Essential Questions For Effective 1:1 Meetings With Direct Reports (Especially For Managing Gen Ys & Zs)
Combing through ~300 hours of 1:1s meeting notes, here are the top 10 questions I found most valuable.
Starting as a new-ish manager, you don’t want to be seen as not knowing what you’re doing. But truth is far from that, you were shooting blindly in the dark in your first few 1:1s.
I could still recall the time when I panicked about what to say next while listening (or not) to my direct reports. After the conversation ended, I thought — great, I just blew up my first impression. Don’t even mention about building trust.
The build-up of anxiety for 1:1s has got to be this —every single management book/article highlighted the importance of running your 1:1s well. That one hour you spent with them impacts their work in the coming weeks. Also from these you-shouldn’t-read-too-much-before-doing leadership books, they stress that 1:1s are the reports’ meeting. They should set the tone and agenda.
But… How exactly is it going to happen? Organically?
Especially in my context, the majority of my reports have a common trait — they have nothing to share before warming up. They are in their 20s, pretty young, and new to the workforce.
To avoid awkward silence and mindless how-are-you fillers, I started collecting questions in my 1:1 questions bank. I tried them out with my reports, took meeting notes, and then went through the notes to hunt down the most valuable questions for effective 1:1s.
This is the results of it — The 10 most important questions to ask in your 1:1s, tested and proven to get you and your reports in the groove 😎
These questions led me to a highly engaged team, doubled productivity (based on team’s output and goals achieved), with near zero turnover over the past year. However, do evaluate my context versus yours, and adapt accordingly.
Structure and Tips
The questions are categorized into 3 buckets with different cadence and timing to be brought up.
- Recurring questions — to bring up in every single 1:1
- Onboarding questions — to bring up in the first few 1:1s
- Monthly or Quarterly questions— to bring up depending on suitability, with lower frequency
TL;DR Illustration
Some helpful tips before diving into the questions:
- There aren’t any one-size-fits-all questions — I’ve deconstructed the WHYs behind each question so you can frame your questions differently yet achieve the same results.
- Keep a shared meeting note for all 1:1s — to align on discussion items, and keep each other accountable on action items.
Don’t worry about being fancy, a simple Google Doc is good enough. - Listen actively to your reports’ replies, then dive deeper with contextual questions, getting to the root cause. You will gain in-depth insights, and your reports will discover their blind spots. If done right, your recurring questions alone will take at least 15 minutes of the session.
Let’s dive in.
Recurring Questions
It is TOTALLY FINE to repeat the same questions in every 1:1. At the end of the day, it is about being present and the actions taken post-1:1s that matter the most.
Of course, it will be great to get creative and phrase these questions differently. But don’t be too worked up on it.
- What’s on your mind lately?
The goal is to know what is going on in their life — be it their personal or professional life; and if anything is bothering them. After learning about their background, values, and priorities, you are equipped with the context to be more sensitive and thoughtful when you speak to them.
To build any relationship, we first need to know about the person.
From this question, I learned that Jayne’s (fictional name) grandmother fell and she had to attend to her grandmother frequently so she might respond late to our work messages. This enabled me to empathize with her, cutting her some slack when required.
2. Your energy level from score 1 to 10 (beaming sun). Why?
You could swap “energy level” out with “happiness level”, whichever makes the most sense.
The goal is to catch any burnout symptoms beforehand, especially in a fast-paced, stressful working environment. Keep an eye on the previous vs current score — take immediate action to resolve any triggers if they’re constantly on the lower scale.
Ask follow-up questions to find out what’s draining your report’s energy. And if any ongoing frustration demotivates him/her.
Similarly, if your report’s score is on the higher scale, find out what energizes him/her so you can replicate more of that.
3. Rate your current bandwidth with a score of 1 to 10 (suffocating). Why?
Request a breakdown of scores into respective projects/ tasks to drill down further.
The goal is to find out if your report requires more challenges, or is already flooded with on-hand tasks. Knowing this enables you to identify your next course of action — to delegate more (or less); or to provide more resources.
The scoring system is useful to compare with previous 1:1 scores — if there’s a sudden jump from 4 to 10; find out the recent changes and the reasoning.
This question usually leads to many more follow-up questions, uncovering the biggest time wasters for your reports, operational issues, misalignment in expectations versus reality, imbalanced workload between reports, task-relevant maturity, and growth opportunities, etc.
4. Any questions you have for me or anyone in the company?
The goal is to uncover any undercurrent feelings/opinions towards anyone (or company), or specific initiatives.
Most of the time, what I heard in return are:
- What is this new project/ initiative about? Why do we need it?
- What is this team/ person working on currently? It seems like they’re busy?
You will discover the common water-cooler topics. Noticing repeated questions across a few reports, some actions should be taken to address their “observation”.
Onboarding Questions
The first few 1:1s are the best time to set things up right. Once a habit is formed, changing is hard. So make good use of the first few sessions to enable productive habits.
Always start with expectation settings — to create a safe space for them.
Set the tone. Let them know it’s alright and expected for the 1:1s to be uncomfortable and awkward, otherwise, we’re not discussing the important stuff.
Set the scope. Let them know that these 1:1s are FOR them, and they can talk about anything they want — personal or professional, including compensation or job offers. Assure them that you have their best interest at heart. They are free to bring up any frustrations, blockers, feedback, etc. in the 1:1s without judgments.
Set the rules. All discussions will be kept confidential; on any rare chance, if there’s a need to disclose, both parties will seek permission prior.
After all expectations are clear, let’s dive into the questions.
- What’s your preference for:
- feedback style (written, verbal, immediate, post-event, etc.)
- task delegation (more or less guidance)
- ad-hoc requests (quick chat or Slack messages)
- productive discussions (morning or afternoon)
The goal is to learn what works best for this person. At the same time making them feel valued and heard. Since both are new to this working relationship, these insights spare you from unnecessary assumptions and trial-and-error in communicating.
Take the chance to share your preference, and reiterate that you are open to his/her feedback to work better together.
2. Tell me about the best manager (or lead) you’ve ever had. What did that person do that you thought was most effective and helpful?
Also ask about the worst manager you’ve ever had.
Other recommended questions:
- What do you like & dislike about my management style?
- What do you wish I have done differently in XXX (replace with a specific managerial activity)?
The goal is to understand what they value the most from their managers. Everyone has a different preference — some prefer a gentler approach, some like it brutal; some appreciate hands-off, some want more guidance, etc.
By asking for their best versus worst manager experience, it paints both opposite ends of the spectrum for you — his/her best versus terrible manager qualities.
3. What do you think about our 1:1 just now?
The goal is to involve your reports in making 1:1s a team sport. The aim is to have the best 1:1s.
It prompts them to reflect on the session just now, uncovering:
- what they liked and disliked;
- topics that they enjoyed vs. dreaded discussing;
- what was helpful vs. unhelpful to them;
- topics they feel uncomfortable talking about, or if you made them feel uncomfortable at any point of discussion.
From here, you can take the opportunity to share improvement areas, address any issues, or apologize if you overstepped any boundaries. Then revise how both of you conduct future sessions.
Monthly or Quarterly Questions (depending on suitability)
- How’s your progress on your OKR/ big projects/ milestones/ PDP?
The goal is to check in with your reports once in a while on their longer-term projects.
It signals to them that you care about their longer-term projects. Probe further for any challenges, and provide guidance or resources when necessary.
If there isn’t progress since the previous 1:1, make sure your report commits to some action steps before the next session.
2. What’s your confidence score towards XXX?
XXX to be replaced with:
- yourself acing this role
- your manager
- your team
- the company and its leadership team
The goal is to realize gaps between your perspectives and theirs, probing self-reflection. As a manager with better visibility, you eventually see things differently. It is useful to pause, take the time to reconfigure, and see things from their lens.
Take the opportunity to celebrate any wins with them if they’re getting more confident! Otherwise, help them to connect the dots, see things they previously didn’t, and align on improvement areas (for themselves, the manager, the team, or the company).
We have NPS surveys for customers in almost every business interaction. But as managers, when was the last time we collected our managerial NPS survey?
3. What do you think about XXX? (only when necessary)
To replace XXX with a recent new initiative/ project/ incident.
The goal is to manage change, proactively. You want to know how they are responding to the new changes. Instead of letting the after-effects take place organically, you can play a role in shaping the outcome.
By asking their opinions, you are preparing them for the changes. By having this discussion, you made them actively think about the issue and whether they should start taking any proactive measures. It helps them to claim ownership of the situation.
Throughout this discussion, you can identify blind spots, provide assurance, and help fill the information gap if necessary.
With this in place, it builds a habit for them to think and see beyond their immediate scope/role, developing their maturity over time.
Back to You
All the questions above are just… Well, conversation openers. It is up to you to bring new depths in your 1:1s with follow-up questions, insights, and replies.
Yes, it might be awkward in the first few rounds. But sit through it, as it only gets easier from here onwards.
When done right, you uncover issues before sh** hits the fan. You’re able to act proactively instead of firefighting. The best part — trust becomes a habit once a routine is formed with these questions. It gets natural for your reports to open up to you. But don’t ever break that trust.
If you cared to read this far, I bet that you are already a great manager, or going to be one! Share with me if you have any other questions identified as your must-dos! I‘m excited to try them out and update this living document with more data points from my future 1:1s.
PS: If it helps to know, the questions above covered all 12 needs for an employee to be engaged and productive, based on Gallup’s survey.
Shoutout to my dearest comrades who have spent countless 1:1s with me! You know who you are, and if you’re reading this, thank you for providing me with the training grounds to inspire these insights! ❤️
