How to Ask Good 1:1 Questions: A Guide for Engineering Managers

You've blocked off time for 1:1s with your team. You understand they're important, and you're trying to be a good manager. But once you sit down to have the 1:1, you find yourself wondering, "What questions should I ask?"

If you've ever started a 1:1 with "How's it going?" only to be met with a simple "Good," you're not alone. This guide will help you transform your 1:1s from awkward checkboxes into meaningful conversations that drive engagement and growth.

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Who This Guide Is For

Engineering managers struggling to get meaningful dialogue in 1:1s
Leaders working with more introverted team members
Managers looking to move beyond surface-level conversations

Note: This guide assumes you're meeting weekly or bi-weekly with your direct reports. If you're meeting less frequently, it becomes much harder to build on conversations effectively.

The Foundation: Building Trust Through Questions

The key to having great 1:1s isn't having a perfect list of questions – it's building trust. The way you build trust is by asking thoughtful questions, listening actively, and following up on the things you've talked about.

When your direct reports feel genuinely valued and supported, they're more likely to speak candidly about their challenges, aspirations, and needs. As one senior engineer put it:

"When you have a manager who's real, honest, and wants you to succeed, you can rest in that assurance and trust. That's when you can talk very candidly about where you're at, where you want to be, and how to get there."

Reminder: Effective management must be personalized to each direct report. What works brilliantly with one person might fall flat with another. While some of your more extroverted team members might naturally share their life story at the slightest prompting, many software developers need more encouragement to open up.

So, the remainder of the guide is meant to offer example questions by category for you to use at your discretion.

Question Categories & When to Use Them

Openers (The First 5 Minutes)

The problem with open-ended questions like "How are things going?" is that they're too broad. For many people, especially those who are more introverted, such questions can feel overwhelming. Instead, start with specific questions that make it easier to express subjective feelings in a more structured way.

One particularly effective technique is the Green/Yellow/Red (G/Y/R) check-in:

"How has this week been in terms of Green/Yellow/Red?"

This works because while it might be hard to express emotions or challenges directly, people can usually identify immediately whether it's been a "green" week or "yellowish/red", for example. Once they voice a color, they typically feel compelled to explain why – and if not, it's natural to ask. You can lead the first few times to help them get the hang of it.

Other effective openers include:

"What's been the best part of your week?"
"What's been the most challenging part of your week?"
"What are you excited about lately?"

Status & Well-being

Once you've broken the ice, you can move into questions about their current state:

"How would you rate your current workload on the Green/Yellow/Red scale?"
- Note: We didn’t ask “How is your workload?” We want to avoid questions that lead to one-word answers!
"What's energizing for you in your work these days?"
"What's draining for you in your work these days?"

💡 Pro tip: Pay attention to non-verbal cues. Sometimes what isn't said is as important as what is. As we like to say at DevClarity, "Everything is data."

After the opening questions and status check, you can continue move into the various areas below, based on the flow of the conversation and employee needs.

Career Development

Great career development questions focus on both short-term wins and long-term growth:

Long-term: "If you could be proud of one accomplishment between now and next year, what would it be?"
Short-term: "What's one thing we can work on over the next [week/two weeks] to help you move toward your long-term goals?"
A casual framing of skill development: "What do you want to add to your resume?"

💡 Pro tip: Document career goals and revisit them regularly. This shows you're invested in their growth and helps track progress.

Technical Growth & Impact

For engineering teams, technical growth is crucial. Ask questions that prompt thinking about both current work and future opportunities:

"What technical challenges are you most excited about right now?"
"If you could improve anything about our architecture, what would it be?"
"What technology or skill would you like to explore more?"

Unblocking & Support

These questions help identify obstacles and clarity gaps:

"Where are you stuck?" or "Are there any decisions you're hung up on?"
"How clear is 'success' for you in the next 3-6 months?"
"What's not fun about working here?"
"What are we not doing that we should be doing?"

Feedback & Improvement

Creating a two-way feedback channel is crucial. Some questions should be asked once to establish expectations, while others may be asked on a more recurring basis.

"What aspect of your job would you like more help or coaching in?"
"What would you like me to hold you accountable for?"
"What are your expectations of someone serving in my role?"
(One-time) "How do you prefer to receive praise (public, private)?"

Advanced Questions

Once you've built strong trust, you can explore more challenging questions:

"When have you disagreed with me but didn't think it was worth voicing it?"
"What's the number 1 problem in our organization? Why?"
"Who is really kicking ass in the company? Who do you admire?"
"If you were me, what changes would you make?"
"What's the biggest opportunity that we're missing out on?"

Common Pitfalls to Avoid

Rushing to fill silence: After asking a question, give your direct report time to think. Silence isn't always awkward – it's often productive.
Sticking to a script: While having good questions ready is important, don't be afraid to go off-script when a response deserves deeper exploration.
Forgetting context: Some questions work better at certain times or with certain personalities. Read the room and adapt accordingly.
Not following up: If someone shares a concern or aspiration, make sure to follow up in future 1:1s. This shows you're listening and care about their growth.

Putting It All Together

The best 1:1 questions aren't just about gathering information – they're about building relationships and trust over time. Start with simpler, more structured questions and progressively move toward deeper, more challenging ones as trust builds.

Remember: the goal isn't to get through a checklist of questions, but to understand your team members better and help them grow. Pay attention to which questions resonate with each individual and adapt your approach accordingly.

Build your own question bank based on what works well with your team, and don't be afraid to experiment with different approaches. The most important thing is showing genuine interest in your team members' responses and following through on the insights they share.

For more insights on effective engineering management, such as our Ultimate Guide to 1:1s for Engineering Managers, check out our EM Canon.

Special thanks to Adam Loftin at Fleetio for sharing his detailed approach to asking good 1:1 questions across his engineering teams!