The Weekly Review

by Chris Bowler

A Framework for Creating a Robust Onboarding Workflow

This post was originally published on the Wildbit blog.

Onboarding is a word that has been around for some time, but has seen increased usage in the world of SaaS in the last 10–15 years. Not surprisingly, this has corresponded with the advent and maturation of customer success as a discipline. And the two are related.

What is onboarding? It’s the process of getting someone up to speed so they can be as effective as possible and achieve success. And you usually want that to happen as quickly as possible. The term can refer to new hires for your own company (employee onboarding). But for most SaaS products, we use the term to describe the process of getting new customers acclimated to our service.

I’d like to share the framework for how we've created some of the onboarding campaigns here at Wildbit.

First things first

Before I talk about some of the activities involved in creating an onboarding campaign, I’d like to step back and talk about onboarding at a high level. There are a couple of important aspects to keep in mind.

First up is one of the most crucial aspects of customer success as a discipline. I hold to the idea that customer success is just that: a focus on the customer. That means I only want a customer to become engaged with our product because it makes their life better. And so I purposefully choose to work for companies where that is the case. I can feel good about helping someone be as engaged as possible with our products because we’re helping people solve real problems.

As Kathy Sierra puts it in Badass: Making Users Awesome:

People aren’t using the app because they like the app or they like you. They’re doing it because they like themselves. What are you doing to enable more of that?

Second, your onboarding is not the first step in guaranteeing the success of your customers. The fanciest, nicest looking, most clever onboarding campaigns cannot help people who do not need your product. If there is no problem that your customer is trying to solve or if your product focuses on the wrong problem, new customers are not going to stick around. Building a successful product starts with understanding your market and your ideal customer, having good marketing, and doing your best to find those people.

Once you have identified the right group of people to help, it’s important to remember that your onboarding should focus on them, not on you. Keep this in mind as you complete the activities below. You should focus on how your product helps the new customer solve their problem. The last thing we all want when we check out a new tool is to see a long list of features or messages that focus on the product or company behind it.

Last, it’s important to remember that anyone in your company can build these campaigns. The responsibility will fall on different shoulders at different companies, but the best onboarding examples are from companies who put the customer at the centre of their entire product development process. Designers, product managers, and customer success teams should all understand the vision of your product and the problem it solves well enough to guide someone new to a successful adoption.

Now, let’s dig into what’s involved.

The Framework

Now, there are many different ways to implement onboarding for a product. Different approaches will work better for some companies than others. I’ll discuss various options below, but remember that there is no one perfect way to do this. The best onboarding is flexible and iterative.

However, there are several exercises you can go through that will help you gain a better understanding of how to guide new customers to success.

Define your levels of engagement

The purpose here is create a tool that allows you to gauge how integrated your product is into someone’s business (again, we can feel good about this when we believe in the value we provide). Think of it in this sense: how hard would it be for someone to switch from your service to a competitor? The harder it is to switch would indicate a higher level of engagement with your product.

Let me illustrate with one of our products at Wildbit. Beanstalk is a development workflow platform where you can host, review, and deploy your code as a team. If someone signs up to Beanstalk, creates a new Git repository, then makes some commits and pushes them to Beanstalk, this would be a low level of engagement with our product. At this point, they could very easily sign up for a Bitbucket or GitHub account, switch the remote URL in their Git config, then push those same commits to their new remote repo in this other service.

But if they had pushed their commits to Beanstalk, then used our deployments feature to update their live website (instead of manually updating their site via FTP), suddenly they gained value they did not previously have. And it’s value they cannot get from some of our competitors. If using this feature becomes sticky and they then considered switching to a different service, they now have to replace the value they get from using ours. They are more engaged.

And that is what we want to outline here: it’s a tool for measuring how engaged people are with our service.

This is not a complicated process at all. Here’s how to create one:

  • list out the possible activities a user can perform with your product
  • group those activities into tiers (the number of tiers doesn’t really matter, but I keep it simple and stick to three)
  • each tier is a level of user engagement

You can then take these tiers and tie them into your user journey. I like to picture an ideal user journey, where someone goes from signup to highly engaged. I document what that journey might look like, and envision where the different activities would occur in that journey.

This does not need to be an precise measurement, but something that gives you a rough idea of how engaged your customers are. It should be flexible as the events themselves may change over time, being more or less important to your customers. But it should help you to identify your core features and what you want to focus on with your onboarding materials.

Identify your Wow moment

Once you have an idea of what an ideal user journey would look like for a highly engaged customer who is getting as much value from your product as possible, you want to identify the Wow moment. If you're familiar at all with onboarding, you may have heard of this term. There are a few other terms that get at the same idea (golden motion, day zero, MVE (minimum viable effort), TTFV (time to first value)). They are all focused on one thing: what is the quickest path to your customer’s success.

David Skok defines it this way:

Wow! is the moment in a free trial where your buyer suddenly sees the benefit they get from using your product, and says to themselves “Wow! This is great!”.

Whether your product has a free trial doesn’t matter. What matters is your new customer experiencing that moment when they realize that your product can make them better at what they do.

That is your Wow moment: when the new customer likes how your product makes them feel.

Now, it’s not always easy to identify where this moment takes place in your product. You may have to take a few guesses to find it. So you take your ideal user journey that you mapped to your levels of engagment, and you make another best guess: where is that Wow moment?

Again, I’ll use Beanstalk as an illustration. Commits are great, but deployments are where people realize the benefit of our product. All our longest tenured, biggest fans tell us that our deployments are what makes the difference when compared with other options they’d considered.

Pushing changes to a remote repo is a good first step, but as mentioned above, it’s easily replicable. But when an agency developer signs up for Beanstalk, then configures their workflow so that they can commit changes to their staging branch, push those changes to Beanstalk, then when those changes are automatically deployed to their staging environment and they can test seconds later …

That’s a Wow moment.

Map out the steps to Wow … in reverse

Once you have chosen a wow moment to guide people towards, start to identify the different steps required to get there. Take your ideal user journey you mapped out in step 1, then work backwards.

Lincoln Murphy describes it this way:

You create a plan to get here by identifying “initial success” and backing out from that goal while identifying success milestones along the way.

And don’t be afraid to go deep on this analysis. When you're very familiar with a process (like using your product), it’s easy to take things for granted. You will want to view your product from the perspective of someone seeing it for the very first time. Where you see 3 or 4 steps, someone unfamiliar with your product may see far more.

As Samuel Hulick points out in Mind the Gap, even the most simple processes involve more than we first think of. He uses the example of listing the steps to create a peanut butter & jelly sandwich (a seemingly simple procedure) . When his grade school teacher followed the instructions given by the students, the results were not as intended:

Our instructions created crappy sandwiches because they failed to bridge the gap between what seemed obvious to us and what actually happened in reality.

What seems obvious to you is not at all obvious to someone new to your product. And it’s important to remember that you're so familiar with your product that you may have trouble identifying all the steps involved with getting started using your product. As Hulick points out in his book The Elements of User Onboarding:

Ironically enough, your product’s first few impressions are SO make-or-break that you simply can’t afford to evaluate them as the expert that you now are — you have to try to forget everything you know and come in with a totally fresh perspective.

Beanstalk also provides a good example here. I mentioned above that getting started with Beanstalk involves making commits in a local repo, then pushing changes to the remote repo in Beanstalk. That sounds like a couple of simple steps. But for someone brand new to Git, it’s actually a complex process.

First, you have to log into Beanstalk and create a new repo. From there, you can open a command line interface (CLI) to take the next step (the words ‘command line’ are scary enough on their own for even some novice developers) with the following commands:

git clone https://accountname.git.beanstalkapp.com/gitreponame.git -o beanstalk
cd gitreponame
echo "This is my new project on Beanstalk." > README
git add README
git commit -m "My first commit."
git push beanstalk master

And this is just one way to get started. Our team has to be ready to support people in many different scenarios. And our onboarding has to do the same and get them started on the right foot.

Map out a list of touchpoints to get them there

Once you have identified your Wow moment and what you believe are the steps required for someone to experience that moment, you can start to create your onboarding materials. This is where there can be a wide variety in onboarding experiences. The type of content, the medium used, and the timing of messages can vary greatly from one product to the next. And that’s how it should be: different products have different audiences and different needs.
Let’s review some of the options.

Types of touchpoints

Email has long been the medium of choice for SaaS products sending onboarding messaging and information to new customers. But with the rise of the mobile web and modern browser technologies, in-app messages and SMS are popular as well.

What works best? It depends.

Context is the key for many messages you may want to send to a new customer. And in-app messages, when well designed, can be delivered at just the right time. However, when overused, they can distract the user from the job at hand and worse, annoy them.

Email is still a great option as it can deliver the required information, but allows the customer to process it at a time that suits them best. However, it’s vital to remember that most people in 2017 suffer from too much email. Your messages need to be well written in order to stand out (that’s an entire subject for its own blog post).

Touchpoint triggers

Another aspect of your touchpoints is how they are triggered. The two basic options are timing and behavioral.

Messages that are triggered by timing are the standard type that have been used for a long time. They are easy to set up and can deliver the basic information about your product that each new customer can benefit from. They may resemble a flow like this:

Sign up > Day 1 > Day 3 > Day 7 > Day 21

However, with the tools we have available today, it’s more valuable to build campaigns based on what you new customers do with your product (or do not do). These are behavioral (aka contextual) messages.

Again, using Beanstalk as an example, if a new customer has not pushed any commits to a repo in their account by 3 days after signing up, we send an email that is focused on helping them get to that point.

Over the past 12 months, this email has had a 43% open rate and, even better, a 12.5% conversion rate. There are so many examples in this category, it could also be a post all on its own. I will stick to pointing you to some great resources:

A solid onboarding campaign that provides real value to your customers will likely involve a combination of message types initiated by different triggers.


To get you started, we’ve provided a collection of resources for your use. It includes an onboarding checklist, a BPI & user journey template, a nurture path template, and some message samples. Enjoy!

There is a lot involved in setting up a robust onboarding workflow. However, it’s (obviously) worth your time and attention. The more people you can help achieve success earlier on, the better you’ll feel. And your business benefits.

Once you have something like the above in place, the next step is to validate and iterate.

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A Return to the Disciplines: Prayer

On the topics of depth and disconnecting from the world (online or off, see more below), a Christian is someone who follows Christ. And further, a Christian is someone who communes with Christ.

His first disciples did it, following him from town to town, breaking bread and serving with him. And when he commanded those early disciples to go and make more disciples, he promised that he would be with them until the end.

And prayer is our primary means to communicating with God.

Caveat: I am the least qualified person to talk about prayer. Study and meditation, the two disciplines we’ve discussed recently, have been something I’ve always enjoyed. Since I first started to read the Bible in earnest, they have come fairly easily to me. But not prayer.

This is something that I have always wanted to improve. Why? Because it’s so vital to a life of being a disciple of Christ. Richard Foster puts it this way in Celebration of Discipline:

Of all the Spiritual Disciplines prayer is the most central because it ushers us into perpetual communion with the Father. Meditation introduces us into the inner life, fasting is an accompanying means, study transforms our minds, but it is the Discipline of prayer that brings us into the deepest and highest work of the human spirit.

Or, as Martin Luther put it:

I have so much business that I cannot get on without spending 3 hours daily in prayer.

Pray Without Ceasing?

Paul lays it down for us in several places. He often uses phrases like, “make mention of you always in our prayers” or “have not ceased praying for you”. It sounds like he’s a man who spent 12 hours per day in prayer. And it’s enough to get you feeling down about yourself because who can hold to that standard?

It took a long time for me to gain a better understanding of what prayer can (and perhaps should) look like.

First, it’s important to note that Paul’s language may not be completely literal. “Always” can mean, “always in my daily prayer session in the morning before I get to making tents”. Continuing to pray for others could mean that each day he would spend time petitioning on behalf of others and would be consistent in who he would pray for. But it does not necessarily mean that he spent each moment of each day in prayer.

Of course, he likely did devote more of his time to prayer than you or I. But when comparing ourselves to the heroes of the faith, it’s important to be encouraged. Not the other way around.

One way to be in prayer continually through your day is to change how you think of God. He’s not far off, he’s right with you as you go through your day. And the second thing that has helped me has been to stop thinking of prayer as formal sessions of petition where I’m on my knees with folded hands. That is a good way to pray and we need to do that, but that’s not praying without ceasing.

Prayer continually, being in his presence continually, is simply to have ongoing dialogue with him as you go about performing the good works he has prepared for you. Being with your family. Doing your job. Chores around your home. Those are all moments where you can commune with your creator.

Why We Need Prayer

Off the top of my head, here are several reasons why we should spend time in prayer:

  • to change
  • to seek guidance
  • to confess and ask forgiveness
  • to make requests, for ourselves and for others
  • to center ourselves
  • to relinquish control and submit
  • to praise him and overflow with thanksgiving

All of the above are vital to walking with God. Am I missing anything? Let me know!

So how does one get better at prayer? Again, I'm not the expert. But here are a few things that come to my mind.

Be bold

Matt 21:22

And whatever things you ask in prayer, believing, you will receive.

Mark 11:22–24

So Jesus answered and said to them, “ Have faith in God. For assuredly, I say to you, whoever says to this mountain, ‘Be removed and be cast into the sea,’ and does not doubt in his heart, but believes that those things he says will be done, he will have whatever he says. Therefore I say to you, whatever things you ask when you pray, believe that you receive them, and you will have them.

Word, that is a challenge. But look at examples in Scripture for “fervent, effective prayer”. Elijah praying for rain or no rain. Moses praying for mercy on hard hearted Israel. The apostles saying to people, “Walk”. There's a simplicity of faith implied in these descriptions.

I want to be more like a little child when I come to my father.

It takes time

Occasional joggers do not suddenly compete in a marathon. It’s the same with prayer; it takes practice.

Richard Foster:

To understand that the work of prayer involves a learning process saves us from arrogantly dismissing it as false or unreal. If we turn on the television and it does not work, we do not declare that there are no such things as electronic frequencies in the air the cable.

We can determine if we are praying correctly if the requests come to pass. If not, we look for the “block”; perhaps we are praying wrongly, perhaps there are new principles of prayer to be learned, perhaps patience and persistence are needed. We listen, make the necessary adjustments, and try again.

Expect failures or dryness … it’s a process.

Come to him regularly

We cannot expect to be able to hear God’s voice if we only seek Him occasionally. And if we’re not studying, meditating, and praying often, how can we expect to understand Him and His will?

Have compassion

Caring for others is another sure way to get us into prayer more regularly.

Matt 20:32–34

So Jesus stood still and called them, and said, “ What do you want Me to do for you?” They said to Him, “Lord, that our eyes may be opened.” So Jesus had compassion and touched their eyes. And immediately their eyes received sight, and they followed Him.

Mark 5:18,19

And when He got into the boat, he who had been demon- possessed begged Him that he might be with Him. However, Jesus did not permit him, but said to him, “ Go home to your friends, and tell them what great things the Lord has done for you, and how He has had compassion on you.

Richard Foster sums it up well:

If we have God-given compassion and concern for others, our faith will grow and strengthen as we pray. In fact, if we genuinely love people, we desire for them far more than it is within our power to give, and that will cause us to pray.

That's a beautiful picture. And isn't it the same heart we see in the parables of the good Samaritan and the prodigal son? If it 

Keep it simple

Remember that you are a child and God is your Father.

Prayer is such a vast topic, it’s almost a shame to say so little about it. Methods, styles, who to pray for, when to pray … the variety is as vast as the people who make up God’s church. But if I think about it in this way, it becomes daunting. And so I try to keep it simple.

  • Jesus taught His disciples to pray with few words (Matt 6:5–15)
  • he also taught them to pray in private
  • follow His example
  • never hesitate to bring the simplest requests to God … Children ask for anything and everything with an expectation their needs will be met
  • be persistent (think of the widow and the judge)

For me, things have improved in recent years. I still go through times where I fail to regularly bring petitions and the needs of others to my father. But I have gotten a lot better at communing with him through my days. More conversational, less formal times of just … talking to my Lord. As Foster stated above, it’s a “perpetual communion”.

And I love how Dallas Willard puts it to Christians in The Great Omission:

But you might wish to think about what your life amounts to before you die, about what kind of person you are becoming, and about whether you really would be comfortable for eternity in the presence of One whose company you have not found especially desirable for the few hours and days of your earthly existence.

I want to want to spend time with my Lord.

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Keynote is King

My past month has brought something new to my workday. I’m a big advocate of writing for any role involved in a SaaS product, but it’s imperative for customer success. And while I’ve had the privilege of writing onboarding campaigns, interacting with customers over email and live chat, sending marketing emails, and summarizing research results in my roles, there is one bit of work I have never done.

Write UI copy. And as it turns out, I freaking love it.

This past month, while our team polished up the first phase of Conveyor in preparation of our private beta, I’ve been reviewing and tweaking the copy for all areas of the product. This has been a big, challenging undertaking. And a fun one!

While I’d love to chatter on about the importance of micro-copy and looking for opportunities to delight in this type of writing, today I want to focus on how to organize an endeavour like this. If you have a product of any size, there is a lot to keep track of. And if there is one thing you want in the copy of your product, it’s consistency.

Once I started to dig in on just seeing what our current copy was and all the bit of the product that include copy, I realized I needed some structure to this work. I immediately read a handful of posts to get some insight here, including re-reading a lot of John Saito’s work, but did not find any in-depth tutorial that laid out a good foundation, toolset, or process.

And so I just reviewed my tools on hand. OmniOutliner and Ulysses got some consideration, but since I would need to share my copy suggestions with my teammates, I went with Paper.

Paper from Dropbox is one of our current favourite tools at Wildbit. We’ve been using it since it first debuted and it just continues to improve. People are using it for so many different types of work (see this example from Noah Stokes and the Creative Market team).

And it has been working fairly well, especially the auto-generated table of contents in the sidebar. Since Conveyor is a Mac client with a full set of cloud services and a web front end, there’s a lot of different places where I need to review copy (as the screenshot below indicates — it does not all fit in the small vertical height of my MacBook screen). I love the ability to work on a bit of copy for the web app, then hover over the sidebar to flip to a corresponding screen in the Mac client. Consistency, remember?

But as time has gone on, this Paper doc has begun to get a tad unwieldy. There have been a couple of times where I wondered if I had missed the best tool at my disposal. Keynote.

And this past weekend, I was reading through the transcript of the second episode of Craig Mod’s new podcast, On Margins (yes, I rarely listen to podcasts and am very thankful for people who publish a full transcript). He was interviewing Frank Chimero, two great minds of our generation, to discuss making books.

Of course, in a 45 minute conversation, a lot of sub-topics pop up and they touched on Keynote. And their dialogue well captured what I love about this app. They begin to talk about their creative process and large walls and putting up materials to meditate on, to move around as the creative juices do their thing. And Frank says this:

And then I buy blue painter tape, and I’ve got a bunch of index cards. And just stray print outs from my crappy little inkjet printer, and I just sort of go to town on it. And sometimes it’s up on the wall, other times I like spread it out on the floor on a table and I’m just trying to sort out these notecards.
Because I have this loosely, blurry idea on my head and I’m trying to find the patterns and all of these things that I’ve been collecting that seem like they’re related somehow. So, the meaning emerges out of that. So, after that, I actually, maybe write a little bit in just like a text editor but I actually go into Keynote. Because what it allows me to do is to get all the images and the quotes arranged in a specific order. And also, I can nest them, I can sort of create a little hierarchy.
So, it becomes almost like a visual outline for me instead of a text outline that you would do in Google Docs or Word or something like that. And that works really well for me, because I can just sort of push things around and type up a quote or I can do a speaker commentary. There’s presenter notes inside of Keynotes so I can just write a full paragraph.

Craig closes this part of the conversation this way:

Keynote really does kind of turn things into objects in a way that text editors don’t. That sort of invite you to move things around in a way that, even in like Google Docs for example can click and drag on images. But I hate doing it, (laughs) like it doesn’t feel good to do it. Keynote I’m constantly shuffling stuff. The nesting works so well with tabs and shift tabs to unnest stuff. Apple really nailed something about tactility in Keynote. To me it feels the closest to like having a wall on the computer, in the same way you can move notecards around on a blackboard or whatever.

I love the descriptions of their process and how Keynote fits into that. It really is one of the most enjoyable tools I work with.

A lot of my teaching material starts in Ulysses as a bunch of bullet points, quotes, and the occasional group of sentences. But it’s when I start fleshing out things in Keynote that it all comes together. One would think that it’s not conducive to the type of usage they describe above, but for some reason it works.

Back to my work with the copy for Conveyor. Paper has been working, but I wonder if Keynote would have been better. I could create the clean outline structure with nested slides, then add suggested copy changes in the speaker notes. It’s certainly not the use case its designers likely had in mind, but that’s the power of a well thought out app. And it’s nothing new for Keynote.

This is one my favourite apps in my tool belt and one I do not mention often enough.

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