I fond an old microblogging post that I posted about 4 years ago. I posted:
When designing technology solutions, ask questions… lots of questions… too many questions. Users have many assumptions they believe you understand, but you don’t.
I decided to see what would happen if I had AI compose a 500 word blog post on the theme. I am not sure it did a batter job than I did, but there it is. I do kow it had an intriguing title!
When building technology to solve human problems, the biggest risk rarely stems from code syntax or architecture choices. Instead, it stems from what remains unsaid. When designing technology solutions, the single most critical habit is to ask questions—lots of questions, and even what might feel like “too many questions”.
At first glance, asking continuous questions might seem inefficient or overly cautious. However, in technology design, inquiry is not a sign of hesitation; it is the fundamental tool for uncovering truth. Without intentional inquiry, solution design quickly falls prey to unexamined premises and misalignment.
The Unspoken Divide: User Assumptions vs. Designer Reality
Every technology project brings together two distinct worlds: the world of the user and the world of the technologist. Users come to a problem with deep context about their daily routines, pain points, and workflows. Because these details are second nature to them, users operate under numerous assumptions that they naturally believe you already understand—even when you do not.
When users assume that designers intuitively grasp their hidden requirements, they rarely state them explicitly. They describe what they want at a high level, taking for granted that the underlying mechanics, edge cases, and unstated preferences are self-evident. On the other side of the table, technologists often assume that a clear user request implies a complete user requirement.
This creates a silent disconnect. When designers move forward without pressing deeper, they build solutions tailored to their own interpretation rather than the user’s actual reality. The result is software or systems that meet initial technical specifications on paper but fail in practice because key user assumptions were left unverified.
The Power of Asking “Too Many” Questions
To bridge this gap, technology designers must embrace the mindset of an Inquiring Technologist. This means intentionally pushing past surface-level requests by asking lots of questions—and never worrying about asking “too many”.
Why is asking “too many” questions so effective?
- It surfaces implicit knowledge: Probing questions force users to articulate habits, constraints, and expectations they normally take for granted.
- It dismantles false consensus: It ensures that concepts like “simple,” “fast,” or “intuitive” mean the exact same thing to both the user and the designer.
- It protects against false understanding: Acknowledging that you do not automatically understand a user’s unstated assumptions prevents costly re-designs later.
By persistently asking questions, technologists transform implicit user assumptions into explicit design requirements. What might feel like tedious probing during early discovery turns out to be the cheapest, most effective risk mitigation strategy in technology solution design.
Conclusion: Cultivating the Inquiring Mindset
Ultimately, successful technology design is as much about inquiry as it is about implementation. When designing technology solutions, asking questions relentlessly ensures that hidden user assumptions are brought to light before a single line of solution architecture is finalized. By accepting that users hold assumptions you do not yet understand, and by committing to asking “too many” questions, you lay the foundation for technology solutions that truly fit