Welcome folks! 👋

This edition of The Product-Led Geek will take 5 minutes to read and you’ll learn:

• 8 common pitfalls that teams fall into when designing upgrade paths

• Why these mistakes undermine conversion

• Practical solutions to avoid each pitfall

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Upgrade Path Pitfalls (And How to Avoid Them)

In my previous post on designing high-converting upgrade paths, I shared a framework for creating upgrade experiences that balance business goals with user experience.

If you haven’t seen that yet, you can catch up here:

But even with the best frameworks and tactics, there are common traps that can throw a spanner in the works and derail your best intentions.

I've seen these same pitfalls pop up a bunch of times, so I thought it would be useful to share them with you, along with some examples.

The good news? They're entirely preventable with the right approach.

Let's dive in.

Pitfall #1: Premature Monetisation

The problem: Pushing for upgrades before users have experienced sufficient value from the free offering.

Why it fails: Users have no basis to evaluate whether the premium offering is worth paying for. This creates distrust and can lead to immediate abandonment.

Solution: Map your aha moments and ensure users experience at least one significant moment of value realisation before seeing any upgrade prompts.

The problem is most acute in a pure freemium model. A reverse trial provides an implicit solution to this in that it:

1. enables users/teams to adopt paid features from day one - effectively giving more opportunity to see, understand and feel the product value

2. defers upgrade conversation until a time or usage based threshold is reached POST value realisation.

Pitfall #2: The False Floor

The problem: Creating a free experience that feels complete, giving users no reason to consider premium options.

Why it fails: Users settle into the free tier permanently because it meets all their perceived needs.

Solution: Ensure your free tier has visible ceilings that users will naturally hit as they grow.

Trello does this well by limiting free teams to 10 shared boards. That's enough to start with, but teams will naturally exceed this limit as they embrace the product more fully. When they hit that ceiling, the upgrade feels like a natural next step rather than an upsell.

Note: There may be segments of uses you don’t want to monetise, preferring to attract their personal use of the product with the bet that they will use and pay for it when they want to apply it in their business context. Snyk takes this approach, and it’s been hugely successful. If you start to adopt Snyk in a team context with higher dev velocity you’ll inevitably hit the 200 free tests per month limit and be asked to upgrade. Individual free user devs are unlikely to hit those limits.

Pitfall #3: The Sudden Cliff

The problem: The opposite of the false floor - a free experience that's so limited it fails to demonstrate value.

Why it fails: Users churn before experiencing enough value to justify an upgrade.

Solution: Calibrate your free limitations to allow genuine value while creating natural upgrade moments.

Zoom's 40-minute limit on group calls strikes this balance perfectly. It's long enough for most casual meetings, but just restrictive enough that regular users will want to upgrade. When that 40-minute warning pops up during an important meeting, users understand exactly why they might want to pay.

Pitfall #4: Mixed Messages

The problem: Inconsistent or confusing communication about what features are included in which tiers.

Why it fails: Users become frustrated by the unpredictable experience and lose trust in the product.

Solution: Create a consistent system for how premium features are indicated and how users are guided to upgrade.

Krisp does this well with uniform Upgrade badges (with a ‘power up’ lightning symbol) on locked features and consistent messaging when users attempt to access them. This consistency creates clarity and builds trust with users.

And Canva’s subtle annotation using the premium crown is great!

Pitfall #5: The Hidden Upgrade

The problem: Making the path to upgrade so subtle that users who want to pay can't figure out how.

Why it fails: You lose conversions from users who are ready to upgrade but can't find the way.

Solution: Provide clear, persistent upgrade entry points.

Making it hard to upgrade when the user/team is ready just creates frustration. Calendly maintains an Upgrade button in their main sidebar navigation, ensuring it's always one click away without being intrusive.

Pitfall #6: The Sudden Downgrade

The problem: Sudden removal of features that users previously had access to in the free tier.

Why it fails: Creates immediate backlash, destroys trust, and prompts users to seek alternatives rather than upgrade.

Solution: When you adjust your free tier (and you shouldn’t avoid doing so - pricing and packaging experimentation is encouraged!), grandfather existing users or provide a generous transition period.

Pitfall #7: The Upgrade Dead End

The problem: Poor post-upgrade experiences that leave users questioning their decision.

Why it fails: Creates immediate buyer's remorse and increases the likelihood of cancellation.

Solution: Design thoughtful post-upgrade onboarding that guides users to the value they just paid for.

Canva does this well by immediately highlighting premium features with tooltips after a user upgrades to Canva Pro. They make sure you understand exactly what you've gained access to and how to use it.

Pitfall #8: One-Size-Fits-All Prompts

The problem: Showing the same upgrade prompts to all users regardless of their usage patterns or needs.

Why it fails: Generic prompts feel irrelevant and are easy to ignore.

Solution: Segment users based on behaviour and customise upgrade prompts accordingly.

If a user frequently exports data, highlight export capabilities in the premium tier. If they collaborate with many teammates, emphasise team features. Context-aware prompts feel helpful rather than intrusive.

A Balanced Approach to Upgrade Paths

It might seem that creating effective upgrade paths requires balancing competing priorities.

Business goals vs user experience.

Perhaps counterintuitively though in PLG these things are in complete alignment.

We can more easily achieve our business goals by putting the user at the heart of our decisions.

When users find genuine value in your product, they're willing - even eager - to pay for it.

The best upgrade paths simply connect users who are experiencing value with the most appropriate path to increased value for their needs.

Think of your upgrade path as a conversation rather than a conversion funnel.

You're not pushing users toward payment.

You're guiding them toward success, with payment as a natural milestone along that journey.

This perspective shift changes how you approach everything:

• Instead of asking "How can we get more users to pay?" you ask "How can we create more value that users want to pay for?"

• Instead of seeing free users as free users you see them as customers at a different stage of their journey

• Instead of treating limitations as monetisation levers, you treat them as thoughtful boundaries that help match user needs to appropriate tiers

The PLG companies that master this mindset inevitably have higher customer satisfaction, lower churn, and stronger word-of-mouth growth. They create upgrade moments that feel like solutions rather than sales pitches.

Embrace this balanced approach, avoid the pitfalls outlined above and you’ll be well set to building upgrade paths that serve both your users and your business.

That’s PLG!

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That’s all for today,

If there are any product, growth or leadership topics that you’d like me to write about, just hit reply to this email or leave a comment and let me know!

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Until next time!

— Ben

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