What to do you do when you're asked for a longer trial?

I agree that you should give it to them unless it causes you a lot of extra work, in which case I'd be scared of wasting loads of time on people who are self-identifying as less likely to pay.

I also think you should use it as an opportunity to talk to them. "Sure, you can have a longer trial if you're able to jump on a 15-min call to talk about how you're finding the product so far". That conversation will be really valuable.

I would just give it to them, or maybe suggest another 30 day trial. Use it as a learning opportunity at your relative early stage.

I know people often recommend to push back on requests like this, or discount codes, but I just tend to give. It's a much more pleasant conversation to have.

I would flat out say no.

Long trials don't convert, there's just too much that can happen that will distract the users away from your product.

There is a logical fallacy that you can supposedly "learn more" from this customer while they are on this extended trial. IMO, you will not learn anything useful from a customer who wants to use your product for free for 90 days. If their problem is not urgent enough for them to get out their wallet, they will just give you irrelevant feedback.

My best advice here is to ask for a commitment for the extended trial.

The easiest and most effective thing to do is to say that if they can commit to a paid plan, you'll be happy to offer a 100% refund if they aren't happy at the end of that additional 60 days.

Longer trials never tended to convert for us. Usually what happens is, without that commitment, they end to checking out of the trial as there isn't that investment to keep them using it.

Asking for a commitment in this way gives them a risk free way to keep evaluating your product but with the commitment to stop them checking out.

I would say yes, always. Except if it adds a lot of work for me! So depends of the product/service.

Commit to give out 30 days at the end of the 30 days assuming they hold a discussion with you about their progress, what they need to do and that they provide feedback. You'll establish that way that a. they use your product b. they aren't freeriding but indeed setting things up c. get feedback d. build rapport.

Plus it may be that they don't need 90 and 30 is enough. In this case you'll be losing on 60 days of revenue. That's fine to give if you're early and need the feedback but no-no later on.

Also, I'd require a review or two in the relevant sites or a mention in their social media, a guest post etc for the extra time. Fair.

Give it. Though 90 days sounds a tad unreasonable.

Try giving another 15 days in addition to the default 30 days.

But never give an extension on top of an extension. They must decide after 45 days.

I've given trial extensions for Zlappo quite a few times, and more often than not they end up converting.

I guess it has something to do with they feel like they owe you something, because you're going out on a limb to cater to them.

Also, I disagree with IHers who are inflexible on this (i.e. "Their feedback is useless if they don't convert," "They're freeloaders," etc.), guess what? Sometimes life just gets in the way, and they forgot to use it. Ever considered that?

Unless they're just flat out taking advantage of your hospitality -- you should be able to see this in your database if they're using it a lot, I'd err on the side of giving them the benefit of doubt.

If it's easy to do - do it.
The reason is that you are still learning from customers and with this specific opportunity you will get a data point (and maybe some learnings) on how a longer trial affects conversion. Maybe suggest a checkpoint conversation after 45 days? It's so hard to get real users to engage with feedback, but here is an opportunity.
If you have 100+ paying customers and generally can predict if a customer will find value, I would say "if we can't convince you in 30 days, we probably cannot convince you."