Run a focused discovery conversation for managed IT services
The Prospecting Show with Dr. Connor Robertson · Editorial sales resource · October 12, 2026
Understand the current workflow before presenting a solution. This guide applies the workflow to selling managed IT services, where a useful conversation may involve the operations director and IT lead and a practical review of recurring support tickets interrupting staff.
The finished result is a discovery summary. Work from information the buyer confirms. The examples below are planning models; replace bracketed fields and unsupported assumptions before using them with an actual account.
Start with the buyer’s operating context
For this selling context, a possible reason to investigate involves support backlog or a planned support-provider review. That event alone does not establish demand. Check whether the team experiences this issue: recurring support tickets interrupting staff. Confirm who owns the workflow and whether a change is worth evaluating.
| Question | Working hypothesis | Evidence to request |
|---|---|---|
| Who should participate? | operations director and IT lead | The contact’s description of ownership and decision roles |
| What is happening? | recurring support tickets interrupting staff | A recent example from the actual workflow |
| What can be measured? | ticket volume, resolution time, and recurring incident categories | A dated baseline with definitions and a named owner |
| What constrains a change? | service scope, escalation ownership, and transition coverage | Requirements confirmed by the people responsible |
A practical sequence
- Ask how the work happens today.
- Explore one recurring exception and its consequences.
- Identify who owns the problem and what has already been tried.
- Summarize the findings and ask the buyer to correct them.
Apply these steps to the same account rather than changing the hypothesis halfway through the exercise. If new evidence contradicts your starting assumption, update the record and reconsider the next action. The objective is a useful decision, not a completed form.
Worked example: run a focused discovery conversation
Illustrative example, not a report of a client result.
Ask: “Walk me through the last time recurring support tickets interrupting staff affected the team.” Then explore: “How do you currently track ticket volume, resolution time, and recurring incident categories?” Finish with: “What would we need to learn before a scoped support assessment would be worth your time?”
Use a concrete artifact
A useful supporting resource in this context is a sample incident register with customer identifiers removed. It should help the operations director and IT lead assess the current situation without forcing them through a generic sales presentation. Keep the scope narrow enough that the buyer can correct it.
For example, connect the artifact to ticket volume, resolution time, and recurring incident categories. Identify which inputs came from the buyer, which are public observations, and which remain assumptions. Do not request private operational records before the buyer has agreed an appropriate purpose and handling process.
Build the working record
Complete this worksheet during preparation, then revise it after the conversation. An unknown is a useful finding when it is recorded honestly.
| Field | What to write |
|---|---|
| Account and owner | [Account] · [Rep] · [Review date] |
| Confirmed problem | The buyer’s description of recurring support tickets interrupting staff, or “not confirmed” |
| Baseline | Available evidence for ticket volume, resolution time, and recurring incident categories, with source and date |
| Deliverable | a discovery summary, including scope and the person who reviews it |
| Open questions | Unconfirmed assumptions, required participants, and unresolved constraints |
| Next decision | Advance, gather evidence, revisit by request, or close the record |
Evaluate the result
Track confirmed problems with agreed follow-up evidence. Define the numerator, denominator, and review window before comparing results. Use comparable accounts and channels; otherwise an apparent improvement may simply reflect a different list or buying context.
For managed IT services, pair the workflow measure with the quality of evidence about recurring support tickets interrupting staff. A reply or meeting is useful only if it helps establish relevance. Record declined and unsuitable opportunities so the team can improve targeting as well as messaging.
A common failure to avoid
Do not ask leading questions designed to manufacture pain. Avoid turning the first answer into a full product pitch.
In this context, the practical consequence is spending time on a scoped support assessment before the buyer has confirmed a reason to do it. Revisit service scope, escalation ownership, and transition coverage early enough to discover a genuine mismatch.
When to move forward
Proceed when both sides agree on the problem and the evidence needed for the next decision. A sensible next step may be a scoped support assessment, but only when it follows from the evidence. If the buyer cannot identify a relevant problem or owner, close or reclassify the record instead of manufacturing urgency.
Continue the workflow
- Set a sales meeting agenda
- Qualify an opportunity
- Run a focused discovery conversation across selling contexts
- Managed IT services sales guides
For the wider collection, visit the prospecting and sales library. Learn about the host on the Dr. Connor Robertson profile or explore the published podcast interviews.