The Question Every Engineer MUST Ask (But Never Does)

Why understanding leadership's real problems matters more than perfecting your technical skills.

Aug 18, 2025

Dear Future Leaders,

Most engineers approach career conversations backwards.

They walk into skip-level meetings asking about their own advancement:

"What do I need to do to get promoted?" or "How can I develop leadership skills?"

These questions make the conversation about you and your needs, which puts your manager in the position of having to coach you through your career development.

There's a better approach.

The Strategic Question Framework

Instead of asking about your career progression, start asking about the challenges that keep leadership awake at night.

For your skip-level manager:

"What are the biggest challenges facing our engineering organization right now?"

For your direct manager:

"What's preventing our team from having more impact?"

For product leaders:

"What could engineering do differently to help you ship better features faster?"

This simple shift changes how they see you. You go from someone who needs development to someone who could help solve their biggest problems.

Why This Changes Everything

When you ask about their problems instead of your promotion, several things happen:

You learn about challenges you never hear about in team meetings. These are the organizational issues that leadership spends most of their time thinking about.

You position yourself as someone who thinks strategically, not just technically.

But here's what matters most:

You discover opportunities to create value that other engineers miss because they're focused solely on their assigned tasks.

Asking the right question is only the beginning, though. The real career acceleration happens when you follow up with action.

After learning about their challenges, identify specific problems you could help solve within your current role. Propose solutions based on your technical expertise. Keep them updated on progress.

When you do this consistently, something powerful happens: your regular work becomes connected to their strategic priorities, making your contributions more visible and valuable.

Understanding What Really Matters

These conversations often reveal a gap between what engineers think matters and what leadership actually cares about.

Engineers focus on:

Code quality, technical debt, system performance

Leadership worries about:

Delivery speed, cross-team coordination, business impact

Both matter, but understanding leadership's priorities helps you contribute more strategically.

This changes how you communicate about your work. Once you understand what keeps leadership awake at night, you can transform how you talk about your contributions.

Instead of:

"Refactored the authentication service"

Try:

"Improved authentication reliability, reducing login failures that were affecting user retention"

Instead of:

"Optimized database queries"

Try:

"Reduced page load times, which should improve our conversion metrics"

Same technical work, described in terms that connect to business outcomes.

The engineers who advance fastest develop awareness of problems beyond their immediate technical scope. They understand how their work connects to business outcomes. They notice inefficiencies in processes and communication. They think about user experience, not just system performance.

The secret? This awareness comes from asking the right questions and listening carefully to the answers.

Your Next Steps

Choose one person in leadership you interact with regularly.

Schedule 15 minutes with them this week.

Ask one strategic question about their challenges and listen carefully.

Follow up within a week with an observation, idea, or offer to help investigate the issue.

Then execute on whatever you proposed.

It’s important to mention here that understanding leadership's real challenges creates a compound effect on your career.

You start noticing problems others ignore. You propose solutions that align with business priorities. You become known for thinking beyond your immediate responsibilities.

This transformation happens through conversation and strategic thinking, not just technical excellence.

Refer a friend

Your Decision Point

You can continue focusing solely on technical excellence and hoping someone notices.

Or you can invest time in understanding what challenges actually matter to leadership and position yourself as part of the solution.

The engineers who advance fastest aren't necessarily the most technically skilled. They're the ones who understand the business context of their work and contribute to solving real organizational challenges.

What strategic question will you ask this week?

Want to get started right away? For a limited time, I'll help you prepare for strategic conversations with leadership, including which questions to ask based on your specific situation and how to follow up with action that demonstrates your readiness for advancement.

Simply reply with the word "STRATEGIC" to get started.