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It Services Managed It Guide
Handling Objections & Following Up
Master the core concepts of handling objections & following up tailored specifically for the It Services Managed It industry.
💡 Core Concepts & Executive Briefing
Introduction
In IT Services and Managed IT, closing a deal is not a one-call event. Your first proposal rarely gets a straight “yes” on the spot. Prospects usually slow down because they’re not just deciding on price—they’re deciding on risk. They want to know: Will this team break something? Will the rollout take over their business? Will we lose visibility or control? At Level 2, your job is to catch those hidden concerns early, then follow up in a way that keeps the decision moving.
Understanding Objections
In managed IT sales, objections are often a wrapper for something more specific. “I need to think about it” usually means the prospect is worried about one of these:
- Disruption: “Will you shut us down, or mess up our systems during migration?”
- ROI and cost control: “How do I know this will reduce incidents and downtime, not add overhead?”
- Credibility: “Have you done this before with companies like ours?”
- Timeline: “When will we be live, and what will it require from our staff?”
Listen for clues in the wording. If they mention “integration,” “timelines,” “onboarding,” or “who owns what,” they’re likely worried about implementation. If they push back on “budget,” they might still be open if you can show a clear path to outcomes and predictable costs.
Building Trust
In IT Services, trust comes from proof and clarity. Prospects don’t want vague promises—they want evidence that you can run a stable rollout and handle real-world IT chaos.
Use three trust builders:
1) Proof from similar work: Share a short rollout story (what you changed, how long it took, and what improved). For example, “We replaced patching and monitoring for 120 endpoints, reduced critical incident repeats by X%, and completed onboarding without extending downtime windows.”
2) Risk-reduction: Offer a bounded commitment that reduces fear. Examples include a pilot with defined success criteria, a fixed onboarding plan with milestones, or an implementation “stoplight” timeline where they always know status.
3) Professional control: Show you have process—documented onboarding, RACI ownership (who does what), change windows, escalation paths, and clear reporting.
The Power of Follow-Up
Follow-up in Managed IT is not “checking in.” It’s helping the buyer feel safe every step of the way.
A strong follow-up rhythm for managed IT looks like this:
- After the discovery: Send a recap email within 24 hours. Include what you heard, the risks you identified, and the next step.
- After the proposal: Follow with a short “implementation reality check.” Explain onboarding phases, what they must prepare (access, contacts, system lists), and what you handle.
- During evaluation: Provide decision support assets—security and backup overview, sample ticket response SLA, monitoring coverage map, and a draft transition plan.
- When they stall: Use a “new information” touch. For example, share a brief note about a common failure point you see (missing MFA coverage, unmanaged endpoint drift, unclear escalation rules) and how your onboarding prevents it.
Follow-up should be consistent for 60–180 days, because many IT buyers compare vendors, request internal approvals, and wait until their schedule frees up. Your system should keep the conversation alive with value.
Conclusion
Objections and delays in Managed IT usually reflect fear about outcomes, implementation risk, and credibility—not just price. If you probe for the real concern, build trust with proof and controlled onboarding, and run a follow-up plan that reduces uncertainty, you turn stalled deals into signed agreements.
⚠️ The Industry Trap
The trap is taking “I need to think about it” as polite hesitation and moving on. In Managed IT, that phrase often hides a specific fear: the prospect is worried you’ll cause outages during migration, that you can’t integrate with their current stack, or that they’ll lose control of security and escalation. I’ve watched deals die because the seller waited for a “decision day” instead of uncovering what they were really protecting. The buyer went quiet, then signed with a competitor who asked better questions, mapped the rollout phases, and offered a scoped pilot with clear success criteria. Meanwhile, your proposal sat in their inbox like an unanswered ticket.
📊 The Core KPI
Stalled Deal Win Rate (60+ Days): Calculate: (Number of deals closed-won that were in your pipeline for 60+ days at the time of closing) ÷ (Number of deals that entered your pipeline in a stalled state with first response sent, and that reached 60+ days age) × 100. Benchmark goal: 25%+ win rate within 90 days of implementing this follow-up process for stalled deals.
🛑 The Bottleneck
The bottleneck is a follow-up system that relies on memory and generic email templates. In Managed IT, deals stall because buyers need reassurance about implementation risk, reporting, and ownership. If follow-up is vague (“Just checking in!”), your lead won’t feel safer—they’ll feel pressured or unclear. A common failure looks like this: a prospect asks to “think about it” after a proposal, and the owner sends another check-in two weeks later with no new implementation detail. The buyer delays internal approval, another vendor reaches out with a pilot plan, and you lose the slot. Without a structured 60–180 day follow-up track tied to the real objection, stalled opportunities go cold even if the proposal is strong.
✅ Action Items
1) Build an IT-specific objection map (1 page): Create a list of the top 8 Managed IT objections you hear (disruption, unclear onboarding timeline, unclear ownership/escalation, pricing predictability, security concerns, bad past vendor experiences, “need internal buy-in,” timeline constraints). For each, write: the probing question, the proof asset you’ll send (SLA sample, onboarding phases, escalation workflow), and the next follow-up step.
2) Run a 90-day “implementation safety” follow-up sequence: Week 1 recap (risk summary + next steps), Week 3 rollout milestones, Week 6 pilot/transition plan overview, Week 10 security/backup coverage explanation, Week 14 decision support (RACI + change windows), then monthly value touches until the buyer goes quiet. Always include one concrete item they can forward internally.
3) Add a “pilot with success criteria” option to your closes: For prospects who hesitate, propose a scoped onboarding/pilot with written entry/exit criteria (endpoint coverage target, ticket response expectations during pilot, reporting delivered, and a clear go/no-go date). This converts vague fear into measurable outcomes.
4) Train the team to ask the real question behind the delay: Practice scripts like “When you say you need to think, what are you most concerned about—timeline, risk of disruption, or cost predictability?” Then send the matching proof asset within 24 hours.
2) Run a 90-day “implementation safety” follow-up sequence: Week 1 recap (risk summary + next steps), Week 3 rollout milestones, Week 6 pilot/transition plan overview, Week 10 security/backup coverage explanation, Week 14 decision support (RACI + change windows), then monthly value touches until the buyer goes quiet. Always include one concrete item they can forward internally.
3) Add a “pilot with success criteria” option to your closes: For prospects who hesitate, propose a scoped onboarding/pilot with written entry/exit criteria (endpoint coverage target, ticket response expectations during pilot, reporting delivered, and a clear go/no-go date). This converts vague fear into measurable outcomes.
4) Train the team to ask the real question behind the delay: Practice scripts like “When you say you need to think, what are you most concerned about—timeline, risk of disruption, or cost predictability?” Then send the matching proof asset within 24 hours.
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