How to Prepare for an MSP Sales Diagnostic with Ian Richardson

An MSP sales diagnostic starts with evidence, not a guess about why the team is missing its number. Before you hire another rep, buy more leads, or change your pricing, get clear on where the sales process is breaking.

If you are preparing for a sales diagnostic with Ian Richardson of Fox & Crow Group, bring a practical view of your business: what you want to achieve, what your sales team is doing, and what happens between the first conversation and a signed agreement.

You do not need a perfect dashboard or a polished presentation. You need honest numbers, specific examples, and a clear explanation of what you can and cannot currently measure.

Start with Revenue, Pipeline, and Activity

At Fox & Crow, the diagnostic framework is Revenue → Pipeline → Activity.

• Revenue: Are you producing the right kind of sales at the margin the business needs?
• Pipeline: Are there enough qualified opportunities, and are they moving toward a real decision?
• Activity: Is the team consistently creating the conversations and next steps that feed that pipeline?

Start with the outcome, then inspect the process behind it. A revenue shortfall does not automatically mean you need more leads. A busy calendar does not automatically mean you have a healthy pipeline.

What to Prepare Before Your Sales Diagnostic

The following checklist is a preparation guide, not a requirement to buy software or create reports you do not already have. As a useful starting point, gather the most recent 90 days of sales data and a** 12-month revenue view** where available. Use the same reporting period across your sales metrics.

1. Your Growth Goals and Current Constraints

• Your current monthly recurring revenue and the growth target you are working toward.
• The amount of new recurring revenue you want sales to produce.
• Your target customer profile, including company size, industries, geography, and service fit.
• Delivery capacity, hiring constraints, and any limits on the customers you can onboard.
• The decisions you want the diagnostic to help you make.

Be specific. “We need more sales” is less useful than knowing how much growth you need, by when, and what the business can support.

2. A Revenue and Margin Snapshot

• New managed-services revenue won during the reporting period.
• Expansion revenue from existing accounts.
• One-time project revenue, shown separately from recurring revenue.
• Revenue lost through cancellations or account reductions.
• Your pricing structure and available gross-margin information.

Distinguish signed business from revenue that has actually started billing. Note whether each figure is monthly, annual, or total contract value.

3. Your Current Pipeline

Prepare a CRM export, report, or spreadsheet showing:

• Opportunity stage and sales owner.
• Expected recurring revenue or deal value.
• Date opened, time in the current stage, and expected decision date.
• Last meaningful conversation and the agreed next step.
• Lead source and whether the opportunity is a new customer or an existing account.

Flag deals with repeatedly moved close dates, no recent contact, or no customer-confirmed next step. These deserve discussion, not automatic inclusion in the forecast.

4. Your Sales Stages and Qualification Rules

Bring the process your team actually follows, even if it is informal:

• What qualifies a lead for a first meeting?
• What must be learned during discovery?
• What evidence allows a deal to advance?
• When is a proposal appropriate?
• What makes an opportunity qualified, stalled, won, or lost?

Include any discovery templates, qualification checklists, or CRM stage definitions. If each rep uses different criteria, explain that rather than standardizing everything before the session.

5. Activity and Conversion Numbers

Gather the measures you already track:

• Outreach activity by channel and salesperson.
• First meetings booked, held, and missed.
• Qualified opportunities created.
• Proposals delivered and deals won.
• Conversion between stages and average sales-cycle length, if available.

Separate activity volume from results. A hundred messages and five qualified conversations tell a different story than a hundred messages and no meetings.

6. Lead Sources and Their Costs

List the sources feeding your pipeline: referrals, outbound prospecting, website inquiries, events, partners, paid campaigns, or outsourced lead generation.

For each source, bring available spending, meeting counts, qualified opportunities, and wins. Mark unknown figures clearly. The goal is to understand which sources produce suitable customers, not simply which generate the most names.

7. Examples of Won, Lost, and Stalled Deals

Select a few representative opportunities and prepare a short timeline for each:

• Why the prospect started looking.
• What business problem your team uncovered.
• Who participated in the decision.
• What was proposed and how pricing was discussed.
• Why the deal moved forward, stalled, or was lost.

Include proposal samples and anonymized meeting notes. Bring call recordings only when you have permission to share them. Distinguish the buyer's stated reason from your team's interpretation.

8. Sales Roles, Capacity, and Coaching

• Who owns prospecting, discovery, proposals, closing, and account growth.
• Which steps still require the owner's involvement.
• Rep tenure, responsibilities, targets, and available selling time.
• Your onboarding and training approach.
• How often managers inspect deals, coach reps, and review forecasts.

This helps separate a people problem from unclear responsibilities, insufficient preparation, or a process that depends on the owner.

9. Account Growth and Retention Information

Prepare a summary of renewals, customer losses, expansion opportunities, account-review cadence, and referral activity. Explain who owns the commercial relationship after the sale.

The close is not the end of the customer journey. New-customer sales and existing-account growth should be visible separately.

10. Your Questions and Known Data Gaps

Write down the questions you most want answered. Examples include:

• Do we need more qualified opportunities or better execution on existing deals?
• Are we hiring before the process is ready?
• Why do proposals stall?
• What should we inspect each week?

Also list information you cannot currently produce. Missing data is part of the diagnosis; do not replace it with estimates presented as facts.

Who Should Join—and What Not to Share

Consider including the MSP owner and the person responsible for sales execution. Confirm attendees and any requested materials when arranging the session.

Use summaries or redacted examples wherever possible. Do not send CRM passwords, API keys, customer credentials, confidential technical configurations, or unnecessary personal information. Agree on a suitable way to share any sensitive business records.

If Your Sales Data Is Incomplete

Bring what you have: a spreadsheet, a few proposals, recent meeting notes, and your team's account of active deals. Identify the source and reporting period for each number.

Do not spend the preparation time making the pipeline look healthier. An accurate incomplete picture is more useful than a polished report that hides stalled deals.

Turn the Diagnostic into a Practical Next Step

Use the conversation to identify the most important bottleneck, the evidence behind it, and what to inspect next. Ask which actions should come first, who should own them, and how progress should be measured.

For more context, explore how The MSP Sales Process works or the Brightworks IT case study.

Ready to prepare your sales diagnostic? Contact Fox & Crow Group to ask about a session with Ian Richardson and confirm the next steps.