Skill Drill: Follow-Up Cadence for IT Managed Services

Direct Answer

This drill builds the skill of running a disciplined, multi-touch follow-up cadence on managed-services (MSP) opportunities — the quotes for managed security, cloud migration, help-desk contracts, and co-managed IT that go quiet after the assessment. A sales manager or sales lead runs it with 3 to 8 account executives or business-development reps in 45 to 60 minutes.

Reps practice building a 6-touch, multi-channel cadence with varied value on each touch, and they leave with a written cadence they can load into the CRM and start sending tomorrow.

Why This Drill Matters in IT Managed Services

MSP deals die in the silence after the proposal. The prospect — usually an office manager, a controller, or an overwhelmed internal IT person at a 20-to-200-seat company — gets the quote for managed security or a cloud migration, says "let me run it by the partners," and disappears.

Reps send one limp "just checking in" email, get nothing, and write the deal off. The skill this drill builds is the cadence: a planned sequence of touches that each carry new value, across email, phone, and LinkedIn, that keeps the deal alive without becoming a nuisance.

This matters acutely in managed services because the buyer is rarely the only decision-maker, the contract is a multi-year commitment ($1,500 to $25,000+ per month), and the trigger to act is often a security scare or an outage that hasn't happened yet. The rep's job is to stay present and useful until that trigger fires — or to manufacture urgency with real risk data.

A single follow-up email cannot do this. A cadence can.

The drill draws on three named systems: the cadence discipline of Predictable Revenue (Aaron Ross), the multi-touch sequencing taught by SalesLoft and Outreach cadence playbooks, and the "give value on every touch" principle from Jeb Blount's Fanatical Prospecting.

Reps build a real cadence against a real stalled deal, not a hypothetical.

What You'll Need (5 min prep)

• Group size: 3 to 8 reps. Each rep brings ONE real stalled MSP opportunity — a quote sent, no response in 7+ days.
• Materials: A printed "cadence grid" (8 rows: touch number, day, channel, angle, message). A timer. A whiteboard for the shared cadence template.
• Room setup: Tables so reps can write; one open wall for the whiteboard. Reps sit where they can see the cadence map you'll draw.
• Handout: A one-page "value angle menu" — the 8 reasons an MSP rep can legitimately reach out (a new threat report, a compliance deadline, a case study, an outage in their industry, a free dark-web scan, a referral, a contract-renewal date for their incumbent, a pricing change). Reps will pull from this all session.

Round 1 — Set the Scene (8 min)

Each rep writes their real stalled deal at the top of their cadence grid: company size, what was quoted, who the contact is, and the last thing that contact said. Read this aloud:

"Pull up your worst ghost. The quote you sent two weeks ago that went dark. By the end of this hour you're going to have a 6-touch cadence loaded and ready to fire on that exact deal. Not a template — a sequence built for that buyer."

Then the leader explains the one rule that governs the whole drill, read verbatim:

"Every touch has to give before it asks. No 'just checking in.' Each message either teaches them something, warns them about something, or hands them something useful. If a touch is only about you, it's not a touch — it's noise."

What good looks like: the rep can name their buyer's role and the last objection, and understands that "checking in" is banned for the rest of the session.

Round 2 — Build the Cadence (15 min)

Each rep builds a 6-touch cadence on the grid, spaced across 18 days, alternating channels. The leader walks the room and challenges any touch that doesn't carry value. The leader writes a model cadence on the whiteboard first:

• Touch 1 (Day 1, email): Recap proposal + attach a relevant threat report for their industry.
• Touch 2 (Day 3, phone/voicemail): Reference the report, offer a free dark-web scan.
• Touch 3 (Day 6, LinkedIn): Share a case study of a same-size client, no ask.
• Touch 4 (Day 9, email): A compliance or cyber-insurance deadline angle.
• Touch 5 (Day 13, phone): Name a real outage or breach in their vertical that week.
• Touch 6 (Day 18, email): The "permission to close the file" message.

Verbatim model the leader reads aloud — Touch 5, the urgency call:

"Hi Dana, it's [name] from [MSP]. I'm not calling to chase the proposal. I'm calling because a manufacturer about your size in the area got hit with ransomware Tuesday and was down four days — the entry point was an unpatched remote-access tool, the exact gap we flagged in your assessment.

I'd rather you not be the next case study. Two minutes this week to walk through closing that one hole, even if you never sign with us?"

What good looks like: no two touches use the same angle, channels alternate, and every touch passes the "give before you ask" test.

Round 3 — Pressure Test the Breakup (12 min)

Reps pair up and role-play the hardest touches: the urgency call (Touch 5) and the breakup email (Touch 6). One rep plays the busy, slightly annoyed buyer who says "we're still deciding" or "we decided to stay with our current guy for now." The leader freezes any rep who sounds desperate, guilt-trips the buyer, or leaves the door fully shut on a "no."

Verbatim model — Touch 6, the breakup that reopens, read aloud:

"Hi Dana — I don't want to keep landing in your inbox if the timing's wrong, so this is my last note for now. I'll close the file on the proposal. If anything changes — a board mandate, a near-miss, a renewal coming up with your current provider — you have my number and the assessment is still good for 90 days.

One thing before I go: the dark-web scan I offered is free either way, want me to run it so you at least know where you stand?"

The breakup email reliably resurrects 10 to 20% of dead MSP deals because it removes the pressure and hands one last piece of value. What good looks like: the breakup is warm, leaves a re-entry trigger, and ends with a no-strings offer.

Round 4 — Debrief & Load It In (10 min)

Go around the room. Each rep reads their Touch 1 and Touch 6 aloud and names the single weakest touch in their cadence. The group suggests a stronger value angle from the handout menu. Then every rep commits to a load date — the day they'll enter the cadence into the CRM — and a partner who'll check they did it.

What good looks like: every rep leaves with a 6-touch cadence on paper, a fix for their weakest touch, and a date plus an accountability partner.

Scaling It: 5-Minute, 30-Minute, and 60-Minute Versions

• 5-minute version (daily huddle): Each rep takes one real "just checking in" email from their sent folder and rewrites it on the spot into a value touch using one angle from the menu. Read two aloud. Keeps the give-before-you-ask reflex warm.
• 30-minute version: Run Round 1 (5 min), Round 2 (15 min), and Round 4 (10 min). Skip the breakup role-play. Best when you need cadences built fast before a quarter-end push.
• 60-minute version: Run all four rounds, then add a multi-threading pass: each rep identifies a second contact in the same account (often the owner or the controller) and builds two touches to reach them in parallel, since MSP deals stall when only one champion is worked.

Common Mistakes & Coaching Cues

• 'Just checking in' touches. The single most common MSP follow-up, and it's invisible to a busy buyer. Cue: "If it doesn't teach, warn, or give — it's not a touch."
• One channel only. Reps email six times and call it a cadence. Cue: "Email, phone, LinkedIn — a buyer who ignores one will see another."
• Same angle every time. Every touch repeats the proposal. Cue: "Six touches, six reasons. Pull from the menu."
• Giving up after touch two. Most MSP closes happen on touch four through six, after the rep would normally quit. Cue: "The deal is in the touches you're not sending."
• A cold, guilt-trip breakup. "I guess you're not interested" burns the door down. Cue: "The breakup is warm and leaves a trigger to come back."
• No urgency anchor. Reps never tie the follow-up to real risk. Cue: "Name a real breach, a real deadline, a real renewal date."

FAQ

Isn't six touches too aggressive? Won't we annoy the buyer? Not when every touch carries value and channels vary. The annoyance comes from repetition without value — six "just checking in" emails. Six touches that each teach, warn, or give are perceived as helpful persistence, which is exactly what an overwhelmed IT buyer wants from a provider.

Our buyers genuinely go silent for months until something breaks. What's the point of a cadence? That's precisely why the cadence works. Your job is to be the name they remember when the breach or outage finally hits.

The breakup email leaves a 90-day re-entry trigger so you stay top of mind, and the urgency touches sometimes manufacture the trigger before it happens on its own.

Should this run in the CRM as automated sequences or manual touches? A blend. Email touches can be templated and queued in your CRM or a cadence tool, but the phone and LinkedIn touches should be personalized per account. The drill builds the thinking; the tool just stores it.

Never fully automate the urgency call — it has to reference real, current risk.

What if the prospect already has an MSP? That's the renewal-date angle. Build touches around their incumbent's contract renewal, a service failure they've mentioned, or a capability gap (no SOC, no 24/7 monitoring). The cadence keeps you present until their current provider stumbles, which they eventually do.

How often should we run this drill? Full version once a month; the 5-minute rewrite huddle weekly. Cadence discipline is the first thing reps drop under quota pressure, so keep the reflex warm. Pair it with a CRM review of which deals have stalled with fewer than four touches.

My reps say they don't have enough value angles to fill six touches. How do I fix that? That's a content gap, not a skill gap. Build the value-angle menu as a team — threat reports, compliance deadlines, case studies, dark-web scans, vertical breach news.

Once the menu has 8 to 10 real angles, no rep can claim they've run out of reasons to reach out.

Bottom Line

After this drill your team can build a 6-touch, multi-channel cadence on a stalled MSP deal where every touch gives before it asks, run an urgency call anchored in real risk, and send a warm breakup that reopens 10 to 20% of dead opportunities. Re-run the full version monthly and the 5-minute rewrite huddle weekly, and pair it with a CRM sweep for any deal sitting under four touches.

Sources

• Predictable Revenue — Aaron Ross
• Fanatical Prospecting — Jeb Blount
• SalesLoft — Cadence Best Practices
• Outreach — Sequence Playbooks
• The Challenger Sale — Gartner / CEB
• HubSpot — Sales Follow-Up Statistics
• CompTIA — Managed Services Resources
• Harvard Business Review — The Right Way to Follow Up

*IT managed services follow-up cadence skill drill — a runnable team training exercise for MSP sales teams, with verbatim scripts, timing, role-plays, and coaching cues.*