How To Execute A Successful Multi-Day Challenge

With a multi-day challenge of combining storytelling and strategy, you can boost engagement and achieve success more efficiently. Enhance your strategy, boost engagement, and become a highly successful coach. In this episode, Kendra Perry reveals how to execute a successful multi-day challenge. She talks about her early days in business, a stressful five-day challenge, and how you can learn from her mistakes. Discover how the three-day challenge can be your golden ticket to engagement and sales. Tune in now!

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How To Execute A Successful Multi-Day Challenge

I’m pumped because I want to talk about this topic. It’s something that I’ve had a lot of success with. It’s something that I’ve done several times over the course of my business, and it’s always been successful. I’ve found a way to do it that is a whole lot less stressful than what I was doing in the beginning and what I was doing previously. I want to talk about how to successfully execute a multi-day challenge.

Challenges are not new. They have been around for a long time. I ran my first challenge in 2016 or 2017. I like to think of it as a mini course over a series of days where, each day, you give the person or the audience something to do as homework. You can give them feedback on that homework. It’s a sell-in to your primary offer.

As a health coach, I ran two different five-day challenges. The first one I ran was for the first launch that I ever did for an online course I created. That was a huge mistake. It was stressful. Planning any multi-day event is a huge amount of work. I was completely ignorant. I was new in my business. I’d never done something like that before, and I was blown away. I did not realize how much content needed to be created. At the time, I didn’t have a team. I don’t think I had anyone. I was doing everything myself. I do not recommend that. If it’s your first launch, please do not do a multi-day event. Start with a webinar or a live stream.

The second time I did a challenge was a five-day challenge, but I was more educated at that point. I had a virtual assistant. I knew more about how to do things. That one was successful, but it was still a lot of work. I did my next one in early 2022 for business coaching. It was for HCA. That one was successful, but it was stressful.

The way that I was taught to do challenges, I’ve talked about this a little bit before on the show, but I was taught to do a five-day event where it’s a four-day challenge, and there’s a bonus training on the final day, which is the webinar. This worked for me, but I found it was so much work. You’re not only putting together a challenge, but you’re also doing a webinar on the final day. If you don’t have any of that content and you have to make the challenge from scratch, plus the webinar, you better give yourself multiple months, like four months, to prepare.

I remember doing that five-day challenge in February 2022. I’m thinking, “Who would do this? This is ridiculous.” It was so much work, and I was exhausted. I was spending twelve hours a day giving people feedback on their challenges because we had hundreds of people in the group, and everyone was engaged, which was amazing. I was on my phone from 7:00 in the morning until 7:00 at night, giving people feedback on their challenges. That was a big no for me. After that, I was like, “Why do I even do this? This doesn’t even make sense.” I decided that I needed to do something different, which is where the three-day challenge that I do now, which I’ve done twice, was born.

That’s what I’m going to be talking about because I found this to be way more successful than my five-day challenge. It was a whole lot less work. With any multi-day event, regardless of what you’re doing, even a webinar, you want to give yourself. If you haven’t created your webinar, I would give you at least a couple of months.

If you’re planning a multi-day event, I would give you at least three months and a little bit more if you don’t have a team. If you don’t have a team, you are doing everything yourself, and it’s a lot. If you don’t have a virtual assistant, at least, I probably wouldn’t run a multi-day event. You are going to want to have support. You want to start planning about three months out, especially if it’s your first one.

The good news is if the challenge goes well, you can rinse and repeat. You want to start planning everything in advance so that everything is ready to go well. When it comes to the actual promotion of the challenge, I started promoting about two weeks out of my email list. I might do two and a half weeks through my ads.

The reason for that is because that gives me time to scale the ads, get the ads going, and if I need to make any adjustments. I always run ads to my challenge. I try to get more challenges to people, but I usually target a warm audience. These are people who already know me because that means that my ads are going to be a little bit cheaper, and the person is going to be more likely to buy because they already know me.

Clear Topic With Clear Outcome

When you’re coming up with a topic for your challenge, you want to have one clear topic that has one clear outcome. You want to ask yourself, “What is the participant going to walk away with?” You want to make sure it’s relevant to what you’re selling. I’ve forgotten what the name of it was, but it was a program on balancing hormones. The problem is that the challenge that I did was on a different topic. The challenge was called the Get Your Sexy Back Challenge. It was all about feeling better after the holidays, which is great. I had a lot of people sign up for it. A lot of people want to capitalize on that, but you can see how it didn’t connect.

I was bringing all these people in who wanted to feel better after the holidays and lose some weight, but they didn’t necessarily have hormone issues. The program was called Hormone Power. It did not sell. Long story short, that wasn’t successful because the topics didn’t align. You want to make sure that you have a topic that aligns with what you’re selling. You want to make sure that the challenge has one clear outcome.

The challenge that I did in January 2023 was called the Six-Figure Wellness Offer Challenge. The clear outcome that people were walking away with was the education that they needed to know on how to build an offer for their business that would help them generate six figures. We help them start to build their online program.

Is that relevant to what I was selling? HCA helps you build an online program. You can see how it’s relevant. This should be relatively easy for you because you should be taking it from your program. It should be an aspect of your program. You’re going to want to break down that bigger topic into three subtopics that you’re going to cover each day. I would choose the most relevant topics. What are the ones that are going to have the most impact?

As an example from my challenge, on day one, we covered the niche or the program topic because I know that you’re not going to have a successful program unless you have a profitable program topic. That’s what we did on day one. Even though a lot of people come into that challenge and already have a niche, they still are happy to get feedback on their niche because everyone feels a little bit insecure about their niche. Don’t worry if you feel like it’s a baseline or intro. If it’s something that they need to have in place to get the result, you want to do that first.

On day two, we talked about how to build the program. We talked about building a unique methodology. I didn’t go into everything that I teach inside HCA, but we went into the first part of that. On day three, we talked about how to set up a sales and marketing framework. When you do this challenge, you’re going to be going live for about 30 to 60 minutes each day. I usually go live for about 60 minutes each day. Sometimes, a little bit less.

Stay Away From Teaching Too Much

What you want to stay away from is teaching too much. We want to give everything in the past when I’ve done challenges, especially the challenge that I did in February 2022, which was the same topic as the one I did. It was five days, and I gave so much away. People didn’t think they needed to join my program because they got everything for free.

There’s something I call the lose the sale line and above this line. Envision this imaginary line. Above the line are concepts, stories, and overviews. Below the line is how to nitty gritty all the details. The more you move below that line, the more you lose the sale. We want to say above the line. We don’t want to get into too much how-to. We want to stay in bigger concepts, paradigms, and stories.

What I did is I took my webinar because these are all the topics that I covered in my webinar. I broke because I have three steps in my webinar. Each day, I did a step. You’re wondering, “A webinar is typically an hour. How did you fill the time?” I filled the space with storytelling and speaking to my own experience. People love stories. They like to be able to see themselves in someone else who they deem as successful.

I spoke a lot about the struggles that I had early on in my business, which they related to. I tried to sell them the dream through my storytelling. As an example, on day one, when I talked about niching, I talked about how when I started out as a health practitioner. I was taught to do it one-on-one. I was charging $100 an hour. That was a huge raise from what I’d been making previously. What I found is that I was in these sessions all day. My clients weren’t getting results, and I couldn’t keep everyone straight.

I talked about all the struggles that I had pre-niching. People in the audience are like, “Yes, that’s me. They get it.” Instead of teaching, I filled the space with telling and talking about my story and my experience. You would think that people wouldn’t find that valuable, but I got way better feedback than my first challenge on building a profitable offer, where I taught a lot.

Dedicated Challenge Post

When you teach too much, you overwhelm people. At the end of each training, you give them a challenge. This is like homework or something that they need to do each day, but it shouldn’t be something that takes them a whole lot of time. You’re not going to ask them to go out, go shopping, and buy their next two weeks of meals. You’re going to get them to do one small task.

 

How you do this will depend on the challenge that you’re having people do. I highly recommend having a dedicated challenge post. I went live at 9:00 AM every morning. At 10:00 AM, we put out our challenge post. Our day one challenge was to post your program promise in the format of my program to help this type of person solve this problem. In order for them to get feedback, they had to do it in that thread.

That was an absolute game changer because in the challenge that I did in February 2022, I told people to post into the group, and I had no rules or boundaries around when they could post. I didn’t say that I wouldn’t go back and give them feedback from the previous day. That’s why I was in the group giving feedback for 12 to 14 hours a day because I had no boundaries.

People were posting all in the group. It was hard to keep track of. Facebook organizes things weirdly in the feed. I was struggling to keep track of everything. I was giving people multiple rounds of feedback. They’d repost. I’d give more feedback and repost. That was crazy. That’s why I hated that challenge. Why it overwhelmed me so much because it was fourteen hours a day of giving feedback. That is not what I want to do.

What we did this time was I made sure I had strict boundaries and rules around the feedback. I said, “This is our post. You have to post your challenge in the comments. I will be in the group giving you feedback from 3:00 to 4:00 PM Pacific. As long as you get your challenge in there by 4:00 PM Pacific, I will give you feedback. I promise that everyone will get one round of feedback as long as they post before 4:00 PM. If there’s time left over, I will go back and answer follow-up questions.” I make no promises. It depends on how much time I have because it’s important that everyone gets one round of feedback.

Bonus Day And Incentivize

What I did to compensate for this is it’s a three-day challenge, but I always have a bonus day. We had a bonus day on Thursday. On day four, we did a live Q&A. I said, “If you have additional follow-up questions, show up to the live Q&A.” The live Q&A is another opportunity for me to pitch and sell the program.

That was a big game-changer. The first time, I would go live, and I would be giving feedback all day long. I’m waking up the next morning giving feedback for the live stream. I was on my phone. It was so much versus this challenge where I got up. I went live from 9:00 to 10:00 AM. I went and did my thing. I went for a walk, had some lunch, did whatever, took the day off, and gave feedback for an hour. It was mellow. It was only two hours of work a day. When I’m running a challenge, I clear my schedule. I let myself do my own thing in between my tasks.

That was a big game-changer, and I highly recommend it. I also recommend that you incentivize people with prizes. It makes it more fun. We give away a $50 Amazon gift card each day, and to be entered into the challenge, all they need to do is comment on the challenge thread and post their challenge. We announce that each morning. You don’t have to do a $50 gift card. You could do $20 or $25. I do Amazon gift cards because it’s the easiest. I’m not a huge fan of supporting Amazon, but it’s the easiest because we have people in many different countries, and Amazon is in every country.

From Five To Three

We also have a grand prize giveaway. Usually, I give away cash with a grand prize giveaway because it’s fun. In order to get entered, they need to have participated in all three challenges, and we will enter them into a draw. I always announce the winner on that bonus Q&A on the bonus fourth day. Traditionally, most of the way that people will teach challenges is that you have this five-day challenge where the fifth day is the webinar. It’s the bonus training.

The reason why I never liked this is because I feel like five days is a long time. It’s a long time for people to lose steam. Your most engaged day will be the first day. We had 120 people on the first day of our challenge on the livestream, which is amazing. On the second day, we had 80. That’s a big drop. That’s 40 less people. On the third day, we had 60. By the fourth day, you have 40. People start to drop off as time goes on. It always didn’t make sense to me that we would do the webinar, which is the big selling point. That’s the selling material that we would do on the fifth day when the people were the least engaged.

I worked with a coach. She was amazing. She taught me to pitch at the end of day two and at the beginning of day three. It’s a lot less formal. Webinar is a sales video, and you have a hard, formal pitch. I kept it informal. That sounded good to me. What I did is we had our day one training and challenge. We did our day two training and challenge. I said, “We’ve had a lot of people reach out.” They want to know more about how to work with me to build their own online signature program. That’s true because we always do have some people reach out at the end of day one, and I went into the day two pitch.

 

What I did was I focused on the emotional selling points. In the last episode, we talked about sales pages, and I talked about how we want to start with the emotional selling points. We want to finish with logistics. We want to back it up with logistics. I focused on the emotional selling points. I spoke to the benefit and the outcome of what it would be like to come into HCA and walk away with your own profitable online program.

I did the pitch at the end of day 2, and I started day 3 with the pitch. When I did this, I was like, “I don’t know. It feels weird to start the day with the pitch.” People were into it, and nobody complained. We focused more on the logistics side of things and the support that they got from the program. After that, I went into the day three training.

Hopefully, you can see how this works. I wouldn’t want to pitch on day 1, but on day 2, I have most of the people. We had 120 people on day 1, but we still had 80 on day 2. All of those people saw the pitch. We still had a good amount of people on day three to see the pitch. When I learned this method, I was like, “It seems weird to pitch on day 2and day 3. It’s early.” Somebody pointed it out to me that they’re like, “Kendra, you sell off a webinar that is a total of an hour.” I’m like, “I do. This isn’t that crazy.”

On bonus day four, I did things a little bit differently in January than I did in October. In October, we brought on a whole bunch of HCA students, both current and past, at all different levels. I wanted people who were newer know who had been in the program for about six months and had started their program. I wanted people who were several years out. That was amazing. I loved doing that.

We had about seven different students who talked about their program. We allowed the audience to ask them questions. People were into that. For January 1, 2024, I didn’t have the bandwidth to find a new group of people. I didn’t want to ask the same clients because it’s a lot of effort to do that. What I did was take the recorded video and post it to the group. That was beneficial. People still loved it. They watched it. They were still able to ask questions.

On the fourth day, I did the bonus Q&A. We had lots of questions about the challenge, but a lot of the questions ended up being about the program. The people who are still showing up at that point are interested. Those people had a lot of questions about the program. I also strategically placed a few questions so that I could reiterate some of the big selling points of the program.

That’s your challenge side of things. It can be a lot of effort to prep for, especially if you don’t have a team. I wouldn’t do a multi-day event if you don’t have a team, but the good news is if you do this multiple times, it’s a rinse and repeat. For the second time I did this, I spent a day working on everything. I updated a few things. I looked over things. I made sure they were still relevant. It took me about a day. It was minor. Keep in mind. I do have a team. I have someone who sets up the tech for me. I have someone who set up the Facebook group and all of those things. I was working on emails and content.

After The Challenge

After the challenge, that’s not everything. You’re not going to have anyone buy at the end of the day two pitch. You may get a couple of people buying on day three, but where people buy is in the follow-up. You’re going to want to follow up on a sequence of emails that goes out with urgency and maybe some bonuses.

Our urgency was, “This was your last chance to work with me inside HCA because I’m shutting down HCA temporarily.” I’m going to talk about why I decided to shut down HCA in the next episode. I’m going to be honest and transparent about what’s going on. That was good urgency because there are a lot of people who want to work with me inside HCA, but they’ve been putting it off, and they’re not sure. There’s a reason to join now.

We also offered a price promotion. It’s important to have some level of urgency. It’s easy to offer urgency if your program is live and there’s a start date and an end date because your cart closes. If you have an ongoing enrollment program, you’re going to want to come up with some bonus or promotion, something that makes people take action. If you don’t have urgency, people aren’t going to take action. It’s human nature. We’re never going to buy something that’s always on sale. We’re never going to feel any urgency if bananas are always on sale. If they’re on sale this week for 50% off, we’re going to buy those bananas.

 

You’ll want that urgency and sales page. If you’re selling through a sales call, your sales page will drive to a sales call versus an order form. That’s how I set up a successful multi-day challenge. The most important thing to consider is that you need a lot of planning time. Give yourself more time than you think you need, especially if it’s your first time. I recommend doing a three-day challenge and pitching the way that I did because that was way more successful than any challenge I’ve ever done. Alright, my friend, I hope you enjoyed this episode. I will see you next episode in the same place where I help you become wealthy AF.