MSP Sales Recovery: A Strategic Guide to Understanding Lost Deals

Troubleshooting a Lost MSP Sale: A Step-by-Step Guide

When a promising MSP sale falls through, it can be a real head-scratcher. Here’s a spunky, no-nonsense walkthrough to troubleshoot where things might’ve gone awry.

A good chunk of what we do here at MKC is setting qualified sales meetings for MSPs. Some of our clients have the budget and time for 1:1 coaching regarding sales process, nurturing and closing, but others don’t. Inevitably those clients often come back to us asking “why didn’t I close that deal?”. So we’ve created a checklist to answer just that!

1.) Revisit the Discovery Call:

Did you really tune into their pain points? Make sure you didn’t miss any subtle cues that could’ve clued you into their real issues.

When revisiting the discovery call in your sales process, consider these deeper insights:

  1. Active Listening and Question Quality: Focus on truly hearing the client’s needs. Listen for the meaning behind their words, asking probing questions that uncover deep-seated challenges and goals. Remember, the real issues often lie beneath the surface.
  2. Engagement and Non-Verbal Cues: Gauge how engaged the prospect was during the call. Reflect on their body language and tone of voice. Hesitation or uncertainty can signal unaddressed concerns or a need for more convincing.
  3. Talk Time Balance: Aim for the prospect to do most of the talking, ideally around 60-70%. This approach allows you to gather in-depth information while making the client feel heard and understood.
  4. Reflection on Responses: After the call, review your responses. Were they thorough and aligned with the client’s needs? Think about how your answers could be more targeted and reassuring.
  5. Recap and Follow-Up: Post-call, summarize and confirm your understanding of their issues to ensure alignment. If any confusion arises, promptly follow up with a clarifying call or email.
  6. Empathy and Personal Connection: Sales involve both emotional and practical aspects. Strive to connect personally, showing empathy and understanding of their situation.

By refining these aspects, you position yourself for more successful sales outcomes. For further enhancement of your discovery call skills, consider a consult with our Chief Consultant, Megan Killion. You’ll also receive our exclusive Discovery Call Cheat Sheet for MSPs, equipping you with tools to win more sales.

2.) Assess Your Solutions Fit:

Were your services the hero they needed? Ensure your solution didn’t just sound good but genuinely fit their unique challenges like a glove.

When analyzing whether your services were the right solution for the client, delve deeper into these areas:

  1. Customized Solutions: Did you tailor your services to meet their specific challenges? This involves understanding their unique business context and providing a solution that addresses their individual needs effectively.
  2. Value Proposition Alignment: Evaluate how well your services aligned with the client’s values and long-term goals. It’s not just about meeting immediate needs, but also supporting their broader objectives.
  3. Problem-Solution Fit: This is about ensuring your service directly addresses the client’s specific problem. Did your solution bridge the gap between their current situation and their desired outcome effectively?
  4. Competitive Edge: How did your solution stand out from competitors? Emphasize if your services offered unique advantages or benefits that others didn’t.
  5. Demonstration of Impact: Did you effectively showcase how your solution would positively impact their business? This could involve case studies, testimonials, or clear ROI projections.
  6. Feedback Integration: If the client provided feedback or asked for modifications, how well did you incorporate these into your solution? Flexibility and responsiveness can significantly enhance the perceived value of your service.

In essence, your solution should not only address the client’s current needs but also align with their long-term goals and provide a clear competitive advantage. Every interaction should reinforce the notion that your solution is not just a good choice, but the best choice for them.

3. Analyze Communication:

Examine your emails, calls, and meetings. Was there a point where the conversation lost its groove? Communication is a dance, and both partners need to be in sync.

The sales communication dance requires rhythm, understanding, and, most importantly, harmony between both parties. As an MSP, it’s crucial to examine your emails, calls, and meetings to identify where the conversation might have lost its momentum. But how do you dissect these interactions effectively?

Enter the world of conversational intelligence tools like Gong,, and Fathom. These platforms aren’t just about analyzing words; they’re about uncovering the hidden dance of communication – the pauses, the tone, the unsaid but implied. They provide insights that go beyond the surface, helping you understand not just what was communicated but how it was received.

For instance, Gong’s AI-driven analytics can reveal patterns in your conversations, pinpointing moments where engagement peaks or dips. offers actionable intelligence on customer interactions, providing data-driven strategies for communication. And Fathom isn’t just another video tool; it’s a way to capture and analyze the nuances of video interactions, giving you a deeper understanding of non-verbal cues.

However, before diving into these technologies, it’s crucial to know what to look for manually. Understanding the basics of effective communication – active listening, empathy, clarity in conveying your message – sets the foundation. Once these fundamentals are in place, tools like Gong and can take your communication analysis to the next level, transforming every interaction into an opportunity to learn and improve.

Simon Sinek wisely said, “People don’t buy what you do; they buy why you do it. And what you do simply proves what you believe.” In every email, call, and meeting, your goal is to embody this philosophy – to make your ‘why’ evident in your ‘how.’ With the right tools and a keen understanding of the art of communication, you’re not just selling a service; you’re building a relationship based on trust and mutual understanding.

Common communication blunders MSPs should be on the lookout for include:

  • Overuse of Technical Jargon: Using too much industry-specific language can confuse clients who may not be tech-savvy.
  • Not Listening Actively: Failing to listen to client needs and concerns can lead to misunderstandings and dissatisfaction.
  • Lack of Follow-Up: Not following up after meetings or conversations can give an impression of disinterest or unreliability.
  • Inconsistent Messaging: Sending mixed messages across different communication channels can create confusion about services and values.
  • Ignoring Customer Feedback: Not addressing or acknowledging customer feedback can lead to missed opportunities for improvement.
  • Overpromising and Underdelivering: Making unrealistic promises about services or results can damage trust and credibility.

Avoiding these common mistakes can significantly improve communication and build stronger, more trusting relationships with clients.

4. Scrutinize the Follow-Up:

Let’s face it, nobody likes the “just bumping this up” or the “can we get on a call?” follow-up emails. They’re like that bad Tinder date who doesn’t get the hint. Desperate and dull. It’s time to revolutionize your follow-up approach.

Think about it. When you’re buying, what kind of follow-up grabs your attention? It’s the one that shows the seller has been listening, not just hearing. It’s about being thoughtful and strategic.

Revisit the discovery phase. What did the client mention about their timeline? Align your follow-up with that. Say something like, “You mentioned needing X problem resolved by Y date. To meet this timeline, we should start onboarding by Z. Given our current schedule, we should aim to have things finalized by [specific date].”

Address any previous concerns directly: “In our last conversation, you had some worries about [insert objections or concerns]. Are these still on your mind? Maybe we could get [all decision-makers] on a call to ensure we’re on track for [positive outcome].”

Good follow-up isn’t just about reminding the client you exist; it’s showing them you understand and remember their needs, concerns, and timeline. It’s proving you’re the right choice, not just the persistent choice.

Persistence is key in sales, but there’s a fine line between staying top of mind and being a Joe Goldberg (stalker for those of you not in the know).

If you fumbled discovery and don’t have a timeline, issues, and positive outcomes to point to – atleast leverage humor. Drop a meme. Tell a joke.

Check our website headline: 

5. Check for Decision-Maker Alignment:

Ensure that the decision-makers were in the loop. Sometimes the person nodding along isn’t the one signing the checks. Make sure you didn’t miss engaging the real shot-callers.

Here are some tactical tips for ensuring decision-maker alignment in MSP sales:

  • Identify the Decision-Makers Early: During initial conversations, ask directly about the decision-making process and who’s involved. Understanding the hierarchy and roles can save you time and effort.
  • Engage All Stakeholders: Ensure that your communications and proposals reach all key stakeholders. Tailor your messaging to address the specific concerns and interests of each decision-maker.
  • Leverage LinkedIn: Use LinkedIn to research and connect with potential decision-makers in the target organization. Understanding their background and interests can help tailor your approach.
  • Validate Understanding: During meetings, ask clarifying questions to confirm that you’re addressing the concerns of the primary decision-maker(s).
  • Follow-Up Strategically: In your follow-ups, reference specific points discussed with the decision-makers. This shows attentiveness and helps maintain engagement with the right people.
  • Seek Referrals: If you’re speaking with a non-decision maker, politely ask for a referral to the person in charge of making the decision.
  • Align Solutions with Business Goals: Ensure your solution aligns with the overall business goals of the company, which are typically set by top decision-makers.
  • Use Testimonials Wisely: Share relevant success stories or testimonials that resonate with the decision-makers’ business challenges.

By applying these tactics, MSPs can effectively engage with the right people in the organization, enhancing the chances of a successful sale.

Ok, but how?

Here are some examples of actionable questions that sellers can ask to align with the tactical tips for decision-maker engagement:

  • Identifying Decision-Makers: “Could you walk me through your company’s decision-making process for a service like ours? Who are the key stakeholders involved?”
  • Engaging All Stakeholders: “Apart from yourself, who else should be kept in the loop regarding this proposal?”
  • Validating Understanding: “From our discussion, it sounds like [summarize key points]. Do these align with your key decision-maker’s priorities?”
  • Strategic Follow-Up: “In our last conversation, you mentioned [specific concern]. Has there been any further discussion on this with your team?”
  • Seeking Referrals: “To ensure we’re addressing all the right areas, could you introduce me to the person who will make the final decision on this?”

These questions can help sellers ensure they are engaging with the right people and addressing the correct concerns, enhancing the chances of a successful sale.

Influencers as a Sales Superpower

While reaching the decision-maker is crucial, don’t underestimate the power of influencers like Office Managers, especially in SMBs. They often have in-depth knowledge of the problems at hand. The real challenge is making these influencers feel safe backing you. Remember, their top priority is security in their role, not making waves. And let’s be honest – the average CEO doesn’t know what their day to day tech challenges are. Who does? The ball-juggling, always overwhelmed office admin or manager. They know who’s frustrated with what, and why.

Here’s how to empower your champion and gather valuable insights:

  • Empowering the Champion: Ask, “How can I support you in presenting this solution to your team? What information or assurance would help you feel confident in recommending us?”
  • Leveraging Influencer Knowledge: Tap into the influencer’s insights with questions like, “Based on your experience, what are some concerns the decision-maker might have about this service?” or “Can you share any insights into the decision-maker’s priorities or style?”
  • Tying it All Together: “I know one of your top priorities is making sure all your resources are aligned. Are their any teams in particular struggling right now? How do you see us integrating with the whole org to make your life easier?”

By aligning with the influencer, you not only gain an ally but also access valuable information about the decision-maker, helping you tailor your approach more effectively. Remember, sometimes the best strategy is not directly targeting the top but nurturing the roots that support the entire decision-making tree.

6. Evaluate the Competition:

Did a rival swoop in with a sweeter deal? Understand your competitors’ offers and how your proposal stacked up against them.

To effectively evaluate competition and understand how your proposal compares, consider these tips:

  1. Conduct Market Research: Regularly analyze the market to stay updated on competitors’ offerings, pricing, and unique selling points.
  2. Gather Client Feedback: Ask clients who chose competitors what factors influenced their decision. This can provide direct insights into your competitors’ advantages.
  3. Analyze Competitor Marketing: Review their marketing materials and sales tactics to understand their messaging and positioning.
  4. Monitor Online Reviews and Forums: Check industry forums and online review platforms to see what clients are saying about your competitors.
  5. Seek Industry Insights: Attend industry events and webinars to gather information on emerging trends and how competitors are adapting.
  6. Perform a SWOT Analysis: Regularly conduct a SWOT (Strengths, Weaknesses, Opportunities, Threats) analysis on both your business and your competitors to identify areas for improvement and potential market opportunities.

By staying informed about competitors and understanding how your offerings stack up, you can refine your strategies to better meet client needs and stand out in the market.

7. Inspect the Timing:

Sometimes it’s all about the ‘when’. Reflect on whether external factors like budget cycles or market shifts played a role.

To get the timing right for MSP sales, especially considering longer contract cycles, sellers can:

  • Understand Client Budget Cycles: Ask prospects about their fiscal year and budgeting process. Align your proposals with their budget planning period.
  • Monitor Market Trends: Stay informed about industry and economic trends that may affect clients’ readiness to buy.
  • Leverage CRM Tools: Use CRM systems to track and predict the best times for follow-ups based on past interactions and client behavior patterns.
  • Build Long-term Relationships: Regularly engage with potential clients, so when the time is right for them, your MSP is top of mind.
  • Ask Direct Questions: During discussions, directly inquire about the prospect’s timeline for implementing new services or changing providers.
  • Utilize Lead Scoring: Implement a lead scoring system that factors in timing readiness, helping prioritize leads who are more likely to convert soon.

By focusing on these strategies, sellers can better align their sales efforts with the optimal purchasing times of their prospects.

8. Seek Feedback:

Don’t shy away from asking why they passed up your offer. Direct feedback is a goldmine for improvement.

For MSPs seeking feedback on closed lost and won deals, here are some inventive ideas segmented for each scenario:

Closed Lost Deals:

  • Send a Parting Gift: Offer a small token of appreciation, like a branded item, to thank them for considering your service. Include a QR code linking to a feedback survey. This approach softens the request for feedback and shows goodwill.
  • Exit Interview Call: Schedule a brief, friendly call to discuss their decision. Frame it as a learning opportunity for your team to improve.
  • Email with an Incentive: Send a personalized email thanking them for their time and offer a discount or special offer for their next engagement in exchange for their feedback.

Closed Won Deals:

  • Scheduled Check-In: Three months after closing the deal, schedule a check-in call to discuss their experience. Ask why they chose you and if you’ve met their expectations. This reinforces your commitment to client satisfaction.
  • Feedback as Part of Onboarding: Integrate a feedback request into your onboarding process, asking new clients to share their initial impressions and decision factors.
  • Client Success Story Request: Invite them to share their success story with your service, which can include why they chose you and how the experience has been so far.

These methods not only provide valuable insights but also reinforce positive relationships with both potential and existing clients.

9. Review Your Pricing Strategy:

Was your service a champagne taste on a beer budget? Or the other way around? Align your pricing with the perceived value.

  • Understand Your Market and Competitors: Conduct thorough market research to understand the pricing strategies of your competitors. This includes analyzing their service offerings, pricing structures, and target markets.
  • Align Pricing with Value Delivered: Ensure your pricing strategy reflects the value you provide. This may mean adjusting prices based on the unique benefits and results your MSP services offer, similar to how Stanley repositioned its products by focusing on a different audience.
  • Adapt to Market Changes: Be flexible and ready to adjust your pricing strategy in response to market shifts, new competitor offerings, or changes in customer demand.
  • Leverage Value-Based Pricing: Consider using value-based pricing where the price is set based on the perceived value to the customer rather than solely on cost. This approach can be particularly effective in differentiating your services in a crowded market.
  • Communicate Value Effectively: Ensure that your marketing and sales communications effectively convey the value and benefits of your services, supporting the rationale behind your pricing.
  • Regular Review and Adjustment: Continuously monitor and review your pricing strategy to ensure it remains aligned with market conditions and your business objectives.

For a B2B example, consider how companies like Adobe have successfully implemented subscription-based pricing, aligning their offerings with market trends and customer preferences for scalable, cloud-based solutions.

10. Reflect on Your Brand Perception:

Is your brand’s reputation opening doors or shutting them? Sometimes the deal is lost before you even pitch.

When it comes to making a lasting impression, your brand’s reputation can either be your key to success or a barrier to entry. It’s essential to ask yourself, “Is my brand resonating with my target audience’s values?” Often, deals are lost not because of the pitch itself, but due to a mismatch in brand perception and audience expectations.

Understanding Through Niching Down:

To truly grasp what your audience values, consider niching down. This means focusing on a specific segment of the market where your MSP services can make the most impact. By niching down, you can develop detailed buyer personas, giving you insights into what your target customers value the most.

  • Create Detailed Buyer Personas: Develop personas that reflect the specific needs, challenges, and goals of your niche market. Consider factors like their industry, company size, typical challenges, and decision-making processes.
  • Analyze Their Value System: Understand what drives your target audience. Is it cost-efficiency, cutting-edge technology, exceptional customer service, or something else? Knowing this helps in tailoring your brand messaging.

Aligning Your Offering:

Once you’ve identified what your audience values, align your offerings and brand message to these preferences. This alignment is crucial in building a brand perception that resonates positively with your potential clients.

  • Tailor Your Messaging: Use the language and tone that speaks to your niche. Highlight aspects of your service that directly address their unique needs and values.
  • Showcase Relevant Case Studies: Share success stories and testimonials that are relevant to your target niche. This not only builds credibility but also demonstrates your understanding and commitment to their specific needs.

Remember, a brand that reflects a deep understanding of its audience’s values is more likely to be trusted and considered. By niching down and aligning your offerings to your audience’s values, you’re not just pitching a service; you’re offering a solution that speaks directly to their core needs.

By systematically evaluating each of these areas, you can identify weaknesses. When identifying the weak spots in your sales process, it’s a continuous learning curve. Embrace it with the spunk of a start-up and the wisdom of the tried-and-true. Remember, every lost sale is just a prelude to your next success story. Keep the dialogue open, stay genuine and creative in your approach, and never stop refining your pitch. Keep your brand voice consistent and your customer’s needs at the forefront, and you’ll turn those near-misses into home runs.

Transforming Your Sales 

Once you’ve pinpointed the hiccup in your sales process, it’s time for transformation. Utilize the “Experience Transformer” concept from Strategic Coach to turn this insight into action. Reflect on the sale, and ask yourself:

  1. What worked?
  2. What didn’t work?
  3. What can be improved?

Then, implement a new strategy in your next sales approach based on these reflections. This is about learning from the past to enhance the future. It’s not just about correcting a single mistake; it’s a strategy to evolve your sales process continuously.

Download the troubleshooting checklist here 

For a step-by-step guide on refining your sales technique and how to implement the “Experience Transformer,” schedule a 1:1 consult.