Part 3: Win-Win Upsells
I know a lot of people restrain from even thinking about creating upsell offers, but if upsells are done the right way, they’re perceived as a win-win (for both you and your clients).
I know a lot of people restrain from even thinking about creating upsell offers, but if upsells are done the right way, they’re perceived as a win-win.
A win for your clients because they can achieve results faster, and a double win for you because you get more testimonials and backend revenue without adding new clients.
When it comes to creating upsell offers for your group program, especially for higher-priced options, relying mainly on emotional urgency is not only outdated - it’s ineffective.
So instead of creating hype and urgency, pressuring people to buy - you need to think differently about your upgrade offers.
Rather than relying on the initial emotional high, dopamine rush, and excitement, at the moment of purchase, you need to focus on your clients' behavior as they progress through your group program.
For example, in one of my latest group programs, implementing this approach led to extra $10,000 upsell revenue, by just sending a simple message at the right time.
Why Does This Approach Work So Well?
Because the upsell offers you create are presented as natural, beneficial options that make achieving results easier.
It’s not about selling for the sake of selling; it’s about providing the right tools and support at the right time, helping your current clients who need extra support.
Each upsell is presented as a specific trigger to make their client journey easier, faster, or more rewarding.
(if you’ve skipped PART #2 of this series - now is the time to go back and read it, since upsells are very connected to understanding 4 key client journey milestones)
#1 ACTIVATE TRIGGER: Keep them focused and motivated
Your clients are excited because they’ve just joined your program, and are hungry to get results. Now, it’s up to you to help keep their focus, attention and momentum from day one.
Ensure they know exactly where to begin, the first steps to take, how to access the materials, and all the ways they can receive support (hint: personalized onboarding sequence).
Many coaches and entrepreneurs overlook this stage, assuming clients’ initial excitement will carry them through, and most will figure it out on their own.
But I always ask:
Why not provide an exceptional client experience right from the start?
EXAMPLE:
In one of my smaller programs, by simply offering a personalized onboarding call with an upsell option, I achieved a 5% upgrade rate of about $5,000 within the first week. To some this may seem like a small amount, but I would’ve done these calls anyway, so it was free money (without ever pushing for those sales).
And it doesn’t happen only once but every time you repeat your launch, so if you launch 3 times per year - this is extra $15,000 without any extra marketing.
I guarantee there are clients who, after just a few days, decide they resonate with your teaching style, values, and overall approach, and immediately choose to upgrade for more direct cooperation and access.
On the other hand, some clients may love everything your program has to offer but feel overwhelmed and realize they need more guidance as they progress.
Even though they’re just starting your group program, this could be the perfect moment to inform them about more direct ways to work with you.
#2 EDUCATE TRIGGER: Deliver knowledge, not overwhelm
The next important milestone occurs when your clients start consuming your educational content.
It doesn’t matter if you do live weekly training sessions, have pre-recorded materials, or offer a hybrid model.
The key is to deliver actionable knowledge that fuels motivation without overwhelming your students.
For example, instead of covering every possible topic under the sun to showcase your “exceptional value”, focus on the key topics they need to learn to take next set of action steps.
Why does this trigger work?
Some clients will want more education and extra materials (templates, worksheet, examples...), regardless of what’s included in your program.
So why not give them an opportunity to upgrade and get access to some of your premium educational materials?
You may think - “yeah right Sherlock! Of course I know it’s important to educate my people”. But I bet you could go over your educational content and eliminate some of the non-essential educational materials.
More is not more in this case! Give exactly what your audience needs, you may add some extra stuff to your bonus section, and save the rest as premium upgrade.
EXAMPLE:
One of my group programs is all about building irresistible offers, and while I show people how to put together and sell offers, I don’t show them how to create products. A lot of my clients were asking about how to structure and record an online course.
So what I did was simply offer a 4-week bootcamp on creating your course and got 15% clients saying yes (you can even do something as simple as offering affiliate deal on course creation).
#3 IMPLEMENT TRIGGER: Inspire action that delivers results
This milestone is the biggest make-or-break point of your program because many clients slow down when it comes to taking effective action.
You need to help them break free from the cycle of binging “just one more lesson” and start seeing real growth through action.
During this phase of your Client Flow Journey, you have the greatest opportunity to present an upsell offer as a natural next step.
Why does this trigger work?
Fast action-takers will achieve results quicker than most of your other clients and will naturally want more access and faster support, which means upgrading to work 1-on-1 with you.
Others may be slower to implement because they need feedback more frequently, which falls outside the scope of the included support in your group program.
Either way, think about how to cater to those clients who need extra support and hand-holding.
We all all want those juicy testimonials and case study stories, and focusing on this milestones and “implement” behavior triggers will help increase your client success metrics the most. So it makes sense to be ready for the moment when your clients need you the most.
EXAMPLE:
That’s why it’s important to know what your clients are doing, and where they are on their client journey. I always have my eyes on fast action takers and when I notice someone is great fit for my premium offer based on their progress - I send them a message.
Just last week I noticed a superstar in making. They initially paid 500 dollars for basic access and after seeing what they were doing, I just sent them a message with where I personally see them in 3 months and how I can personally help them. It resulted in them upgrading to my 5,500 dollar offer.
Key? Being able to track individual client progress and activity, so you can easily identify rising stars.
#4 CELEBRATE TRIGGER: Celebrate their wins and plan next steps
The final important milestone is all about what happens at the end of your group program.
While many people talk about onboarding, few pay attention to the “offboarding” process, especially in time-limited programs (e.g., a 12-week journey).
By the end of your program, clients will be at different stages of progress. Some will have already achieved results and become success stories, while others will be progressing at their own pace.
This one depends on the type of your group program, but the most important question you need to answer for your clients is:
“What are my options if I want to keep going?”
Some will be excited and eager to say yes to a more premium offer, others will want to buy longer access to your materials, and some will be ready to move on. Whatever the case, make sure to clearly communicate their options.
I have a ton more examples and ways to create and position your upsell offers, but this should be more than enough to get you going and see the importance of 4 milestones I’ve been harassing you with.
(HINT: part five has a special PDF with in depth win-win examples and even a step by step case study on how to create proper upsell offers).
Time for part 4 and to learn how to keep personalized experience at scale…