Playbook: Alex for Sales Professionals

Your personal reference for using Alex to close more deals. Ready-to-run prompts for prospecting, discovery calls, proposals, and objection handling.

What This Guide Is Not

This is not a habit formation guide (see Self-Study Guide for that). This is a sales toolkit — the specific ways Alex can help you sell smarter, and the prompts that get results.

Where to Practice These Prompts

Every prompt in this guide works with any AI assistant — ChatGPT, Claude, GitHub Copilot, Gemini, or whatever tool you prefer. The prompts are the skill; the tool is just where you type them. Pick the one you’re comfortable with and start today.

For an integrated experience, the Alex VS Code extension (free) was purpose-built for this workshop. It understands sales context, lets you save effective prompts with /saveinsight, and brings your playbook and practice exercises into one workspace. VS Code is a free editor that takes minutes to set up, even if you’ve never used it before.

You don’t need a specific tool to benefit. You need the habit of reaching for AI when the work is genuinely hard — not just when it’s repetitive.

Core Principle for Sales Professionals

The best salespeople don’t push products — they understand problems deeply and connect solutions precisely. Alex’s highest value is helping you prepare better, personalize faster, and respond smarter.

The key pattern: context is everything. The more you tell Alex about your prospect, their industry, their challenges, and your product — the more useful the output. Generic prompts produce generic results.

The Seven Use Cases

1. Prospect Research and Preparation

When to use: Before a first call, demo, or meeting. Preparation is where deals are won.

Prompt pattern:

I'm preparing for a sales call with [prospect name], [title] at [company].

What I know:
- Industry: [their industry]
- Company size: [employees, revenue if known]
- Their product/service: [what they do]
- Recent news: [any press, funding, launches you've seen]

Help me:
1. Identify 3 likely challenges they face based on their industry and role
2. Find potential connections between their challenges and my product: [describe your product]
3. Suggest 5 discovery questions that show I've done my homework
4. Flag any industry terminology I should know

Follow-up prompts:

What objections might someone in their position typically raise?

What's happening in [their industry] right now that I could reference?

How would I describe my product's value in their language, not mine?

Try this now: You are preparing for a discovery call with the CTO of a logistics company. They currently use a competitor’s platform, they posted on LinkedIn about frustrations with its reporting, and their company just raised a Series C. Paste the company details and your product’s differentiators into the prospect research prompt. The output will give you talking points specific to their pain, not your pitch deck.

2. Discovery Call Questions

When to use: Designing your discovery approach for a specific prospect or segment.

Prompt pattern:

I sell [your product/service] to [target persona/industry].

The problems we solve:
[list 3-5 core problems]

Help me build a discovery framework:
1. Opening questions that uncover current state
2. Pain-amplifying questions that reveal the cost of the problem
3. Future state questions that help them envision success
4. Qualifying questions that help me understand timeline and authority

Make them conversational, not interrogation-style.

Follow-up prompts:

These feel too generic. Make them more specific to [industry/role].

Add follow-up questions for when they give a vague answer.

How do I transition from discovery to presenting my solution?

3. Personalized Outreach

When to use: Writing cold emails, LinkedIn messages, or follow-ups that don’t sound templated.

Prompt pattern:

Write a cold outreach message to [name], [title] at [company].

What I know about them:
[paste LinkedIn info, company news, or anything relevant]

What I sell: [your product/solution]

The hook: [why they specifically might care — be honest if you're guessing]

Write a [email / LinkedIn message] that:
- Opens with something specific to them (not "I hope this finds you well")
- Creates curiosity about one specific outcome
- Asks for one small action (not "let me know when you're free")
- Stays under [100 / 150 / 200] words

Follow-up prompts:

The opening is still too generic. Make it more specific to their role/company.

Write a 3-touch sequence: initial outreach, follow-up if no response, final attempt.

Write a warm follow-up for after they [opened my email / viewed my LinkedIn / attended our webinar].

4. Objection Handling

When to use: Preparing for common objections or thinking through a specific pushback you’ve received.

Prompt pattern:

I sell [product/service] to [target buyers].

Help me prepare for this objection:
"[exact objection — be specific]"

Context: This typically comes from [type of buyer] at [stage of deal].

Give me:
1. What's really behind this objection (the unspoken concern)
2. A clarifying question to understand their specific situation
3. A response framework: acknowledge → reframe → address → confirm
4. A real example or proof point I could use

Follow-up prompts:

They said "[their specific response]" — how do I continue the conversation?

What are the 5 most common objections for [my product/industry] and how should I handle each?

This objection keeps killing deals. What am I missing?

5. Proposal and Follow-Up Writing

When to use: After a demo or call, creating a proposal or follow-up that advances the deal.

Prompt pattern:

Write a follow-up [email / proposal summary] after my call with [prospect].

What we discussed:
- Their challenges: [list what they said]
- Their goals: [what success looks like for them]
- Their concerns: [any hesitations they expressed]

What I proposed:
- Solution: [what you're offering]
- Key benefits for them: [specific outcomes]
- Next steps discussed: [what you agreed to]

Write a follow-up that:
- Recaps in their language, not mine
- Reinforces the connection between their problem and my solution
- Addresses any concerns they raised
- Makes the next step crystal clear

Follow-up prompts:

Add a section that handles their concern about [specific objection].

They've gone quiet. Write a check-in that adds value, not just "checking in."

Write executive summary language for when this gets forwarded to their boss.

6. Competitive Positioning

When to use: When you’re up against a specific competitor or need to differentiate.

Prompt pattern:

I sell [your product] and I'm competing against [competitor].

My product's strengths:
[list key differentiators]

Competitor's perceived strengths:
[what buyers typically say about them]

The prospect cares most about:
[their priorities based on discovery]

Help me:
1. Position my strengths against their priorities (not against competitor directly)
2. Create questions that expose competitor weaknesses without badmouthing
3. Develop talk tracks for when they say "We're also looking at [competitor]"
4. Identify proof points or case studies that would resonate

Follow-up prompts:

They said [competitor] is cheaper. How do I reframe the value conversation?

The prospect already uses [competitor]. Help me build a switching narrative.

What do deals we lose to [competitor] have in common?

7. Pipeline Review and Deal Strategy

When to use: Weekly pipeline review, diagnosing stuck deals, prioritizing where to spend your time, or preparing for a forecast call.

Prompt pattern:

Here's my current pipeline:

Deal 1: [company] — [stage] — [deal size] — [days in stage] — [last activity]
Deal 2: [company] — [stage] — [deal size] — [days in stage] — [last activity]
[etc.]

Help me:
1. Identify which deals are at risk based on time in stage and activity gaps
2. Prioritize where my time should go this week (highest impact actions)
3. For each at-risk deal, suggest a specific re-engagement strategy
4. Flag any deals that should be disqualified so I stop wasting time on them

Follow-up prompts:

[Deal] has been in proposal stage for 3 weeks with no response. What are my options beyond "just checking in"?

I need to forecast this pipeline for my manager. Help me categorize these deals as commit, best-case, or upside — and tell me what evidence supports each.

What patterns do you see in my pipeline? Am I heavy on early-stage and light on closing, or vice versa?

Your AI toolkit: These prompts work in ChatGPT, Claude, Copilot, Gemini — and in the Alex VS Code extension, which was designed around them. Start with whatever you have. The skill transfers across all of them.

What Great Looks Like

After consistent use, you should notice: shorter prep time with better prepared calls, higher response rates on outreach, more confident objection handling, and deals progressing faster through pipeline. The goal isn’t for Alex to sell for you — it’s for Alex to help you sell smarter.

Practice Plan

Month 2–3

Shift from guided exercises to independent workflows — build templates, integrate AI into your real projects, and create reusable prompt libraries for repeating tasks.

Track Your Growth

/saveinsight Prospect research: [description]

/saveinsight Objection handling: [description]

Continue your practice: Self-Study Guide has weekly challenges to keep building your skills after the workshop ends.