GUIDED WORKBOOK

25 Questions Before You Buy Technology

Ask better questions before you buy a tool, app, platform, system, vendor solution, or AI-enabled product.

A tool looks promising. A vendor demo feels persuasive. A peer recommends a platform. AI gives you a shortlist. A free trial is easy to start. A monthly price looks manageable.

But buying before the decision is clear can lead to hidden costs, poor adoption, manual workarounds, team frustration, reporting gaps, and buyer’s remorse.

25 Questions Before You Buy Technology helps you slow down just enough to think clearly, ask better questions, and move forward with more confidence.

60%

of software buyers regretted a purchase made in the prior 12 to 18 months*

58%

of U.S. software buyers regretted at least one recent software purchase*

56%

of regretful U.S. buyers described the financial impact as significant or monumental*

The problem is rarely intelligence. It is decision-readiness.

Smart people still make expensive technology mistakes when they move into evaluation before they have done the decision-readiness work.

Before your team compares tools, starts free trials, books demos, asks AI for recommendations, or narrows a shortlist, you need to know:

• What problem must the technology solve
• Who will use, manage, approve, and pay for it
• What success should look like
• What requirements are truly must-have
• What the technology will really cost after setup, support, training, migration, add-ons, and internal time
• What questions still need answers before you commit

Without that decision-readiness work, the buying process can be shaped by the flashiest demo, the safest brand name, the loudest internal voice, a peer recommendation, a vendor’s sales process, or a generic AI answer.

This easy-to-use workbook puts you, the technology buyer, back in charge.

Before you ask AI what to buy, get clear on what matters.

AI can help you research tools, summarize vendor pages, draft questions, compare notes, and surface risks. But AI works best when the decision structure is clear.

If you ask AI for recommendations before you know what problem you are solving, who needs to be involved, what requirements matter, what tradeoffs are acceptable, or what risks need to be verified, AI may simply help you move faster through an unclear process.

This workbook gives you the structure first. Then it gives you AI pressure-test prompts and guardrails to help you clarify gaps, test assumptions, prepare better vendor questions, and separate what is confirmed from what still needs to be verified.

Use AI for speed. Use the workbook for decision-readiness.

What’s inside the workbook

The workbook walks you through 25 practical questions across five decision stages:

• Clarify the Decision
• Align the People
• Define the Requirements
• Understand Cost, Setup, and Ownership
• Compare and Pressure-Test Options

Each question includes:

• Why the question matters
• Who should help answer it
• Weak and stronger answer examples
• Follow-up questions
• An AI pressure-test prompt

Use it on your own, with your team, or as part of a more formal vendor review.

Built for business buyers, not technology experts.

You do not need to be technical to use this workbook.

It is designed for business leaders, founders, marketers, product managers, operators, team leads, and decision owners who need to choose technology but may not have a formal procurement process or technical buying team.

Use it when you are:

• Buying a tool online with a credit card
• Comparing a few options
• Choosing a platform for your team
• Replacing a system that no longer fits
• Evaluating an AI-enabled product
• Preparing for a vendor review

The goal is not to become a technology expert.

The goal is to become a more prepared buyer.