The strategic conversation playbook for Customer Success Managers - Glide Consulting
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The strategic conversation playbook for Customer Success Managers

When your manager tells you to have “strategic conversations,” your first instinct as a Customer Success Manager might be to hit the panic button.

Am I not being strategic? Isn’t that my job? Am I not doing my job?!?!

Let’s take a step back.

“Strategic conversation” is, unfortunately, a really vague term. It means something different to everybody—including two people on the same team. This lack of clarity about what a strategic conversation is—and how to go about having one—is an enormous source of friction in Customer Success.

And yet, conducting them is one of the most important aspects of a Customer Success Manager’s job.

If your manager doesn’t know a lot about CS, they might think strategic conversations can magically drive upsells and increase revenue. For other managers, it’s just another buzzword to toss around. The truth is that CSMs don’t get enough guidance and direction to have an effective strategic conversation.

If this describes your reality, you’re setting yourself up for failure. In order to have a successful strategic conversation, you need to know exactly what your manager wants and employ some specific strategies to help you achieve that goal.

Bonus Content: Get the Strategic Conversation Checklist to take with you

How to define a *strategic* conversation

Before you pick up the phone to call a customer, define what a “strategic conversation” means to your manager. It’s important to get on the same page regarding what the end goals of these discussions are—especially if your manager is the one instructing you to have them.

At a high-level, strategic conversations are discussions with customers about big-picture items. They might take the form of a Quarterly Business Review, onboarding, or a check-in call, but no matter what the context is, they’re completely different from tactical conversations. They focus on the long-term instead of the nitty-gritty. Here’s the main difference:

tactical conversation is about your product. You will discuss it's features and functions.

strategic conversation is about the impact of your product. You will learn how your product impacts, affects and helps your customer. You will also learn about your customer's organizational goals and what their future holds.

Strategic conversations are your best opportunity to build trust with customers—which is a cornerstone trait of any Customer Success professional. The ability to have a strategic conversation also separates elite CSMs from newbies. When you show that you truly care about your customers' day-to-day pains, as well as their future goals, you'll gradually level up from a 'resource' to a 'partner'.

Questions for your manager

If your manager tells you to conduct more strategic conversations and you don’t know what that means, ask a couple of clarifying questions. Here are some to get you started:

1. Can you help me understand what you mean by “strategic?”
2. How would you know I was having more strategic conversations?
3. What would be different if I were having more strategic conversations?

If your leader can’t answer those, then Houston, we have a problem.

Your manager has some work to do before you can execute.

If you don’t know where to begin, try framing the discussion with your manager around the qualities a strategic conversation should have. In order to get to a higher-level conversation, you need to keep a couple of things in mind.

A good strategic conversation:

  • Always puts the client first, not the company
  • Moves the customer closer to the end goal of where they want to be with your product
  • Builds trust by asking powerful questions
  • Shows that you’re genuinely curious about how the customer’s world works

Strategic conversations will be different for different products and different managers. As soon as you get a clear sense of what your manager wants, and how you can best help your client, you’ll be ready to actually get started.

Get customers to dig deep

Strategic conversations require a level of depth that doesn't exist in tactical conversations. But if you’re used to interacting with a client on a tactical level—let’s say, talking about specific bugs in your product—you’re going to need to coach them into giving you the answers they need.

Customers might be used to giving you short and sweet answers, especially if they normally interact with Customer Success only when a problem crops up. But rote responses aren’t going to cut it for a strategic conversation. You’re never going to understand a customer’s day-to-day experience with your product unless you do some digging.

Let’s say you just rolled out new analytics metrics for your platform. You ask your client what she thinks of them and she responds, “Yeah they’ve been helpful.” In a low-level conversation, you might just accept that answer and move on. In a strategic-level conversation, you need to ask a follow-up question.

This can feel counterintuitive.

When something is going well, the last thing you want to do is probe further, in case the customer changes her mind. But in reality, asking probing questions is the best (and only) way to get your hands on juicy customer insights.

Good questions to ask

In order get this information, you must push past generic, surface-level answers.

Listen for the places where you can open up the conversation a bit more. Whenever a client uses a generic word like “helpful,” or “useful”—go deeper. You might have a definition of that word, but what does it mean to the client you’re speaking with?

When you ask a customer a follow-up question, use “what?” questions instead of “why?” questions. A “why” question, like “Why was that helpful?” feels interrogative and questions the customer’s judgement. A “what” question, like “what exactly was helpful?” demonstrates genuine curiosity.

Try these follow-up questions on your next strategic call:

  • What exactly is helpful about the new metrics?
  • What’s the impact this part of the product has had on your business?
  • How has that affected you professionally?

You’ll build more trust if you show a genuine interest in your customers. In a study on customer loyalty in hospitality, researchers found that having high-quality conversations—that is, ones that went beyond the superficial level—significantly increased customers’ relationship with and loyalty to the brand.

Bad questions to ask

If you only ask ready-made questions and don’t tailor them to your individual client, you’ll just wind up sounding like a robot.

Never begin a QBR by saying something scripted, like “Hi, my name is x. I’m conducting a Quarterly Business Review. In this review, we will cover x, y, and z.” You will get surface-level responses and lose your customer's interest.

Don’t get bogged down in the wrong details

A good strategic conversation gives you a 50,000-foot view of your relationship with a customer. In order to get to this viewpoint, you need to make sure you’re not tripping over the small stuff that doesn’t matter. If the conversation is getting derailed, get out of the weeds.

A common tripping point is benchmark data. If you’re in a strategic conversation and talking about high-level goals, customers might ask how they measure up against your other clients. A lot of the customers I worked with at my former company were focused on increasing their average revenue per user (ARPU). In this data-driven world, it’s unsurprising that they were eager to hear how they compared to my other clients. How did their ARPU stack up?

They knew I had the data, and they wanted to see it. Without carefully navigating the situation, I was at risk of making clients feel like I was actively withholding useful information from them.

But if you share benchmark data with clients, not only will it confuse them, it will throw the entire strategic conversation off course.

Turn the conversation back to the customer

In this situation, it’s important to remind clients that with benchmark figures, it’s never an apples-to-apples comparison. Explain exactly why this information is irrelevant. For example - everybody’s app is different—they’re at different stages of development, they operate in different markets and they have different goals. Of course their ARPU is going to be different!

Once you’ve done that, it’s time to re-orient the conversation to your customers’ strategy. Try asking this one question:

When we met last time, you said this metric was most important—how’s that going? How can I help you move the needle?

It loops you back to having a strategic conversation and moves the focus right back to them. That’s what we’re all here for in the first place, after all.

Above all, use strategic conversations to build trust

Ultimately, a CSM’s job is to make the customer look like a rock star. You want to help them use your product the best they can, achieve their personal career goals, and grow their company in the right directions. You simply can’t help your customers do this if they don’t open up to you about what their goals are.

In order for them to open up, they need to trust you. Strategic conversations are your opportunity to build trust by showing customers you're there for them in the short-term, but also looking forward to the future.

When done right, this level of trust creates more than a good CSM-client relationship—it creates lasting friendships. A lot of CSMs, myself included, are still friends with clients from years ago because we developed real relationships. When you have a meaningful strategic conversation, you won’t just check off boxes—you’ll align goals, strategize together, build trust, and maybe even build a friendship along the way.

Bonus Content: Get the Strategic Conversation Checklist to take with you
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