MSP Sales Discovery

3 Tips for MSP Sales Discovery Success to improve your MSP Sales Close

Written by Ian Richardson

March 4, 2024

MSP Sales Discovery Success

By Ian Richardson, Principal Consultant, Fox & Crow

My friend Walter Crosby from Helix Sales Development clued me in on a “secret” early on in our friendship. We were on my porch in East Lansing, enjoying a pair of Cuban cigars in summer. Walter leaned over and dropped a proverbial bomb in my lap about MSP sales discovery.

“Ian, Sales are won or lost in discovery. Your proposal doesn’t matter at all.”

That golden piece of wisdom has changed the way I sell and improved my close percentage by over 300%. Throughout the journey, I’ve found 3 big tactics that have helped that continued success. You can use these tips to improve your own MSP sales discovery success. Without further ado, here are 3 tips for MSP Sales Discovery Success:

  1. You should be asking questions when you speak.
  2. You should be comfortable with silence.
  3. Dig Deeper.

Let’s explore each of these tips.

Asking questions when you’re talking:

Discovery is about being a student, not a teacher. You will have ample time to share your expertise and wisdom with your client during proposal. You’ll do it all the time during the paid engagement. In discovery keep your focus on learning. Explore the client’s organization. Understand the issues they’re experiencing, and the impact those issues have.

Almost all your “talk time” should be asking questions. Even when you have a question asked of you, find a way to end your response with a question. This technique is a “reversal”. It makes sure you keep control of the conversation and remain in “student” mode.

Be comfortable in silence:

Part of asking questions is letting your prospect respond. The interesting commonality about people is that everyone will fill silence. When you ask a question, stop talking and wait. Your client will answer you. Sometimes they might say a response and stop. Count to 5 in your head before asking for more information or moving on. Many times, people will pause to collect their thoughts before continuing.

Dig Deeper:

The adage “slow down to move fast” comes to mind. Move past the surface to find the real problems. What does your prospect care about that is driving this concern? Understanding true impact and root cause of problems sets up successful closes.

That understanding of the individuals and organization sets your organization apart from competitors. It makes a competitive bid seem shallow and weak in comparison.

Good MSP Sales Discovery wins deals

The point of discovery is alignment between yourself and the client. That alignment occurs around what matters to the client, and how you can help them in ways that make sense to them. This doesn’t mean being “the best/fastest/biggest” in your market. It definitely doesn’t mean talking technology at your client.

Alignment occurs through your questions. The exploration of problems will help both you and your client. You both will learn throughout the process – often the true problem is hidden under 3 to 5 “why does that matter?” (see Toyota Five Why’s here: )

Spending time gaining understanding builds trust with your client. They “know” you understand their situation. That understanding allows them to hear your plan. Present your plan  and they can judge if they believe it will help. That belief creates the “yes”.

Spoiler: This means no “geek-speak” in proposals. Leave tech terms at the door.

MSP Sales Discovery needs Sales Management

Good MSP sales discovery needs sales management. Review of the three tips should occur after your discovery calls. Items done well get reinforced, those that have room for improvement get coached on. Below are 3 actions to take today to help with this effort.

  1. Record your discovery sessions. Transcribe the recordings. Use AI to analyze the transcripts against set parameters to highlight outliers.
  2. Review Time speaking versus Time Listening. A ratio of 30:70 is good.
  3. Focus on exploration of issues presented by the client. Did you get to the root cause? Did you monetize Pain & Gain? Do you understand what good looks like for the solution?

These tips are not all encompassing, but they’re enough to get you on the path to steady improvement.

Sales Management Help

It can be hard to see problems with your own work, or your team’s work. If you’re focused on improving your MSP sales management Fox & Crow can help. Our MSP Sales Process can help level up your MSP sales discovery.

We help with MSP Sales Discovery. We also provide training on MSP Sales Management, and coaching for reps and managers. You can reach us here:

Contact | Fox & Crow Group (

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