Unlocking Client Trust: Deep Dive Conversations For MSP Growth

Sitima Fowler & Ray GreenMSP Marketing

As MSP owners, we often find ourselves in the thick of sales conversations, trying to showcase the value of our services. Yet, the key to truly winning over clients lies not in the hard sell, but in understanding the nuances of their frustrations and needs. Today, I’m sharing insights on transforming these client conversations into opportunities for deep connection and business growth.

Understanding The Problem

Our journey begins with a crucial step: diving deep into the client’s challenges. It’s not enough to scratch the surface; we need to ask pointed questions that reveal the real issues at play. For instance, when a client mentions dissatisfaction with their current provider’s response times, don’t just nod along. Ask, “Why is that a problem?” This invites the client to share their story, offering us a clearer picture of their situation.

The Three Key Questions

When we engage with clients, our goal is to peel back the layers of their IT challenges to uncover the core issues impacting their operations. This process is not about showcasing our solutions upfront but about fostering a deep understanding of the client’s situation. Let’s delve deeper into the three key questions that form the cornerstone of our client conversations.

1. Why is that a problem?

This question might seem straightforward, yet its simplicity belies its depth. Asking “Why is that a problem?” invites the client to articulate the issue in their own words, offering us insights we might not have uncovered otherwise. It’s not about our assumptions; it’s about their reality. For instance, if a client’s issue is slow response times from their current IT provider, we must resist the urge to fill in the blanks with our assumptions. Instead, let them express how this delay affects their daily operations, their staff’s productivity, and ultimately, their bottom line.

2. How long has that been a problem?

Understanding the duration of the problem offers a glimpse into its impact on the client’s business. A long-standing issue suggests deep-rooted operational inefficiencies and possibly, a significant toll on the company’s morale and financial health. This question also signals our commitment to not just a quick fix but a long-term solution that addresses the root cause of their frustration.

3. How is this affecting your business?

The third question is where the conversation pivots from identifying a problem to understanding its tangible impact on the client’s business. Here, we’re not just tallying up the operational hiccups; we’re quantifying the problem’s cost to the business in real numbers. For example, if slow response times mean employees are idle, missing deadlines, and productivity is hampered, we ask the client to consider the financial implications. “If you have 50 employees and their average burden rate is $30 an hour, and it’s affecting one hour per employee per week in lost productivity, what does that cost your business?” This approach not only highlights the issue’s financial drain but also sets the stage for a compelling ROI argument for our services.

Transitioning From Problem To Pain

Moving the conversation from identifying problems to understanding their deeper impact is crucial. We must encourage clients to think about how these issues affect their business, staff, and even customers. This requires us to slow down, listen, and really digest what they’re saying.

This process isn’t just for our understanding; it’s a reflective journey for the client too. As they voice their challenges, they’re also piecing together the broader impact on their business. This moment of realization is crucial. It’s where the problem, previously a frustration, becomes a pain point with clear, measurable impacts on their operations, security, and bottom line.

Avoiding Premature Solutions

It’s tempting to jump in with a solution as soon as a problem is mentioned. However, offering solutions too early can make us seem more interested in selling than in understanding the client’s needs. We must first fully understand their situation, which in turn, positions us as consultative partners rather than mere vendors.

Moreover, by fully understanding the problem before proposing solutions, we gather valuable insights that inform a customized, impactful proposal. This thoughtful approach not only demonstrates our expertise and commitment but also significantly increases our chances of winning the deal. It’s about creating an emotional connection, showing we understand not just the technical aspects but the real-world impact on their business.

Crafting A Winning Proposal

The insights from these conversations are golddust when it comes to crafting proposals. They allow us to tailor our pitch to address the client’s specific concerns and needs, using their language and emphasizing how our services can alleviate their particular pains.


Deep engagement and understanding are the bedrock of successful MSP-client relationships. By adopting a strategic, empathetic approach to sales conversations, we can improve not only our sales outcomes but also client satisfaction. Let’s strive to master the art of client conversation, transforming every interaction into an opportunity for growth and connection.

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