Based on the Proven SPEAK Framework

The Ultimate Guide to Finding Paid Speaking Gigs in Chicago

Use our proven methods to find (and book) highly-paid speaking gigs in Chicago — regardless of your speaking experience or the size of your platform!

Written by Grant Baldwin

Table of Contents

First Things First: Yes, YOU Can Find and Book Paid Speaking Gigs

Public speaking is something that is either incredibly terrifying or incredibly fascinating to most people. Being in front of a group of people presenting is an incredible rush. There’s nothing quite like it. Once most people get a taste of it, they can’t wait to do it again. But most people also don’t know how to get speaking engagements and turn that rush into a full time career.

For over a decade, I made my living as a full-time professional speaker. I’ve given literally hundreds of presentations for thousands and thousands of people. I’ve spoken to classrooms with a handful of people and in an arena with 13,000 people (which was pretty cool I might add :). I also made over $2 million in speaking fees along the way.  It’s been an amazing and unforgettable journey, and I wouldn’t trade it for the world.

But let me be clear about something: all those numbers are nice; they’re cute and cuddly and make me feel good inside. But I don’t share any of them to pat myself on the back. I share all this to say if I can do it, you can do it. 

If you have a message the world needs to hear, then it’s up to you to find a way to share it.  Building a career out of paid speaking is entirely possible, even if you’re just a regular person without a huge platform or big following on social media.

Speaking is a great way to grow your audience or platform. It’s a powerful medium to share an idea or concept. It’s an incredible tool for building relationships. And it’s really freakin’ fun. No wonder so many people are fascinated by this topic. So if we all agree that speaking is a great skill to possess for both personal and professional reasons, then comes the question…

How do I actually get booked (and preferably paid) to speak?

Well, I’m glad you asked.

The SPEAK Framework

Select A Problem to Solve

Prepare Your Talk

Establish Your Expertise

Acquire Paid Speaking Gigs

Know When To Scale

What Is The SPEAK Framework?

Here at The Speaker Lab, we’ve created a proven system called the SPEAK Framework that thousands of students have used to build successful speaking businesses and earn millions of dollars in speaking fees.

In this post, we’ll talk specifically about the first four steps — the S, P, E and A of SPEAK. Once you’re landing paid gigs regularly, you can check out our other resources on K (Knowing When to Scale).

There are 4 main parts here, along with some foundational questions you’ll need to answer in order to get those elusive paid gigs:

  • Select a Problem to Solve — Decide who you want to speak to and what you want to speak about
  • Prepare Your Talk — Create a presentation that delivers value and leaves your audience wanting more
  • Establish Yourself as an Expert — Showcase your experience and knowledge through key marketing assets
  • Acquire Paid Speaking Gigs — Build relationships with decision makers that ultimately lead to paid speaking opportunities

Ready to get started? Let’s get you Booked & Paid to Speak®!

“Choosing an industry is one of the most challenging steps to becoming a professional speaker. The worst thing you can do, though, is nothing.”

3 Questions to Select Your Problem to Solve

Where do we begin? With a problem, of course. Why is this the first step? Because if you don’t get this part right, nothing else will work. 

When I meet speakers who are struggling, even experienced communicators who aren’t gaining traction, I always come back to the same question: “What problem are you solving?” If you don’t know that, you can’t expect to be booked, because speaking doesn’t start with what you want to say. It starts with the problem you want to solve.

Your job is to solve someone’s problem, not deliver a speech. The speech is the way you get the job done.

When people ask you what you speak about, they’re really asking, “What problem do you solve? And why should I care?” No matter how great you are, the audience will always be wondering what’s in it for them. Why should they pay attention? What are you helping them with? When we’re starting out in our speaking careers, it’s not a topic we need to select as much as it’s a problem we want to solve.

When someone asks what problem you solve, you should be able to answer with the following: I help [GROUP] do [TOPIC] so they can [SOLUTION]. 

For example: I help corporate executives maximize their productivity so they can spend more time with their families.

The main goal is to keep your solution short, clear, and simple. Don’t complicate it. My seven-­ year-­ old should be able to understand what you mean. If you’re clear on the problem you solve, it will be clear to clients whether they should book you.  You need to figure out who you’re speaking to, what problem you’re going to solve, and how you can stand out from everyone else.

Let’s start with some foundational questions…

Question #1: Who Do You Want to Speak To?

If you could talk to any audience, who would it be? What is the group of people that gets you excited to speak to? Teenagers? Entrepreneurs? Executives? Moms? Model train enthusiasts? Moms of model train enthusiasts? Who is it that makes you say, “YES…those are my people!”?

There are 7 major industries for speakers that you should be aware of:

  1. Corporations
  2. Associations
  3. Faith-Based Organizations
  4. Nonprofits
  5. Government and Military
  6. Colleges and Universities
  7. Education (K-12)

If deciding who your audience is right now feels overwhelming, that’s totally normal. Choosing an industry is one of the most challenging steps to becoming a professional speaker. The worst thing you can do, though, is nothing. Don’t assume you have to absolutely know who you’re speaking to for the rest of your life. Just pick the industry that seems like the best fit for you right now. Worst-­case scenario: you pick the wrong industry, get a few gigs, and have to go back to square one.

Question #2: What Problem Are You Going to Solve?

So let’s assume you could speak to that ideal audience…what would you say? What would you want to share with them that will enrich their lives, businesses, etc?

Now here’s a little bonus tip: just because you know who you want to talk to and what you want to talk about doesn’t mean someone will actually pay you for it. There are topics that the market will generally pay for and others that they generally won’t. How do you know the difference? Keep reading 🙂

Question #3: What Makes You Qualified to Speak on This Subject?

Of all the other speakers on the planet who could present on this topic, why you? Perhaps you have a fancy degree on the subject. Maybe you have significant experience. Maybe you have produced serious results with what you want to share.

The good news is you don’t have to have some fancy or lengthy pedigree to be able to speak. You don’t need to have been on Survivor (is that even still on?) or have won the Nobel Peace prize (because that’s on par with being on Survivor :).

Now I understand that you may not know the answers to these questions at this moment. That’s okay. I’ve found the more you speak, the better you’ll be able to answer these questions. But in the meantime, at least come up with some broad answers so we have somewhere to start.

“The best marketing a speaker can do is not making the right connections or having the slickest promotional material, but simply delivering a great talk. Let me say that again: the best marketing you will ever do is to give a great speech.”

2 Steps to Prepare Your Talk

It may seem out of order to jump right into preparing and delivering your talk before you even have your first speaking gig booked, but this is the next layer in the process. 

Don’t rush this step because you’re eager to get out there; this is important. 

The best marketing a speaker can do is not making the right connections or having the slickest promotional material, but simply delivering a great talk. Let me say that again: the best marketing you will ever do is to give a great speech.

Before we get too far into creating and delivering a talk, we need to discuss the different types of talks to choose from. This decision will likely have the biggest impact on how you go about creating and delivering a message and how successful you are as a speaker.

Step #1: Choose the Format of Your Talk

There are three main types of talks: keynotes, workshops, and seminars.

Keynotes

What is a keynote presentation? A keynote is any speech that captures the main focus of an event. Larger keynotes are often held in convention centers or even stadiums, but a keynote can include giving a talk at your local Rotary Club, a business meeting, or the chamber of commerce.

Workshops

Workshops or breakout sessions typically range from forty-five to ninety minutes in length. The audience is typically smaller, though often more engaged, than that of a keynote. Depending on the size of the event, you may expect anywhere from twenty-­ five to a couple hundred people at a workshop. They are usually more intimate and relaxed in nature. Whereas keynotes are more polished and practiced, workshops are a little more loose and interactive.

Seminars

Seminars and trainings can last anywhere from a few hours to a few days and allow you to go deeper on a given topic. Typically, speakers who offer these types of in-­depth trainings are hired by companies to help with a specific topic. But you can also do your own trainings if you have built a large enough audience interested in hearing from you.

Step #2: Create Your Talk

Now that we’ve explored the three different types of talks, it’s time to create one. 

The goal in preparing a speech is to become clear on your destination so that everything in your talk points to that one insight, principle, or application. You never want to leave the audience wondering, “What was the point of that talk?”

A good talk should always answer two questions:

Question 1: “So what?” What is the one thing you want your audience to know by the end of your speech? You never want them to feel confused about the message you were trying to get across.

Question 2: “Now what?” What do you want them to do about it? What’s the next step? Where do they go from here?

Answering “So what?” and “Now what?” is your first job as a communicator. That’s your objective. Before you begin practicing your speech, you must be clear on the answers to those two questions. As you develop your speech, consider these questions with each step of the journey. They will help you stay focused and clear.

“Once you’ve prepared a great talk, the next step in your journey is establishing yourself as an expert. As a speaker, you want to be the go-­to authority event planners consult to solve a specific problem for their audience.”

3 Things You Need to Establish Your Expertise

Once you’ve prepared a great talk, the next step in your journey is establishing yourself as an expert. As a speaker, you want to be the go-­to authority event planners consult to solve a specific problem for their audience. This is the problem you defined in step 1 and why we started there.

Before you can start booking gigs, you have to define who you are, what you do, and who you do it for. But just because you know something, that doesn’t make you an expert in the eyes of others. What do you need, then? A brand.

Before we start connecting with decision makers, we want to get a few other foundational marketing pieces in place.

Marketing Asset #1: A Speaker Website

Do I really have to tell you this?! In this day and age, a website is your business card. If you’re serious about speaking, you must have a website. If someone is considering hiring you to speak, they will want to do their homework on you and your website is where they will do it. It doesn’t need to be complicated or fancy. Just a few pages to tell how you are, what you talk about, any recommendations or testimonials and a contact page. Really that’s about it.

If you already have a website, then you’re a step ahead. Just make sure your site communicates that you’re a speaker. People won’t think to book you as a speaker if they don’t know you are one. If someone you know was looking for a speaker, would they think of you? Not because of how good or not good you may be, but do they even know speaking is something you offer?

Marketing Asset #2: A Demo Video

Think of a demo video like a movie trailer. You take a 90-minute movie and boil it down to 2-3 minutes of the best stuff. You can watch a trailer and have a pretty good idea what the movie is about and whether or not it’s a fit for you. That’s exactly what your demo video needs to be. It’s just a few short minutes showing highlights from your talk. Just like your website, a demo video is a must. You can tell a potential client you’re really good and that you’d be a good fit for their event, but they’ll want to see it themselves.

But how do you make a demo video if you don’t have any footage of you speaking? Like with anything, you start with what you’ve got. Do you have any speaking engagements coming up? Even just a small workshop, Sunday school class, or boardroom presentation will work. If not, can you find a small environment where you could speak (for free) just so you could film it? Worst case scenario, I’ve seen some demo videos of speakers just talking to an empty room. Now of course you can’t tell that it’s empty. You just need footage of you speaking.

Marketing Asset #3: Testimonials

Testimonials provide social proof that you know what you’re doing. Now I know what you’re thinking…”Grant, how do I get testimonials if I’ve never spoke before?!” Glad you asked! You have to start with what you’ve got. Have you given a presentation at a work meeting? Pitched a proposal before? Spoke at a PTA meeting at your kid’s school? Any public speaking experience will work.

Now, think back to who was in the audience that could provide some form of testimonial (side note: the fancier their title, the better). You don’t need them to lie or make up something that didn’t happen. But if you spoke for 10 minutes in a boardroom and someone has a testimony that you were “very well prepared and inspiring in your presentation. The audience was engaged with the talk and hanging on every word.” If that happened and someone will give you a testimonial for it, then use it!

Find Out Exactly How Much You Could Make As a Paid Speaker

Use The Official Speaker Fee Calculator to tell you what you should charge for your first (or next) speaking gig — virtual or in-person! 

5 Steps to Acquire Paid Speaking Gigs in Chicago

Now the fun begins. 

This is where a lot of speakers make a crucial mistake, thinking, “Well, I’ve got my website online and my speaker video up, so I’m done.” But your phone isn’t going to start ringing just because you have a website; your inbox isn’t going to be flooded with speaking requests now that you’ve finished your speaker video.

In many ways, the work is just beginning. Now your job is to identify potential clients and reach out to them to find out if they need a speaker for their upcoming event. If you’re lucky, some people may find you through your website; certainly, that happens on occasion—­ in fact, the longer you speak, the more it may happen—­ but the quickest way to start booking gigs is to ask for them.

After you’ve identified who you want to speak to and what you want to speak about, here’s the next big question to ask…

Step #1: Determine the Events/Conferences Your People Go To

When I started my speaking career, I focused primarily on marketing to existing conferences. Why? Because I knew they already booked speakers. I didn’t have to convince an organization who had never hired a speaker that they needed to spend money on me. It’s much easier to get someone to use your service if they’re already used to paying for that service in the first place.

So where do your people gather? Spend some time on Google using related keywords to find conferences, associations, conventions or other gatherings of that audience. Pro Tip: Search by state as well. So for example, instead of just searching for “financial planners conference,” search for “Chicago financial planners conference” or “Illinois financial planners conference.”

Here’s why that is so important…not only will you discover a whole plethora of other options that exist, but often times, it’s much easier to get booked with state, regional or local conferences than it is with bigger national conferences. So start small in your search.

How to Use the Intel Engine to Find Speaking Gigs in Chicago

One of the ways you can make this process much faster is by using the Intel Engine. The Intel Engine is a special framework built for The Speaker Lab to allow you to run customized searches for conferences or events based on things like date, location, industry and more.

Even better — it also allows you to find the contact information of decision makers at those events, giving you a fast track to starting a conversation and getting that gig. 

If you want to learn more about how you can access the Intel Engine, book a call with our team here or click the button below!

Step #2: Start A Conversation

Once you’ve identified some possible events, then it’s time to find the meeting planner or conference organizer. This is usually on the “about page” or “contact page”. Depending on the size of the conference, there may be a bunch of people to choose from or it may be pretty clear who the decision maker is. That’s the key…we need to find the decision maker.

Here’s where a lot of speakers make a big mistake. We’ve discovered a conference we would LOVE to speak at. We did some searching and identified the decision maker. So what do most speakers do?

Send a ridiculously long email (that will never get read) about how great you are and why they should book you to speak. Please don’t do this!

Think of this whole process like dating. You’ve identified someone that you’re interested in and think there might be potential for a relationship. You don’t send them a cold email proposing marriage. That’s a horrible life decision.

But that’s exactly what we do when we send those ridiculously long email pitches to someone who has no idea who we are.

Instead, here’s what I try to do…

Send them a SHORT email asking about the conference. Preferably something they can answer with a short reply. Here’s an example…

Hey John!

I noticed your “Association of Beautiful Brewing Baristas” conference is coming up in a few months in Chicago. And I have a presentation about helping your baristas go from Tall to Venti that I think would be a great fit for your conference!

I was curious if you have started taking proposals for workshop presenters yet?

Thanks John!

Grant
————————–
www.beautifulbaristaspeaker.com

Notice what all happened in this email…

  • I did some basic homework to see when and where the conference is. Don’t email them asking when the conference is when it’s plastered all over their site.

     

  • I didn’t pitch why I would be the perfect speaker…I just offered an idea of what I might be able to speak about. I know what you’re thinking…”But Grant…I don’t have a talk about helping baristas go from Tall to Venti?” Well, they haven’t booked you yet, so you don’t need it. One of the best ways to sell a talk is to presell it. If they reply that they want you to present on that topic, then you can get to work. Now of course, if you throw out a one line topic of a possible presentation, it should be something you can actually present on 🙂
  • It was short and easy to reply to. No long rambling email with an unclear reason for why the email was sent in the first place.
  • I concluded with a clear question that could be answered with a simple yes or no. Easy for the recipient.
  • I included my speaking website at the bottom. I didn’t tell them to go to the site. If they’re interested, they’ll go anyway. When someone new follows you on Twitter, what do you do? You read their short bio and if what they do sounds interesting, you’ll go to their link! You don’t need the bio to tell you to go to the link.

So at this point, all you’re trying to do is build a rapport with the decision maker. Another idea is to research last year’s conference. Who did they have speak? What did those presenters talk about? Do you know any of those speakers? If you’re already in that industry, then hopefully you’ll know a few speakers who have been there before.

If so, it’s a good idea to reach out to them and get some more context on the event. Is the person you emailed about the conference the actual decision maker? Depending on the relationship with your friend, could they give you an intro to the decision maker?

Again, let’s go back to the dating analogy. You see someone you’re kind of interested in, so what do you do? You start stalking researching them online! You want to discover who they’re connected to and if you have any mutual friends.

All of this is about building a relationship and establishing rapport with the decision maker.

Step #3: Schedule a Discovery Call

Once you get a promising response from one of your leads, ask to schedule a discovery call as soon as possible. If you have a scheduling link you can send with a software like Calendly, that’s great! Or ask for their number and their earliest availability. Then, use that call to learn as much as you can about the paid speaking engagement while also communicating the most important information about the speaking services you offer.

The discovery call isn’t just about showing your potential client how great you are. In addition, it’s about getting a feel for their needs and their event so you can quote them an accurate speaker fee. 

You might be tempted to keep using email for this part of the process, but we can’t recommend a real-time conversation enough. Showing the best parts of your speaking business is much harder over email!  Think of your discovery call as the first audition for the part of speaker. 

In addition to subtly selling yourself, you should expect to answer three main questions in the discovery call. They are: 

  1. What do you speak about?
  2. Are you available on that date?
  3. What are your fees?

The discovery call is not a decision-making call. It’s your chance to make a great first impression and learn enough about the client to set an appropriate fee. It is also a chance for you to decide if the client is a bad fit. The next step, the proposal email, puts the ball in the client’s park.

Step #4: Send a Proposal Email

It’s impossible to communicate all the details about your speaking business over the phone. After all, the person on the other end might not remember them anyway. That’s where the proposal email comes in. At the end of your discovery call, let your potential client know you will send them a follow-up email with your speaker proposal. 

Your speaker proposal should include everything a decision-maker needs to know about you. At the end of reading your proposal (and presenting its contents to a board, committee, or any other decision-makers), they should be able to confidently say a) “you’re hired!” or b) “our event isn’t a great match, but we will recommend you to an event planner who might want to work with you.” Remember, it’s not the end of the world if a potential client doesn’t hire you. Those leads can still lead you to speaking engagements through referrals and recommendations. 

Your proposal should include at minimum: 

  • A headshot. 
  • Your contact information
  • The title of your proposed talk.
  • A short paragraph explaining the premise of the talk.
  • Any testimonials from previous event planners (if you have them). 
  • Learning objectives (what your audience will learn from you).
  • References (who have consented to being contacted by your clients). 
  • Your speaker fee (based on what you learned from the discovery call).

Step #5: Follow Up 

I would argue that this step is as important as the initial proposal. Following up with an organizer indicates you are really serious about the event and are super keen on being involved. Send thank you notes to the organizers for considering your proposal and reinforce your enthusiasm for the opportunity. Keep it brief and professional, but with a friendly tone.

After an appropriate amount of time, follow up and check on the status of your proposal. Be polite and concise when you ask and express your continued interest. Be willing to give any more information they may want. It’s worth remembering that the organizers are probably pretty swamped, so respect their timelines and processes. You can follow up more than once, but do your best not to come across as overbearing. And of course, be sure to show appreciation for any feedback or updates.

“Once you’ve prepared a great talk, the next step in your journey is establishing yourself as an expert. As a speaker, you want to be the go-­to authority event planners consult to solve a specific problem for their audience.”

A Few Final Tips

Here are a few more tips as you get started with this…

You’ll often speak for free before you speak for a fee.

If you’ve never really spoke much and you don’t have a massive platform already, there’s a good chance you won’t get paid the first few times you speak. That’s not to say you’ll never get paid, but to get your foot in the door, you’ll often be speaking for free. Remember, you’re trying to build a relationship with the decision maker, so if you can present an insanely good workshop at their conference for free one year, there’s a better shot at getting paid the next year.

Know what speakers get paid for

Just because you’re an expert on a topic doesn’t mean people will pay for it. There are lots of topics that work well as a free workshop but the event planner wouldn’t pay you to talk about. If you notice, most keynote speakers talk about broad topics that most all the audience can connect with. But the workshops or breakout sessions are generally on more niche subjects that appeal to narrower groups of people. As a general rule, keynote speakers are paid and workshop presenters are not (unless that presenter is a “name” in that space, then maybe).

In the corporation/association world, speakers generally get paid for things that tangibly affect the bottom line. If you can help improve sales, customer service or company morale, you can get paid. If you want to talk about how Quickbooks can make accounting more fun…good luck.

Your best marketing is a great presentation

Marketing for a speaker is telling someone what to think about you until you show up and open your mouth. Someone who is a good marketer but a poor speaker can get booked initially but that won’t last. With any service, you still have to be able to deliver. If you’re good, word travels.

One of the best ways to get booked is to get other people to see you live – Any time I go speak somewhere, I always ask myself who is in the area (or at the conference) that has the potential to book me for something else? I know that if I can get them in the room and deliver a great presentation, there’s a good chance they’ll book me in the future. Why? Look back at the previous point…your best marketing is a great presentation. So make sure you pack the room with potential decision makers!

Here’s one final thing to remember….relationships take time. Getting to speak (and preferably paid) is not an overnight process. It’s a slow growth process that takes time. Don’t rush that process.

But if you’re committed to not only the craft of speaking but also the marketing and hustle it takes to get started, you can become a great (and frequently booked) speaker.

Conclusion

Becoming a successful speaker can change a person’s life, whether your goal is to travel the world, make more money, or reach a wider audience with your message. For me, it was all of the above and more. I wanted to know my life had a purpose, to share my gift with the world, and to make a living doing it. And I knew I couldn’t do that if I didn’t understand the actual process to achieve success as a speaker.

I want that for you too. Whatever success means to you, and you are free to define it however you’d like, I hope this article and all of our resources here at The Speaker Lab helps you find your way. Keep doing the work, keep getting your message out there, and I’m confident you’ll discover a life of deeper meaning and purpose. You’ll become the communicator you were meant to be—a truly successful speaker—­ and the world will thank you for it.

Now go make your message matter!

Learn How You Could Get Your First (Or Next) Paid Speaking Gig — Guaranteed

We receive thousands of applications every day, but we only work with the top 5% of speakers.

Book a call with our team to get started — you’ll learn why the vast majority of our students start booking paid speaking gigs even before they finish our program.

If you’re ready to control your schedule, grow your income, and make an impact in the world – it’s time to take the first step. Book a FREE consulting call and let’s get you Booked and Paid to Speak®.