Jul 19, 2019

Read Time 6 min

CSM Confidential – Part 1: Difficult Customer Conversations


Being a Customer Success Manager is difficult enough. 

Based upon the premise that customer support should be more proactive than reactive, the value of Customer Success cannot be understated. Between responsibilities like onboarding, advocacy, upsells and renewals, Customer Success Managers (CSMs) have cemented themselves as drivers of corporate growth. 

That said, thriving in this relatively new discipline is not always easy. Between difficult customers, a lack of executive buy-in and other challenges, being a CSM isn’t always a walk in the park. Wondering how CSMs really feel about some of the intricacies of working in CS?  

Continue on to read the first installment of CSM Confidential – where real-world Customer Success practitioners give their unfiltered responses to some of the most challenging, frustrating and cringeworthy situations that every CSM experiences. 


The Customer is Always Right, Right? 

solve customer success challenges

As the adage goes, The Customer Is Always Right. But are they actually? According to two CSMs, the majority of the time, the customer is indeed right. While this isn’t always the case, (missed deadlines or a lack of adoption), it’s important to hear out customer concerns. Sometimes you’ll even have put your foot down in order to position your customer for success. 

“Nope! [the customer is not always right] Luckily, as a CSM for a software product, I don’t usually have to worry about my customers feeling like they are always right. I tend to work with really tech-savvy people who understand the difference between “technically as designed” and “bug.” They tend to be open to the idea that it could have been designed this way for a reason…. we just maybe don’t know what that reason is! 

One thing to note is how much I’ve learned from my customers. My organization’s product team has made some really big (and lots of really small) changes to our processes (and product, of course) as a result of Customer feedback. So even though they may not always be right, you’d be a total fool to not listen to them. We’re a much smarter company because of it.” 

-CSM for B2B Software Company 

Another practitioner added that while there is a lot to learn from customers, sometimes you need to draw a hard line. Reestablishing yourself as the product expert in situations like these are essential: 

The customer is always right? Allegedly! I always work hard to let the customer think they are right, but sometimes, as the expert of my software, I know better. As the person who works with the platform day in and day out, I am familiar with what the software needs to be utilized successfully. Sometimes that means gentle persuasion until the customer agrees with my point of view, and sometimes that means forcefully putting my foot down to adjust their perspective.” 

-Implementation Specialist for SaaS Startup 

 Should You Tell Your Customer That They’re a Poor Fit? 

For most CSMs, one of the most dreaded situations is managing an account that just isn’t a good fit. It can be frustrating to deal with a customer whose prospects aren’t bright from both a professional and personal perspective. Whether the result of an overzealous buyer or an overpromising AE, poor fit customers are never good news. So, should you communicate to your customer that they are a poor fit? Or is it better to just sit back and accept that this account will likely churn? 

“You should, but not right away. A customer can be a poor fit and still find a lot of value out of your software. Chances are that you will be able to find some viable workarounds in your platform that will provide value. If there are no workarounds, then you can have the discussion with your internal sales team to see where the miscommunication in the sales process existed. If you decide to tell the customer they are a poor fit, I personally believe there should be a contractual discussion to follow, but each organization handles it differently.” 

-Implementation Specialist for SaaS Startup 

Another CSM, however, suggests a softer approach. They suggest digging deep to find the root cause of the poor customer fit: 

“Telling a customer that they’re a poor fit is a bad idea. That said, it should absolutely be something that you address, and challenge head-on as opposed to letting it go off the rails. First and foremost, your team should absolutely have an avenue to “rate” the deals that come across from Sales. Are they a good fit for your offering and solution? If they’re not a good fit, how does that impact the person that sold the deal? Sales has a tough job as-is so damning them for selling a deal can be a double edged sword, however, identifying trends with a Sales Rep that consistently sells the wrong deal could have major upside in the long-term for your company as they are less likely churn, more likely to be an advocate as a result of meeting their desired outcomes, and more.  

Tip: Create a field in your CRM that shows whether the customer is a Great Fit, OK Fit, and Poor Fit along with a corresponding notes field. This will allow you to keep tabs on which Accounts are good/bad fits and why.” 

-Customer Success Strategist for a SaaS Company 

 Handling a Customer Who Ignores Deadlines and Misses Calls and Demos 

For CSMs who are working with strict implementation deadlines, an unresponsive customer can undo many weeks of preparation. Facing these types of customers can be one of the biggest challenges in delivering an on-time implementation, as the success of many accounts rely upon one or two stakeholders 

One CS professional explained that the best way to deal with a troublesome customer is through communication: 

“As a CSM, my priority is to make sure my customer is happy, successful, and finding endless value in my product. When they aren’t invested at the same level as I am, it drags me down. Here, I try to focus on value and I make that clear to the customer. 

I try to schedule a quick phone call, and if that’s not possible, I write out my concerns in an email where I speak very frankly and say something along the lines of “Hi Jane, I’m really concerned about us not meeting your goal timelines on this project. Originally, you expressed that you wanted your team to be live on the first of next month, and at this rate I don’t know if that is possible. I fully recognize that you have a full-time job outside of this project, and I’m extremely grateful for any time you or your team can give me. When is a good time to spend 10 minutes clarifying our open items, next steps, and discussing a new timeline?” – and if that doesn’t work, don’t hesitate to say “My manager is really on my back because she’s not seeing this project move forward at the speed we anticipated and she wants to set up a time to speak with you to see what we can be doing to move this along.” 

-CSM for B2B Software Company 

The anonymous Implementation Manager we spoke to is no stranger to customers who miss deadlines. Besides establishing a communication line, they suggested taking a step back and looking at the big picture. When dealing with difficult customers, be sure to consider all factors that could be in play. 

“Ain’t nobody got time for missed deadlines! This is one that continues to baffle me whenever I come across this scenario. When an organization chooses to spend a large sum of money on a product, wouldn’t you want to put the manual work into it to make it a success? Now I must take a step back and remind myself: my customers are also human. There could be extra factors, inside or outside of their workplace environment, that can cause them to be this way. It’s key to remember to always be human and offer a second chance or two. I find that when you have a conversation with a customer to reset and inform them that they’re behind on a project, it kicks them into high gear to get back on track. If that doesn’t work, then sometimes you must loop in managers to ensure that you’re being heard, but that is as rare as it gets!” 

-Implementation Specialist for SaaS Startup 

Regardless of your Customer Success experience, difficult customer conversations never come easy. Whether dealing with missed deadlines or poor fit customers, always be sure to facilitate effective communication and be conscious of other factors that may be at play.  

While there is never a one-size-fits-all approach to these conversations, take comfort in knowing that CSMs before you (and well into the future!) will experience similar challenges.  

Ready for more unfiltered views on life as a Customer Success Manager? Subscribe to the Fighting Churn Blog and stay tuned for our next installment of CSM Confidential. 


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