Level Up Challenge

present with people Jan 23, 2023




When I was in my 20’s, I spent a good amount of time sending VHS tapes to leaders around the country. Okay, before I go any further, let me make sure we’re on the same page. A VHS tape was this black rectangle made out of plastic that you could record video on.

Now, it wasn’t like I just sent VHS tapes to any and everyone I could. As I built a relationship with speakers and leaders who I respected and wanted to be at their level of caliber, I would ask them to critique my speaking. I would record myself speaking in front of an audience on a VHS tape and send it to them. I would then hold my breath until the critique came in. Once I received the critique, I did everything I could to not blow it off in my pride but to learn from it. It was such an amazing season with an incredible learning curve and experience.

Early on, I learned that every leader and communicator needs people in their lives that will challenge them to grow, such as leaders who are a level or two up from where you are and who can speak to the struggle you’re going through. These are leaders who know exactly what it feels like to be where you are and who can help you become the leader and communicator you long to be.

I had plenty of people in my life I could ask about my speaking: my spouse, my employees, and the people I communicated with regularly. However, there’s something special about finding a voice who has an expertise in the discipline that you’re wanting to grow in and who can challenge and push you to the next level.

In my 20’s I thought I was a very talented speaker. Let’s just say I didn’t struggle with confidence when it came to my communication ability. I always loved speaking, I loved to get in front of people and I loved to deliver my message. I really thought I was something special. At the same time, my intentions were pure in that I really did want to grow. I didn’t want to just be a good speaker who could hold an audience’s attention. I wanted to be the best speaker I could be.

I spent my childhood reading every book on the great Boston Red Sox player Ted Williams. In my opinion, Teddy “Ballgame” was the greatest hitter to play in the majors. He always practiced, always swung his bat and studied everything he could about hitting. One of my favorite quotes of his undoubtedly shaped my desire to keep growing. He said,

“When I walk down the street, I want people to say, look, there goes Ted Williams, the best ever.”

That inspired me to be the best speaker I could be. I genuinely wanted to improve my speaking ability and was looking for ways to grow.




During my formative years, John Maxwell had a monthly leadership tape club and once a month this cassette tape filled with an amazing leadership talk would be mailed to you. It was the greatest day! Again, let me backup. For those of you who don’t know what a cassette tape is, it is basically just a smaller version of the VHS tape.

John talked about making lists of leaders you admired and wanted to rise to their level of leadership. He taught you to reach out and try to connect with them. If they agreed to meet with you, then be prepared with a legal pad and ask three questions. Ask your questions and take copious notes so you can learn and remember everything they said. John also recommended that you offer to pay them, but I was in my 20’s and didn’t follow that part.

So, that’s what I did. I made my list and I started to connect. I built relationships with leaders all across the country. I was so surprised how receptive they were to either an email with questions, a phone call, or a sit down. This was huge especially when I went to conferences. I would spend months ahead of time contacting leaders and asking them if they had time to connect at the conference. 8 out of 10 times they said yes. It was incredible.

The learning that I experienced during that time was catalytic. I really believed it vaulted me ahead in many areas of my life and speaking. I learned and experienced a lot about new levels:

  1. A new level of humility. I tried sending my tapes as prideless as I could, but down deep there was definitely some pride motivating me to send those tapes. I wanted them to say what a good communicator I was. But, when they’re comments came back, they took me to a new level of humility. Seldom were they mainly filled with compliments and platitudes. They were filled with painfully rich constructive criticism that in the end, did wonders for my growth as a speaker. 
  2. A new level of speaking. Spending time one-on-one with those leaders was absolute gold. Being able to ask questions, listen to their responses and hear their stories not only inspired me, but it catapulted my desires to get to the level they were at. My speaking and communication skills increased exponentially because of that inspiration. 
  3. A new level of experience. Because I took the time to hear exactly how those leaders got to where they are, it gave me incredible insight about how I could level up. That wisdom came from seeking out challenging words and it helped usher in a new level of experience for me. 

What I learned from the conference meet ups, the sit downs, and the critique that came my way from sending those VHS tapes was incredible! It was priceless. Did I agree with all of it? Of course not. I didn’t agree with it all because sometimes I had blinders on. I had blinders of pride, arrogance, immaturity, and overestimating about my speaking ability.

We all have blinders. I don’t know what blinders you may have on. I don’t know if they could be holding you back from experiencing a new level in your speaking or leadership, but my encouragement would be to do everything you can to identify what your blinders are and then seek out the necessary challenging words so you can experience the next level.




Step 1: Make a list of every leader and speaker you admire. Create a spreadsheet of all their names, website, speaking video and contact information. Learn as much as you can from their social media and websites. Find out if you’re already connected with anyone that knows the leader you’re reaching out to. This is not for leverage or to manufacture a connection. But, people are inclined to connect with you if someone they already know vouches for you. If you find any mutual connections, reach out to them and kindly ask if they would facilitate a connection with you.

Step 2: Send an email with a short video of you speaking. In your email, be humble and introduce yourself. Make sure the email isn’t incredibly long and read through it multiple times. Make it clear that you’re wanting to connect with them and you would love to ask them questions about their expertise. Be specific. If you want them to critique your speaking, then send them a short 5 minute clip and ask them exactly what type of feedback you are looking for. If you want to meet with them, ask if they would consider connecting in person. Be clear.

Step 3: Receive their critique with an open heart. If they don’t respond in a week or two, reply to that email and send one more request. When they do respond, thank them for being open and willing. If they’re open to meeting with you, drive the extra miles to meet them wherever is most convenient for them. Be willing to do whatever it takes. Remember that this is for your benefit. Be clear in asking for constructive criticism and use it to grow. Thank them for their honest feedback and not holding back.

Trust me, this process is going to help you! When I would receive a letter in the mail after sending someone my speaking VHS tape, it was a great day! Just the fact that someone would take the time to do this was huge, but it also meant that my leadership and speaking was about to go to the next level. And that’s what you want as a speaker.

In my 20’s I let my pride guide me way too often. I relied too heavily on my gift and the fact that I could stand in front of any audience and captivate them. Even if you’re a natural, it won’t last forever and you have to learn how to seek out, receive and use challenging words to level up your leadership and speaking.

To start your leveling up journey, I’d love to offer myself to be on your list of people to ask for constructive feedback. Just email me at [email protected] and let's talk.


By Jason Raitz - Founder of Speak with People