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July 09, 2020
Best Practices

An Introduction to Good Customer Onboarding

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By Calendly

There are many ways to onboard a customer; here's the right way.

You pitched the sale. You shook the hands. Now it's time to deliver on the solution that you know will help make your customer's life better, easier or more productive. 

Initiate customer onboarding. 

It's time to train your customer to become proficient with your product or service while answering their questions and offering your expertise along the way. At the same time, you’ll benefit from understanding how to best adapt your customers to a new solution. 

What is onboarding?

The easiest way to think about customer onboarding is to see it as a process that provides a user with two key takeaways:

  1. Knowledge of how to use a product

  2. Understanding of how to make the product work for them

The onboarding process includes all of the activities that get you to that end goal, such as introductions, account setup, training calls, webinars, question-and-answer sessions, follow-up meetings and more. Companies plan these activities in advance, typically with built-in flexibility and a loose timeline. It's not about how quickly you can onboard a new customer—it’s about how well you can do it.

The head of customer support at Pipefy, Isabelle Salemme, explains that onboarding builds “a pathway that converges the value your customer expects and what you can offer.” It's the intersection of your solution and a customer's goals. 

Once that sale is made, you and the customer are on the same team. Onboarding is that space in time that connects you together and allows you to write a playbook for success. 

For your customer, that success will come from having their expectations about the new product or service met. For you, success means a lasting relationship with the customer—renewals, product add-ons or upsells. Ultimately, you're both invested in making this partnership work from the start.

Why does onboarding matter?

Think about the last time you saw a commercial for a new technology that you had to have. It was probably presented as a sleek, intuitive tool with hundreds of options for customization, convenience and effortless problem-solving.

Now cut to the moment you opened the packaging and could barely figure out how to power it up, let alone use it like the expert you saw on TV.

That same disconnect happens in your customer's life once they sign on the dotted line for your product. The demos they watched or heard from you during the sales phase looked simple, but there is a learning curve that happens for any beginner once they are in the driver's seat. 

Even if you offer a free trial phase, there is still a big difference between a user tinkering around with a platform and actually using it to bring about measurable change for their business.

This is why onboarding is so important. It's a step that takes the pressure off and allows for some time in limbo to educate and adjust.

Wyzowl reports that 86% of customers surveyed said they're more likely to stay loyal to a business that offers onboarding content that welcomes and educates them. The flip side of this is that 90% of people surveyed were not impressed by the current onboarding efforts of other companies.

This all means that successful customer onboarding can have a huge payoff for a company. However, it's likely that there's something that many companies are missing.

The “aha moment”

The missing factor might be what Ed Shelley identifies as the customer's "aha moment" in the process. As Shelley explains it, "When a new user follows the path to an aha moment, they understand how your product can help, and they want to keep getting the results. Without an aha moment, a user will feel lackluster about their success and lose motivation to keep going."

You don't just want your customer to be able to rattle off facts about your product. You want them to click with it. 

Onboarding is crucial in maintaining the momentum of the sale and the excitement of the product. It also ensures that your customer will find long-term happiness with your company and want to continue coming back for more.

So let's dive in and explore seven best practices for customer onboarding to help you give your customers their own "aha."

1. Know your customer

A new customer is a blank slate when it comes to interacting with your product. Even after a lengthy courting phase with free trials and demos, your tool won’t have the weight of importance until your client invests in it. 

Onboarding, then, is your customer's first real point of motivation for taking in all there is to learn about your product. 

Your job is to feed your customer everything they need and want to know while being careful not to overwhelm them with features and tutorials they might never use. It's an exciting undertaking— this is where you get to personalize the onboarding experience to help a new user grow to love your product. 

How do you figure out the key features and tools that your customer should know? It starts with understanding the key aspects of your customer’s job and how they will be using your product. You’ll need to know several critical pieces of information about your customer, including their:

  • SWOT analysis—strengths, weaknesses, opportunities, threats

  • User structure (single vs. multiple users)

  • Expectations of the product or service

  • Goals that your tool will help them to accomplish

The more you understand your customer's challenges and goals from the onset, the more you can avoid the pitfall of overwhelming them with information about your tool that they might not ever need.

You already know what you're offering your customer, inside and out. Once you get a general sense of where the client wants your offering to take them, you can deliver a streamlined onboarding experience.

2. Vary your customer onboarding activities

It's one thing when your customer is so eager to use your tool that they fly through the onboarding process at warp speed. It's another when they're asleep during it.

A boring onboarding experience slows the pace of excitement that a new user feels at the beginning of your partnership. Keep the energy high by switching up onboarding activities. Present a variety of ways to learn about your product. Vary the length of time and circumstances of your meetings. You might include:

  • Shared-screen interactions

  • Webinars

  • Team introductions

  • One-on-ones

  • Q&A check-ins

  • Tutorials

Everyone has a different way of taking in information, so cast a wide net to ensure you're reaching your users and keeping their attention.

Strikedeck offers an eight-week timeline that illustrates a number of customer onboarding techniques. Activities range from a simple welcome email to meetings to a best practices webinar and more. They even include checkpoints that lie solely with the onboarding company, like usage monitoring and cross-sell opportunities. We've amended their timeline with our own and focused on the seven emails that drive each conversation:

Week 1

Welcome email


1st onboarding meeting. (Introduction and expectation setting)

Product overview webinar

Week 2

2nd email


2nd onboarding meeting. (Project plan and responsibilities)

Advanced set up, user creation, tutorial

Week 3

Tips and Best Practices Email


Extensive Q&A

Begin user monitoring and refinement

Week 4

Advanced Onboarding Email


Introduce cross and upsell opportunities

Week 5

Customer Satisfaction Survey Email


Identify issues and introduce possible solutions

Week 6

Special cases email


Continue review of survey feedback and address customers with heightened concerns personally

Week 7

Final onboarding email


Discuss customer ROI and evaluate ways to add sustainable value

A varied approach like this one comes in handy when you have a more independent user. They might be more likely to take in information and assistance from you if you approach them from a number of angles.

Of course, some of your onboarding activities will be standard procedural elements, such as account setups and product demonstrations, but other aspects can benefit from your creativity.

Other elements that you may want to consider adding to your onboarding schedule include:

  • Videos embedded in emails

  • Website FAQ pages

  • User messaging portals

  • Reminders to use, renew, upgrade, rate/review, etc.

  • Well-designed infographics

  • Surveys to assess current knowledge of the product or service

3. Have systems in place for a professional process

Onboarding is a chance to show off your company along with the solution you're offering to customers. Show your new client how excited you are to have them on the team by beginning the onboarding phase quickly and running it smoothly.

Each customer is unique, but your process for onboarding should have a standard framework. You can repeat it and implement it consistently for positive results while tweaking it for each individual customer. 

There are onboarding tools that can make for a smooth and quick transition into the onboarding phase for your client and help you manage a professional experience. You can use scheduling tools like Calendly to easily set up meetings, webinars, training calls and more without the hassle of back-and-forth emails that waste time. 

Scheduling tools make it easy for teams of people to seamlessly figure out a time to connect without losing focus on the task at hand. Automating your systems in this way lets the busy work happen in the background and keeps the communication between you and your customer succinct and relevant.

For larger email campaigns, automated email tools like Mailchimp allow you to design, schedule and save whole email sequences and track the progress of user engagements. Your customer will receive attractive emails letting them know to schedule a meeting or check out a new product. 

The best part about automating your emails is that you only have to write them once. As long as you have an email list, you can reproduce these emails over and over again for all new users without wasting time and effort.

Hubspot offers another resource to check out for onboarding help—free templates to guide you through the process.

Tip: Test your systems on new employees

Take new employees at your company through the same onboarding process you have in place for customers.

At each point of contact or training, ask employees for feedback and assess how well they are learning how to use your product. This insider information you’ll gain can help you spot consistent wins or bumps in the framework of your onboarding strategy. You can then tweak them for clients.

This process makes for a win all around. Your employees get trained, and you get to take a closer peek inside a user's head while it happens.

4. Commit to a collaborative effort

The onboarding process involves your team—your whole team. 

Rather than just including the sales rep and account manager in the onboarding process, why not get a few key heads from each department involved to welcome new users? After all, new business concerns everyone in your company, and what better place to align yourselves than at the very beginning?

Go through client goals, challenges and questions during this collaboration. Work out a strategy that encompasses your long-term plans for new clients, from marketing and upselling to product adjustments. Define what customer success looks like to all parties involved in your business. You’ll be better able to stay on the same page throughout the customer's life cycle with your company.

Also, let your customer know who the key people in your company are. They will appreciate the wide umbrella of support you're offering to help them in their journey. The takeaway for them is the feeling of VIP status. For you, it's customer research and awareness at every level. 

5. View the process as the first step on a journey

Onboarding is not necessarily a step that ends. Ideally, it will be a process that has more beginnings than endings.

With each new customer onboarded, there are countless opportunities for upsells, upgrades and product add-ons. That means there's potential for additional onboarding sessions in the future. 

It's a good idea to have multiple onboarding programs in place—one for new customers who are unfamiliar with any of your offerings, and one for repeat customers upgrading to a tool with enhanced features. This may mean a different timeline and set of activities, or it could mean a whole new team that your repeat customers will meet. 

Be prepared for the possibilities of upgrades or add-ons that could mean a new set of onboarding activities for your team. But however you decide to structure your onboarding strategies, be sure to always include:

  • An introduction to the team of people dedicated to the customer's success

  • An account setup or adjustment

  • Demos or tutorials of new features, products or services

  • Progress check-ins

As your company's offerings expand, your clientele will need more attention, information and assistance from you, just as they did in the beginning stages. 

Think of onboarding more as a series of events on a long voyage, rather than a one-and-done step in a set period of time. Ride the waves, and your customer will be sure to hang on to the success you know you can deliver. 

6. Provide opportunities for feedback

Successful onboarding is a two-way street—a chance for you to learn from each other and find a connection point for a solution.

Your customer has heard that you're available at any time to help answer questions and concerns, but being proactive and asking them about their concerns during key onboarding meetings often produces better opportunities for feedback.

As you set up your first meeting with a new customer, prepare a set of questions to find out more about their problem—the one they're hoping your product can fix. It helps for everyone to be on the same page from day one. 

Beyond knowing your customer's expectations, you can check-in with them throughout the first several weeks to see what sticking points they are having with using your product. If it's a major issue, bring your IT expert back into the conversation (this is where the team strategy pays off) to talk with the client directly. Minor hiccups might prompt another walkthrough of key features. 

A few months down the road will call for another check-in. Here's where you'll assess how your product is meeting original expectations. Are there any surprise benefits the customer has found? What would they like to see offered in the future from your company? 

Listening to your customer is a constant process. The faster you see any potential hiccups or difficulties with your customer's experience, the more likely you are to eliminate churn.

Tip: Build feedback into sign-up forms

If you offer a free trial for a service you provide, consider creating a unique signup form page for free trial users. On that form, include a few short questions to gather their initial feedback from their trial experience. Any data helps piece together the puzzle of how visitors become users and what keeps them hooked.

7. Measure

The next step in the process is one of the most important aspects of customer onboarding—measuring your results.

As with just about any element to business, you will need to gather metrics on your onboarding success. Collecting as much data as you can for all of your business processes can only benefit you in the long run. If you’re running an online platform, for instance, this might mean gathering initial stats on:

  • Number of customer logins

  • Number of days each week that the customer logged in

  • Average time spent logged in

  • Which features are being used

  • Which features are being ignored

If you detect a concerning trend in any of these over the first week or so, communicate immediately with your client. This can help to answer a question or two that customers might not be asking you. Most importantly, it can also eliminate stalls in energy and excitement for your product on your user's end.

Along with short-term data, you'll want to keep tabs on how well your clients are meeting their own long-term goals when it comes to their expectations for your product. Revisit those expectations you talked about on your first meeting. 

How has your product succeeded in matching your customer’s expectations? Where has it fallen short? What stats, if any, does your customer have to back up their answers? Digging deep into your own lead, sales or retention figures can help you better assess what each of your clients can be adjusting in order to reach their goals. 

A final checklist

Now that you understand the best practices of customer onboarding, the big question is when is onboarding completed.

You will know that you’ve properly onboarded your customer when they figure out the strategy they’ll need to use with your product and can harness its abilities to fulfill their expectations. 

This discovery may take a couple of weeks, or it may take months. It may take even longer than that, and that's ok. Performing all of the following key steps, however, is an indicator of a solid onboarding program:

  • Uncover key expectations and challenges facing the customer's organization

  • Provide the customer with relevant information and training

  • Provide exceptional customer service from a wide range of team members

  • Gather data surrounding customer interaction with the product to detect early issues

  • Ask for feedback from the customer about their onboarding experience and initial reactions to the product

  • Build a strategy around future opportunities for customer interactions and usage of additional offerings

Keeping your onboarding game strong is just as fulfilling for you as it is for your customer. After all, it's awesome to see your users discover for the first time the same value that you see in your product every day. 

Even a little "aha" goes a long way.

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About the Author

Calendly LLC.

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