Start With the Problem: The Executive Approach to Tool Fit

Start With the Problem: Executive Tool Fit Strategy for Better Software Buying Decisions An executive decision making playbook for AI and SaaS tools using a problem first approach to avoid tool sprawl and maximize ROI on software tools. Learn how to evaluate business tools, design a technology purchasing strategy, and choose the right software with confidence and clarity.

What You'll Learn:

• How to apply a start with the problem mindset before you ever look at AI or SaaS tool features.
• A simple framework executives can use to define the business problem, quantify impact, and link it to strategic goals.
• Practical criteria for how to evaluate business tools so they solve real problems instead of creating tool sprawl.
• Questions to ask vendors that reveal true fit, hidden costs, and realistic ROI on software tools.
• How to build a technology purchasing strategy that aligns with current workflows and change-management capacity.
• Red flags that signal a tool-first, shiny-object decision—and how to redirect back to a problem-first approach.
• A quick reflection exercise to identify one area in your own org to apply this tool fit strategy right now.
• A step-by-step action plan to take one small, low-risk move this week to improve your software buying decisions.