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A Quick Guide to 1-on-1 Meetings
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A Quick Guide to 1-on-1 Meetings

Such a personal meeting may seem stressful, but it doesn't have to be.

September 22, 2020
Rob Lennon
Customer Education Lead at Hugo
Marketer and author with experience spanning a diverse 16 years in retail and SaaS startups across healthcare, mar-tech, and ad-tech, and productivity software sectors.

Looking to run 1-on-1 meetings with your team that build connections and get things done?

Or, perhaps you’re on the other side, wondering how to best prepare for 1-on-1’s with your boss.

Either way, we’ve got you covered with our Quick Guide to 1-on-1 Meetings.

1-on-1 Meetings For Managers:

Setting Up Your First 1-on-1 Meeting With an Employee

Whether you’re new to running 1-on-1 meetings, new to an organization and just meeting your team, or welcoming a new hire, first impressions are always important. Your first 1-on-1 meeting with an employee is your chance to set the tone for your work relationship moving forward.

To ensure success, make sure you clearly convey what the meeting aims to achieve. 1-on-1 meetings are a rare opportunity to provide individual guidance, support, and insights for team members and their projects. This shouldn’t be a meeting about updates and progress, but rather a space to connect about concerns and needs.

As a result, your meeting invitation should offer a suggested agenda (here are some great 1-on-1 meeting templates if you need one) and include a few 1-on-1 meeting questions as prompts.

Ask your team members to add to and adjust the agenda to include their concerns. Meeting software like Hugo can create interactive agendas that both parties can change as needed. Additionally, ask for team members’ input on the desired length and frequency of their 1-on-1 meetings.

1-on-1 Meeting Questions

Not sure what questions to ask? Here’s an abbreviated list from Inc’s 25 Questions to Ask in One-on-One Meetings:

  • What do you feel best about in the work we’re doing?
  • How can we set each other up for success?
  • When did you recently get an opportunity to learn and grow?
  • What should I know about you that would help me support you better?
  • What are you doing here that you feel is most in line with your long-term goals?
  • What are you doing here that you wish you could set aside so you can concentrate on your most important work?
  • Is anything holding you back from doing the best work you can right now?

Include a few of these questions in your meeting invitation or agenda to help team members prepare. Save the rest for the meeting itself. You don’t have to use them all, of course—just the ones that make sense for your team and projects.

How to Start a 1-on-1 Meeting

Fortunately, having a shared agenda makes starting 1-on-1 meetings a snap. With a meeting agenda in hand, the only real concern is setting a welcoming tone that makes it clear to your team member that they are free to speak openly about their concerns, goals, and needs.

Consider starting by asking how your employee is doing overall and really listening to their answer. You can also share some thoughts about an aspect of your own work that you’re grappling with at the moment. Sharing details like this helps build understanding and trust, which are great foundational pillars for team success.

Once everyone seems comfortable, simply follow the 1-on-1 meeting agenda to keep the ball rolling.

1-on-1 Meetings For Team Members:

How to Prepare For a 1-on-1 Meeting with Your Boss

So, your boss scheduled a 1-on-1. How can you go about preparing for the meeting to get the most out of it?

Ideally, you’ll receive an agenda before the meeting date. Take time to look over the agenda and consider the answers to any questions it presents. Additionally, ask yourself what isn’t included in the agenda that you think should be there. For example, is there a part of your work that is taking up a lot of time and energy, but isn’t represented by any agenda items? This is probably worth including in the meeting.

1-on-1 meetings are a great place to bring up roadblocks and frustrations. Just be sure to come with both a clear description of the struggles you’re facing as well as an open mind to feedback

1-on-1 Meeting Agenda

If your supervisor asks you to provide a meeting agenda, don’t panic. Simply browse free 1-on-1 meeting templates online to help you get started.

As you consider the pain points you’d like to discuss, take time to think about the sources of these challenges. The clearer a picture you can paint for your manager, the better. You may also want to try ranking your concerns in order of urgency. That way, if you’re short on time, your most important items will be clear.

If you’re unsure whether your 1-on-1 meeting agenda meets expectations, ask if you can share it ahead of time and get feedback. Ideally, meeting agendas are collaborative, living documents between managers and team members that change to meet needs. Don’t be afraid to open the door to pre-meeting agenda review and editing.

Having a Successful 1-on-1 Meeting with a Manager

To make the most of your 1-on-1 meetings, it’s important to remember their purpose. 1-on-1’s are all about personal connection and problem-solving. So, open up! Be honest and open to ideas. Use your agenda to convey your goals and priorities and ask for the things you need to succeed.

1-on-1 meetings can become a significant source of innovation, professional growth, and organizational success. Approach them with an openness to connection and feedback, and you’ll both leave these meetings energized and informed.


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Rob Lennon
Customer Education Lead at Hugo
Marketer and author with experience spanning a diverse 16 years in retail and SaaS startups across healthcare, mar-tech, and ad-tech, and productivity software sectors.

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