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These days, buyers have more choices, are better informed, and expect a superior customer experience.


As Customer Success Managers, we have a narrow margin to bring value to a customer, or else we risk losing them. So, it’s not surprising that many Customer Success teams spend tremendous energy on keeping customers “happy” or doing whatever they can to adapt to customer desires.


The problem with this approach is that it assumes customers know what’s best. In reality, Customer Success Managers are the authority on best practices with their tool / service. If CSMs always bow to the requirements of the customer (who isn’t the product expert), the result is often a lack of success.


Have you had a customer churn because they refused to use your product in the manner that would produce the best results?  


Sometimes, a customer’s habits are the biggest hurdle to their success. This is why “challenging” your customers can have a positive impact on retention and growth.


The Challenger Concept


The “challenger” concept was popularized as a sales strategy by Matthew Dixon & Brent Adamson in their book, The Challenger Sale. In their view, the sales landscape had fundamentally shifted, and prospects were now too busy, too well informed, and had too many options for a long-term relationship strategy to work. Instead, Dixon and Adamson proposed consultative selling that wasn’t afraid to challenge the customer’s assumptions.


They broke the model into three steps:

  • Teach: Teach prospects how their product solves common industry challenges.
  • Tailor: Tailor the solution to the potential customer’s specific needs.
  • Take Control: Push the prospect by challenging their assumptions.


Although the challenger model was originally designed for sales, it also has a lot of application in Customer Success!


How to leverage the Challenger Concept for Customer Success


Today, customers increasingly expect that Customer Success will help them not only achieve value with a product but also impact their business as a whole.


As mentioned before, a customer’s habits can often be the roadblock to achieving success. So, if that expected impact is what customers truly want (and for the most part it is), then we need to challenge them to modify their behavior and enact true change management. Using the Challenger Sale strategies are a great place to start.


What does this mean in practice? “Challenging” the customer comes down to getting them to change. It may involve changing their processes, goals, preconceived notions, strategy, or anything you feel is currently inhibiting their success. Some examples of areas to challenge customers are:

  • Pushing against their success criteria – Some customer’s expectations of your product can either be unrealistic or lacking enough detail to give you measurable ROI.
  • Scrutinizing bad workflows – Are customers using your product in a way you think fails to deliver value? Be candid and let them know how their behavior will decrease the potential value they receive. Give examples of the success other customers have seen following your best practices.
  • Addressing low engagement or usage – A customer who has low engagement has a low likelihood of success. Be upfront and let them know that you are worried that they are not heading for success based on their engagement. Confirm their expectations and compare that to their current path.


Then, you need to convince them to change. This is the most difficult part as it requires asking tough questions or voicing concerns that may produce some friction. It’s important to conduct this part with respect and with the goal of helping them and their business.


Some examples of the types of questions or statements you can use are:

  • “You mentioned you want to be able to improve X, but how will you quantify and measure it? In what time frame?"
  • “I understand your workflow is to do X, then Z, then Y, but from my experience, when customers have done that in the past they end up seeing less value.”
  • “You signed up to achieve X, but your team hasn’t logged in regularly since the beginning. Most customers who don’t make our product a habit from the start won’t see an improvement in X. Will you be able to work with me to get them engaged?”
  • “I’ve recently been working with customer X who is in a similar industry, and they’ve been successful in increasing Y. You haven’t mentioned that as one of your criteria for success, but I think you should consider it as a future goal.”
  • "I understand you want us to prioritize a new feature but it’s outside the scope of our product’s intended workflow. What is the fundamental business problem you are trying to address?"


While it isn’t easy, “challenging” customers is a powerful tool in a CSMs arsenal to help customers whose biggest hurdle is their own behavior.


Note: Alex also runs a newsletter for Success leaders. Check it out.



The top articles this week: 

This week's newsletter features posts on: 

  • Remote Happiness, How to Create It
  • Slick B2B SaaS Onboarding and Fantastic User Adoption
  • How to Take Personal Development Off the Backburner
  • 21 Questions to Help You Understand Your Customer




Remote Happiness, How to Create It

“Humans need 4 things to feel mentally balanced: connection to nature, connection to tribe, blood flow, and uninterrupted work space. Pre-COVID, we could each achieve these to some degree simply by going to an office.” It’s challenging for some of us to adjust to remote working. Matt Mochary (CEO coach to companies like Coinbase, Opendoor, Clearbit, and more) offers some tips on how we can achieve those four elements, and encourage others to do so, in a work-from-home environment.

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The Key to Slick B2B SaaS Onboarding and Fantastic User Adoption

Where Alex Bakula-Davis (above) explains how to use the “Challenging” concept to get a customer to change, Dean Colegate (Customer Success Consultant) offers a high-level blueprint for creating a Change Management Plan in this post.

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How to Take Personal Development Off the Backburner

Here’s a compilation of sound advice on how to approach personal development, meaning the ongoing work of up-leveling yourself in pursuit of your longer-term goals.

Read the Full Post




21 Questions to Help You Understand Your Customer

Here’s a solid list of questions you can use to unpack your customers’ wants and needs, while increasing buy-in. Some examples include, “What’s working well right now?” and “What might happen if you do x/don’t do x?”

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