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📖 Chapter 7: Managing Your Challenge – How To Keep Engagement High

The complete guide to running a high quality challenge inside the system

Jordan Plotkin avatar
Written by Jordan Plotkin
Updated this week

The Story That Keeps Repeating Itself

Your launch worked.
127 people joined your challenge.

Day 1: everyone is excited. The group is buzzing.
“I am so excited!”, “Let’s go!”, “I have been waiting for this!”

Day 3: fewer messages. Some people did not open that day’s content.

Day 7: the group is quiet. Only 45 people opened today’s content.
Where is everyone?

Day 14: 23 people are still active.
The rest? Gone.

What happened?

You assumed that once people paid, they would automatically finish the challenge.
But reality looks different.

Why?

  • The content is not engaging enough

  • There is not enough community and interaction

  • There is no clear feeling of progress

  • People get lazy and drop off

The good news:

If you manage your challenge the right way, you can reach a 60 to 80 percent completion rate.

And people who finish a challenge:

  • Become loyal customers

  • Buy your premium offer

  • Recommend you to friends

  • Share you on social media

In this chapter you will learn:

  • How to deliver daily content that people actually look forward to

  • How to build a group that increases engagement (without spamming)

  • How to keep momentum throughout the challenge

  • How to finish with strong conversions into your premium offer


🎯 How CommuniPass Works – The Technical Basis

Before we go into management tactics, let’s understand how content is delivered to participants.

The Enrollment Flow

Participant pays → chooses where to receive daily content → joins the group automatically (if there is one)

Receives a welcome message

Every day: new content is sent directly to them

Content Channels

Each participant chooses where they want to receive the daily content:

✅ WhatsApp
✅ Telegram
✅ Discord
✅ Email

What Happens After Someone Joins?

  1. Welcome Message

    Sent automatically right after payment.
    It explains what is going to happen, when the content will arrive, and how to get the most out of the challenge.

  2. Daily Content

    Sent automatically at the time you defined.
    Directly to the channel the participant chose.

  3. Support Group (Optional)

    The participant joins automatically.
    This is the place for sharing, mutual support, and engagement.

What The Creator Sees – Your Data

Inside your dashboard you can see:

  • 📊 Who opened the content – day 1, day 2, day 3, and so on

  • 📊 Who answered tracking questions – if you added a follow up question, you see the answers

  • 📊 Completion rate – what percentage of participants are still active


📝 The Structure Of A Perfect Daily Lesson

Your daily content is the heart of the challenge.
If it is boring – people drop off.
If it is exciting – people wait for it.

Here is the recommended daily structure in CommuniPass:

The Structure Of One Day In Your Challenge

  1. Warm opening – daily framing (30 seconds to 1 minute)

  2. Main teaching content (3 to 7 minutes)

  3. Implementation task (one clear action)

  4. Encouragement and motivation (anchors) (around 30 seconds)

  5. Reminder to share in the group, tag you, or do an engagement action

Let’s break this down.


1. Warm Opening (Hook)

Goal: grab attention immediately, focus people, and set the frame.

Example:

  • “Today is day 3 of the challenge.”

  • “By the end of today you will be able to do X.”

Short, warm, and clear.


2. Main Teaching Content

Goal: teach one clear thing that can be implemented today.

Principles:

  • One day = one main point – do not overload

  • Short and focused – 3 to 7 minutes max

  • Practical – not theory, something they can actually do


3. Implementation Task

Goal: get the participant to do something today, not just understand.

Principles:

  • One task per day

  • Simple and clear

  • Takes 10 to 20 minutes maximum

  • Easy to understand what “done” looks like

Example – AI Marketing Challenge, Day 5

✅ Your task today:
Write a Facebook post using ChatGPT.

  1. Open ChatGPT

  2. Paste the prompt I gave you

  3. Get 3 versions of a post

  4. Choose your favorite one and share it in the group

Anyone who shares their post in the group will get personal feedback from me 🔥

Why is the task so critical?

People remember what they do, not what they hear.

If they just watch content and never act – they will not see results, and they will drop out.


4. Encouragement And Motivation

Goal: make the participant feel good about themselves and want to keep going.

Examples:

  • 💪 “You are already on day 3! That means you have taken 3 real steps toward [result]. Keep going.”

  • “I am seeing all your shares in the group – you are amazing. Keep posting, it really inspires everyone.”

  • 🔥 “Remember: a small change every day = a huge change by the end of the challenge. You are on the right track.”


5. Reminder For Engagement Action

Goal: leverage the momentum into more sharing, tagging, and group engagement.

Examples:

  • “After you finish today’s task, share it in the group.”

  • “Tag me if you post it on your stories.”

  • “Write one thing you noticed in the group tonight.”


👥 How To Build A Group That Boosts Engagement (Without Being Overwhelming)

Your group can be your most powerful tool – or your biggest headache.

Here is how to do it right.

The Golden Rule: Quiet Group With Defined Activity Hours

The problem with “open” groups:

People start writing 24/7:

  • “Good morning!”

  • “Is anyone here?”

  • “I have a question…”

  • “I did not manage to do today’s task…”

Result: 200 messages a day.
People feel like they are always behind.
They mute notifications.
The group dies.

The solution: a quiet group with defined activity hours.

How it works:

  • The group is closed to messages for 22 hours a day

  • It opens for 2 hours at a fixed time – for example 20:00 to 22:00

  • During those hours people share, support, and respond – according to what you decide

  • After that – it is quiet again until tomorrow

Advantages:

  • ✅ People know exactly when to “show up”

  • ✅ No FOMO – everyone sees the same content

  • ✅ Focused energy – everyone is active at the same time

  • ✅ Not overwhelming – just two hours per day


The Daily Group Rhythm – Example Of A Winning Structure

08:00 – daily content is sent directly to participants (not in the group)

15:00 – follow up question: “Did you do it?”

20:00 – group opens

20:05 – you send an opening message, for example:

🔥 “The group is open!
I want everyone to post the piece they wrote today.
Pair up with someone and give each other one piece of feedback.
I will pick one post that nailed all the criteria and break it down for you.”

21:50 – you send a closing reminder:

⏰ “10 more minutes until the group closes.
If you have not shared yet – now is the time.”

22:00 – the group closes until tomorrow.


What Should People Share In The Group?

It depends on your niche. Here are examples:

Example 1: AI Marketing Challenge

Task: write a post with ChatGPT.

In the group:

  • Everyone shares the post they wrote

  • Others give feedback: “Loved this intro”, “Maybe add an emoji here”, “The hook is strong”

  • You give personal feedback to a few posts

Result: people see how others are doing, learn from each other, and feel like part of a real community.


Example 2: Dog Training Challenge

Task: “Sit” exercise for one minute.

In the group:

  • Everyone uploads a short video of their dog doing the exercise

  • Others respond: “Your dog is so smart!”, “Mine did it too today!”, “I am still practicing…”

  • You respond with tips and encouragement

Result: dog owners feel supported, proud, and less alone.


Example 3: Baby Sleep Challenge

Task: create and apply an evening routine.

In the group:

  • Each parent shares a picture or screenshot of the routine they wrote

  • Others comment: “Love the massage idea!”, “I also do bath + story”, “How did your baby react?”

  • You answer questions and guide them

Result: parents feel seen, get practical ideas, and stay engaged.


Tips For Running A Successful Group

1. Give Personal Feedback To A Few Shares Each Day

Do not try to respond to everyone (that is exhausting),
but choose 5 to 10 people each day.

Example:

“Sarah, I loved your post. The headline is really strong.
Just add a clear call to action at the end and it will be perfect 🔥”

Why it works: people want to feel that you see them personally.


2. Encourage Participants To Give Feedback To Each Other

Example:

“If you posted your task today, go and give feedback to someone else in the group.
Let’s support each other 💪”

Why it works: this builds a community, not just a broadcast channel.


3. Share Participant “Wins”

Example:

🎉 “I want to share something amazing!
Dana wrote that her baby slept 6 hours straight last night for the first time 👏
This is exactly why we are here. Keep going.”

Why it works: it proves the challenge works and inspires others.


4. Do Not Let The Group Turn Into A Q and A Box

If people start asking lots of questions inside the group:

“I have a question – what if…?”

You can:

  • Ask them to send technical or personal questions privately

  • Or define a specific time window for Q and A (for example, once a week)

Why?
Because if you answer everything in the group, it becomes a support forum instead of a focused space for sharing and motivation.


5. Do Not Forget To Close The Group On Time

Exactly at 22:00, send a closing message:

“That is it for tonight. The group is now closed.
See you tomorrow at 20:00 🔥”

Then switch the group to “admins only”.

Why?
To keep the structure clean and prevent 24/7 noise.


Why Do People Drop Off?

Common reasons:

  • The content does not feel relevant – “This is not what I expected.”

  • There is no sense of progress – “I do not feel like I am getting better.”

  • No engagement – “No one sees what I do.”

  • Content is too long – “I do not have time for this.”

  • Life gets in the way – work, kids, trips, holidays


How To Reduce Drop Off

1. Automatic Notifications For People Who Stop Opening

CommuniPass lets you see who has not opened the content for 2 to 3 days.

Action:

Send a personal message:

“Hey [first name],
I noticed you have not opened the content in the last 3 days.

Is everything OK?
Is there anything holding you back?

I am here if you have questions or need help 💪”

Why it works: it shows you care and reminds them they are part of something.


2. “Milestones” – Creating A Feeling Of Progress

Every 3 to 5 days, remind participants how far they have come.

Example (Day 7):

🎉 “Congratulations – you finished a full week!

Look what you have already done:
✅ Built an evening routine for your baby
✅ Started teaching them how to self soothe
✅ Reduced night wakings by 50 percent

That is huge. Another week and you will see even bigger changes.”

Why it works: it reminds them they already invested effort, and that it is worth continuing.


3. A “Mini Challenge” Inside The Challenge

Around day 7 to 10, when people start to get tired:

🔥 “Special mini challenge!

Anyone who completes the tasks for the next 3 days in a row
will get [a bonus / gift / surprise] from me.

Who is in?”

Why it works: it refreshes motivation and gives a short term goal.


4. Share Success Stories

Example (Day 10):

“I want to share an amazing story.

Michal joined this challenge 10 days ago.
Her baby was waking up 5 times a night.

Yesterday he slept 7 hours straight.

How did she do it?
She did every single task, step by step.

This can happen for you too. Keep going.”

Why it works: it proves the process works and gives people hope.


📱 Turning Engagement Into Organic Reach – The Algorithm Is Your Friend

One of the smartest things you can do in a challenge is turn your participants into your ambassadors.

How?
By leveraging their engagement on social media.

Why This Matters

When participants share content from your challenge on their own social accounts:

  • ✅ You get free exposure to their followers

  • ✅ The algorithm sees engagement and boosts your reach

  • ✅ You get strong social proof – “look how many people are doing this”

  • ✅ Future participants see it and want to join the next round


How To Do It

Strategy 1: Create A Unique Hashtag For The Challenge

Create a specific hashtag for your challenge.

How to encourage using it:

On day 1, in your opening message:

📸 “Want to be part of the community?

Every time you do a task, post a story and use the hashtag #YourChallengeName

That way we can all see each other, cheer each other on, and stay connected.

If you share a story, tag me at @[your handle].”

During the challenge, keep reminding:

“If you did today’s task, post a story and tag me!

I will reshare my favorites 🔥
#YourChallengeName”


Strategy 2: Tagging And Resharing

Ask people to tag you in their stories.

Why?

Because then you can:

  • Reshare their stories

  • Show your audience that many people are doing the challenge

  • Build strong social proof


Strategy 3: Viral Style Content Challenges

Once during the challenge, give a task that is very “shareable”.

Examples:

  • A specific physical move with a recognizable song in the background

  • A simple “before and after” photo format

  • A fun, visual mini challenge

Why it works:

  • It is easy to do

  • It is interesting content, not just “salesy”

  • It creates FOMO for people who are not in the challenge

  • The algorithm pushes content that gets reactions and shares

  • Participants like sharing things that feel fun and “cool”


What Happens When Participants Share?

  1. Organic Exposure

Each participant has 200 to 500 followers on average.

If 30 people share a story → that is 6,000 to 15,000 free views.

  1. Social Proof

People see their friends doing the challenge and think:
“Maybe I should join next time.”

  1. Building Anticipation For The Next Round

People who saw all the stories but did not join this time
will sign up to your waitlist for the next round.

  1. The Algorithm Boosts You

Instagram and Facebook see that your account gets lots of tags and shares →
they increase your reach.

Result: your posts reach more people, even without paid ads.


Tips To Maximize Engagement

Tip 1: Reshare Every Tag

Whenever someone tags you in a story → reshare it.

Tip 2: Give An Incentive To Share

Why it works: people love contests and rewards.

For example: a prize for the most creative story, or a random draw among people who shared.

Tip 3: Create A “Share Contest”

Why it works: it turns sharing into a game and encourages healthy competition.

Tip 4: Emphasize The Impact Of Sharing

Explain that:

  • Their shares help other people discover a solution

  • They help grow the community

  • They help you keep offering challenges at a good price

Why it works: they feel their action has real meaning, and they are more likely to keep sharing.


🎯 Building A Daily Routine – The Key To Real Results

One of the smartest things you can do in a challenge is build a simple daily routine that participants repeat every day, in addition to the daily task.

Why Is A Routine So Important?

  1. It Guarantees Results

If participants only do the daily tasks, they might still not do enough to see meaningful change.

When there is a fixed daily routine they do every day, results become much more predictable.

  1. It Builds A Habit

Routine = habit.

If someone does something 21 days in a row, it becomes a habit that often continues after the challenge ends.

  1. It Is Easy To Follow

Tasks change every day.
The routine stays the same.

That makes it easier for participants – they always know “this is what I do every day, no matter what.”


Example – Weight Loss Challenge: 3 Daily Actions

Your daily routine:

1️⃣ Drink 2 liters of water
2️⃣ Eat 30 grams of protein in the morning
3️⃣ Walk for 30 minutes


Example – AI Marketing Challenge: Daily Practice

Your daily routine:

1️⃣ Write one new prompt in ChatGPT
2️⃣ Create one piece of content (post, email, or video)
3️⃣ Publish it on one platform


Example – Dog Training Challenge: 10 Minutes Per Day

Your daily routine:

Practice with your dog for 10 minutes a day:

1️⃣ Sit
2️⃣ Down
3️⃣ Come

Do this every single day, in addition to the specific daily task.

Why?
Because daily repetition = a well trained dog.


🧠 Varying The Syllabus – Strong Days And Lighter Days

Not every day in your challenge has to be equally intense.

If every single day is “huge and heavy” – people will get exhausted.
If every day is flat and boring – they will drop out.

The key: smart variety.

  • Start very strong in the first 3 days

  • Finish very strong in the last days, especially before your premium offer

This way:

  • People are hooked at the beginning

  • They finish with high energy and are ready for the next step


🎓 Ending The Challenge – Converting To Premium

The end of the challenge is actually the beginning of the sale.

Most participants who complete your challenge want more.

They:

  • Saw real results

  • Got a “taste” of your method

  • Trust you and your process

Now is the right time to offer your premium product.

What Is A “Premium Product”?

This is your higher priced, deeper offer, such as:

  • A full course

  • Personal coaching instead of general content

  • A monthly or yearly membership instead of a one time payment

  • An advanced program (level 2 after the challenge)


What’s Next?

Now that you know how to run a successful challenge and keep people engaged,
it is time to learn how to debrief and improve for your next round.

Ready to learn how to analyze your first challenge so you can build the perfect one next time?
Let’s dive into the next chapter. 🚀

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