The Ultimate Guide to One-On-One Meetings for Managers

All managers struggle with the fine balance between doing work that achieves short term goals vs. investing time in activities with long term benefits. 

Output that’s immediately visible may give a feeling of satisfaction in the moment, but it soon fades away and demands more energy to keep up with the pace of growth and scale of the company. Focussing too much on progress in the short term eventually slows down every manager in the long run. 

Energy spent in growing business may help you achieve some outcomes, but the same energy invested in growing people can produce remarkable results. 

What you quickly realize as a manager is that the single most effective way to setup a team for success in the long run is to focus on the people. - Julie Zhuo

Navigating the path to each employee’s success is not trivial and requires a commitment to be patient, dedication to push ahead despite failures and devising unique ways to inspire and bring out the best in every individual. It’s a slow process, but done right it can be your ultimate advantage as a manager.

What you need as a manager is to utilise the power of one-on-one meetings by designing them with a clear purpose in mind. 

Without a purpose-driven approach, every one-on-one meeting sooner or later turns into a time-wasting mandate where neither party adds or derives any value from the discussion. It’s a mindless execution of duties as opposed to a benefits-driven exercise. 

What’s the purpose of one-on-one meetings

One-on-one meetings designed to address the core needs of your direct report works best since they instantly connect to every individual at a personal level. 

Before you put together an agenda for a one-on-one meeting or scrounge for a list of questions, the really important question to ask yourself is “what do people really need from me as a manager?”

While core needs may vary across individuals, here are the 5 things most people desire from their managers:

1. To be seen

These are not external motivators like recognition, rewards or promotion. It’s the knowledge that you as their manager genuinely care about them. Do you notice when they are feeling sad, miserable, joyful, distracted or angry. Do you care enough to recognise subtle changes in their behaviour?

Observing even small things like “they did not say hi” when they entered the one-on-one meeting like they typically do and asking “Hey, it appears to me that you are upset about something. Is everything alright?” goes a long way in building a meaningful connection. 

It’s a small observation, but indeed a very powerful one to communicate that you care enough to take note of their feelings. 

Great managers notice when your normal energy level changes, and will hopefully care enough to ask you about it - Camille Fournier

2. Treated as an individual 

Every person is unique. 

Work that excites one person may annoy another and what’s easy for some may require others to stretch beyond their comfort zone. Each individual also has different life goals, learning practices, productivity measures, interest levels and tolerance limits shaped by their own environment and experiences. 

Putting everyone together and packaging them into a single unit without taking time to understand their unique traits is the most ineffective way to utilise the strengths that every person brings to the team. 

As a manager, your direct reports want you to be curious about them as an individual. There’s a certain sense of security in the knowledge that you are being seen for who you are and not an imagined persona created by your manager in their minds. 

3. Supported in their growth

Human beings are designed to find joy in building new skills and strengthening existing ones.

People expect their managers to be candid and speak openly not only when things are going well, but also when things are not going as expected. No one wants a manager who ignores the conflict with the hope that it will disappear on its own instead of handling it maturely. 

They look for support from their managers in their desire to grow by connecting how their work is aligned with the skills they need to develop, the resources they need to develop those skills and the mechanisms they need to put in place to measure progress along the way.

4. Empowered to think 

Everyone at work craves the satisfaction that comes from finding their own solutions as opposed to being told what to do and how to do it.

Your direct reports want you to empower them to put their critical thinking skills to use, challenge them to think differently and feel comfortable in making their own decisions. 

Human beings have an innate inner drive to be autonomous, self-determined, and connected to one another. And when that drive is liberated, people achieve more and live richer lives - Daniel Pink

There’s a ton of difference in telling: 

“Let’s have a demo of this product on Thursday” 

vs asking

“When do you think will be a good time to demo this product”

They desire responsibility with empowerment, not without it. 

5. See you do things you say you will do

Managers who say one thing and then do another without bothering to explain or worse never act on the things they say they are going to do loose the trust of their people. Soon people realise that it’s all in saying and nothing actually gets done. 

People don’t want managers who speak big words or try to paint a pretty picture by making false promises. They want someone who speaks the truth, lays down the reality of the situation and makes only those commitments they wish to put to action. 

With the understanding of what your direct reports need from you as a manager, let’s structure the one-on-one meetings aligned to their core needs.  

5 components of effective one-on-one meetings 

Engage with your direct reports in 1-1 meetings and carve out a path to each individual’s success by

1. Making observations
2. Exploring curiosity
3. Discussing growth
4. Encouraging a shift in mindset 
5. Taking action

Put these 5 components into practice:

1. Observations: Connect beyond words 

Observations are non-verbal cues that form an important part of effective listening. 

To connect with your direct report, you need to go beyond words to these signs - watch out for their emotions, body language, tone, energy level and make a note of anything unusual from their usual behaviour. Even a small change like "not showing enthusiasm to engage in a conversation" could be a sign to dig deeper. 

Questions to ask yourself

1. What was their energy level
2. How was their tone during the conversation
3. What did their body language indicate
4. Anything unusual that you noticed

How to make observations in one-on-one meetings

Observations require a high degree of presence of mind as well as the body. Make sure you are leaving all your other commitments and worries at the door to be fully present and engage in a productive 1-1 conversation. 

Disconnect from the phone - it can distract you without your awareness making you incapable of observing anything useful about your employee. 

For true listening, no matter how brief, requires tremendous effort. You cannot truly listen to anyone and do anything else at the same time - M. Scott Peck

Take note of these observations at the end of the meeting. Capture as many details as possible. Even minute details can help when/if you plan to have a conversation. Don't rely on your memory - it's limited and can be put to better use elsewhere. 

In some cases, it’s best to not talk about these observations during the one-on-one meeting, unless it's something very awkward and demands immediate attention. 

Take time to explore your observation further. Use informal chats and other interactions with them to determine if your observation was a one-off thing or something noticeable demanding attention. 

Depending on the severity of the observation, either have a chat right away or talk about it during your next one-on-one meeting. 

Make sure to mention it as an observation instead of passing an opinion or a judgment. There’s a difference between saying “You look upset” vs “Why are you upset.”

2. Curiosity: Learn about your employee

Curiosity is the exploration journey that you can take with your direct report as an individual - personally as well as professionally. 

It’s the path to learn about their background, experience, aspirations and discover their strengths. By investing in this knowledge, you can align different opportunities with strengths and personalise your conversations to bring out the best in each individual.  

The most important thing you can do for your team collectively is to understand what growth trajectory each person wants to be on at a given time and whether that matches the needs and opportunities of the team. To do that, you are going to have to get to know each of your direct reports at a personal level - Kim Scott

Questions to learn about your employee

1. What prevents you from doing your best work
2. What makes you tick
3. What kind of work helps you stretch your limits 
4. What would you like to do more, stop doing and do less to be effective in your work
5. What have you learnt recently 
6. How do you view team dynamics [Is it a positive or negative source of energy]
7. Who do you find most helpful in the team [why]
8. How do you measure your own progress
9. How do you strive for continuous improvement
10. What catches your attention 
11. What seems like a complete waste of time at work
12. What bothers you about work
13. How do you suggest we communicate to be in alignment [progress, concerns, how to reach out, what needs my attention] 
14. What's your opinion about the processes followed in the team
15. What's the one thing interesting about you outside of work [any information that helps you get a peek into their personal life]
16. Which book, blog, video or podcast inspired you recently [what specific information inspired them]
17. What are your most productive hours [What enables that level of productivity]
18. What's your favourite movie [share yours and why you like that movie]
19. What's your source of inspiration
20. What are your life goals

How to explore curiosity in one-on-one meetings

Learning about each individual requires asking good open-ended questions with the idea to enable deliberate thinking and engage in a meaningful conversation instead of asking questions that lead to a simple yes/no. 

These questions can be covered over multiple one-on-one discussions and some can be repeated over a period of time to understand how they are evolving as an individual.  

The most important part of being curious is to ask really good follow-up questions to connect with and understand each person at a deeper level. 

3. Growth: Carve out a path to strengthening skills

Growth discussions are focussed on sharing and receiving feedback with the objective to understand what’s going well and what can improve. It’s a necessary tool for continuous improvement. 

Regular check-ins on these discussions enable your employee to be in alignment with their goals, understand how they are progressing against them and what else they can do to strive for excellence. 

As a manager, you need to help your employee grow by carving out a path to strengthen existing skills and build new skills in their role. 

Questions to engage in a growth discussion 

1. Use Feedback Equation to engage in a growth-related discussion
   Feedback Equation = Describe the situation + Talk about your observation + Describe the impact + Ask Open-ended question + Silence
   E.g. For missed delivery deadlines, state "I want to talk to you about your last 2 projects [situation]. I noticed that you missed delivery timelines on both the projects [observation]. When we miss to deliver the project on time, it not only reflects badly on the team, we also lose our chance to get the product out in the market on time [impact]. What do you think? [open-ended question]. 
   Then embrace silence. It may be awkward to be silent for even a few seconds at first, but silence is a very powerful tool to let the other person chew on the information and express their point of view.
2. What level of clarity helps you in doing great work by having an opportunity for enough mental stimulation
3. What practice helps you learn something new daily to build the skills important in your role
4. What challenges do you see in applying what you are learning 
5. How do you seek help to grow in your role
6. What's the conflict in your mind regarding work, priorities, expectations or any other point of concern
7. How do you learn from your mistakes and failures
8. What skills are you currently focusing on 
9. How do you see your individual goals as an extension of the team's goals
10. How can you contribute to the growth of your team members
11. What's your most valuable skill that can be useful to others in the organisation [by teaching this skill, you will strengthen it further]
12. What can I do more to help you be effective in your work
13. What about my behaviour bothers you and impacts your work
14. Share with me one thing I did well and one thing I did wrong recently that impacted you [even a small thing is fine]
15. How do you view your relationship with other teams and their members [getting their views on cross functional team collaboration]
16. What value do you derive from engaging with employees beyond your team [other functional units as well]
17. What challenges do you face when working with other cross functional units [and how do they solve these challenges]

How to discuss growth in one-on-one meetings 

Feedback should be delivered in a constructive manner with the intent to learn more about the employee instead of jumping to conclusions about their abilities. Use a collaborative approach to seek solutions together instead of simply sharing your advice.

The single most important thing [you can do] is to shift [your] internal stance from "I understand" to "Help me understand." Everything else follows from that. . . .Remind yourself that if you think you already understand how someone feels or what they are trying to say, it is a delusion. Remember a time when you were sure you were right and then discovered one little fact that changed everything. There is always more to learn - Douglas Stone

Ask really good follow-up questions to enable them to inquire and learn more about themselves. Most people do not actively think about these areas. So, when you bring up these questions, they need a moment to collect their thoughts before speaking up.

When receiving feedback, do not react or try to justify anything. Definitely ask questions to understand it better and take time to chew on it later.  

4. Coaching: Enable a shift in mindset 

Coaching is a means to drive autonomy within the team by enabling your employees to solve problems on their own, take initiative, make decisions and develop critical thinking skills.

The coaching mindset requires you to shift from giving answers to enabling your employees to find solutions on their own. It's difficult to resist what you know and it may seem to slow you down, but it will speed up things in the long run. 

Questions to enable learning and solution mindsets

1. What prevents you from moving forward
2. What can you do to change your current situation
3. Why do you think this is the only possible path
4. What will be the effect of staying where you are vs taking action
5. What does this situation teach you about yourself 
6. How do you plan to solve this problem
7. Tell me more about your thought process
8. Describe this issue you are facing
9. What are some of the solutions you have tried
10. Where can you find more information on this idea
11. Share with me your thinking that went into designing this product
12. Who can be helpful to share ideas on this work
13. Explain how you intend to grow in your role  
14. What resources do you need to find solutions

How to coach in one-on-one meetings

Coaching requires resisting every cell in your body that wants to spurt out advice and instead ask questions that will make your direct report shift from problem to solution mindset.

It’s absolutely fine if they aren’t able to think through solutions in the moment. Give them time, ask them to work on it, speak to others and then connect later to discuss further. 

Coaching requires patience.   

5. Execution: Turn intent to action 

Execution requires establishing the importance of one-on-one meetings and demonstrating your seriousness to make them effective.

One-on-one meetings become ineffective when there’s discussion without action. It’s great to discuss ideas, but if those ideas are not implemented, they do not add any value to the discussion. 

How to turn intent to action in one-on-one meetings

An important element of turning intent to action is to summarise the key takeaways, clearly state the action items with their owners and set aside a date to connect/update on them. 

Action item1, owner, date to connect

Action item2, owner, date to connect

Action item3, owner, date to connect

...

By setting expectations in the form of action items, you leave less room for confusion later.

Document each action item, setup calendar reminders to connect on them and encourage your employee to do the same.

After a few initial discussions, invite your direct report to contribute to the agenda. It will help them think beyond their day-to-day work to the areas they need to invest in and learn how to manage up to take charge of their own growth and success instead of relying only on their manager.

Also published here.