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7 Grove-inspired questions Engineering Managers should ask in their one-on-ones

7 Grove-inspired questions Engineering Managers should ask in their one-on-ones

November 26, 2022

7 Grove-inspired questions Engineering Managers should ask in their one-on-ones
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Legendary CEO and investor Ben Horowitz considers one-on-ones vital enough that he was willing to fire a senior leader if he didn’t start holding them.

The one-on-one is where managers and their reports:

  • Build trust
  • Learn how to best work together
  • Exchange vital information that doesn’t come up in any other venue

So why do so many managers skip their one-on-ones? One reason may be because they’re not using them to their highest potential.

As a manager, do you find yourself talking through most of the meetings? In High Output Management, (foreworded by Ben Horowitz) Andrew Grove wrote that managers should spend the vast majority of their one-on-ones listening.

As a manager, it’s your job to get your reports to tell you everything relevant to the task at hand. Including things that might be hard for them to bring up. Talking to a boss is intimidating, uncertain, and high-stakes. Your first task is to make employees feel safe opening up.

“The key is to build a relationship with your team so that they can trust you,” Engineering Manager and Coach Ling Abson wrote. “Having a trusting relationship is important as it allows your team to surface any issues that may be preventing them from delivering and trusting that there’s safety in bringing those issues to you.”

Show your Engineers that you care about them and are interested in what they have to say by actively listening. Once you’ve gotten the hang of active listening, bring some targeted, effective questions to the meeting.

“Since the one-on-one meeting is for your team member, asking questions is one of the single best ways to bring the focus to them,” according to the Lighthouse blog.

You can heavily influence the quality of your conversations with high-quality questions. Toward that end, I’ve scoured the web for questions that get to the heart of what you need to know to get the best work from your Engineers.


1. “What’s been on your mind recently?”

If your report came in with an agenda or something they wanted to address, this gives them the opportunity to broach it. If not, you can move on to more specific questions. It also signals that the meeting is for them. It’s their opportunity to bring up topics that don’t fit in any other context. Another way to ask this could be, "What makes you anxious right now?" Maybe they hate the team’s bug-tracking software. Maybe they want to work from home one day per week. Whatever it is, this is their chance to talk about it.

This serves as a subtle hint that they should be preparing for these meetings going forward as opportunities to discuss topics that don’t come up in other contexts.

2. “How are you? How’s life outside of work?” source

Some of your Engineers might feel awkward bringing up their home life with their boss. This question gives them explicit permission to do so. This can be extremely valuable, if not now, at some point in the future. There are myriad examples of times when managers thought their employee was a bad fit but in actuality the employee was going through something tough at home and needed support. You never want to wait until performance suffers to know about anything that might impact their performance. The time is now to start making it safe to talk about home life at work.

One way to make this kind of sharing safe is by modeling vulnerability yourself. “Creating the space to be vulnerable is the only way to foster trust,” Matt Martin, Co-Founder and CEO of Clockwise said. “People take to these cues very quickly: Is this a place where I'll be judged for not having the answer? But vulnerability really needs to be lead-by-example. It's tough to ask a report to be vulnerable to start. So, I find for this one, it's really important for the manager to open the space by going first.”

3. “What are you struggling with lately?” source

This is a can’t-lose question. You might find out some new things you can do to make your employee more effective. Maybe they need training in the new database or with a new framework. Maybe they need more Focus Time.

This could also be a place to address the quality of this person's relationships with their functional or cross-functional counterparts. You might say something like, "I'd love to hear more about your relationship with your tech lead/product manager/program manager/designer/other engineers..."

“The depth of these relationships can be instrumental in their success, and it also gives the manager the ability to discover trends and learn what else to dig into,” VP of Engineering Nathan Broslawsky said.

Or you might learn they’re still struggling with something you thought had been fixed. But what if your Engineer says they’re not struggling with anything and have no barriers? Well, that’s a hint that they may not be growing or being challenged enough!

At the same time, getting an accurate answer requires trust. At the beginning, it might work better to ask "What are we struggling with lately?"

No matter what, this question lets your report know that you care about not just the work they’re doing, but the context they’re working in.

4. “If you had to pick one skill you want to level up -- be it technical skills, leadership skills, speaking skills, soft skills — what would it be?”

Another way to ask this question is, “How can I create opportunities for your growth?” source If that doesn’t yield much, try “What are your long term goals? Have you thought about them?” If your Engineer hasn’t been thinking about career advancement or life goals, this may be a good nudge/reminder to reconnect with their ambition and think a little more long-term.

It’s also a valuable question for retention, because the average worker values opportunities for career growth more than any other workplace perk according to Gallup, Deloitte, and Google.

Millennials most valued work benefits
Training and development was the most-cited most valuable work benefit for Millennial workers Get Lighthouse
Top priorities when job seeking
"Opportunities for career progression” was the most-often cited attribute that makes an employer attractive. Get Lighthouse

5. “What would make you not just willing but excited to stay with us for the next two years”

This is another good retention question. Engineering is famous for die-hard individual contributors. Not everyone is climbing the corporate ladder at all times. Some people at certain times value flexibility, autonomy, or other perks more than career advancement opportunities. Find out where your Engineer sees themselves going so you can help them get there.

6. “How do you prefer to receive feedback?”

Engineers get feedback constantly from each other in the form of code reviews, project plan reviews, etc. Yet no matter how much you get, criticism is hard to take, and compliments can be embarrassing. So giving your Engineers feedback in their preferred manner can save a lot of unnecessary friction. It’s worthwhile to understand how your Engineers are receiving feedback from their teammates and from you.

Ask your report about their preferred medium and timing for accolades and constructive feedback. Do they prefer in-person or via email or Slack? Do they like to get feedback in real-time or batched at regular intervals? Do they want recognition in front of their peers or one-on-one? Giving and getting feedback is challenging enough. Make it easier on you both by doing it in their preferred way.

“Knowing how someone wants to receive recognition helps to ensure they’re able to enjoy the moment rather than feel really uncomfortable,” Hogan wrote. “For example, for a big-deal promotion, I once gave an introverted direct report a handwritten congratulatory note and a loaf of banana bread—his favorite baked good—which he chose to share with his teammates. His celebration, his terms.”

7. "What do you wish I better understood about you or your work?"

Generally the last thing you want as a manager is to be surprised. This question helps head off surprises at the pass. It’s a good gut-check to be sure you and your Engineer are really on the same page about things they think are important. It also invites them to re-explain something that they may have tried to communicate earlier but didn’t quite get across for whatever reason.

Going forward

These seven questions should help you establish trust with and get to know your Engineers, helping you both get the most value out of your one-on-one meeting. You’ll notice all these questions are open-ended, as yes or no questions don’t get people talking as effectively.

One more tip: Consider taking notes. Engineering Manager and Management/Leadership coach Lara Hogan maintains an Evernote file for each report for this purpose.

“Over time, I’ve learned that getting some particular data during an initial 1:1 can be really helpful, as I can refer back to the answers as I need to give a person feedback, recognize them, and find creative ways to support them,” Hogan wrote.

The tip I want to leave you with comes from the aforementioned High Output Management. It’s Grove’s Principle of Didactic Management: “Ask one more question!” Keep asking follow-up questions until both you and your report are satisfied that you’ve addressed everything important.

What questions have helped you build rapport in your one-on-ones? Let me know at cathy at

Next, check out what makes a great manager of software engineers.

About the author

Cathy Reisenwitz

Cathy Reisenwitz is the former Head of Content at Clockwise. She has covered business software for six years and has been published in Newsweek, Forbes, the Daily Beast, VICE Motherboard, Reason magazine, Talking Points Memo and other publications.

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