• Set your next meeting before ending the first one – This simple habit eliminates the chase and keeps momentum alive
• Replace “check-in” emails with value-driven content that positions you as a trusted advisor, not just another salesperson
• Use educational materials strategically to guide prospects through their decision-making process while building trust
• Automate your follow-up system to ensure consistent, professional touchpoints that never get forgotten
• Track engagement metrics to know exactly when prospects are ready for your next conversation

The Hidden Problem: Where Most MSPs Drop the Ball

Here’s what I’ve learned after helping hundreds of MSPs optimize their sales process: the appointment isn’t the finish line, it’s the starting gun.

Most MSP owners I talk to have this backwards. They spend weeks perfecting their sales presentation, crafting the perfect proposal template, and rehearsing their pitch. But when it comes to what happens after that first meeting? They wing it.

The result? According to recent industry data, only 23% of MSP prospects who attend a discovery call actually become paying clients. That means 77% of your hard-earned appointments are walking away, often to competitors who have a better follow-up game.

But here’s the good news: this is completely fixable. The MSPs who crack the code on post-appointment conversion don’t just get lucky. They follow a systematic approach that turns casual interest into signed contracts.

Step 1: Set a Meeting from a Meeting (The 5-Minute Game Changer)

Before your first call even ends, schedule the next touchpoint. This might be the simplest, most effective habit that separates top-performing MSPs from everyone else.

Here’s exactly how to do it:

As you’re wrapping up your discovery call, say something like:

> “Based on everything we’ve discussed today, I’m confident we can help solve these IT challenges. I’m going to put together a customized proposal that addresses your specific needs. Let’s schedule a quick 15-minute follow-up call for next Tuesday so I can walk you through the recommendations and answer any questions you might have.”

Why this works so well:

Eliminates the chase – No more playing phone tag or wondering when to follow up 

Maintains momentum – Keeps your solution top of mind during their decision process 

Shows confidence – Demonstrates you’re organized, professional, and expect to move forward 

Creates accountability – Both parties have a clear next step 

I learned this lesson the hard way early in my MSP career. I had a fantastic call with a local manufacturing company. They loved our approach, asked detailed questions about our monitoring services, and seemed ready to move forward. I sent the proposal and said I’d “follow up soon.”

Three weeks later, I finally reached the owner. “Oh, we already signed with another provider,” he said. “They called us the next day with a clear timeline and next steps.”

That stung. But it taught me that urgency and organization win deals.

Step 2: Don’t “Check In”, Add Value Instead

After you send your proposal, resist the urge to send generic “checking in” emails. These messages scream “salesperson” and often get ignored or deleted.

Instead, follow up with content that helps them make a better decision while subtly reinforcing why choosing you makes sense.

Replace this:

> “Hi John, just checking in to see if you had a chance to review our proposal. Let me know if you have any questions!”

With this:

> “Hi John, I wanted to share this helpful guide: ’15 Questions to Ask When Evaluating an IT Provider.’ Many business owners find it useful when comparing proposals to ensure they choose a provider that’s transparent and proactive. I’ve attached it here, and I’m happy to discuss how we address each of these areas when we talk next Tuesday.”

The psychology behind this approach:

Reframes your role from “salesperson” to “trusted advisor” 

Provides genuine value that helps them regardless of their decision 

Builds trust by showing you care about their success, not just your sale 

Keeps you top of mind without being pushy 

Step 3: Use Educational Content to Build Trust and Guide Decisions

After your appointment, prospects enter what I call the “research and doubt phase.” They’re comparing options, second-guessing their needs, and often feeling overwhelmed by technical details.

You can guide this process by strategically sharing educational content that builds confidence in your expertise while addressing their specific concerns.

Here are the most effective types of post-appointment content:

Buyer’s Guides

– “15 Questions to Ask When Changing Your MSP”

– “The Complete Guide to IT Due Diligence for Business Owners”

– “How to Evaluate Cybersecurity Proposals: A Non-Technical Guide”

Case Studies and Success Stories

– Industry-specific examples showing similar challenges you’ve solved

– Before/after scenarios with measurable results

– Client testimonials from businesses they can relate to

Process Overviews

– Your onboarding methodology (shows professionalism)

– How you handle emergencies and after-hours support

– Your approach to cybersecurity assessments and compliance

Comparison Resources

– MSP vs. break-fix model explanations

– In-house IT vs. outsourced IT cost breakdowns

– Feature comparison charts (your services vs. typical competitors)

Pro tip: Timing matters. Don’t dump all this content at once. Space it out over 7-10 days to stay engaged without overwhelming them.

Step 4: Create a Systematic Follow-Up Sequence That Never Fails

Consistency wins deals, but remembering to send personalized follow-ups manually? That’s a recipe for dropped balls and missed opportunities.

Here’s the proven sequence that high-converting MSPs use:

Day 0 (Immediately After the Meeting)

– Send a thank-you email with the proposal attached

– Include the “15 Questions to Ask When Evaluating an IT Provider” guide

– Confirm your scheduled follow-up appointment

Day 3

– Share a relevant case study or success story

– Brief email: “Thought you might find this interesting…” approach

– No hard sell, just valuable information

Day 7

– Send a short video or PDF about your onboarding process

– Focus on how smooth and painless the transition will be

– Address common concerns about switching providers

Day 10-14

– Final value-add touchpoint before your scheduled follow-up call

– Could be a cybersecurity checklist, compliance guide, or industry report

– Gentle reminder about your upcoming conversation

The secret sauce: Each touchpoint provides value while subtly reinforcing your expertise and professionalism. By the time you have your follow-up call, you’re not just another vendor, you’re the obvious choice.

Step 5: Automate the Process (But Keep It Personal)

Here’s the reality: manually tracking and sending all these follow-ups for every prospect is unsustainable. You’ll forget, get busy with other priorities, or send generic messages that don’t convert.

The solution is strategic automation that feels personal.

Modern CRM systems can trigger customized email sequences based on where prospects are in your pipeline. When someone moves to “Post-Appointment” status, the system automatically begins sending your proven follow-up sequence.

What to automate:

– Thank-you emails with proposal delivery

– Educational content delivery (spaced appropriately)

– Appointment reminders for your follow-up calls

– Task reminders for personal outreach

What to keep manual:

– Responses to their questions or concerns

– Proposal customization based on their specific needs

– Phone calls and personal conversations

– Adjustments based on their engagement level

Step 6: Track Engagement to Know When They’re Ready

One of the biggest advantages of a systematic follow-up process is the data it provides. You can see exactly how engaged each prospect is and time your personal outreach perfectly.

Key metrics to monitor:

Email open rates – Are they reading your follow-ups? 

Link clicks – Which content resonates most? 

Proposal views – How many times have they reviewed your proposal? 

Time spent – Are they spending significant time reviewing materials? 

Device tracking – Are they viewing on mobile (quick scan) or desktop (serious review)? 

How to use this data:

– High engagement + no response = Perfect time for a personal phone call

– Low engagement = They may need more education or aren’t ready yet

– Multiple proposal views = They’re seriously considering; time to address any concerns

– Shared with others = Decision involves multiple stakeholders; adjust your approach

Step 7: Handle Common Objections Before They Become Deal-Killers

In my experience, most post-appointment objections fall into predictable categories. By addressing these proactively in your follow-up content, you can eliminate many concerns before they derail your deal.

The Big 5 Post-Appointment Objections:

1. “We need to think about it”

Translation: They’re not convinced of the urgency or value 

Solution: Share case studies showing the cost of waiting, or time-sensitive incentives

2. “Your price is higher than other quotes”

Translation: They’re comparing apples to oranges 

Solution: Send comparison charts showing what’s included vs. excluded in different proposals

3. “We’re worried about the transition process”

Translation: Fear of downtime or disruption 

Solution: Detailed onboarding timeline and testimonials about smooth transitions

4. “We need to discuss this internally”

Translation: Multiple decision-makers are involved 

Solution: Offer to present to the full team or provide materials for internal sharing

5. “We want to wait until next quarter/year”

Translation: Budget concerns or timing issues 

Solution: Flexible payment options or phased implementation plans

Pro tip: Address these concerns in your follow-up content before they bring them up. This positions you as someone who understands their business and anticipates their needs.

Step 8: The Psychology of Persistence (Without Being Pushy)

There’s a fine line between helpful persistence and annoying pushiness. Understanding the psychology behind effective follow-up helps you stay on the right side of that line.

The Rule of 7: Marketing research shows that prospects need to see your message at least 7 times before taking action. Most MSPs give up after 2-3 touchpoints, missing the conversion window entirely.

How to be persistently helpful:

Always lead with value – Every touchpoint should benefit them, not just you 

Vary your communication methods – Email, phone, video, written materials 

Reference previous conversations – Show you remember their specific needs 

Set clear expectations – Tell them when you’ll follow up next 

Give them an easy out – “If this isn’t a priority right now, just let me know” 

Story time: I once had a prospect who didn’t respond to any of my follow-ups for six weeks. I was ready to give up when I decided to send one final email: a simple industry report about new cybersecurity threats affecting his sector. He responded within an hour, apologized for the delay (family emergency), and signed the contract the following week.

The lesson? Sometimes persistence pays off in unexpected ways.

Step 9: Leverage Social Proof Strategically

During the post-appointment phase, prospects are often researching you online, checking references, and looking for validation that you’re the right choice.

Make this easy for them by strategically sharing social proof:

Client Testimonials

– Video testimonials from similar businesses

– Written reviews highlighting specific benefits

– Before/after case studies with measurable results

Industry Recognition

– Certifications and partnerships (Microsoft, ConnectWise, etc.)

– Awards or recognition from industry organizations

– Speaking engagements or published articles

Community Involvement

– Local business partnerships

– Charity work or community sponsorships

– Chamber of Commerce membership

Timing matters: Share social proof naturally within your follow-up sequence, not as obvious sales material. For example: “I thought you might be interested in this case study about how we helped [Similar Company] reduce their IT costs by 30% while improving security.”

Step 10: Know When to Walk Away (And How to Do It Professionally)

Not every prospect will convert, and that’s okay. Knowing when and how to gracefully exit a sales process actually strengthens your brand and sometimes resurrects dead deals.

Signs it’s time to move on:

– No response after multiple value-driven touchpoints

– Budget constraints that can’t be overcome

– Timeline that doesn’t align with their actual needs

– Poor cultural fit or unrealistic expectations

The professional exit strategy:

Send a final email that:

– Acknowledges their decision (or lack thereof)

– Keeps the door open for future opportunities

– Offers to be a resource even if they don’t become a client

– Provides one last piece of valuable content

Example:

> “Hi Sarah, I understand you’ve decided to explore other options for your IT needs, and I respect that decision. If circumstances change or you need any IT guidance down the road, please don’t hesitate to reach out. I’ve attached our 2025 Cybersecurity Planning Guide. Feel free to use it regardless of which provider you choose. Wishing you and your team continued success.”

Why this works: It shows professionalism, keeps you top of mind for future needs, and sometimes prompts a response from prospects who were just busy or overwhelmed.