3 onboarding email mistakes you're probably making (and how to fix them)

The goal of onboarding emails is very simple: get people to do a specific thing. You might be a software company with a bunch of users trialling your product, who you’d like to convert into paid users. Or you might be a construction company with a bunch of leads, and you’d like them to schedule a consultation with one of your salespeople. There’s a zillion different examples, but they all boil down to the same thing - you have a bunch of people in state A, and you’d like to convert them to state B.

Email is a great way to do this. Email catches peoples’ attention in a way that other advertising does not, because it’s going straight to their inbox. It’s also relatively inexpensive, especially if you automate the process. But time and time again, I see the same mistakes in onboarding emails. Here’s a few of them:

Making people click through to content

One of the first things you want to do in an onboarding process is build trust with your readers. A great way to do this is by sending them interesting, relevant content that they get value out of.

Lots of email marketers do this, but for some reason, they hate putting any actual content in an email. Here’s an example from a CRM software provider:


To be honest, those five content writing tips look pretty good - but I didn’t click the link. That may sound precious, but I am probably in a similar position to most marketing email recipients. I got the email while I was in the middle of something else. I would have welcomed a brief distraction, but clicking a link was a bridge too far. I don’t know where that link’s going to take me - will it take me straight to the content? Will it insist that I fill out a form? Will it make me watch a video? I don’t know, so I’m just going to go back to what I was doing.

The goal of that email was presumably to get me to read the content, and I did not read the content, because I didn’t want to click a link. Goal not achieved.

Here’s an example of someone who does a good job of this. This is a guy called Mehdi, who runs a website called stronglifts.com. It’s a weightlifting programme, and if you give him your email address, you’ll get emails like this:


Fundamentally, this approach isn’t that different from the CRM provider. He’s sending me interesting emails that keep me engaged in his app and his exercise programme. Every email has a call to action at the bottom in the form of a “PS,” asking me to convert to the paid version of his app (I did). The only difference is that the content of his emails are right there in the email. I don’t have to click off to somewhere else to see it -  I just have to open the email, read it, and move on.

This approach is better because it’s more in line with the way people use email in the first place. When I email somebody, I don’t type my email in a google doc, then send them a link to it. That would be ridiculous. I just write them an email. By integrating his marketing emails in with the way I use email day-to-day, Mehdi is better-able to get me to read his content - which in turn keeps me interested in hearing from him, and eventually buying what he has to sell.

Asking for too much

The ultimate goal of your onboarding process is to get people to commit to something. So it follows that each email in that process should ask for smaller commitments. By getting people to take an action, you’re gradually building their commitment and interest in whatever you’re selling. It’s like a car salesperson getting you to take a car for a test drive before they ask you to buy the car.

The problem is that many onboarding emails ask for completely unreasonable things, far too early in the process. For example, I recently signed up for some time tracking software. I signed up for a trial on the 16th. On the 19th, I got an email inviting me to a forty five minute webinar.

M8 - no.

I can see why organisations do this. Once you’ve got someone in a webinar, it’s probably a lot easier to convert them. So you can justify that invite by arguing that even if not many people sign up, the revenue from those who do sign up will make up for the vast majority who don’t.

This would make sense if each person was worth thousands of dollars, but this particular time tracking software costs $12/month. What’s more, it doesn’t take unsubscribes into account. Every email you send is going to have an unsubscribe rate of between half a percent and a percent. That doesn’t seem like much, but half a percent is 5 people on a list of 1,000. If you send them 5 emails (not unreasonable), then you’ve lost 25 people. This is costly because once someone unsubscribes, that’s it, forever - it’s incredibly hard to get them to re-subscribe, because you’ve lost access to the main channel you would use to do so. So you need to look at that unsubscribe rate as a cost of sending the email. If you ask for too much, too early in the process, then you’re “paying” that cost and not getting much benefit in return.

Just like a salesperson would have you look at a brochure before asking if you want to go for a test drive, your onboarding process should start with smaller commitments - starting with opening the email in the first place, and working its way up to the bigger asks.

Over-reliance on offers

All this trust building and gradual increasing we’ve been talking about is nice, but eventually you’re going to want to actually ask people to buy your product. A lot of companies do this by using discounts to get people over the line. I think they’re making an expensive mistake. Let’s say you’re a SaaS company with 1,000 people who have signed up for a trial version of your product in the last three months. So you email all of them with an offer of 50% off for a couple months if they convert to the paid version today.

Then, lucky you - 200 people take you up on your offer. 20% conversion rate, nice!  But here’s the problem: if all it took to switch from trial to paying was a relatively small offer, then most of those people were probably going to convert anyway. Maybe there were a couple at the margin, but I doubt it was enough to justify the revenue you sacrificed from everyone else.

While it might feel like you single-handedly brought in tons of revenue, in reality, you probably just paid a bunch of customers to bring their purchasing decision forward. You’ve also infuriated any customers who converted the day before you sent out your offer. That’s second bit is a harder cost to quantify, but  it’s certainly not great.

That’s not to say that offers should be avoided at all costs. After all, Briscoes has an entire business model built around constantly having sales, and they seem to be doing okay. But when you do use them, you should try to do them in a targeted way that converts the people at the margin without paying too many people who were going to convert anyway. That’s what Briscoe’s is doing with the endless sales, accompanied by TV ads and mountains of circulars. They’re getting people to come into the store who wouldn’t have otherwise come in. But if you’ve already got someone’s contact details, they’re essentially “in your store” already. So don’t pay them to buy a blender they were already going to buy.

Getting it right

So with all this in mind, here’s some things to think about to create a more effective onboarding process:

Build trust by sending people relevant content, that’s easy to consume. The body of the email is the natural place for this kind of thing.

Gradually increase the level of commitment you ask from your readers. There’s nothing fundamentally wrong with watching a video, going to a webinar or booking a demo - but you need to warm people up first.

Use discounts sparingly. Otherwise, you pay people to do something they were already going to do, which is incredibly expensive.

Or, as always, just have me do it.

Photo by Mikaela Wiedenhoff on Unsplash