Leveraging Thought Leadership featuring Tony Alessandra

In this LinkedIn Live interview, host Peter Winick talks with veteran speaker and assessment entrepreneur Dr. Tony Alessandra about the role of assessments in thought‑leadership businesses. They begin by defining a validated assessment, noting the American Psychological Association standards and the need for a Cronbach’s alpha of 0.70 or higher, and explain why independent validation (e.g., via Hummro) is essential to avoid bias. The conversation moves to business models: free, lead‑generation assessments versus paid, validated tools that can be monetized. Tony stresses that enterprise clients—especially Fortune‑100 companies—treat validation as a non‑negotiable gatekeeper, making it a decisive factor in B2B sales. They discuss practical design considerations such as mobile‑first delivery, full automation, and user‑friendly interfaces, noting that younger professionals expect app‑based experiences. Different assessment formats are explored, from simple Likert‑scale questionnaires to sophisticated weighted‑average algorithms like DiSC, and the added value of 360‑degree feedback for coaching and development. Re‑testing after interventions is highlighted as a way to turn subjective insights into objective progress, likened to a diet‑scale analogy. Tony shares that his assessment business grew 50% in 2021, positioning it as a scalable asset that could be an exit opportunity, unlike a traditional speaking practice. The discussion then shifts to the speaking industry: Tony recounts his calendar shrinking from ~100 live gigs pre‑2000 to about 25 in‑person events post‑COVID, while virtual presentations now allow multiple daily sessions with high production value. Peter and Tony agree that virtual formats are efficient but lack the networking, community, and serendipitous interactions that in‑person events provide. The interview closes with Tony’s personal philosophies—generosity, evergreen principles, and giving back through scholarships—illustrating the broader values that guide his work.
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And welcome, welcome, welcome. This is Peter Winick. I'm the founder and CEO at Thought Leadership Leverage, and you're joining us on the LinkedIn Live, which is an extension of our podcast, which is Leveraging Thought Leadership. So I want to introduce our guest today, Dr. Tony Alessandra, because he's got a great bio and some cool stuff to share with us today. So Tony has a streetwise, college-smart perspective on business, having been raised in the housing projects of New York City, and eventually realizing success as a graduate professor of marketing, internet entrepreneur, business author, and a Hall of Fame keynote speaker. He's the founder and chairman of Assessments 24/7, which is a company that offers a variety of online assessments. He's a prolific author. Prolific, I think, is an understatement when he's got 41 books under his belt. He has been inducted into the Speakers Hall of Fame in the '80s, a Legends in Speaking Profession, Speakers.com Top 5, inaugural class of the Top Sales World Hall of Fame, and number 1 world top communication guru. And that's— that is not all of the accolades, but let's just dive in. Tony, welcome aboard. Thank you so much for spending some time with us this afternoon.
My pleasure, Peter. Thanks for having me on the show.
So you've been around the this thought leader keynote business through many, many, many cycles, right? The good, the bad, the ugly. Pre-9/11, post now COVID. I want to start with assessments though, and and this is where we could geek out a little bit. So I love assessments, and the reason I love them there's there's a couple of reasons. From a business model standpoint, they're the best, right? So you can produce a tool once, use it again and again and again. But I want to get your take because what we see a lot of is people that don't know or don't understand, and this is similar to the problem we have in instructional design, think, oh, I can just scribble out 10 questions and, you know, do this and do that and whatever. But there are assessments and there are assessments, right, in terms of a validated instrument that always gives a consistent outcome. So give us sort of the an overview of what a validated assessment is, and then we'll get into the business side of it.
Yeah, so a validated assessment is one that meets the requirements of the American Psychological Association. They use, from a statistical point of view— and I don't want to get too down that rabbit hole— we want a a score of a 0.7 or above, you know, from what we call the Cronbach's alpha, which is a statistical measure. And what we do internally at Assessments 24/7 is we have an outside independent company do our validation. And the reason is—
Yeah.
When you do it internally and you look at the numbers and let's say the number says, no, it's a 0.68, You say to yourself, hmm, can I just jack it up to a 0.71 or whatever? There's just some monkey business that can happen if, uh, if you do your own internal validation. So we have a whole separate company, and sometimes when they do the validation, it doesn't come out, and we have to go back, uh, get hundreds of more data points for them. with data points being people.
But I want to go to the point of the validation is basically you're saying to the buyer, to the market, this is a true and reliable instrument. So if I were in the business of selling rulers, and every time I sold the ruler, people got different measurements, I would be bankrupt pretty quickly. So all the validation is ultimately doing is giving proof positive to the buyer that that if we're measuring whatever, a personality trait, an ability, a capability, whatever, that in a certain set of circumstances, you give the same inputs, you get the same outcomes, right? And I think—
Exactly, exactly. And, you know, it's sort of like validation is like the Good Housekeeping seal of approval. And the proof of the pudding is when people take, for instance, our DiSC assessment, almost Almost 100% people look at this and say, this is me. I mean, it really creates an accurate description of the individual.
Right, it's not fortune-telling. So I think what happens is, and I'd love your thoughts on this, early on in someone's journey as a thought leader, they've got, maybe they've got a book, they've got a keynote, and they see other folks have an assessment. So they say, I'm a smart guy or gal, I can create, let me ask a couple questions, let me do this, let me, you know, whatever. And if you're selling to consumers, the reality is consumers just don't know what they don't know. So they will not care necessarily if something's validated or not. Where we tend to put our energy and efforts in, and I think this is where you are as well, Tony, is on the B2B side, on the enterprise side. So what happens is you might get away with an unvalidated instrument for a period of time. It might even be viably commercially successful. And then you go, into the B2B side, and there will be someone on the client side, particularly at a Fortune 1000, that says, great, show me your validation study, show me this. And if the answer is no, it's going to be a really short meeting, right?
Exactly.
So can you talk to that?
Yep, yep. And we do have a lot of people who have a book coming out and, and basically say, you know, we'd like to create an assessment. And what we tell them to do is to go to an independent company An example would be a company called Hummro, H-U-M-M-R-O. And what they do is they create assessments and validate them, but it's a very expensive process to do that. And that's why a lot of individuals say, you know what, I'm just going to do a simple process, sort of like what you would see in a magazine, you know.
Right, the Cosmo thing. So, yeah. So your focus is more on the distribution side of assessments as opposed to the validation side of 24/7?
Absolutely. Yeah, we— so we don't validate, we have somebody else do that. But we do validate. That's crucial because most of our business is either through business coaches that are working with business clients. And And those clients want to know that the assessments really do work and are telling us the truth. And also our end-user corporate clients, which could be anywhere from Starbucks to Microsoft to Tesla or whatever.
Yep, yep. So any advice or recommendations on someone that's maybe a little bit early in the journey that is thinking of developing or deploying or monetizing their thought leadership through an assessment? Any tips or recommendations you'd have for them, Tony?
Yeah, so what we typically find, Peter, is people either want an assessment so that they can generate leads, right? People are interested. So it would be, I want an assessment simply to Have people take the assessment and maybe allow me to sell them something else, whether it be my book or a virtual training program, whatever. And—
So wait, let me pause you there. So I think there's— I want to make sure I'm getting this right. There's kind of a continuum. There's the free assessment. So I'm not monetizing that assessment directly, but the benefit is I'm collecting emails. it's giving people another level of depth into my IP. Maybe they've read the book or an article, but it's another way for them to interact with me pre-buy-sell, right? So there's certain assessments that are on the marketing side is what you're saying, I think.
Yeah, and people are going to do that free version, uh, they're not going to put the money into, uh, to validate an assessment. It's way too expensive.
Sure.
At the other end would be people who really want to to monetize their assessments. So they're charging money, they're charging per person.
Sure.
And those are the people that will in fact put the money in and, and develop validated assessments.
Got it. And are there some best practices that you've seen there in terms of, you know, interface? And because one of the things that I'm starting to see now, there are assessments that have been out in the market for a long, long time that Not, not from a validation standpoint, but visually, maybe they're a little bit dated or they're not available mobile on an app. And maybe touch on that a little bit.
Yeah, well, I can tell you right now that being mobile on an app is crucial because more and more of the people in business now are younger people, whether it be millennials or Gen X, Gen Y, and they do a lot of stuff on their mobile devices. So we're totally mobile. You also want it totally automated. You know, the more steps that you're asking people to take to do an assessment, the less likely they will get to the end and finish it.
Right.
So, you know, when we, when we talk to people about building an assessment, we first ask them, how complex is the assessment that you are building? Some people simply want questions with what's called a Likert scale, strongly agree to strongly disagree, always or never. That's a Likert scale, typically a 5-point scale. Or is there some sort of mathematical algorithm that you use to compute things? A good example of a mathematical algorithm would be the DiSC assessment, where we use a very sophisticated—
Sort of weighted averages against each piece to get the outcome.
Exactly. We also ask people, okay, if you're doing this assessment, is it a self-assessment only, or do you want what's called a 360 or rater-based? A 360 would be, I take the assessment to determine how I see myself and my behaviors, and then I send it out to a representative group of other people.
Right.
Which could be, if I'm in a company, it could be my, my direct manager, my peers, and my direct reports. That's a 360 where they tell me how they see my performance. And then I got—
So stay there for a minute because the data tells us that most of us are pretty lousy at self-rating, right? So this is the Lake Wobegon effect. I'm a better than average driver, I'm better looking, I'm smarter than— like, mathematically, not everybody could be better than average. Right? But when you ask, how am I? So there's also— and I forgot what the word is for this, but you probably know— there's a way to get people to sort of self-rate, but finagle the language a little bit to say, people around here, dot, dot, dot, right? So you can play with that a little bit.
Yeah.
But I love the 360 piece, because then if you're a coach or consultant, you say, well, hey, Peter, you think you're agreeable, easy to get along with, but everybody else around here sees things a touch differently. Let's talk about that, right? And that becomes the, the basis of a good coaching call or a good consulting call.
Exactly. So we, we have seen leaders do this, and you get what the direct reports may say, and it tells you how I can develop coaching or training built around improving their performance. From a salesperson's perspective, what we'd love to do is to have the sales manager, their fellow salespeople, and their customers, their customers giving feedback. Hey, I think I'm really good at, quote, closing the sale, but my customers are saying no, you know, that's—
Your follow-up's terrible or whatever.
Basically tells us what we should do to improve and develop. And usually with 360s, if you are using it as part of a a development program for the employees, you want to have people retake it, whether it be 3 months or 6 months or maximum a year down the road, to see if in fact they have improved by sending the, the regular assessments to the same people, not different people, same people.
So, so let's stay there for a minute. And herein lies the beauty of part of the business model, right? So you take a test, you take an assessment, And it shows you things that you do great, things that you need to work on, things that may be not so great, whatever. Then you commit to some sort of an intervention, right? I'm going to do X, Y, and Z over the next 6 months. And then I'm going to check it again, right? And the reality is, you know, if I use the analogy of a diet, if I was on a diet for 6 months and got on the scale pre and post and the needle didn't move, it's clear that that was a failure. We can get into the whys, but it just didn't work. So one is when we're going back and remeasuring 6 months later, click, you know, the cash register rings again, right? That's the beauty of it. And we get to see, we get to turn subjectivity into objectivity. Hey, look, this didn't move. It says you are still a 7 and the goal was to get you to a 9, right?
Right.
So, right, um, I love the business model there. Are you seeing anything In terms of exits and acquisitions that thought leaders are having of their assessment tool side of their business, right? Nobody's buying anybody's speaking business. That's not news to anybody. But an assessment does potentially position that part of the business to have an exit. Any thoughts or things to share there?
Well, I can tell you, you know, For the last 30-plus years, I have been a motivational speaker. And in the last 2 years, that business has really, really dried up. But the assessment business, you know, our revenue last year, 2021, went up just slightly more than 50— 5-0%. So because of the virtual nature of assessments, because of the accuracy—
Yep.
It allows us to, to reach people, not necessarily in live environments. And just like we're doing right now, where we can actually see each other and talk to each other, you and me.
Sure.
We could actually have— let's say I'm a manager, you're one of my employees, you've taken a 360 or a DiSC assessment. We could actually do our coaching and personal development Right here, not necessarily face-to-face, you know, live, but here we are.
Well, I think the other thing is, if we look at a company making an investment into you or anybody else as a speaker, that's a big-ticket item. If they took those same dollars and poured it into an assessment investment, they're going to touch a lot more people at a different level. It's at a better level. It's a different, it's a different touchpoint. Right? You can reach dozens, hundreds, whatever, depending on your speaking fee. So let's go back to the speaking side, because you've been, you know, sort of as I opened with, you've been around this speaking thing for quite some time, the good, the bad, the ugly. Give us a sense of what you're seeing now. Obviously, everything's going digital, going remote. I mean, I guess my big question is, do you think it ever gets back to 2019 and pre-levels in terms of in-person event living on airplanes, doing 80 gigs a year? What are your thoughts and experiences?
Yeah, no, no, we have, we've definitely had structural differences. And by the way, this all started probably right around 2000, 2001 when, you know, the stock market, especially technology, and then 9/11. So maybe before 2000, like in 1999, I remember this vividly, 1999, I had 99 gigs booked. Paid speeches. That—
and you weren't trying to get to 100 and it still bothers you, were you? No, no.
It allows me to remember 1999 and '99. And typically a full calendar was about 100 speeches a year prior to 2000. After 9/11, my personal thought was that the full calendar dropped to about 80. After 2008, the Great Recession, a full calendar dropped to maybe 50 or 60. Now, after the coronavirus, you know, COVID, et cetera, et cetera, you know, you're now maybe looking at a full calendar at 25.
And that's in person at 25 or—
In person, maybe, maybe 25. And the reason is because of the technology over the years that has gotten so good. And some speakers now are doing 3 and 4 speeches a day on Zoom or platforms like this and still charging enough money that they're making more money than they would have made on a single live speech. So, and You know, the, the, the technology, the equipment that you can use that can, you know, change screens and pull up video segments. Some speakers have gotten so good at this that actually the, the virtual presentation is better than a live presentation in terms of what they can do, what they can show, production values.
And I mean, I mean, The technology is a piece, and then the cost is another piece. It doesn't take much to produce like amazing high-quality stuff from your desk at home without spending tens or hundreds of thousands of dollars. I mean, you could, you could trick out whatever you need for a really reasonable price now. So I think that's interesting. I also see and would love to get your take on this, that this is a great way to deliver content. Right, we're having a conversation. I can, I can see your body language. We can talk. It's better than audio, whatever. It's kind of a lousy way. When I say this, it's not just this platform, any of them. Not a great way to create community and not a great way for connection, right? So those are the pieces that are still, I think, human needs that that in-person event satisfies in a way that the technology either can't or can't as of yet. Right, because why do we go to all these events, right? We go, part of it is the program, but the other part is, you know, random, you know, it's interesting when you talk to event planners about the best events they did, they'll repeat the theme and the look and the feel and the venue. Ask participants about the great event they went, they'll say, oh, 2006, that's the time I met Alessandra and we were at, you know, we're at the bar together and we became really good friends, or, you know, that was the other time where, you know, such-and-such happened. So I think there's a difference between the producers and the participants.
Yeah, yeah. I have always found that the interaction, the networking during breaks and meals has as much, if not more, impact on the attendee at a live conference than actually the speakers.
Right. Said the speaker, right? Said the speaker, that's right.
I mean, you know, gotta be honest with this.
Yeah, no, and listen, there's nothing, there's nothing like a great speaker in their element doing what they do best. So any other, as we start to get ready to wrap up here, Tony, any other thoughts or reflections for folks on either the speaking side, the assessment side, life in general?
Well, you know, I just have certain philosophies as, as you know, we've come through a couple of really tough years and I don't think we're still over it yet. I'm flying to London on Monday, but to get back into the United States, I've got to take a COVID test within 24 hours, even though I'm totally vaccinated. But, you know, so it's still there. I just live by certain philosophies that I keep telling myself, no matter how good or how bad, especially how bad, this too shall pass. Right. And it will, it will. What goes around comes around. Uh, you know, I always— I'm always out there helping people, not expecting anything in return. But believe it or not, I always get something in return. Maybe not from them, but some— somehow, somewhere. Uh, and, uh, you know, I just, uh, I, I tend to be generous with my time and my money. You know, I went to college, I went to the University of Notre Dame on a scholarship for need, not academics. And now that I have been successful, I've actually endowed a scholarship at Notre Dame for students who were accepted but can't afford to go there.
Oh, wow.
Because that's what happened to me. So, you know, again, what goes around comes around.
Yeah.
Before diagnosis is malpractice. These are rules that I live by that it— they're, they're evergreen. They're evergreen, which means they were, they were valid 20 or 30 years ago. They'll be valid 20 or 30 years from now.
Well, this has been great. I appreciate you spending time with us and sharing, uh, your experiences, your thoughts, your expertise, uh, an example of the principles that you just talked about, of the generosity and such. I appreciate you and appreciate your time, Tony. Thank you so much.
Thank you very much, Peter. My pleasure.










