We just interviewed eight engineers to learn how they view and approach one-on-one meetings. We asked them how they prepare, what stresses them out and what they expect from their managers. But more on that later.

There are so many different personalities on your team. They each like to be managed in different ways, receive feedback differently, and expect different outcomes from a one-on-one meeting with their manager.

Managers, if you take away one thing from this article, it’s this: your one-size-fits-all approach to management is killing your team. You’re going to end up with a group of disengaged people who will likely start responding to those recruiter InMails.

So…

😖 If you think that your employees should adapt to your management style…

😡 If you’re using the same talking points across all of your one-on-ones…

🤬 If you’re too busy to prep well ahead of time for your employees…

…Your team probably wants a better manager 😳

“But, wait, isn’t engagement an HR problem?”

No. It’s a you problem.

For the past 40 years managers accounted for at least 70% of the variance in employee engagement scores. You, the manager, have the most power to influence how engaged your employees are.

Don’t worry. The bad manager curse can be lifted. 🧙🏻‍♂️ But, in order to do that you’ll need to be willing to learn how to be a better manager — it’s a career change after all.

There are a lot of factors that play into being an amazing manager and a great place to start is by reflecting on your one-on-one meetings.

So let’s talk about that.

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To make your life easier, here’s a quick break down of content:

1. Commonalities among the 8 engineers interviewed
2. The 8 engineering personalities (we chatted with)
   🤡 The class clown
   🤫 The undercover whiz who puts their career path on the back-burner
   👨‍💻 The “10x” engineer who could care less about one-on-ones
   🤗 The new Team Lead who seems arrogant (but actually isn’t)
   🙅🏻‍♀️ The one that keeps their personal life private
   🤔 The one that asks thoughtful, pointed questions
   🐤 The think out loud, rubber duck-er, problem solver
   🧐 The mentor who doesn’t want to manage people
3. The actual questions your engineers want you to be asking in your one-on-ones (according to them)

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Commonalities among the 8 engineers interviewed

• They are feedback-oriented but want specifics. When getting feedback they all like to have concrete examples, whether it’s verbal or written so that they can improve their overall performance.
• Unorganized meetings are your fault. They expect that you, the manager, prepares for the one-on-one. Whether it’s completing next steps that were set in your last meeting or simply just coming prepared to give feedback, talk about company or team updates, you should be prepared… even if it’s “their meeting”.
• They expect you to prepare for meetings ahead of time. These engineers want ample time to review any questions or talking points you may bring up during the meeting. They want to come prepared to one-on-ones and expect that you give them the time they need to properly think through their answers.
• They don’t want to waste time (yours or theirs… and expect you to feel the same).
• They prefer to have one-on-ones outside of the office. If it’s a beautiful day, go for a walk. If it’s the ice age, a coffee shop will do. ☕️

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The 8 engineering personalities (we chatted with)

Below is a non-exhaustive list of personalities we’ve found in our interviews. If you talked to 8 more engineers I’m sure you’d find 8 more personalities.

Hopefully this will give you insight into who’s on your team… but nothing replaces actually talking to your team.

And, at the very end: Questions they want you to ask (+ bonus gift! 🎁)

№1 — The class clown 🤡

Whether it’s in a one-on-one, at the lunch table or just straight up yelling across the office, this individual finds every opportunity to crack a joke. They’re very focused on building meaningful relationships within the office and jokes are the best way they know how. This person is extremely confident on the surface, but can be insecure when it comes to their work. It’s that insecurity that pushes them to consistently overachieve because they want to leave the best impression possible.

Ideal one-on-one: 

Bi-weekly for 45 minutes outside of the office

What annoys them in a one-on-one…

• When the manager owns and dictates the agenda (they feel that it stifles learning and removes focus from the employee)
• When there is no radical candor (and as a result, not being able to build a meaningful relationship with their manager)
• Using Google Docs or equivalent to document one-on-one notes (they find it very unorganized and hate having to scroll through several pages to recap notes)

What bores them

• Being given feedback in a roundabout way
• One-on-ones that turn into status updates

What stresses them out

• Leading up to the one-on-one: The thought of getting negative or constructive feedback as a result of not meeting performance expectations
• Not having enough to talk about, leading to awkward moments of silence
• Fear of wasting their managers time by not being prepared enough for the meeting

How they prepare for one-on-ones

• Plan some talking points, while hoping that some talking points come up organically so the conversation still feels natural
• Think about areas in which they would like to receive feedback
• Reflect on the past week to provide their manager with any feedback

How they expect you to prepare for one-on-ones

• You should have a good understanding of the work that they’ve done since their last one-on-one
• When questions come up regarding performance, feedback and company-related news, the manager should be prepared to answer with detail or actionable advice
• You should tailor any questions you may have to this direct report. The meeting shouldn’t feel like a one-size-fits-all conversation.

What they find most valuable in one-on-one meetings

• Giving and receiving feedback
• Discussing overall happiness (from work they’re doing to their stress levels)
• Having uninterrupted time to build more trust and camaraderie with their manager

Questions they want you to ask them in a one-on-one

• What do you dislike most about your job?
• What area would you like to improve in? How can I help you do that?
• How do you feel about your workload for this sprint?

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№2 — The undercover whiz who puts their career path on the back-burner 🤫

A hyper-focused engineer with a passion for learning. This individual puts a heavy emphasis on quality and it shows in their work. They have a ton of potential but won’t necessarily step outside of the boundaries of their role unless pushed or asked to do so (even when they have the skills to do so). They’re extremely self-critical and, as a result, tend to speak up less even when they have an opinion that really should be heard. This undercover genius needs to be pushed out of their comfort zone to be able to reach their full potential.

Ideal one-on-one: 

Bi-weekly for an hour on a walk

What annoys them about one-on-ones…

• When the conversation feels forced
• When one-on-ones are too frequent (resulting in them not having enough to talk about)
• When the discussion isn’t documented anywhere, making it hard to reference later

What bores them

• Small talk that goes on too long
• Conversations that provide little-to-no value for both individuals

What stresses them out

• Getting negative feedback that’s focused around poor performance
• When questions get brought up during a one-on-one that weren’t on the agenda and not having enough time to think through the answer

How they prepare for one-on-ones

• Leading up to the one-on-one, as questions pop up they will add them to the meeting agenda
• Skim through the shared agenda and prepare answers for any questions or agenda items that the manager has added

How they expect you to prepare for one-on-ones

• Come with questions or talking points you’d like to discuss
• But, give them time to think about these questions, so they expect you to add in agenda items at least two hours before your one-on-one meetings.
• Be present, be open and be ready to answer questions about this individual’s performance or other topics related to the business

What they find most valuable in one-on-one meetings

• Feedback and constructive criticism as it relates to performance
• Having the time to learn about what’s going on in the business (both good and bad)
• Getting updates about the team if there are any changes and getting more context into the why behind that decision (letting someone go, someone leaving the organization, organizational restructure, etc)

Questions they want you to ask them in a one-on-one

• How do you feel about your performance relative to the rest of the team?
• What is something you’ve learned in the past month that you’d like to apply to your work?
• What is one thing that you would like to improve on between now and our next meeting?

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№3 — The “10x” engineer who could care less about one-on-ones 💻

This individual is a very technical developer, looking to automate anything and everything that they can to improve the product or process they’re working on. They’re extremely easy-going and are very enthusiastic about technology. They’re better in team settings, willingly sharing their opinions within this environment. But, as soon as they step into a one-on-one setting… All you’re going to get is crickets. This engineer loves to take time to think through problems in their day-to-day work, and that includes one-on-ones. You’ll want to provide this individual with agenda items and talking points prior to the meeting to be able to have a more productive, two-way conversation.

Ideal one-on-one: 

Monthly for an hour on a walk or at a coffee shop

What annoys them about one-on-ones…

• Poorly timed meetings.
• Being put on the spot with surprise questions
• Less than 3 days of prep time before the meeting

What bores them

• When the manager comes to the meeting without anything to talk about
• Small talk

What stresses them out

• Never stressed going into a one-on-one

How they prepare for one-on-ones

• Unless they have anything major to talk about, they will review the agenda set by the manager and be ready to address any questions or comments

How they expect you to prepare for one-on-ones

• Manager should come with some points to talk about (personal and professional growth, if the manager is unhappy with this person, etc)
• Come curious and ready to ask questions, otherwise you’ll likely sit in awkward silence

What they find most valuable in one-on-one meetings

• Growth conversations (they won’t be the one to initiate this type of conversation, but when it’s brought up, it sparks great conversations)
• When something is really bothering them, it’s a great time to bring things up and try to resolve the issue
• Although they find some value in one-on-ones, they get more value out of team meetings because they are more opinionated about how the team works together rather than themselves as an individual

Questions they want you to ask them in a one-on-one

• What are you most excited about working on in the next sprint?
• How do you feel the team is performing? What’s one thing we should continue doing and one that we should improve?
• Is there a process that you feel can be automated? What is it and how would you go about automating it?

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№4 — The new Team Lead who seems arrogant (but actually isn’t) 🤗

This engineer recently started leading a team of engineers. They’re an extremely extroverted, confident and vocal individual. This sometimes gives off the impression that they’re very arrogant and it can come off as intimidating to new faces. However, when you actually get a chance to speak with them one-on-one, you quickly learn that they’re super thoughtful, caring and is really trying to refine their management skills to be the best manager possible. This fashion-loving individual is extremely social within the organization, constantly making the effort to connect with people cross-departmentally and getting involved in every social activity happening at the company. When it comes to their work, they’re a go-getter and is constantly looking for ways to improve, as an engineer and a leader.

Ideal one-on-one: 

Once a month for an hour on a walk or at a coffee shop

What annoys them about one-on-ones…

• Having a meeting agenda and not sticking to it
• When the meeting becomes a one-sided conversation
• Being told how they should feel about a situation rather than being able to share how they’re feeling with their manager

What bores them

• When the meeting is used as an opportunity for their manager to receive status updates
• When a manager isn’t able to jump between light joking and radical candor during the meeting

What stresses them out

• The anticipation of learning how (or if) big changes on the team will affect their role
• Conversations about career growth and salary (if there’s misalignment in views, career progression, salary, etc.)
• Receiving negative feedback on their management skills

How they prepare for one-on-ones

• Review the agenda prior to the meeting and add notes or comments where necessary
• Sum up one good or bad conversation they recently had with a direct report to discuss and ask for ways they can do better next time

How they expect you to prepare for one-on-ones

• Be observant of how this individual communicates with their direct reports and be ready to answer questions related to their management skills
• On at least a quarterly basis, get feedback from direct reports on how this individual is doing as a manager and address any areas of improvement
• Be self-aware; make sure your communication fosters a safe space for open dialogue and that you’re having a two-way conversation

What they find most valuable in one-on-one meetings

• Conversations about personal growth
• Receiving advice on how to be a better manager and how to approach different types of conversations (PIP talks, providing feedback, ice breakers, etc)
• If this engineer feels like they have a weak spot, checking in with their manager to understand ways to improve

Questions they want you to ask them in a one-on-one

• What is your biggest challenge when it comes to managing your team?
• How do you feel your one-on-ones are going?
• Do you feel like you’re a good manager? Why or why not?

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№5 — The one that keeps their personal life private 🙅🏻‍♀️

This engineer is all business when they’re in the office. They are a strong believer that work and life should be two completely separate things and it reflects in their relationships. When in the office, they don’t want to talk about their kids, their weekend plans or anything else that isn’t related to the job at hand. When it comes to their work, they are highly driven by learning opportunities, whether it’s video tutorials, books, feedback from one-on-one’s or more, they love to learn. One-on-ones have proven to be a great opportunity to receive really detailed feedback for this engineer.

Ideal one-on-one: 

Bi-weekly for 30 minutes outside of the office

What annoys them about one-on-ones:

• Not having one-on-ones frequently enough
• When the meeting focuses on tasks that need to be done rather than the employee’s growth
• Small talk, especially questions like, “How was your weekend?”

What bores them

• When the conversation isn’t relevant to the work that they’re currently doing
• When feedback isn’t part of the conversation

What stresses them out

• Whether or not there’s enough time to cover everything they want to discuss

How they prepare for one-on-ones

• Take notes leading up to the meeting about things they want to talk about
• Reflect on the work they’ve done since the last one-on-one, what went well and what didn’t and share that during the meeting
• Create a list of languages and technologies they would like to learn with the intention of receiving resources to facilitate their growth

How they expect you to prepare for one-on-ones

• Prepare talking points related to learning opportunities and feedback
• If there are issues you’d like to bring up or feedback to provide, gather concrete examples that you can share

What they find most valuable in one-on-one meetings

• Feedback when it’s accompanied by specific examples
• When the conversation is related to something they’re working on/have worked on and there are learnings for them to take away
• Conversations related to learning opportunities and how they can continue to expand their knowledge

Questions they want you to ask them in a one-on-one

• What are some areas you would like to work on in the future?
• How would you like to use your education budget? Would you like me to suggest things to consider?
• What would you like the next step in your career to be? How can I help you get there?

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№6 — The one that asks thoughtful, pointed questions 🤔

This engineer is the methodical individual on their team. They take ample time to think through a problem or question and it shows. When they show up to a meeting, you better be prepared because they will come having thought through an issue from every possible angle and ask questions accordingly. As smart as this individual is, they can be very insecure about their skills and need that extra vote of confidence to make them feel secure in their role. They need to be reassured that they’re adding value to the team and the best way to get that is through feedback. When receiving feedback, they need it to be presented verbally and in writing so that they have something to reference back to in the future.

Ideal one-on-one: 

Bi-weekly for a half-hour at a coffee shop

What annoys them about one-on-ones:

• Not having an agenda or plan for the meeting (the conversation becomes disorganized)
• When the meeting gets canceled and not rescheduled for a while, resulting in them being treated as a performance review rather than a one-on-one
• When the manager shows up to the meeting with no knowledge of any of the work this individual has done (or was expected to do)

What bores them

• When a manager uses this time to sort through past conversation notes rather than coming to the meeting prepared
• When the conversation feels very repetitive and less valuable as a result

What stresses them out

• When they haven’t had much time to chat with their manager in between one-on-ones

How they prepare for one-on-ones

• Put together a list of everything they’ve been working on since their last one-on-one to keep their manager in the loop
• Have a list of any asks they have (vacations, work from home days, etc)
• Think of areas or projects in which they would like more feedback on

How they expect you to prepare for one-on-ones

• Have a centralized place where you can both share questions prior to the meeting to allow time for both individuals to prepare
• Come prepared; Have a good understanding of what they’ve been doing since your last meeting so that you don’t waste time trying to catch up during the meeting
• Make time for the meeting (do everything you can to avoid canceling or rescheduling)

What they find most valuable in one-on-one meetings

• Getting feedback on their performance, as well as feedback from their peers
• Getting clarification on what is expected of them and how they can better contribute to projects
• Learning about potential opportunities within the organization that can help expand their skill set and overall knowledge

Questions they want you to ask them in a one-on-one

• How would you approach tackling the challenges we’re currently facing on this project?
• What are you most proud of this past sprint?
• How do you feel about our one-on-one meeting frequency?

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№7 — The think out loud, rubber duck-er, problem solver🐤

This engineer is outgoing, “painfully” extroverted and very social. They feel very secure and comfortable asking questions when they are unsure about how to approach a problem. They work through problems by talking through ideas, whether it’s with another individual or a rubber duck; words work better than screens. As an employee, they are a very approachable individual who likes to socialize and joke around with peers.

Ideal one-on-one: 

Monthly for an hour outside of the office

What annoys them about one-on-ones…

• When issues have been brought up in the past and there are no updates from the manager
• Being asked the same questions at every meeting
• When a manager isn’t very receptive to talking through a problem or challenge this employee is facing

What bores them

• When the small talk at the start of the meeting isn’t genuine (feels like a forced dance that needs to be done to get to the good stuff)

What stresses them out

• The anticipation of having to voice a concern without knowing what the reaction of their manager will be

How they prepare for one-on-ones

• They will review the meeting agenda prior to the one-on-one and prepare an answer if required
• They get very wrapped up in their work and want to get as much done as possible so they put little-to-no preparation into their one-on-one meeting

How they expect you to prepare for one-on-ones

• If there’s a specific topic that’s been brought up and next steps have been discussed, action on those next steps before the meeting
• Come prepared to talk about progress as it pertains to the company, product, and the employee’s growth as an engineer

What they find most valuable in one-on-one meetings

• Conversations that focus on their place within the company, how their career will progress within their organization and what they need to accomplish to get there
• Setting milestones for a specific project or feature they’re working on to help guide how they’ll approach the task at hand

Questions they want you to ask them in a one-on-one

• What is a problem or challenge you’re currently facing?
• How do you feel about your performance since we last spoke?
• What languages or technologies would you like to learn more about between now and our next one-on-one?

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№8 — The mentor who doesn’t want to manage people 🧐

This engineer is very social, both in and out of the office. They’re very active in helping their team out in a mentorship capacity but would be miserable if they were put into a management position. They want to focus on their work and are keen to help others grow, they just don’t want to have to be accountable for their growth. They don’t want to deal with operation-focused tasks like salary negotiations, HR complaints, etc. When it comes to one-on-ones with their manager, they value this time A LOT! They view this time as an opportunity to receive valuable feedback.

Ideal one-on-one: 

Bi-weekly for 30 minutes outside of the office

What annoys them about one-on-ones…

• Not receiving clear feedback during the meeting
• When their career growth plan (within or outside of the org) is not clear
• If the manager does not create a safe space for the employee to feel comfortable enough to talk about things like growth, salary and more.

What bores them

• They love one-on-ones and don’t find them boring, but rather a valuable opportunity to discuss their path and performance within the company

What stresses them out

• Not having any agenda items to discuss and feeling like they have to force a conversation

How they prepare for one-on-ones

• In SoapBox, they will add agenda items prior to the meeting and add talking points to any items their manager has added to the agenda
• Come prepared to talk about at least one area in which they would like more feedback

How they expect you to prepare for one-on-ones

• They expect you to take one-on-one preparation seriously
• Have at least one piece of feedback ready to share with examples

What they find most valuable in one-on-one meetings

• Receiving and giving feedback
• Conversations revolving around career path and growth
• Learning how their manager feels about the company’s trajectory and the team’s overall progress

Questions they want you to ask them in a one-on-one

• How can I improve as a manager?
• What do you think is your biggest strength? Weakness?
• How do you feel you are performing against the goals we have set?

Questions your engineers want you to be asking in your one-on-ones

Below is a list of questions that you can share with your direct reports to help you brainstorm conversation topics for your next one-on-one. It’s a mix of questions from the eight engineers we interviewed, and from SoapBox’s Agenda Template library.

Questions you can ask:

• What do you dislike most about your job?
• What area would you like to improve in? How can I help you do that?
• How do you feel about your workload for this sprint?
• How do you feel about your performance relative to the rest of the team?
• What is something you’ve learned in the past month that you’d like to apply to your work?
• What is one thing that you would like to improve on between now and our next meeting?
• What is a technology or language that you would like to start learning more about?
• Let’s have a look at your goals and how you have progressed. How can I help you reach those goals?
• What was your work or non-work related highlight this past month?
• What, if anything, feels harder than it should be in your day-to-day work?
• How have you felt about my level of presence/support over the past month?
• Do you feel you’re getting enough feedback on your work? If not, where would you like more feedback?
• What’s one thing you’d like to do more outside of work this coming month?
• If there was one thing I could do differently to help you more, what would it be?
• One a scale of 1–10 how happy are you with your work-life balance? How can we get closer to 10?
• What are you most excited about working on in the next sprint?
• How do you feel the team is performing? What’s one thing we should continue doing and one that we should improve?
• Is there a process that you feel can be automated? What is it and how would you go about automating it?
• How would you approach tackling the challenges we’re currently facing on this project?
• How do you feel about our one-on-one meeting frequency?

Bonus! Questions your engineers will likely ask you

Part of being prepared for a one-on-one is being able to answer questions that your direct reports may ask you. This doesn’t mean that you have to have all of the answers right off the bat, but understanding things like their performance, what feedback you’d like to give them, and how you see them progressing at your organization are great pieces of knowledge to have going into each one-on-one.

Questions you can expect to be asked:

• What’s the area in which I can improve most? How can I do that?
• Have you seen me grow over time? In what ways?
• How am I performing relative to my direct team?
• Are there any major company updates that I should know about?
• I’m interested in learning more about [a specific language or technology]. Can we keep that in mind so that I have the opportunity to learn more about this in the next coming months?
• What peer feedback have you received that I can work on?
• Do I have any blind spots that I can improve?
• What are some areas that you think I will be working on in the future?
• What’s coming up in the future for our product? What languages or tech should I spend time learning about so I can work on it in the future?
• What am I doing well and what’s something that I can improve on? Can you provide me with examples?
• Here are some of the roadblocks and challenges that I’m facing with this project. How would you approach this problem?
• Where do you think we should be heading from a technology perspective as this project comes to fruition?
• What am I not doing currently that you think I should do more of? Can you provide me with examples and specific things that I can do to improve?
• What can I do to move forward with my career? What skills or technology should I be learning to achieve this next milestone?
• Can we go over the goals that we have set and talk about my progress?

What should you do now

You made it to the end of this article! Here are some things you can do now:

1. Our YouTube channel is full of tips on management skills and team building.
2. You should try Hypercontext to see how it can help you run a high performing org.
3. If you found this article helpful, please share it with others on Linkedin or X (Twitter)