How to Hold Better 1:1 Meetings with Your Remote Team

In this time of increased remote work, maintaining connections and building strong organizational culture is more important than ever. One of the best ways to achieve this with remote employees is through regular one-on-one meetings. 

One-on-one meetings ensure consistent, real-time communication between an individual team member and their leader, providing a space for open and honest discussion along with robust exchanges of ideas and creative problem solving.

However, 1:1 meetings don’t just happen on their own, and their success is almost entirely dependent on the set up and follow through from the scheduling leader.

In order to ensure you and your colleagues are getting the most from your 1:1 meetings, we put together some useful tips and guidelines.

If you don't already, start scheduling regular 1:1 meetings with your remote colleagues.

Effective managers know the importance of creating and adhering to an established communication cadence, especially as it relates to remote team interactions. This is true for project reports, periodic progress reviews, and weekly recaps. 

In addition, managers often use these forums for open-ended interaction, such as brainstorming or business development, or even pulse checks on the remote employee’s disposition and outlook.

Explore their challenges.

Remote workers face obstacles that don't exist in co-located working arrangements. Combining work and home in the same square footage can prevent the workday from ever ending and is creating a new level of stress needing immediate attention.

In her recent Deloitte article, "How working remotely impacts employee wellbeing," Erin Sindom shares how a

“United Nations report found 70% of the respondents reported that technology led to a blurring of boundaries because it brought work into their personal lives, and 48% of them also reported that telecommuting creates more work–family conflicts.”

1:1 meetings are a unique opportunity to address issues like work-life balance in a meaningful, constructive, and psychologically safe environment.

Keep it constructive, positive, and most of all, human.

Just as critical for ensuring a strong remote workforce is to create a personal, human environment.  Using a platform that supports high-fidelity communication can make a big difference here.  The importance of picking up on facial and body language cues triggers the manager to ask questions differently.

“How’s it going?” becomes “Tell me how you’re doing”, “What do you want me to do?” becomes “How may I help?” “Why isn’t this working?” becomes “How do you think we can improve the process?”

1:1 meetings should open constructive conversations that improve work processes and form stronger connections while identifying and working through issues.

Keeping a personal tone encourages employees to speak freely and candidly about challenges, which is key to resolving them. 

Ben Balter, Senior Product Manager at GitHub recently shared this insight 

“Feedback is inherently human, and as such, it deserves a human face. When working remotely, it’s on you to take that extra step to be able to connect on a human level, so don’t forget to turn on your camera, especially these days when it’s really nice to see other faces.”

Seed the discussion in advance with thoughtful questions.

Any scheduled conversation should not only come with a well-defined agenda, but also with at least some questions that are established before the meeting occurs.

Questions are a tricky thing, because if asked the wrong way or with the wrong words or wrong tone, they can elicit the exact opposite of the desired response. 

Consider a question's purpose before asking it.

Is it to identify or solve a problem, explore a new idea, uncover facts, or discover a new direction?  Any of these are strong examples of the basis for a good question. 

So, start at the beginning. Great examples of solid questions include: 

• Why are we undertaking this project?
• What is the desired outcome?
• What resources do we need?
• How can we work together to be more effective?
• How much time do you think this will take?
• How should we plan to meet the deadline?

These questions are non-threatening, non-rhetorical, and they are asked in a manner that encourages an exchange of ideas, rather than a defensive response.

Ray Zinn, author of Tough Things First, wrote in an article for Entrepreneur:

“There is an old adage that says one should seek to understand before seeking to be understood. I say, we have two ears and only one mouth for a reason -- because we need to listen twice as much as we speak.”

Well thought out questions lead to an increase in the amount of information that is contained in the answer, and tend to lead to new ideas. 

Match your questions to the medium

With a multitude of remote platforms for 1:1 communications, questions must be formatted to fit the characteristics of that particular medium, whether it be email, Slack, Microsoft Teams, or something else.  What reads well on one platform may come off totally different on another. 

Zinn also offered this advice:

“Most of all, ask questions as you would like to be asked by them. Take that brief second to think about how you would answer the question you are about to ask, and if you feel uncomfortable, then you need to rephrase it.”

Cover ground on a strategic, tactical, and cultural level.

In an article for Forbes, Serenity Gibbons shared that:

“When it comes to communicating with remote employees, the best method is to use multiple channels of communication — but each needs to have a default “best use” setting. Video chats, emails, phone calls, Slack: All of these can help to open (and keep open) lines of communication, therefore creating a successful working relationship.”

There has always been a standard for tactical meetings, and it becomes more critical to have those standards when setting remote task-related meetings.

With that in mind, make sure to create a recurring time that fits both manager and employee schedules. Simplify this by scheduling recurring notifications in the meeting platform, and set it to send timely reminders.

Allow time for all critical items

In order to make sure you cover everything you need to, it can be helpful to have a consistent, predictable agenda. A few ways to help achieve this are to:

• Establish time limits for topics to guide the meeting forward and eliminate ‘wandering’ into non-essential discussion.
• Within the meeting allow time for non-structured conversation and idea generation.
• Reserve the final moments of the meeting for wrap-up and action item recap.

Establish a balanced, collaborative agenda prior to the meeting.

Whether it’s for a large team or a 1:1 meeting, managers tend to drive the agenda, but the reality is that with collaborative input on some well thought out advance questions, the agenda creates itself.

As Steven G. Rogelberg explains in his Harvard Business Review article "How to Create the Perfect Meeting Agenda"

“attendees should be asked for input as the agenda is being created...when employees are encouraged to openly share their thoughts and ideas – and the leader actually listens to those ideas — they’re more likely to feel a greater sense of commitment to the team and the organization.”

If the desired result for the 1:1 is to review and define an employee’s career goals, then ask a pre-question that will open the door to relative agenda items.

Try a question such as, “Where do you see your skills being best utilized in this organization over the next 5 years and what additional skills do you think you will need for these future positions?” This will lay out a clear roadmap for areas that should be discussed on the agenda. 

Suddenly the door opens for an agenda that covers education, training, mentorship, soft and hard skill development -- all with a single purpose -- increasing the mutual value shared between an employee and their organization. 

As with any agenda, create parameters on time limits for discussion topics to keep the discussion focused.  At the end of each point, recap it for clarity sake, and of course at the end of the meeting recap it with agreed upon action items. 

While everyone is still at the remote ‘table,’ this is the perfect time to set the time and prospective agenda for a follow-up meeting.  This ensures continuity and purpose.

Ask for feedback.

You're learning and practicing this new skill together. One of the best ways you can improve that skill is to ask for mutual feedback. Find out how valuable the content of the meeting was, how well the format worked, and if your remote colleague has any suggestions on improvements. 

Find out if there are any changes you can make that would increase the sense of psychological safety in the meeting so ideas can be shared more freely.

In Conclusion 

Managers of remote employees must accept the challenges that come with these expanding workplace logistics, and shouldn't try to solve them alone. Creating, fostering and maintaining positive and constructive 1:1 communication is critical to the success of all involved.

With these challenges comes an opportunity to develop a more robust team capable of working independently and productively, while ensuring the team dynamics are still firmly in place.