Defining Difficult Conversations in Customer Success

Meeting room with people in

Difficult Conversations come in many forms: 

  1. The what happened conversation… The blame game. 
  2. A feelings conversation that is emotionally charged, and
  3. An identity conversation where personal complexes are challenged (or added to!)

Sometimes emotions can run high, vulnerability may make an appearance, and/or legal matters may be involved –  It’s termed a difficult conversation for a reason. 

When you see this in Customer Success, it’s easy to get defensive based on the topic of conversation, but it’s crucial neither party walks away slotting your discussion into any of the above-mentioned categories. 

So what are you supposed to do?

It’s a big ball of matter, so let’s start at the beginning. 


The Nature of Difficult Conversations in CS

Where a difficult conversation is an occurrence of differing opinions, empathy is the name of the game. You can work to remain objective by putting yourself in your Customer’s shoes’. Being in Customer Success it’s no surprise that sometimes – as much as we wish it wasn’t the case – your Customer will have a different perspective of what they expect and/or believe they deserve. 

Sometimes it’s an ask that comes completely out of the blue, other times it’s a misunderstanding from a previous conversation or interaction. It’s not their fault, but it’s not yours either.

So, you’re in a position of needing to find mutual ground and work on identifying the best way to overcome this obstacle (even if it is a large leap). 

The No.1 reason most conversations become difficult is because it becomes emotional and not objective. You have to carry the baton and you lead on navigating through the different viewpoints and not grow frustrated.  


Taking a Step Forward

Facts are significantly easier to lean on as a base for a successful move-forward plan. If you’re in a Customer facing role, it’s likely that you already know that. But, that doesn’t mean it’s always smooth sailing. 

Just because you know to keep emotion out of the conversation and the facts are on your side, doesn’t mean you won’t come across some customers who like to unload their frustrations onto you. What do you do? You accept it, after all, we are all human. You just need to know where you’re going to go next. 

One of the best ways to navigate difficult conversations in Success is, yes, to learn on the job, but also to prepare yourself for the likelihood. 

If your customer is unhappy about a service, wants to challenge a fee or wants to report a bug, most of the time you as their account manager will already know they’re not best pleased. So why not prepare in advance for your next call by following a four-step process?

  1. Identify the root cause of your upcoming difficult conversation. 
  2. Use a framework for designing a mutual success plan.
  3. Mitigate your challenges.
  4. Measure your impact and hopefully celebrate your win!

If you use the steps above, you’ll not only be prepared for their emotions and challenges, but you’ll also have a strategy and immediate plan should calm any tensions. The feeling that their account manager cares and is ‘all over it’ will nine times out of ten, cause the customer to take a step back and let you fix it. 


Pressing Toward Proactivity

After you’ve outlined the way you’re going to get through the one difficult conversation you should prepare yourself for the inevitable that you’ll have more similar conversations in future. 

Invest time in researching success plans for a customer in your industry, stay awake and listen to podcasts, read books, watch the news; learn about your customer, understand their pains and be prepared to respond to them when it’ll inevitably pivot the reason they’re investing in your solution. 

Most of the time root causes for discontent when you’re managing a B2B Customer account, fall into one of these brackets:

  1. Unmet expectations
  2. Challenges for the Value <> Cost ratio
  3. Disbelief in the solution and success
  4. Cutbacks

Whilst you’re likely going to struggle when working to overcome financial cutbacks as listed in point four, there is a way to make knowledge your power for the remaining factors. 


Unmet Expectations

Standards are high. They just are. Lesson one is to make that your morning mantra. Work with them, not against them. 

This is often the result of accounts that are experiencing a dynamic with either your company or a specific product – that doesn’t feel like it aligned with the customer account. You’re not living up to their expectations. 

OR, it could be the other way around. Internal efforts to get the deal approved so they could purchase your solution may have come with some internal commitments. Internal commitments that they may not have achieved. 

Work to achieve and maintain organizational clarity with your customer at all times. Ask yourself ‘Do I know why Company X are using our solution?’. If yes, dive a little deeper… Do I know what they are trying to achieve? What metric needs to move to represent success?’. 

Make sure you know the answer to these questions – as a minimum – throughout the full lifecycle of the account. Double-check regularly, especially if there is a change in your point of contact. You’re much more likely to know when the needle isn’t going the right way and you can work with them to reignite passion and get the account back on track. That way whether it’s a you or them issue, it won’t become a larger issue that needs results in a more difficult conversation. 


Challenges for the Value <> Cost ratio

A challenge against the value and cost of your product gets a little trickier. If not fully understood, it can be seen as a matter of ‘unmet expectations’. Which it can be, but it also goes another level deeper.

Value <> Cost = Reasonable expenditure that equates to the core reason they bought your solution in the first place. 

This doesn’t always mean there’s a cutback on the financial side.

Is your product worth the cost? 

It could be financial value, moral value, or personal value. 

When the value of a solution is outlined and not achieved, it can be upsetting. The value you’re aware of might be that the customer wants to get X amount of ROI. And yet, the real value for them could be to move forward in their career and showcase other elements.

‘It’s not my fault that they made it personal when we couldn’t achieve that. What am I supposed to do?’

It’s your job in Customer Success to provide value and determine where the value gaps are. It’s a big challenge to be investigating how value pieces influence other value pieces, which connects back to the continued discovery mentioned earlier.


Disbelief in the Solution and Success

Finally, you’ve got the most personal objection of them all. Disbelief in your solution and what they will be able to achieve with it. As you can imagine, this is multifaceted. 

  1. Disbelief in an individual’s ability to be successful. It’s not connected to your product, nor the features your whole team has banged on about. It’s down to them and not thinking they’re good/smart/strong enough to carry it forward. 
  2. Disbelief that the studies they’ve seen from your other customers are totally factual. All marketers and legal teams know that there’s no way you’d be able to falsify a testimonial, but it doesn’t stop people from wondering. Particularly if your product is solving an untapped issue and it’s almost unbelievable that you can overcome it.
  3. Disbelief that the way you’re solving the issue is the best way to do it. Why your solution over the next?

Now, it’s not difficult to think that this should’ve been covered and overcome during the Sales cycle, and it’s likely it was discussed. But that doesn’t stop an individual from falling into their old traps and having the negative thought pop back up after they’ve signed.

These are hard conversations that centre around the customer’s obstacles and require you to push the customer towards an end goal. It can be difficult because it’s all about moving them as a CSM or a sales representative, which we will touch on in a moment. 

It’s often more centered on mindset than fact.


Who Should You Expect to be Working With?

When you’re thinking about these root issues, it’s important to stay aware that they can be seen with both your own internal stakeholders and external customers – Which will likely have a different impact on the situation. 

With internal customers, management and departmental figures tend to overpromise, which can create an unmet expectation later down the road. 

Plus, internal customers are not always aware of best practices as it relates to customer success. They’re experts in their own departments, so you can’t expect them to be the expert of yours as well. So, typically you’re going to see some misinformed opinions which is completely normal. 

It’s for reasons like this that internal customers may say ‘no’ without understanding all of the involved factors and may go around you to get the answers they need. Understandably this can cause conflict, as it limits the communication between you and them and harms the overall working relationship, which over time, can affect external communication when other departments support external customers. 

You’ve also got your external customers. They’re customer and business-facing. You may have an external customer who doesn’t want to participate in a conversation with you or is not looking to develop a relationship with you. 

This, granted, can make it easier for difficulties to arise, as communication is not up to par. 

Other times you may have customers who find it easier to move on to a new product or service and there is no amount of communication or solution-building that can change that. So it’s important to remember that it’s not a reflection of your management of a difficult conversation, as it may be a reflection that they had no interest in discussing mutual success at all.

To conclude, it’s important to understand your audience, as how you respond to them will look different on an individual level. 



To learn more about how to further research and carry out Difficult Conversations in Customer Success, why not take a look at our course? Not a member? We can help there, too.