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Create a mutual action plan for customer onboarding software

The Prospecting Show with Dr. Connor Robertson · Editorial sales resource · October 12, 2026

Coordinate the work required to evaluate and implement a purchase. This guide applies the workflow to selling customer onboarding software, where a useful conversation may involve the customer success leader and operations partner and a practical review of new customers waiting on unclear setup tasks.

The finished result is a shared action plan. 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 a new onboarding program. That event alone does not establish demand. Check whether the team experiences this issue: new customers waiting on unclear setup tasks. Confirm who owns the workflow and whether a change is worth evaluating.

Account facts to confirm before advancing
QuestionWorking hypothesisEvidence to request
Who should participate?customer success leader and operations partnerThe contact’s description of ownership and decision roles
What is happening?new customers waiting on unclear setup tasksA recent example from the actual workflow
What can be measured?time to first useful outcome, task ownership, and blocked stepsA dated baseline with definitions and a named owner
What constrains a change?implementation dependencies, handoff rules, and customer participationRequirements confirmed by the people responsible

A practical sequence

  1. List the buyer’s evaluation steps.
  2. Assign an owner on each side.
  3. Record dependencies and realistic dates.
  4. Agree how changes or missed milestones will be handled.

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: create a mutual action plan

Illustrative example, not a report of a client result.

Buyer confirms the owner of time to first useful outcome, task ownership, and blocked steps; seller prepares a customer milestone checklist; both review implementation dependencies, handoff rules, and customer participation; buyer decides whether to proceed to a demo centered on one onboarding milestone. Put a real owner and mutually agreed date beside each step. Leave unknown dependencies visible.

Use a concrete artifact

A useful supporting resource in this context is a customer milestone checklist. It should help the customer success leader and operations partner 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 time to first useful outcome, task ownership, and blocked steps. 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.

FieldWhat to write
Account and owner[Account] · [Rep] · [Review date]
Confirmed problemThe buyer’s description of new customers waiting on unclear setup tasks, or “not confirmed”
BaselineAvailable evidence for time to first useful outcome, task ownership, and blocked steps, with source and date
Deliverablea shared action plan, including scope and the person who reviews it
Open questionsUnconfirmed assumptions, required participants, and unresolved constraints
Next decisionAdvance, gather evidence, revisit by request, or close the record

Evaluate the result

Track buyer-confirmed milestones completed. 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 customer onboarding software, pair the workflow measure with the quality of evidence about new customers waiting on unclear setup tasks. 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

A seller-only timeline is not mutual. Do not force a procurement or implementation step into an arbitrary quarter-end date.

In this context, the practical consequence is spending time on a demo centered on one onboarding milestone before the buyer has confirmed a reason to do it. Revisit implementation dependencies, handoff rules, and customer participation early enough to discover a genuine mismatch.

When to move forward

Proceed when the buyer accepts the plan and the dependencies are workable. A sensible next step may be a demo centered on one onboarding milestone, 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

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.