More time selling. Fewer misses.

Module 00 / 13

Start here

Objective: learn the three moves behind every good result, and how to use this guide.

Treat an AI assistant like a sharp new teammate on day one. It is fast and well read, and it has never met your customers. It fills gaps with confident guesses unless you give it the facts.

How to use this guide

1. Read the Foundations, modules 00 to 03. They apply to every tool.
2. Walk through the account plan example in module 04.
3. Open the chapter for the tool your company approved. The tool picker at the top remembers your choice.
4. Practice with the fictional account below before using real customer data.
5. Keep the Play library and Guardrails open as reference, or print the prompt card.

Practice account

From: Dana Ruiz, IT Director, Northbeam Logistics
Thanks for the call. Three things before we go further. Our CFO wants a comparison with simply renewing our current vendor. We have 14 sites, and two run on outdated equipment. My team is small, so anything that adds work is a hard sell. Can you send something by Friday?

From: You
Thanks, Dana. I will send a comparison Friday and bring in our solutions engineer on the site question.

From: Dana Ruiz
One more item. Our board is asking about ransomware risk. Can the proposal cover that?

Attendees: Dana Ruiz (IT Director), Marcus Lee (CFO, joined late), me, our solutions engineer
Current state: contract with current vendor renews next quarter. Security team of three. Too many alerts.
Pain: remote sites hard to manage. Board worried about ransomware.
Budget: not confirmed. CFO wants a cost comparison.
Decision: CFO signs. Board briefing in March.
INTERNAL, do not share: Dana sounded frustrated with the current vendor's support.
Next steps: comparison to Dana by Friday. Site design call next week.

Account	Stage	Amount	Close date	Last activity
Northbeam Logistics	Discovery	180000	2026-12-15	2026-09-10
Oakmere Schools	Proposal	95000	2026-09-30	2026-07-22
Kestrel Bio	Negotiation	240000	2026-08-29	2026-08-14
Cardinal Mills	Qualification	60000	2027-02-01	2026-09-02
Harrow Bank	Proposal	310000	2026-10-31	2026-06-30
Tidewater Ports	Negotiation	420000	2026-09-25	2026-09-08
Juniper Retail	Qualification	45000	2026-08-15	2026-05-19

Module 01 / 13

Where AI helps in the sales cycle

Objective: see where AI saves real time, and where the judgment stays with you.

Module 02 / 13

Prompts that work

Objective: write requests that get a usable first draft.

Goal: [what you need]
Context: [who it is for, the deal, the stage, what they care about]
Source: use [the thread, notes, or files] only. Leave out anything marked internal.
Format: [length, tone, layout]
If you are not sure about something, say so instead of guessing.

Steer, do not restart

The first answer is a draft. Tell it what to change: "Shorter." "Write it for a CFO." "Sound more like me." Then ask the two questions that expose guesses:

Module 03 / 13

Ground your deals

Objective: make the AI answer from your account material instead of general guesses.

Grounding means pointing the AI at specific material so it answers from that material. Every tool in this guide has a place to collect it. The habit that pays off most: one workspace per key account.

Workspace instructions

This workspace covers [account]. Answer only from the files here.
If the answer is not in them, say so. Name the file each point comes from.
Write short and plain, for an account executive. No marketing language.

Weekly routine

Module 04 / 13 · worked example

Build an account plan with AI

Objective: follow one real process from start to finish, and see exactly where AI helps and where you decide.

Use this for a new strategic account or an annual plan refresh. Try it first with the Northbeam practice account. Each step below shows what AI does, what you do, a prompt to copy, and the checkpoint before you move on.

1. Gather the sources

   ai

   Reviews what you added and lists what is missing or out of date.

   you

   Create the account workspace. Add the current plan if one exists, key email threads from the last quarter, call notes, a CRM export, any RFP, and approved product sheets.

   step 1 · gap checkCopy

   I am building an account plan for [account]. Review the files in this workspace. List what a solid account plan needs that is missing here, and flag any file that looks out of date.

   checkpointNothing in the workspace breaks your company's data policy.

2. Profile the account

   ai

   Runs research and writes a short, cited brief: what the company does, its strategy, recent news, and likely priorities.

   you

   Confirm each fact and its date. Cut anything you cannot verify. Add what you know from the relationship.

   step 2 · cited briefCopy

   Write a one-page profile of [account]: business model, strategy, news from the past year, and likely priorities for the next twelve months. Cite a source for every fact. Label anything that is your inference.

   checkpointEvery fact has a source you opened. Inferences are labeled.

3. Map the stakeholders

   ai

   Lists the people in your emails and notes: role, what they care about, last contact, and apparent stance, with the evidence.

   you

   Correct stances, add people the AI cannot see, and name the gaps, such as no contact with the budget owner.

   step 3 · people mapCopy

   From the files here, build a table of everyone involved at [account]: name, role, what they care about, last contact date, and stance (supporter, neutral, skeptic). Quote the evidence for each stance. Then list the roles we have not reached.

   checkpointStances rest on evidence, not guesses. Personal opinions stay out of shared versions.

4. Find the opportunities

   ai

   Matches the customer's stated needs to your approved offerings and lists where you could grow, each tied to a source.

   you

   Validate fit with your solutions engineer. Drop any idea without a real customer need behind it.

   step 4 · fit and growthCopy

   Compare [account]'s stated needs with the approved product material here. List each opportunity: the need, the offering that fits, the evidence, and your confidence. Do not claim any capability the material does not state.

   checkpointNo product claim goes further than approved material.

5. Weigh the risks

   ai

   Lists risks such as budget, timing, competition, and relationship gaps, with evidence and a suggested response for each.

   you

   Rate each risk for likelihood and impact, then decide which ones you will act on this quarter.

   step 5 · risk listCopy

   List the risks to our position at [account]: budget, timing, competition, and relationship gaps. For each, give the evidence from the files and one practical response. Mark any risk that rests on thin evidence.

   checkpointYou, not the AI, rank the risks.

6. Set goals and actions

   ai

   Drafts a 90-day plan: a few goals, actions with a suggested owner and date, and how you will measure progress.

   you

   Commit to realistic owners and dates. Agree the plan with your manager and anyone named in it.

   step 6 · 90-day planCopy

   Using steps 2 to 5 above, draft a 90-day plan for [account]: three goals, the actions under each with a suggested owner and date, and one measure of progress per goal. Keep it to one page.

   checkpointEvery named owner has agreed. No dates you cannot keep.

7. Publish and keep it current

   ai

   Assembles the plan document, and a short review deck if you want one. Each week, it reports what changed.

   you

   Review, share with your team, and run the weekly routine from module 03.

   step 7 · assemble the planCopy

   Assemble the account plan for [account] as a document with these sections: summary, account profile, stakeholder map, opportunities, risks, 90-day plan, and open questions. Use only what we agreed above. List the sources at the end.

   checkpointThe plan is internal. Run the Guardrails checklist before any part goes to a customer.

Where to run each step

Module 05 / 13 · tool chapter

Microsoft Copilot

Objective: run the sales plays inside Outlook, Word, Excel, PowerPoint, and Teams.

Best when your company runs on Microsoft 365. Copilot works inside the apps you already use and can reach your email, calendar, chats, and files, depending on your license.

Check your license first

To check, sign in at m365.cloud.microsoft, scroll to the bottom of the home page, and read the label under your name: Copilot Chat (Basic), M365 Copilot (Basic), or M365 Copilot (Premium). Premium means you have the add-on license. Microsoft explains the labels in What Copilot license do I have.

Set it up once

• Create a Copilot Notebook for each key account and add its emails, meetings, and files as references.
• Add the workspace instructions from module 03 to each notebook.
• Save your best prompts so you are not retyping them.

Plays

I meet with [customer] tomorrow. From my recent emails, meetings, chats, and files about them, summarize where things stand, their open questions, and anything I promised to send. List your sources. Then suggest three questions to ask.

Module 06 / 13 · tool chapter

Claude

Objective: use Claude for research, careful writing, and account work grounded in Projects.

Best when the job is careful writing, long documents, or research you need to trust. Proposals, executive rewrites, RFP analysis, and objection practice are strong fits.

Set it up once

• Create a Project for each key account. Add its files and the workspace instructions from module 03.
• Turn on the connectors your company allows, such as Microsoft 365 (Outlook, OneDrive, SharePoint, Teams), Gmail, Google Drive and Calendar, or a CRM from the connectors directory.
• Save a skill for recurring work, such as your proposal format or an email template. Your company can also provide skills to everyone.

Plays

Act as a skeptical [buyer role] at a [industry] company evaluating [product category]. Raise the objections a real buyer would, one at a time. Push back when my answer is vague. After five exchanges, score each answer and tell me what to fix.

Module 07 / 13 · tool chapter

Gemini

Objective: run the sales plays inside Gmail, Docs, Sheets, Slides, and Meet.

Best when your company runs on Google Workspace. Gemini appears in the Ask Gemini side panel in Gmail, Docs, Sheets, Slides, Drive, and Chat, and can take meeting notes in Meet.

Set it up once

• Build a Gem as your deal coach: paste the workspace instructions from module 03 and add your approved product material under Knowledge. Files you add from Drive stay current as they change.
• For deep account work, create a Gemini Notebook (formerly NotebookLM) per key account, if your admin has turned it on. You can add a notebook to a Gem as a source.
• Turn on Take notes for me in customer calls you organize in Meet, with the customer's agreement.

Plays

Summarize this thread. List decisions, open questions, and anything I have been asked to do, with who asked and by when. Then draft a short reply that confirms [next step].

Module 08 / 13 · tool chapter

ChatGPT

Objective: use ChatGPT for research, drafting, and multi-step work across your connected apps.

Best when you want one flexible assistant across many apps. Switch from Chat to Work for multi-step tasks that end in a document, spreadsheet, presentation, or report.

Set it up once

• Create a Project for each key account with its files and the workspace instructions from module 03.
• Set custom instructions with your role, your market, and how you like drafts written.
• Connect only the apps your company allows, from Settings or the plugin directory. Admins decide which apps, and which actions inside them, are available.

Plays

Using only the files in this project, summarize where the [account] opportunity stands: goals, decision makers, timeline, open objections, and the agreed next step. Name the file behind each point and flag anything that looks out of date.

Module 09 / 13

Which tool, when

Objective: pick the right tool without overthinking it.

For deeper tool comparisons, model tiers, and automation, see the AI Operator's Manual.

Reference · 10 / 13

Play library

Objective: copy-ready prompts for the sales cycle. Fill in the highlighted parts.

Research [company] before my first meeting. Cover what they do, news from the past year, likely priorities for a company like them, and anything in my connected apps that mentions them. Cite a source for every fact and keep facts separate from your inferences.

Plan my next call with [name, role]: the goal, three questions to ask, likely objections, and the one follow-up I must not forget. Use [notes or workspace].

From the files here, build a table of everyone involved at [account]: name, role, what they care about, last contact date, and stance. Quote the evidence for each stance, then list the roles we have not reached.

Draft a one-page 90-day plan for [account]: three goals, actions with a suggested owner and date, and one measure of progress per goal. Use only the files and decisions in this workspace.

Turn these call notes into a one-page summary for the customer: their goals, what we heard, and next steps with owners and dates. Remove anything marked internal. Mark anything unclear as [confirm].

Draft a follow-up email to [name] that answers their questions at a high level, confirms [deliverable] by [date], and proposes [next meeting]. Under 120 words. Make no commitments beyond these.

List every requirement in this RFP as a table: requirement, section number exactly as written, must-have or nice-to-have, and deadline. If unsure whether something is a requirement, include it and mark it [check].

Rewrite this for a non-technical [CFO / executive]. Keep the meaning. Lead with business risk and cost. Under 200 words. Add no capability that is not in the original.

Today is [date]. From this pipeline, list deals with no activity in 30 days or a close date that has passed. Show account, stage, amount, close date, and days since last activity.

Act as a skeptical [buyer role] evaluating [product category]. Raise real objections one at a time and push back on vague answers. After five exchanges, score my answers and tell me what to fix.

Review the draft above against the source material. List every claim, number, or commitment the sources do not clearly support. Do not rewrite anything yet.

No plays match. Try a different word or choose All.

Reference · 11 / 13

Guardrails

Objective: keep AI use safe for you, your customers, and your company.

Reference · 12 / 13

Glossary and sources

Glossary

Account plan

A living document that sets out an account's profile, people, opportunities, risks, and your next actions.

Agent

An AI that takes several steps toward a goal and can act in your apps.

Connector (app)

A link that lets an AI search or act in another tool, such as email or a CRM.

Custom instructions

Standing directions applied to every chat.

Gem

Gemini's reusable assistant with saved instructions and files.

Grounding

Pointing the AI at specific material so it answers from it.

Hallucination

A confident answer that is wrong or made up.

Notebook

Copilot's workspace that collects references for one piece of work. Google's similar tool is Gemini Notebook, formerly NotebookLM.

Plugin

In ChatGPT, a package that can bundle apps and skills for a workflow.

Skill

A saved set of instructions an AI loads for a repeatable task, such as your proposal format.

Project

A workspace in Claude or ChatGPT that keeps files and instructions together.

Prompt

What you type to tell the AI what you want.

Research mode

A slower mode that searches many sources and returns a cited report.

Sources

Checked against each maker's help pages on September 16, 2026. Features change often, and those pages have the latest details.

• Microsoft: What Copilot license do I have; Copilot Chat in Microsoft 365 apps; Copilot plans compared; Copilot Notebooks; Researcher; Create a presentation from a file
• Anthropic: Projects; Research; Create and edit files; Microsoft 365 connector; Skills; Claude for Microsoft 365; Claude in Chrome; Claude Tag
• Google: Gemini in Workspace; Gems; Gemini Notebook; Take notes for me; Deep Research in Workspace; Gemini in Slides; Fill with Gemini
• OpenAI: ChatGPT Work; Creating files with Work; Apps in ChatGPT; ChatGPT for Excel and Google Sheets; Workspace agents; Business release notes