Not Having Strategic Conversations with Customers? Here’s How to Fix That


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I keep hearing “our Customer Success Managers need to have more strategic conversations with our customers.” I’ve heard this in numerous discussions with customer success executives over the last year. And more recently, I continued to hear the same thing while attending customer success conferences and meetups in San Francisco, Toronto, Denver and Pittsburgh. This is a big problem. If CSMs aren’t having strategic conversations with key customers, it will be very difficult to proactively move their accounts forward in any significant way. This keeps us all up at night.

I want to share a technique that customer success executives can use to help Customer Success Managers be equipped for strategic conversations with key accounts. For years, I worked with newer product managers to help them think more strategically. The technique I used was to ask three key questions that pushed them to seek the fundamental knowledge and insights they need for effective strategy discussions. Below, I’ll share and unpack these questions which I’ve adapted for customer success managers.

Three questions CSMs need to answer to engage in strategic customer conversations

1. Where is your customer going?

Strategy is what one intends to do to move from its current state to a desired future state. Therefore, a CSM’s readiness for strategic conversations must begin with knowledge of a customer’s objectives and goals. If a CSM doesn’t know where a customer is going, how can they have any hope of engaging that customer strategically? When your CSMs knows this answer – down to the level of the organizational unit that purchased your solutions – they can add value in several ways:

  • focusing attention on actions that will have the most impact on a customer’s goals
  • providing meaningful guidance to a customer
  • evaluating a customer’s progress
  • demonstrating the value they’ve realized.

When a customer is lacking effective goals, a CSM can help them. I discussed how a CSM can do this in a recent blog post.

2. How will your customer get there?

I’d want a CSM to understand three items: (a) the primary approach a customer is taking to get to their desired future state; (b) the initiatives the customer will take to execute it and when; and (c) the role your solutions play in this. This knowledge of their customer’s strategy is important for several value-adding tasks including:

  • Identifying opportunities to add value with your existing products, services and programs
  • Anticipating and prioritizing unmet customer needs
  • Aligning the roadmaps for products, services and programs with the needs of key accounts
  • Relating the actual use of your products, modules and features to the customer’s desired outcomes
  • Sharing best practices and lessons learned from other customers with similar strategies

3. Where is your customer today?

The current state of the customer is often the focus of a CSM. But, for this question, I’d want to know if a CSM understands how a customer is doing versus their goals and versus benchmarks created from the results achieved by other similar customers. More specifically, do they know (a) Where is the customer doing well? (b) Where could they improve? (c) What has changed? (d) Where have we helped them effectively? (e) Where have we held them back? When a CSM has these comparative insights, they have the basis for adding value in several more ways including:

  • prompting exploration of the reasons behind the results
  • sharing potential remedies known to work with other customers
  • demonstrating the additional value a customer has realized with a solution

Ask these questions regularly

Strategic conversations with customers begin with understanding the strategic context of a customer. If your CSMs need to have more strategic customer conversations, try asking these questions on a regular basis in your internal customer review meetings. Because of your interest, your CSMs will put more emphasis on getting this information and understanding it. Plus, you’ll gain opportunities to coach and develop their strategic thinking skills. Ultimately, when your customers and Customer Success Managers are talking strategically, customers will move closer to their goals and you’ll move closer to yours.

Jim Berardone
Jim Berardone is an entrepreneurial executive with over 20-years of experience leading new technology companies. Currently, he is the Chief Customer Officer at OnlyBoth where he focuses on customer success and value creation. When off duty, he teaches a product management course for master's students at Carnegie Mellon University, mentors entrepreneurs and assists the customer success community in Pittsburgh PA. In all the above, he promotes using a customer-centric view of the customer's journey, experience and desired outcomes to achieve success.


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