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Building rapport can take time and is often hard to do during designated meetings or video calls. Icebreakers can take away some of the awkwardness by offloading the creative curiosity to a lighter question that gets the conversation juices flowing. Adding variability to these questions keeps things easy and fun and you're likely to learn new and interesting things about your team that you otherwise might not have.
Pick a topic of the week and design questions around it, or choose from a list of questions to ask in a 1:1 meeting online.
The evidence is clear that frequent and productive conversations about individual and team goals need to happen on a weekly basis. Goal check-ins don't have to be an in-depth review, but they do need to happen very often. The frequency increases attention, information retention, and accountability for all.
A quick green/yellow/red scoring or check-in on your work OKRs/goals should give you the proper framing for the rest of your week.
The power of this question comes from the follow-up.
Let's pretend the answer to this question is "7/10". The context of why anyone said 7 is helpful, but it's not always actionable. Following this discussion with "What do you think would make you an 8/10?" gives you a more actionable road map of what we need to do first to positively impact this person at work.
Often you'll find a bunch of little quick wins that can add up in big ways to impact the morale of your team.
Before feedback is a habit, it's often awkward and painful for everyone.
We've found creating an explicit expectation and time for it enables more feedback to happen. We're breaking the ice with their feedback for you. This will help you model how to receive feedback and turn it into something positive.
While the previous question is about gathering data on yourself, and modeling how to receive feedback productively. You should not gloss over the fact that you're now modeling how to give high quality feedback.
Spend the last 1-5mins reviewing any next steps. Document these somewhere (or in a meeting tool built to track next steps.)
Each next step should have a clear due date and a directly responsible person assigned to it. The extra clarity documented now helps foster a culture of accountability later as you should review all outstanding next steps at the start of your next meeting.
Setting the frequency of this meeting to weekly means you'll always have natural time to sync up on these outstanding topics without feeling the need to nudge, pester, and micromanage.
About 1/4 of managers find developing a clear vision and strategy to be their largest challenge.
Often managers find immense value in sharing that burden (or opportunity) with their team. Visions, strategies, and goals should change with new data and ideas. Your team should be the source of the majority of that new information. By turning this conversation into a monthly discussion with each report you'll be generating themes and ideas as you prepare for that next quarterly planning session.
Take notes, ask why, and set aside time at the end of the quarter for the entire group to bring the vision together.
When it comes to supporting career development and performance, 14% of people agree it’s where their manager needs to improve. Similarly, 15% of managers find it to be their single biggest challenge; and after seeing the reasons why your team is quitting, the cost of that, and the impact a great 1:1 can have towards retention, it should be a no-brainer why bringing up this topic monthly/quarterly can lead to increased retention on your team.
The goal of having this conversation is to build and evolve a roadmap for this person's career at your company. Find and develop projects that they'd be great at and allow them to unleash more of their passion during their day-to-day.
While you might feel you have goals covered with the weekly questions, this question is more about coaching. By requesting an area of focus for the upcoming month you get an invitation to narrow the feedback you'll share in the following meetings to a specifically identified area of improvement.
You should think about helping identify potential areas for improvement by looking at historical performance or projects that you can use for learning.
Often people can have the wrong idea about 1:1s from their previous workplace or manager — For some, they consider it to be an annual review, while for others it’s the weekly, bi-weekly or monthly meeting that employees have with their manager.
Use your first one-on-one to reset expectations on these meetings and how they should be run. Some messages to consider sharing include:
One-on-ones are a type of meeting held between a manager and their employee, often on a routine cadence that involves discussing growth, performance, development and motivation. Both people have a responsibility for the agenda, however it's the direct report who should eventually take it over.
A dependable, weekly routine cadence is the consensus on the most valuable frequency.
Understanding both party's communication styles and preferences can sometimes take time. It might be helpful to be upfront about any desires or patterns you've noticed about yourself — and ask for the same from the other person. Do you prefer email? phone calls? chat messages? Do you send email after hours or schedule it for the next day?
It turns out people have very different preferences when it comes to feedback. While this question can help you get at the ideal form of feedback to give in a 1:1 the main benefit is setting the expectation that it's going to happen.
Whether or not you use the full hour, you're going to want to make sure you have enough time to get to know each other better and understand how you can work best with one another. At this point in time, your direct report has likely gone through the hoops of orientation for their first week, learning about the company, how each team operates, etc. So this time should be focused more on your relationship with one another.
Maybe you touched on this a bit during the hiring process, but if not, this is a great get to know you question. Maybe you have common interests, and maybe their interests can prove to be valuable for the company. Either way, breaking the ice by talking about yourselves and spending time getting to know one another is super important for building rapport from day one.
Learning about one another's preference is a great way to make sure that nothing falls through the crack. Keep in mind that this isn't a one-size-fits-all answer. Where and how you communicate can be easily broken down by what's being communicated:
Remember that this is a get-to-know-you meeting so you should both be answering this question.
Are they a morning person? Is the time of day less relevant, whereas the location is more important? Understanding when and where your direct report is most productive will help you avoid interrupting that time, whether it's through meetings or from popping by their desk.
Start off the relationship by letting your direct report know that you care about what motivates them. If it's possible to have them focus on the work that excites them the most, they'll be more engaged at work.
Your direct report doesn't need a very specific answer to this. However, getting a better understanding of their bigger goals will give you a compass for areas you can coach them in, projects you can include them on, and generally give them opportunities to work towards their career goals.
At the end of the day, you should be rooting for your direct report to achieve those goals, whether or not it's at your company or not. This mindset will help you build a truly awesome relationship between you and your direct report.
A great book that many professionals look to when starting a new role is The First 90 Days by Michael D. Watkins. It's a book that helps you plan out your first 30-60-90 days at a new company.
When you're able to break up your onboarding into these three milestones, it sets you up for success. So, planning and understanding what success looks like for your direct report's first 30 days on the job is a great way to collaboratively plan 1-3 tasks that will help them reach their 30-day goal.
When you're able to help a new employee build confidence and build it fast, they'll feel more comfortable and excited to come to work every day!
End off your first one-on-one by deciding how frequently you'd like to meet and for how long. Remind your direct report that this isn't set in stone; If you need to increase or decrease the frequency or length, you can do that over time. But, it's important that you decide on when your one-on-ones will be. Try deciding on the following:
Ending off your first one-on-one with deciding on when you'll meet next is a great way to give you and your direct report something to look forward to post-meeting.
Why have 1:1s weekly?
If you've got a team that is small enough (around 5 people) or you have a team whose roles are different. You'll want to consider a weekly 1:1 meeting to help them perform to their fullest. If you have a larger team doing very similar roles monthly 1:1s might be right for you instead.
Why one hour?
At the start of your relationship, it's usually good to spend more time together building trust and rapport, helping with onboarding, and getting feedback flowing. It's also better to overbook time and regain 20 minutes back in your days, versus rushing through the agenda.
Often the best way to kick this off is to say "I'm going to book this for 1hr and we can always leave early. In a few weeks, we can adjust this to 30 or 45 minutes if we both agree it's the right call."
It’s always good to break the ice with something easy. What's the best thing that happened (personally or professionally) for each of you? Be curious: Why was it the highlight?
Managers: Be vulnerable first! Share your lowlight and explain why it sucked. When you open up first, it makes it easier for direct reports to open up to you too.
It’s good to keep your goals at the top of the agenda because it focuses your week towards the things that should matter most. If you feel like these goals don't matter weekly, maybe you need different goals?
Think about it this way: If you talk about your goals weekly, then you have 52 chances each year to make the adjustments needed to hit them. If you only talk about them monthly, then you only have 12 chances. Wouldn’t you rather have more?
The previous two questions should set you up nicely to discuss blockers that exist. Keep in mind that this isn’t just about blockers your direct report is facing, it’s also about the things they can do to better unblock you.
This question gets at the same answer in an indirect way: Addressing "known problems" versus "unknown problems". This question offers a great opportunity for you to discover and discuss any issues that need to be solved.
The unfortunate truth of management is people can be intimidated by you, and therefore you'll get less and less feedback. This sucks for your personal growth. The best way to change that is to address it head on and ask the question.
If you keep hearing "no, all good" you might want to read up on psychological safety.
This is a great way to end a 1:1. Not because of their answer, but because of the follow-up.
For example, let's say they say "7." You say, "Awesome, why?" And they'll tell you. The real super power is asking, "What would make it a 7.5 or 8?"
Let's be real, not everyone can be a 10/10 every week. And jumping from a 7 to a 10 means that all problems have gone away. But getting to a 7.5? All that needs to happen is to get rid of that nagging little thing.
That's a win. That's likely something you can help get rid of between this week and the next. Do that enough times and your team will feel lucky to have you as a manager.
Why have 1:1s monthly?
If you lead a larger team of people who are doing similar roles, monthly one-on-one meetings are great. If this is the case, don't forget to still sync up between meetings via other communication tools.
Why one hour?
If you only meet once per month, there's likely a lot to talk about between each 1:1. By scheduling an hour for this meeting, you'll give yourselves the time needed to work through the meeting agenda and have meaningful conversations.
It's always great to start every meeting off on a positive note. Maybe they completed something at work that they're extremely proud of and excited to share with you. Celebrating workplace wins is a great way to motivate your team.
Asking about a personal highlight also offers some great benefits. First, it works as a great icebreaker, easing you and your direct report into the meeting. It also allows the opportunity for each of you to learn something new about one another!
Remember that this is a two-way question. You should both come prepared with an answer.
It’s good to keep your goals at the top of the agenda because it allows you to focus on how you can best move the needle. If your direct report isn't feeling great about the numbers, maybe they're running into a lot of blockers, or they weren't realistic in the first place.
When you're able to discuss your goals on a frequent cadence, it allows you and your team the flexibility to pivot and/or improve processes.
Whether it's processes that need improving or something is going on in their personal life that requires them to spend more time working remotely; This question offers a great opportunity for you to discover and discuss any issues that need to be solved.
This question is open-ended enough to allow for a wide range of conversations to spur, from growth-focused ones to workplace culture improvements.
As a leader, you want to know whether or not your team feels supported. After all, employees feel more motivated and engaged in the workplace when they feel like they're heard and cared for.
This is a great way to ask for specific feedback from your direct reports. Maybe they want to meet more frequently, or maybe they're happy with your level of support. You won't know until you ask (and continue to ask!)
This is a question to ask direct reports. For any employee, upward feedback can be scary and intimidating. However, using a word like "experiment" feels less like a demand or that something is wrong. Instead, it gives off the impression that you're more open to changing things up. This makes it easier for direct reports to provide valuable feedback.
During this conversation, be curious. Dig for more information. Most importantly, be supportive. Once you receive an answer, make a small commitment and be sure to follow-through. Then, when you meet again a month later, you can ask them how they felt about the change.
Similar to the previous question, this is another way to help direct reports feel comfortable sharing upward feedback with you. If they don't feel supported enough, a consistent stream of feedback is a great way to ensure that they feel this way.
However, remember that every direct report is different, so what is considered frequent or enough for one, could feel very minimal for another. That's why it's so important to add this agenda item to every one-on-one meeting across all of your direct reports.
This is a great question to end off every monthly one-on-one because it gives you a guaranteed talking point for your next meeting. If a direct report shares that they'd like to network more in the next month, it gives you an opportunity to introduce them to valuable and relevant professionals. After a month passes, you can ask, "What was the most memorable conversation you had this past month with people you networked with?"
On the flip side, they can share that they'd like to dance more outside of work. Not only will it offer you a fun and personal talking point for your next one-on-one, but you'll also learn a little bit more about their interests outside of work.
If you manage a remote team, you know that building rapport is essential to a cohesive and productive work environment. And while there are many ways to build rapport, one of the most important is the regular one-on-one meeting. This document will show you exactly how that meeting should go down.
One-on-one meetings are a chance for you to check in with each of your team members individually, and to get to know them on a personal level. This is important not only for building rapport, but also for getting a pulse on how they're doing both professionally and personally. This is important because it helps you create a team that feels comfortable and supported, which helps them do their best work.
So, if you manage a remote team, make sure to set aside time each week for one-on-one meetings. Here's a quick rundown of how to make the most of your one-on-one meetings:
How long, how often, and who's invited?
To get the most out of your one-on-one meetings, they should be held weekly and should last around 60 minutes. Just you and the team member you're meeting with should be in attendance.
This is a broad question that can help you get a sense of how your team member is doing both professionally and personally. If they're struggling with something, this is a chance for you to provide support. If they're doing great, this is a chance for you to celebrate their successes.
Getting to know your team members on a personal level is important for building rapport. This question can help you learn more about their interests and hobbies, and can help you find common ground.
This question helps you stay up-to-date on what your team member is working on, and can help you provide support and feedback.
This question helps you understand what's going well and what's not going well for your team member. If they're struggling with something, this is a chance for you to provide support. If they're doing great, this is a chance for you to celebrate their successes.
This question helps you stay up-to-date on what your team member is working on, and can help you provide support and feedback.
This question gives your team member a chance to identify any areas where they need support. It also gives you a chance to offer help and guidance.
This question helps you gauge how your team member feels about the level of communication. If they're not happy with it, this is a chance to make changes. If they are happy with it, this is a chance to reinforce the importance of communication.
This is an open-ended question that allows your team member to bring up any concerns they have that haven't been addressed yet. It's also a chance for you to provide support and guidance.
A skip level meeting is a one-on-one meeting where an employee meets with upper-level management, bypassing their direct manager. In other words, an employee is "skipping" a level of management to connect directly with senior leaders.
What is the goal of this meeting?
The goal of skip-level meetings is: - For employees: To learn about company goals, objectives, and strategies from senior leaders in an organization. - For senior leaders: To create a shared space to discuss career progression, professional goals and exchange feedback with employees.
Skip level meetings are not intended to dig up dirt or spy on middle managers. If there are any issues, they should be handled between the employee and their direct manager.
This is a great opportunity for employees to get a deeper understanding of company goals and overall strategy from someone outside of their direct team. In many cases, senior managers have more information at their disposal about things like how the work of one team will work in tandem with another, enabling everyone in the organization to collaborate on company-wide goals.
Growth conversations don't have to be limited to employee-manager relationships. When employees feel that their growth is a priority for the company as a whole, they become more motivated and engaged in their work. They feel like they have more than just one person (or team) in their corner to get them to where they want to be professional.
Asking employees for the why is also a great way to dig deeper into what excites them. Maybe someone on your marketing team has decided that they want to start transitioning into a product role. If there's an opportunity to build up their skills in that domain and a need for it in your company, it should be a no brainer. Hard skills can be taught; Soft skills, work ethic, and culture fit can't.
This is your opportunity to gather useful information on how things are going in the company, straight from the front-line. Leaders higher up may know more about the health of the business, fundraising updates, and how much money is in the bank... But the front-line employees are the ones who feel organizational pains the most, from a toxic culture to workplace silos.
Skip-level meetings offer a great opportunity for senior management to learn more about these issues straight from those who experience them the most.
However, be mindful of how employees might feel, and aware that they might have difficulty sharing opinions and being vulnerable with you. You're their boss's boss. It’s your job to foster an environment of open, honest communication by setting the pretext for your one-on-one before and during your meeting.
Performance review meetings are an important part of every employee's development. They give employees the opportunity to assess their performance, receive feedback, set objectives, and align their priorities with their manager's. This meeting is a great way to ensure that employees are meeting their objectives and identify areas for improvement. This is also an opportunity for employees to ask questions and clarify any concerns they may have.
Why run this meeting?
Quarterly performance review meetings are a great way to:
How long should it take? When should you run it? Who should attend?
This meeting should last for 60 minutes and occur quarterly. You should run this type meeting with every employee on your team. Only yourself and the employee being reviewed should attend.
What should you talk about in a quarterly performance review meeting?
Review the employee performance data collected in via surveys, one-on-ones with others, project management systems, and self-reports.
Self assessments and peer feedback are a great way to:
Reviewing performance against objectives is a great way to:
Highlighting wins, strengths, and opportunities to grow is a great way to:
Identifying areas for improvement is a crucial part of the performance review process. It will:
This is an important part of the performance review process. It: