How to Win A Toastmasters Speech Contest (Strategically!)

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Are you interested in competing and winning a Toastmasters speech contest?

You have come to the right place.

But be warned: this is a different guide.
It’s a guide grounded in the realpolitik of life, including power dynamics, human psychology, as well as Machiavellian strategies and social manipulation (but ultimately, win-win manipulation).

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In all evaluation contests I have competed at, I only have finished either 2nd, or 1st

#1. Train At Club Level To Get A Feel For Time

Evaluations are usually the role where people go the most often over time. In many clubs, mine included, people don’t even try to stay within the time. 

I personally never try to stay within the allotted time because I couldn’t care less. My focus is giving value, not nailing the time or “staying within the rules”.

However, that always puts me at a great disadvantage when it comes to competitions because I haven’t developed a good feel for the time. 
I never know how many of my observations I can safely deliver and as I speak I need to double-check the time every so often, which is distracting.

When it gets red and I then rush to finish and my evaluations end abruptly.

That’s why if you care about winning a speech evaluation contest, you should get used at a club level to staying within the time limit.

#2. Make Friends With The DTMs

Here is the biggest “secret” to coddling with the judges: it’s always the same people who are judges.

And of course, the DTMs are the people who most often end up being judges.
Make friends with them, and you’ll have friendly judges for as long as you want to compete.

DTM Profiling

WARNING: Skip this section if you’re a feminist, male feminist, or virtue signaler

DTMs are more often women than men.

They either don’t have a job, have an easy one, or are retired.
If they do have a job, it’s either part-time, or not too demanding (and that’s why they got time to dedicate to TM).
Some of them are attracted to Toastmasters because it gives them the chance of climbing the hierarchies that they never managed to climb in actual business.

Sometimes they are strong women, even domineering.
They enjoy the hierarchical organization and the “power” that comes from their experience and from judging others (so first hint: make them feel good about their TM accomplishments).

They tend to be very conscientious -otherwise, they wouldn’t have stuck so long with Toastmaster-.
And with high doses of conscientiousness often come an eagerness to obey the rules. 
So don’t to be too rebellious or “too different”: show that you respect the norms.

Finally, some of them are after status and recognition.
They shoot for DTM because they crave status and respect. These women often wear armor and present an aggressive facade that keeps most people at bay. 
You must learn to see behind the appearances because once you get past the armor, they’ll love you for it.

Befriending DTMs

So if you’re not sure where to start from, always make good friends with the DTMs (they always have a pin and the older DTMs have a golden plaque).

Here is what you can do to be friendly:

  • Talk to them face to face
  • Always go to say hi first when they enter your club
  • Make them feel important
  • Add them on Facebook / Linkedin
  • Like their status updates (yes, this is super important)

No Friendly Judges, No Trophies

How important is it being friends with the judges?

It’s crucial.
Either almost as important as your performance or equally important.

I know a couple of people who are very, very good speakers and are top table topic performers with decades of experience.
They are far better at what they do in speeches and tables topic than I am at delivering evaluation speeches.
And yet never went past district level in competitions and fail to go past the area level more times than not.

I don’t think it’s purely a coincidence that they are not friends with the DTMs who always end up being contest judges.

#3. Flirt With The DTMs in Your Area

Flirting is the next level of friendship.

Avoid too openly sexual flirting, but if you are around the same age and if it’s applicable, do hint at the sexual.
This is an art in and on itself and can’t be explained via a short paragraph.

But just be aware that “flirting” is not necessarily sexual.
As long as you make them laugh by broaching racier subjects that most people wouldn’t dare talk about, you’re golden.

Below are some ideas for you.

Most people don’t dare to talk about personal life in their first or second conversation.
But you’re not most people and you ain’t got time to waste. It’s personal life that makes people feel bonded, so go there as soon as it’s safe.

And then use that information to get closer:

You: Whaaat, your children are in their 20’s? You’re so young yourself!

Use small daily occasions to build them up and make them feel important:

Them: Can I sit here?
You: As if you had to ask, everyone here wants to sit next to you, you’re a legend!

Build them up via third parties, this is all done in jesting and good fun. You make them feel great while also making everyone laugh.
Very socially powerful and leader-like as well:

Random Pawn: DTM Marta here is my mentor
You: Wow, congratulations, now tell me, what does one have to do get a legend like Marta as your mentor, are there some secret steps to follow?

If some of these might seem “over the top” to you it means you’re not yet as socially skilled as you could be.
If you execute anything similar to the above well and naturally they will take a huge liking on you.

#4. Make DTMs Your Mentors: Ask For Recommendations

Most guides tell you to ask for recommendations because it makes people feel good.
That much is true. But in this case, it’s actually dangerous.

The more you ask for recommendations and the more you act like you are taking it all in, the more power you give them… and the more of a beginner you look.

And judges don’t elect beginners as the winners.
So you must watch out for what you ask for and how you position yourself. Making them feel good, yes. Looking like a total beginner, no.

I recommend you ask questions, but more like an equal who respects their great knowledge and experience.
It’s also great if you can ask something that they will see you follow up on.

Here is an example:

You: do you think it’s better to go on stage with the badge on or without?

Of course, it’s better to go on stage without the badge, you know that already. But by asking you can make it look like you’re later going to follow their suggestion.

And when they see you on stage they will think “my boy is following my recommendation”.
They will feel like your win is also their win. And they’ll rate you higher.

#5. Visit Other Clubs: That’s Where Your Judges Come From

When you compete you can’t have judges from your own club. 

Theoretically, you could be despised by your own club members but have very friendly judges. 
And the opposite is true: everyone could love you in your club but that means nothing when you compete.

This why it’s crucial that you visit other clubs.
Especially the clubs that DTMs and judges frequent, and mingle mostly with the senior members there.

#6. Travel With The Judges

If the competition is outside of your town, don’t be the lone wolf going by himself.

Travel with as many Toastmasters you can, but focus specifically on the ones who most often end up being contest judges.

And then work them up along the way, offer breakfast, drink with them, listen to their stories and make them feel good.

#7. On Contest Day: Network With Possible Judges You Don’t Yet Know

The higher you go, the more judges there will be. 

Remember that by the time you got to the higher level contests, you already should know all the judges from your areas and most DTMs from your district.
But of course, you can’t know everyone.

So on contest day, you want to increase your odds of adding a few more friendly judges to your squad.
Focus on the DTMs and senior Toastmasters you don’t yet know and do this:

  • Go early in the morning (don’t be the guy who gets there late as I did)
  • Attend all contests (don’t be the guy who only attends his contest)
  • Take supporting roles (judge of other contests, ballot counter)
  • Talk to everyone, but prioritize with the DTMs you don’t yet know
  • Congratulate every speaker (even the ones who sucked)

Be aware that the judges of one contest are also often judges of other contests, so always take the opportunity to be a judge yourself and make friends with the other judges.

Good speakers in a contest are also likely to be judges in another contest, so always make friends with the speakers as well.

#8. Pick Low-Competition Markets

There are two ways to win: get better yourself or lower the competition.

You might think I’m joking, but in many instances, it’s much, much easier and much, much more practical to move to lower competition markets than working on yourself (same for dating, by the way, see: sexual market value hacks).

Look at my results for example.
I am very good at evaluating (modesty aside: I have never met a better observer, which is why I do what I do on
But I didn’t prepare myself for the contests. And I am not that good at public speaking (I haven’t even delivered 10 speeches so far!). And to win an evaluation speech contest you do need to be a good public speaker.

How come then I have been relatively so successful?
The main reason for my success is that I competed in easy markets.

What’s an “easier market” in Toastmasters?
For example, it’s competing in your mother tongue in areas where Toastmasters is not that popular (TM is most popular in English-speaking countries).
Or it’s competing in English in regions where English is not the competitors’ native language.
In my case, I competed in English in continental Europe, and that made it much easier for me.

On the other hand, I would expect the US to be a highly competitive market for Toastmasters. 
India is also a highly competitive market as many people there grow up in a culture that glorifies academic achievements. And they carry that hard-working mentality to Toastmasters.

#9. Take Friends With You: The Stooge Effect

Listen to this one:

In my last district contest where I placed second everyone told me I was superb, and the win was going to be between me, and another guy.

In the end, I didn’t win.
But here is the funny thing: neither did the other guy that everyone tipped off!

It might be a coincidence of course, but do you know who won? It’s the guy who had the most friends in the audience who won.
He had the most friends from his club who all made a huge ruckus when he went on stage and who all laughed hard when he cracked a joke.
And who all applauded and cheered like it was 2019 when he finished (this was a Covid-19 joke :).

Having people support you from the audience is huge.
It’s so important that in the old days of theater, there was such a thing as “hired clappers“, and performers paid them (and still do) because it works. 

If you crack a great joke people will laugh anyway.
But it’s when your attempt at humor is average, poor or “too difficult for most” that having friends in the audience will make a difference.
Their laughter can make the difference in the judges’ minds between a “what was that” and “that was good” (remember that judges also evaluate depending on the audience’s reaction).

Why World Championship Is Waste of Time

If you have been reading around here you know that I’m all about efficiency and efficient use of time.

And in a nutshell, this is what I think about preparing yourself to become a Toastmaster world champion speaker:

Working hard to become a Toastmasters world champion is the equivalent of working hard to win a lottery

And if that’s not yet clear, it means that it’s not an efficient use of your time and your resources (As Warren Buffet once said: gambling is a tax on ignorance).

Difference between evaluation and speech contests

I actually could recommend to prepare yourself well for winning an evaluation speech contest at the district level.

So why don’t I recommend the same approach to the international speech contest?

Here is why:

Large Numbers = Random Results

The difference between the speech contest and the evaluation contest is in the word “world”.

The evaluation contest ends at the district level while the speech contest keeps going to the world stage.
But that also means that there are many more people competing for the world champion.
And when we are talking about very large numbers, there is no reliable path that will significantly increase your chances of winning.

The keyword is “significantly”.
Sure, you can “significantly” increase your skills. And you can increase your personal chances of winning going from, say, 0,1% chance of winning to a 0,2% chance of winning.
And that’s a “significant” increase in relative terms: you double your chances of winning.

But you are still competing against so many people that you still face a 99.8% chance of losing.

Is it worth it to work so hard in a field where no matter what you have 99% chances of losing?
I don’t think so.

No matter how good you are, a speech contest still leaves you with 99+% chances of losing.

Compare it to entrepreneurship instead.
Working on your business -or in your job- you have a much more direct control over your chances of earning more.
Many people can get rich. And one person getting rich does not take away from your chances of getting rich but actually increases them.

Nassim Taleb and Seth Godin say something similar.
You’re better off competing in a field that has many winners than in a field where one wins and hundreds lose.

It’s irrational to seek victory in a field where one wins and thousands lose

Especially when you consider there are plenty of fields where thousands can win.
As a matter of fact, I would say that it’s irrational -and even idiotic- to invest days and days of your time to go after what is, in practice, a lottery ticket.

Working on Skills Matters Little

Working on your skills will not help much.
Most people competing are good, which means that high skills are a minimum requirement, but not a differentiator.

Sure, you can get better.
And you can get slightly better than the competition. Maybe even slightly better than any other competitor.

But that’s still not that helpful and certainly not a guarantee of winning.

Just think about it.
Even if you reach a level of a 10/10, there will be plenty of people that score between 9 and 10.

And skills are only one variable to influence victory.

Too many variables are outside your control

Here are a few variables that are partially or wholly outside of your control:

  • How well you sleep the night before
  • What the judges subjectively think of your speech
  • How much the judges like the others
  • The skill of all the other competitors
  • Howe well all the other competitors prepare

Investing too much of your time in a field where the results are so out of your control might not be the best investment of your time and resources.

My Toastmasters Background

I have been a Toastmasters now for a little over two years.

I wasn’t a good speaker when I started. I’m not that good today either to be honest, speaking is not my strong suit.

My specialty is evaluations, and my skills at evaluating derive from the same analytical skills that I use for this website.
I analyze speeches for structure, body language, confidence cues, persuasion techniques, etc. etc.

And it’s the high quality of my analyses that make me a very good evaluator. 
I can often come up with observations that lead people to think:

Wow, that’s true! I hadn’t thought about that!

And when you can make people think that, you’re on your way to deliver a “wowing” evaluation.

toastmasters international speech contest

My Competitions Results

At my first competition ever as a greenhorn, I won the club contest, the area contest and I placed 2nd at Division level.

At my second competition ever I reached the international finals of district 95 in Gothenburg, where I placed 2nd (2nd sucks, lemme tell you that :).

In every single evaluation competition I competed, I either placed first, or second.
And, finally, I probably win the “best evaluator” award around 90% of the times at club level, and mine is quite a competitive club.

I say this not to brag, albeit that doesn’t hurt :), but to provide you with the credentials that allow me to write a guide on how to win a Toastmaster speech contest (or evaluation contest).

See here how to brag, by the way:

How To Brag Without Bragging: The Covert Brag Technique


You have just read an advanced guide on how to win a Toastmasters competition.

This article focused on a speech evaluation contest, but most of the steps apply to any Toastmasters competition.

I don’t think it makes sense to prepare too hard for a Toastmasters speaking contest because the numbers are skewed against you, no matter how good you are.

Speeches evaluation contests are better because they require less preparation and they have fewer knock-off rounds on the way to “ultimate champion”.

In this article, I showed you the less-known “tricks” to win a Toastmaster speaking contest.

2 thoughts on “How to Win A Toastmasters Speech Contest (Strategically!)”

  1. This was a very offensive article about women and their place in business and networking. Flirt with the judges? Women that never succeeded in ACTUAL BUSINESS or don’t have a job are the judges? Excuse you, but do more research before making such claims. Most women in Toastmasters ARE successful in business BECAUSE of Toastmasters. And if flirting is what you need to do to think you win anything in life, I feel sorry for you.

    1. Lucio Buffalmano

      Sometimes reality can be offensive, Sarah.
      I only write what I study from research and evidence, or what I observe from first-hand experience, over and over -ideally, both-. Neither are foolproof, but they’re more reliable than describing reality as what’s we wish it were.
      The vast majority of the higher-up people -especially women- whom I have observed in the organization did not have equally high-flying careers. That’s been my experience. Yours might differ. But it’s possible you might be writing not on experience, but on what you feel is correct to say.

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