delivered the NGO’s full presentation more than 300 times, and the short version more than 1,000 times. I’ve seen my share. The 2nd lesson I have to share here is that practice can help and practice with real-time feedback can help even more. Speak in front of everyone that’s willing to listen and ask them to write down 2–3 comments. This is preferable to multiple comments and to verbal feedback because you can get lost in multiple comments, and because verbal, immediate, feedback will threaten your ego and is, therefore, harder to use to your benefit.

The times where I myself found it harder to achieve my goal in a presentation were when I had a complex story to tell. The challenge I like to focus on is not to tell the whole complex story but rather to simplify it. Furthermore, simplifying a complex story shouldn’t be about flattening it, making simplistic statements, and assuming pre-existing knowledge among listeners. Rather, it should be about extracting the main thread of thought that makes the story and focusing on it. This is the 3rd lesson I want to share. Draw a diagram of your presentation (on paper or in your mind) and try to figure out what leads to what. What’s the common ground everyone shares, agrees on, and build on it from there. This is harder than you’d think but has nothing to do with your oratory skills, so you can be great at it even if you are naturally terrible at presenting. The human mind gets stories far better than it does lists or numbers and extracting your main thread of thought should help you create a story people can relate to.

It can be equally hard to present to senior professionals as it is to teenagers with ADHD. Can also be equally fun by the way. I think one of the key reasons people doze off while listening is the speaker being too focused on himself. Perhaps counter-intuitively, when speaking, you are not what matters. This is my 4th lesson: look at your audience. Keep your eyes and mind on your listeners and try to engage them. Ask questions, let them speak, agree with what they are saying, use their own words. People listen when they speak, they listen when they are told how smart they are. You do not matter and no one cares about your thoughts. Extremely ironic writing this while sharing my thoughts but written text is very different than oral presentations.

Modern behavioral psychology shows you are extremely unlikely to convince someone of their mistake and you should let go of trying. People, as a species, are very bad at changing their minds. Much of our ability to accumulate deal with complex situations by nature is built on our quality of sticking to what we were previously taught. This was particularly hard for me to learn, and I am still struggling to live by this principle, but my 5th lesson is to stop trying to change people’s minds. A brilliant story about this idea is on this episode (#736) of the wonderful podcast “This American Life”, and the specific story starts at 32:24. Back to our topic, I’d say that it is preferable to build on top of your listeners’ thoughts rather than going against them. If you’re pitching your company to investors, or customers, ideally everything you say should start with “yes, exactly”, relating to what your listener said.

There are a million other good tips. Keep your sentences short, avoid clichés, stick to what you know best, be enthusiastic. As mentioned above, there is an abundance of written, video and audio content about public speaking. I like looking or listening to people I find fascinating and drawing out things they do well. Some of my favorite storytellers are Ira Glass, Dave Chappelle, Sarah Koenig, Louis C. K., Aaron Sorkin, Oprah Winfrey, but you can learn from anyone.

I’ll finish by sharing the challenge I’m dealing with at the moment:

I come off as arrogant and it bothers people. As I don’t have an urgent need to convince people of things, at this moment in my life, I tend to just drop my take and let go of the conversation. This makes people feel I’m condescending and pushes them away from my message. I’m working on this but it is not very easy. Happy to hear tips if you have them.

Entrepreneur (Approve.com) and VC (Entree Capital). Love the startup hustle.