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Nine Onboarding Steps to Turn Demanding Customers Into Raving, Revenue Generating Fans

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It started out like any other day until you received that text, email and phone call from one of your top customers. In an instant, your day went sideways and blew up in your face.

Needless to say, this customer wasn’t calling to give you stellar accolades. They were mad, frustrated and were ready to fire you and work with one of your competitors. Customers often recall the negative experiences over the positive ones. Even if you get it right 99% of the time, that one mistake could be enough for a customer to leave.

Hours later, promises made, and discounts offered, you were able to convince the customer to give you just one more chance before you lose them forever.

So, the eternal question is, “Are difficult customers and service issues inevitable or avoidable, and what role doe we play in this?”

Client Retention IS Your Growth Strategy

Unfortunately, today’s marketplace still hasn’t caught on to the fact that you can avoid problematic customers. Invesp reported that 44% of companies have a greater focus on customer acquisition, where only 18% focus primarily on retention. This is one of the main causes of this conundrum.

The Hüify agency found that the likelihood of converting an existing customer into a repeat customer is 60 to 70%, while the probability of selling to a new prospect is 5 to 20%. That same study showed that increasing customer retention by 5% could lead to an increase in profits by 25 to 95%.

This study also reported that it’s slower and costs five – seven times more to acquire a new customer, than to retain an existing one. Think about your hiring and onboarding process. It’s always more efficient and cost-effective to retain good talent and turn around an underperformer.

If you consider the lifetime value of each customer, Client Heartbeat reports that loyal customers are worth up to 10 times as much as their first purchase.

This Isn’t Just About Retention—It’s Your Post-Sale Onboarding Process

Retention issues don’t start when a customer is frustrated. They start the moment the deal is closed, and most companies are dropping the ball here.

Too often, businesses celebrate the sale, hand things off to account management, and assume the customer will just “figure it out” from there. But this gap between closing the deal and ensuring success is where expectations get misaligned, frustration brews, and customers start looking elsewhere.

Your post-sale onboarding process is the foundation of retention. Without a structured, intentional onboarding experience, customers feel abandoned, confused, or worse; buyer’s remorse sets in. And once that happens, you’re already on the defensive, scrambling to keep them.

A strong onboarding process should:

  • Reinforce why they bought in the first place. Customers need to feel validated in their decision, not left wondering if they made a mistake.
  • Clarify expectations early. Clearly outline what success looks like, what they should expect from you, and what you need from them.
  • Proactively address common pitfalls. Instead of waiting for complaints, educate them upfront on best practices, common missteps, and how to get the most value.
  • Ensure fast and easy adoption. Make it ridiculously simple for customers to start seeing results, eliminating friction from the get-go.
  • Create checkpoints to re-engage. Follow-up isn’t just about checking a box. It’s about keeping them engaged, ensuring satisfaction, and identifying small frustrations before they become deal-breakers.

Retention isn’t just about fixing problems; it’s about preventing them. Your onboarding process is the first (and most critical) step in that strategy. Most companies don’t have a clear process in place, and that’s why they’re losing customers or not maximizing their lifetime value.

A Proven Retention Strategy to Boost Profitability and Exceed Customer Expectations

Here’s your retention strategy to improve relationships and set or re-set expectations with your customers. If you’ve never had this conversation with your current customers, it’s never too late! Otherwise, your costly assumptions will create the situations you want to avoid.

This retention conversation will boost sales, customer satisfaction and loyalty, re-set relationships, and insulate your customers from your competition.

1. Set Intentions to Ensure Alignment

“Hi Mr./ Mrs. Client. Thanks for taking the time to discuss the best way to work together. What I want for you is to ensure we’re delivering the level of service and the value you expect. We respect that every customer has different priorities and expectations around customer service. In addition, while we do our best to mitigate problems, we find that most problems are a result of communication breakdowns and not having a clear strategy around how to work together. That’s why I wanted to take a few minutes to discuss what we can do to continue meeting your expectations. Is it okay to ask you a few questions to ensure we develop and maintain a great relationship?”

2. Benchmark Current Performance

  1. Why did you decide to hire us?
  2. What’s your expectation or definition of exemplary, 5-Star customer service?
  3. If you were to rate our customer service with one being unsatisfactory and ten being exceptional, how would you score us? What do we need to do to score a ten with you?
  4. What stands out most regarding the quality of our service and deliverables?
  5. What data/key performance indicators or metrics do you use to assess the impact of our deliverable and customer service, and if your expectations were met? How do you collect this data?

 

3. Meeting Client Expectations

  1. How would you define a successful vendor partnership and engagement?
  2. What can we do to maintain our positive relationship? What role can you play in ensuring this?
  3. What would negatively impact our relationship?
  4. Can you share a positive experience with another vendor so that we can deliver on your expectations?

4. The Customer Engagement Strategy

  1. When you need something or have a question, what’s your expectation around our response/delivery time to your requests (email, phone, text, and so on)?
  2. Can we take a moment to discuss our typical timeline/turnaround times to ensure they’re aligned with what you can expect?
  3. How often you would like us to contact you to ensure you’re getting the service, information and results you expect?

 

5.  Strategies to Handle and Avoid Problems

  1. Can you describe a bad experience with a prior partner/vendor and things we should avoid doing?
  2. If a problem arises, how would you want to work together and resolve it so it doesn’t happen again?
  3. If I’m not able to reach you to discuss something urgent, how else can I get in touch with you?
  4. Other than you, who else would you want us to contact in case of a timely need or challenge, whether it’s something you need from us or we need from you that if we don’t resolve, could delay the project and/or delivery time. What’s the best way to contact them?

 

6. Communication Strategy

  1. How much involvement and visibility do you want regarding the work flow and stages we’re at with your project/engagement?
  2. How often do you want to be updated? What specific data points? Format?
  3. How would you like us to share these updates? (Call, text, email, phone, social media, document)

 

7. Understanding the Company’s Business Cycle, Policies and Compliance Regulations

  1. Let me share how we bill and the expectations around payment. Can you share your typical payment process/guidelines so we align them with our billing process?
  2. There may be times when you experience fluctuations in your business. Do you have a busy season or experience downtime so we understand how you allocate your resources, how this would impact the way we work together and what to expect regarding response times from you?
  3. To ensure we stay in compliance, what business or regulatory compliance regulations, laws or policies do we need to be aware of as it relates to your industry and business?

 

8. Creating Future Selling Opportunities

  1. As one of the (decision makers, influencers, advocates, end users), what can we do to ensure we make you look great?
  2. Is it okay to reach out to you from time to time regarding product or service updates or new services that you could benefit from?
  3. As long as we continue to provide the value and results you expect, how open would you be around making introductions or referrals to other departments or people you know who can benefit from the value we deliver?

 

9. Finalizing Your Retention Strategy

Document the conversation and send an email recapping what was discussed and agreed upon. Then, ensure you get a response to confirm alignment and avoid miscommunications.

Think about the additional revenue and countless, stressful hours solving problems you just saved by proactively managing client expectations. After all, if you’re not taking care of your customer, someone else will. When salespeople start transforming into better coaches for their customers, and sell with questions rather than answers, better opportunities, results, retention and revenue will follow.

The post Nine Onboarding Steps to Turn Demanding Customers Into Raving, Revenue Generating Fans first appeared on Keith Rosen.

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