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Challenges are all the rage right now, probably because they provide a super engaging experience for potential clients and customers. They're a fantastic way to show off your expertise and provide real, tangible results, which then leaves your audience begging for your (paid!) next steps.

If you're reading this, chances are you want to set up the tech/emails for your challenge in ConvertKit.

I hope so – because that's what this whole post is about!

I've helped loads of clients set up both live and evergreen challenges in ConvertKit, and I've learnt a whole load of stuff along the way.

There are 3 main scenarios when it comes to setting up a challenge in ConvertKit:

  1. A fully evergreen challenge
  2. A fully live challenge (but if they sign up late you want to help them catch up)
  3. A live challenge (but if they sign up late they enter an evergreen sequence)

1. A fully evergreen challenge

This is arguably the easiest type of challenge to setup in ConvertKit. You're basically just going to create a sequence, create a form, create a tag, and link them all up with an automation rule:

Things to consider when setting up a fully evergreen challenge:

  • Do you want the challenge to always start on a specific day of the week? e.g. Monday? If so, you need to set that up in the ‘Delay Sending By' section of the first email. I recommend you still send them an email immediately to let them know that they'll get the first email on Monday (otherwise they might be waiting almost a week and hear nothing from you!):

  • If you're adding sales emails to the end of your sequence (which you totally should be), then you might want to exclude people who've already bought the product from receiving those emails:

  • If your challenge is one of your main opt-ins, you may want to consider setting it up so this sequence takes priority over all other sequences. In this blog post I talk about creating ‘In Sequence Segments'. Exclude this segment from receiving any other sequences. The effect is that as soon as they start this challenge they ‘pause' in all other sequences, and then resume once they've finished this challenge.
  • If your challenge is going to lead into selling something, as part of a funnel, you may want to consider using something like Deadline Funnel to truly make the offer time-limited in an evergreen setup. It integrates nicely with ConvertKit.

2. A fully live challenge (but if they sign up late you want to help them catch up)

You know the deal, you're running a live 5 day challenge, with Facebook group support. It's only happening that week. Now or never. This type of challenge you're going to run predominantly through Broadcasts.

You create a form, create a one email sequence that sends immediately, create a tag – and then connect them all up with an automation rule.

What goes in the one email sequence? Just some info about when the challenge starts, what it's going to involve, join the Facebook group, invite your friends, that kinda thing.

Each day of the challenge you then want to send/schedule a broadcast that you just send to the ‘Live Challenge' tag.

The catching up bit…

On Day 2 of the challenge, go into the report for the Day 1 email, and get the direct link to share the Day 1 content:

Then in the Day 2 email (and Day 3, and Day 4….) you want to put P.S. Missed Day 1? Click here to catch up. And you link to the Day 1 Broadcast.

3. A live challenge (but if they sign up late they enter an evergreen sequence)

This is a combination of the two scenarios outlined above. First up you start as though it's a live challenge. You create your form, your welcome email sequence and your tag, and you connect them up (like in Scenario 2).

You send/schedule the live challenge emails as Broadcasts to the ‘Live Challenge' tag.

Immediately after sending the Day 1 email, you want to copy the content from the Day 1 email into the 2nd email of the welcome email sequence. Probably set the delay to 1 day, and publish it. You're also going to want to tweak the copy in the first email in sequence because it's now an evergreen challenge sequence. Change the name of the sequence to ‘Evergreen Challenge'.

Immediately after that you want to go into the automation rule you already had set up for the challenge, and change it to this:

So anyone who signs up now is going to flow into the Evergreen Sequence (and not receive the live challenge broadcasts.

The Live Challenge Welcome sequence has now become the Evergreen Challenge sequence.

You also want to change the Live Challenge form to the Evergreen Challenge form. (And probably some of the copy that's date specific).

Notes/Other Ideas

  • Instead of telling people to share the challenge on social media, I really love Social Link Generator so that they can share with one click. It's also fun to do things like “Click to tweet that you're doing the challenge!” and then you create link using Social Link Generator that tweets something like “I'm doing @marchingstars 5 Day ConvertKit Challenge – join me: “. Click here to see a demo of that exact tweet!
  • If you're encouraging your existing list to sign up, please please please don't make them put in their details on the same form as everyone else. There's no need. You can use link trigger automation rules to sign up them up. I recorded a quick video on how to do it:

  • Pick a subject line for your challenge emails and be consistent with it! It makes it so much easier for people to keep track of what's going on. e.g.
    • [Email Challenge] Day 1
    • [Email Challenge] Day 2
    • [Email Challenge] Next steps
  • Consider timezones! Unlike some systems, ConvertKit sends broadcast/sequence emails to everyone at the same time. If your audience is predominantly American, then an American timezone is fine. If they're more mixed, then 9am PST is 5pm in the UK… and that's not great for ‘taking daily action' kinda challenge. You have to work out what works for you and your audience. If you've got an evergreen challenge you can try something, then duplicate the sequence, and try and different time – and see which has higher open/click rates. (Make sure you connect up the 2nd sequence via automation though and remove the 1st one!)
  • For both evergreen and live challenges you may want to consider setting up a specific email template with custom unsubscribe links at the bottom. If you're doing an evergreen challenge, then the action in the automation rule is to unsubscribe them from the challenge sequence and remove the challenge tag. If you're doing a live challenge, then the action in the automation rule is to remove the live challenge tag. If this challenge is one of your main opt-ins, then you want people to be able to unsubscribe/opt-out of the challenge, but not your entire list. Make sure you also tag them newsletter or they don't fall into a black hole though!

I'm probably going to think of extra things to say as soon as I hit publish on this, but hey ho.

I’d love for you to share in the comments how you're using ConvertKit to run your email challenges!

If you’d like to learn more about using ConvertKit to its full potential, definitely check out ConvertKit Club, my monthly membership site! We cover loads of advanced uses of ConvertKit, and you’ll have my support to make it relevant to your specific business.

Alternatively, if you’re new to ConvertKit or even just considering it, check out my free 40 min A Beginner’s Guide to ConvertKit video.