10 Speaking Failures and 10 Lessons Learned

If you haven’t failed as a speaker, you haven’t spoken enough. It’s inevitable that some engagements won’t go the way you want. However, the experience you gain from those failures can make you succeed much more often.

But here’s something you know as well. You can learn from other peoples’ failures as long as they’re willing to share them. That’s what this lesson is about…having you learn from my failures.

Ten of My Failures and 10 Lessons You Take from Them to Succeed

When I think back to the engagements that were less than successful, I can usually pinpoint the major reason(s) why. Below are 10 of those reasons along with ways to avoid them so you can have successes more often.

Failure One: Not enough relevant material  

In the first year of my speaking career I gave lots of speeches to Toastmaster’s Districts, clubs, etc. Well, when you speak to Toastmasters, you can talk about things an individual wants to hear such as living your dreams. You can’t necessarily talk about living your dreams to a corporate audience. Why? Because most people are dreaming about working somewhere else!

In fact, listen to me explain what happened once in Nebraska in 1999 (57 seconds).


Most of my material at the time was geared towards entrepreneurs and individuals rather than corporations and teams. As a result, I had a few failures because my material wasn’t relevant or aligned with my audience.

What’s the solution? It’s as easy as ABC (Always Be Creating). Constantly create material for the specific niche audiences you plan to address. Make sure the Foundational Phrases they walk away with are relevant to them.

Failure Two: Squeezed too much in

The old speaker proverb says, “When you squeeze your information in, you squeeze your audience out.” There’s no time to connect with your audience when you are rushing through your material. When I first started speaking, I said to my mentor, “I can’t seem to fit what I have to say into the time-frame that they’ve given me. What should I do?” Unfortunately he said, “Talk faster.” I followed that advice for some time until I realized, “I need a new mentor.”

Do you want to hear proof of how fast I talked? Click the audio below and see how fast I spoke 13 years ago (17 seconds).


The solution is to understand that less is more. If you are scheduled to speak for 45 minutes, prepare enough material for 35. That way you won’t have to rush, you can take advantage of the spontaneous moments, you’ll leave enough time for the introducer, and you’ll promote a smooth adjournment/transition, which meeting planners love.  

Failure Three: I Spoke to impress

Early on after winning the World Championship of Public Speaking, I felt like I had to prove to everyone why I won and that made me temporarily forget why I got into speaking in the first place. Every speech I gave during that time-frame was a failure. Then I heard Willie Jolley say, “Don’t speak to impress, speak to inspire” and I was transformed. My goal once again was not to impress but to touch lives.

The solution is to ground yourself into your WHY. Why are you speaking? If you connect  with your WHY before you speak, you will connect with your audience as you speak.  

Failure Four: Didn’t know the audience well enough

One of my worst failures was a free speech I gave to an audience but I didn’t have a good enough understanding of who would be there.  It turns out that 95% of the audience had already seen the program I presented and they saw me present it only a few weeks earlier. I had no idea I would have so many repeats. So what they loved the first time around they hated the second time. And, at that point in my career, I didn’t know how to instantly guide the ship in another direction. So I hit the iceberg and the whole room turned cold. I failed.

The solution is to have a pre-program questionnaire that you have every client fill out before you speak. Then use that questionnaire to have conversations with the client. When all is said and done, you should know who is going to be there, what their pain is, and what relief you can provide for them.

Failure Five: I forced my humor

I remember one speech in Baltimore where I started with about 5 straight minutes of humor. Someone in the audience finally yelled out, “What are you a comedian?!” There’s no problem with humor. However, if you are forcing it the way I was (i.e. little jokes and puns that have nothing to do with anything), you are reaching for the humor while your audience is reaching for the exits.

The solution is to realize you’re a speaker and not a comedian. Also, the lesson I learned was to have detour-free humor. That means you can have humor that you don’t need to reach outside and get but you can reach inside and uncover. The best place to uncover your humor is inside of your stories and within your characters’ dialogue with each other. That’s organic, uncovered, detour-free humor. Look for it. It’s already there.

Failure Six: I didn’t rehearse enough to leave what I rehearsed

There comes a time in many speakers’ lives where they think, “I’ve given this program hundreds of times, do I really need to rehearse it so much this time?” If you answer “No,” there’s a good chance you will fail with that speech. Why? Because, to me, rehearsal is not about remembering what I’m going to say. It’s about allowing me to abandon what I’m going to say.

That’s right. Rehearsal is about internalizing my message so much that I can temporarily leave what I’ve planned, jump on the spontaneous moments that are bound to come up, and then seamlessly transition back into my planned program. That’s what diligent rehearsal allows you to do. I’ve found that, when I don’t rehearse adequately enough, I don’t connect deep enough because I end up too tied to what comes next rather than to who’s in front of me now. The solution is to rehearse diligently no matter how many times you’ve delivered the program.

Failure Seven: I didn’t connect to myself first

One failure I had years ago (at least I perceived it as a failure even though they’ve invited me back again) was due to something I couldn’t put my finger on right away. I remember before the speech when the meeting planner said, “You look very calm.” She was right. I was too calm. Usually I have nerves before each speech and I’m glad they’re there because they focus me. It might sound silly but I always thank my nerves. However, on this day I had no nervous energy. As a result, I wasn’t as focused as I should have been.

The key was I really hadn’t connected with myself before I attempted to connect with my audience. Speaking is not all about what you say and do; it’s about who you are. It’s about who you bring to the stage that day. It’s about the energy you give them. On this day, the whole me didn’t show up. I wasn’t completely present.

The solution is to have a pre-speech routine that connects you with yourself before you take the stage. Some of the things I do are the following

  • Sit in all 4 corners of the audience (if it’s an empty room before I speak)
  • Go over my opening silently with my eyes closed
  • Say, “May I forget myself, remember my speech, and touch my audience.”

Having a pre-speech routine gives you a charge that helps you create a spark for your audience.

Failure Eight: I didn’t have 100 percent conviction

Thirteen years ago when I was at the World Championship of Public Speaking, the coordinators brought all the contestants together in a room the day before the contest so they could go over logistics. They asked, “Do any of you want to change the title of your speech?” I was thinking, “What?! Are you kidding me? Why would anyone…” but then my thought was interrupted when one of the contestants said, “Yes, I do.” Then another one said, “Me too.” I believe at least 4 of the contestants changed their titles the day before the speech! I remember thinking, “I’m going with what I have.” At that moment I realized I had 100% conviction with my title, my message, and my everything else. Win or lose, I knew I had 100% conviction. I was going with what I had.

Unfortunately, I have not always had that same 100% conviction each time I’ve spoken in the real world. If you are at all unconvinced that you are delivering the message you should deliver, there is a good likelihood that you will not connect with that audience. Why? When you’re not completely sold on your own message, chances are you don’t get them to buy into it. You can’t give what you don’t have.

The solution is to do what I heard Ed Tate call “Freeze the design.” Eventually you need to come to a point where you say, “This is what I’m going with” and then you need to commit to it. Yes you can make adjustments on stage and uncover spontaneous moments but at least you go into the speech knowing “this is it.” Your conviction is convincing.

Failure Nine: I let the beginning ditch become a huge hole

I used to think that all is won or lost in the first minute of a speech. In other words, if I heard some laughs and saw good energy in my opening, I was in good shape for the rest of the speech. On the contrary, if they didn’t laugh and didn’t show good energy, I was doomed. I would think, “This will be a rough one.” I thought this for years. Whenever I had a bad start, I would let that ditch turn into a huge hole.

Then, in one speech years ago, I had a bad start. I didn’t get the laughs I expected and I didn’t feel connected. But I told myself, “Something I have for them will connect. Something coming up will connect with them.” And guess what happened? I connected. Then I deepened that connection as I went along. That was a real breakthrough because it let me know you can get out of a ditch and even build something significant on top of it.

Yes the first 30 seconds can help you or hurt you. However, please know that it’s not over if you don’t connect right away. Know in your mind that “something coming up will connect” with them. If you keep that confidence, even if it takes a little longer than normal, you will find yourself connecting to your audience. At the end of the speech, they won’t think, “Wow, it took him a while to connect with us.” Instead they will simply walk away feeling the connection.

Failure Ten: I didn’t have enough material.

My first time speaking overseas was a disaster. Why? Because they said, “We want you to do eight 45-minute speeches in six days and four of them will be to the same audience.” Whoa! I was so excited to fly overseas and speak that I completely neglected to consider something very important…I only had material enough for one or possibly two 45-minute speeches! I certainly couldn’t give four different speeches to the same audience. I ended up failing with 6 out of the 8 speeches.

One of the successes on that trip

The solution is to follow the same formula I mentioned above in mistake number 1…the ABC formula, which stands for Always Be Creating. Now I have material enough for several days of speaking. The key is to set up a system of testing and tweaking. Consistently try out new material and test it and tweak it. That’s the only way you’ll know what resonates.

Also, I should still have taken that engagement but under my own terms of speaking only once or twice to each audience. You do have a say in the negotiations so don’t set the bar too high for you to reach.

Final Thoughts on Failure as a Speaker

Some people say, “Craig, you didn’t really fail. You just didn’t succeed as much as you wanted to with those speeches.” Well, call it what you want. I believe facing reality is the key to changing reality so, to me, the reality is those speeches were failures. I know because I was there.

You can succeed much more than you fail if you avoid the 10 mistakes illustrated in this lesson. Remember that you master what you measure. When you record your speeches and find out what went right and wrong, you will reward yourself with better speeches, better connections, and better speaking opportunities.

And, of course, the subtext of this entire lesson is the following:

Even if you fail, you can eventually prevail

Craig Valentine

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