Are you interested in competing and winning a Toastmasters speech contest?
You have come to the right place.
TPM Note: This realpolitik guide helps, but never forget to focus on skills
This is a different guide that goes into more Machiavellian approaches and even some manipulation dynamics. Not because we recommend them, but because they’re part of life. We never advise making these your focus, but to be aware of them to better navigate life, focusing on skills first, and always preferring an honorable approach to achieving goals.

In all evaluation contests I have competed at, I have only finished either 2nd, or 1st
Contents
- #1. Train At Club Level To Get A Feel For Time
- #2. Make Friends With The DTMs
- #3. Flirt With The DTMs in Your Area
- #4. Make DTMs Your Mentors: Ask For Recommendations
- #5. Visit Other Clubs: That’s Where Your Judges Come From
- #6. Travel With The Judges
- #7. On Contest Day: Network With Possible Judges You Don’t Yet Know
- #8. Pick Low-Competition Markets
- #9. Take Friends: The Boost of a Supportive Audience
- Why World Championship is a Waste of Time
- My Toastmasters Background
- SUMMARY
#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 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
DTMs are more often women than men.
Some are not very busy with work, or they wouldn’t have time for TM.
Toastmasters may attract some because it provides a platform to feel significant, climb hierarchies and acquire status.
I’ve encountered several who could be defined as ‘strong women‘, even domineering.
Some enjoy 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 Toastmasters-.
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 want to be seen as strong and professional.
Learn to get to know the person behind the role, and you will be able to better bond and connect with them.
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, it matters)
No Friendly Judges, No Trophies
Performance always matters, of course.
But so does personal liking. Judges may not even willingly ‘favor their favorite’, but biases are often unconscious.
I know a couple of people who are exceptional speakers and top table topic performers with decades of experience.
They are better with their speeches and tables topics than I am at evaluations.
And yet they never went past the district level and fail to go past the area level more times than not.
I don’t think it’s a coincidence that they are not friends with the DTMs who always happen to be contest judges.
#3. Flirt With The DTMs in Your Area
Some people take it to the next level with mild social seduction.
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.
Machiavellian operators may broach racier subjects that most people wouldn’t dare talk about, and that creates a ‘level of connection’ that’s more unique to them.
Some techniques they may use include starting with more personal matters that make people feel bonded, to then lace in a personal, mildly flirtatious comment. For example:
Mach Player: Whaaat, your children are in their 20’s? You’re so young yourself!
Or they may use small daily occasions to build them up and make them feel important:
Them: Can I sit here?
Mach Player: As if you had to ask, everyone here wants to sit next to you, you’re a legend!
Or they may build them up via third parties, all done in jesting and good for extra smoothness. Plus, it’s socially powerful and leader-like. For example:
Random Pawn: DTM Marta here is my mentor
Mach Player: 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?
#4. Make DTMs Your Mentors: Ask For Recommendations
Some social skills guides tell you to ask for recommendations because it makes people feel good.
That is true in several situations, but not in this one, because asking for feedback can frame you as a beginner.
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 walk the line between asking for feedback, making others feel good, and still projecting competence and authority.
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 mentee 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 as you can, but focus specifically on the ones who are most often 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.
This applies to any area of life including, for example, dating, with new trends promoting moving to more congenial ‘sexual marketplaces‘.
Back to Toastmasters, look at my results for example.
I am good at evaluating (modesty aside: I never met a better observer, which is why I do what I do on ThePowermoves.com).
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: The Boost of a Supportive Audience
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? The guy who had the most friends in the audience 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 they had won the lottery when he finished.
Having people support you from the audience is a massive help.
In the old days of theater, there was such a thing as “clappers“. Today, TV shows have ‘laugh tracks’ for the same reason. Many actors hate them, but they’re still there because they work.
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 a Waste of Time
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 Buffett 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.
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 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.

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:
SUMMARY
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.