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5 Keys for Coaching CSMs to Have Strategic Customer Conversations

Coach your CSMs to lead strategic customer conversations with 5 keys—planning, listening, flexibility, results, and action—to move accounts forward.

5 Keys for Coaching CSMs to Have Strategic Customer Conversations

TL;DR

  • The five keys to coaching CSMs for strategic customer conversations are planning, listening, flexibility, results, and action.
  • Planning is the most critical key—CSMs should set a clear meeting goal, share it with the customer beforehand, build a detailed agenda, and prepare answers to likely objections.
  • Every strategic conversation should end with documented results shared in writing and a concrete follow-up action, so customers see that raising concerns leads to movement.

Customer success managers are tasked with being great at a lot of things. Project management, sales, issue mitigation, etc. – the list could go on and on. This is why requiring CSMs to be excellent at leading strategic planning conversations with customers can sometimes be a little tricky. For many customer success departments, however, CSMs are responsible for managing customer relationships and moving them forward as well. So, like it or not, these strategic conversations fall on the shoulders of CSMs themselves.

If you’re a customer success leader working with a team of CSMs, don’t panic. Most of the ‘how to’ for managing strategic customer conversations comes down to planning, and the rest can be easily taught and learned. Here are the five keys for coaching CSMs to having successful strategic conversations with customers:

1. Planning:

As mentioned above, planning is critical for any strategic conversation, which makes it doubly important for customers. Your CSMs should have a clear goal of the meeting and share this with the customer beforehand. A detailed agenda is also a good idea, with notes and points that the CSM can reference throughout the conversation. Another good habit is to develop any objections, questions, or concerns a customer may have beforehand and prepare a few answers to these points, so the CSM is well prepared for anything that comes their way.

2. Listening:

Whether the strategic conversation with a customer is around journey planning, feature expansion, or renewals, there are bound to be some areas where your two teams don’t see eye-to-eye. Instead of doubling down and barreling through with a speech, CSMs should step back and listen to any concerns the customer brings to the table. Listening serves two purposes: it helps the CSMs know precisely what the customer is looking for and makes them feel more comfortable and respected by your CSM team members.

3. Flexibility:

While planning things out to a tee is a recommended step for any strategic conversation, there will be times when things won’t go as planned. In these situations, the worst thing a CSM could do is panic and flounder. Flexibility – aka being able to pivot to a new path or idea – is a critical skill that CSMs need. This presents a chance for CSMs to show off their inherent project management skills and put all the information they know about the customer on display.

4. Results:

After a strategic customer conversation, was the end goal achieved? Every strategic customer conversation must have some wrap-up component that reminds the team why the meeting was called and what the result of the meeting was. One part of gathering results is sharing them with both your internal team members and the customer via email so everyone can see what was achieved there in black and white.

5. Action:

And, finally, a final key skill to coach your CSMs involves taking action. Regardless of the initial focus of the meeting, every strategic customer conversation will result in some to-do for your customer management team. Whether it’s following up with a data team member or escalating a feature request to the product team, your CSMs must take action after a meeting. This will keep things from backing up and let your customers know that it’s okay to share these kinds of concerns with your team.

You can learn more about building a successful CSM team with these other executive resources and tools:

Frequently Asked Questions

How do you coach CSMs to have strategic customer conversations?
Coach them on five keys: planning, listening, flexibility, results, and action. Most of the "how to" comes down to planning, and the rest can be taught—setting a clear goal, listening to concerns, adapting when things go off script, capturing the outcome, and following through with a concrete next step.
Why is planning the most important part of a strategic customer conversation?
Planning gives the conversation direction and prepares the CSM for anything that comes up. A CSM should define a clear meeting goal, share it with the customer in advance, build a detailed agenda, and anticipate the customer's likely objections so they can respond confidently in the moment.
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