The Power of Questions in Tech Leadership

First in the “Art of Technical Communication” series

Communication is often about *how* you say something, not just *what* you say. As technology professionals, we sometimes get a bad reputation for poor communication or brusque behavior. Even when technical jargon feels natural and we prefer the TL;DR version, developing strong communication skills is worth the effort. In fact, it’s our responsibility to communicate effectively—not just with peers and leaders, but with clients and stakeholders too.

Questions in tech leadership

One of the most powerful tools for clear and effective communication? Well-timed, thoughtful questions.

Learning from the Ultimate Questioners

Spending time with my young nieces and nephews is something I love. We often find ourselves in fascinating conversations, and if you’ve ever been around children, you know their favorite question: “Why?”

• “Why don’t the clouds fall down?”

• “Why do cars only have 4 wheels?”

• “Why can’t I have ice cream for breakfast?”

While their questions stem from pure curiosity about the world, as technologists, our questions serve an even broader purpose. Good questions help us:

• Exchange vital information

• Build trust

• Improve outcomes

Better Understanding Through Better Questions

Throughout my career across various roles, one thing remains constant: the need to comprehend, evaluate, and estimate work. This includes requirements, hypotheses, analysis, and outcomes. While assumptions can be costly, asking questions is virtually free.

In technology roles, understanding the ask is crucial. Good questions might be the only thing preventing:

• Unidentified skill gaps

• Missed resource requirements

• Overlooked dependencies

I’ve lost count of how many times a well-placed question led someone to realize they hadn’t considered a crucial factor. The answer might be easy to obtain, but imagine where a project might end up if that question was never asked.

Building Clarity and Alignment

Getting clarity throughout the software development lifecycle directly impacts:

• Solution quality

• System stability

• Estimate accuracy

Understanding the “why” behind the “what” helps you see work from different perspectives—crucial when discovering missing requirements or addressing blocked work. While this isn’t about taking on product owner or management responsibilities, it is about aiding in the successful translation of work details and considerations.

Sometimes this means asking who, what, when, and why multiple times, to multiple people, uncovering as much as possible for everyone involved. Turns out my nieces and nephews were onto something with their persistent “whys.”

Improving Partnerships Through Questions

After using your expertise to ensure everyone has the necessary information, a natural byproduct emerges: stronger partnerships and collaboration. It’s invaluable to identify teammates who can help solve challenges you couldn’t tackle alone.

Keys to Question-Based Collaboration:

• Challenge assumptions and ideas, not people

• Verify understanding rather than pointing out wrongs

• Maintain an open posture for fruitful engagement

• Assume positive intent

• Build trust through layered questions

Establishing Your Expertise

Asking meaningful questions isn’t just a communication strategy—it’s career development. It helps:

• Showcase your expertise

• Improve leadership skills

• Demonstrate emotional intelligence

• Bridge communication gaps between technical and non-technical audiences

The toolkit for bridging these gaps consists of:

• Thoughtful questions

• Genuine caring

• Empathy

Types of Questions to Master

1. Open-ended Questions

   • Feel less like interrogation

   • Reduce unintended bias

   • Leave room for discussion

2. Direct Questions

   • Focus on fact-finding

   • Help counter vague answers

   • Limit response options when needed

3. Follow-up Questions

   • Allow conversation expansion

   • Demonstrate active listening

   • Show comprehension

4. Leading Questions

   • Guide conversation direction

   • Should be used sparingly and appropriately

Best Practices for Questioning

Do:

• Research before asking

• Follow conversation flow

• Check your bias

• Read room dynamics

• Be brave in asking difficult questions

• Stay engaged and listen actively

Don’t:

• Ask questions just to ask them

• Lead people unnecessarily

• Rush responses

• Derail conversations

• Forget to be respectful

The Art and Science of Questions

While asking questions might seem straightforward, there’s both art and science to doing it well. Context, venue, tone, sequence, and framing all matter. The good news? Anyone can learn to do it effectively with practice.

Developing strong questioning skills helps break the stereotype of the ill-mannered technologist. It’s worth the effort to:

• Have more productive conversations

• Get your point across effectively

• Demonstrate expertise naturally

Next in the series: “Questions That Transform Tech Conversations” – practical examples of different question types in technical scenarios.

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What questioning techniques have you found most effective in your technical role? Share your experiences in the comments below.