8 Practical Tips for Managers Struggling with One-on-Ones

Most manager’s generally agree that 1:1 meetings are essential. These meetings are known as “the employee’s meeting” and it is a time for you as a manager to connect with your employee, listen, answer questions, give feedback, and coach. 

As Kim Scott, author of Radical Candor points out: 

“1:1s are your must-do meetings, your single best opportunity to listen, really listen, to the people on your team to make sure you understand their perspective on what’s working and what’s not working.”  

Read on for how to make your one-on-one meetings something you and your direct report can look forward to!

• Benefits of one-on-one meetings
• Common struggles and key challenges
• 8 tips for managers struggling with 1:1s
• A final word of advice

Benefits of one-on-one meetings

Countless top-notch Managers have spoken to the benefits of one-on-one meetings:

• “One of the first things that happen when you start doing one-on-ones is you notice you start getting less questions during the week,” says Mark Horstman, on the Managers Tools podcast. “Things aren’t quieter… People just aren’t coming to you with hundreds of small questions because they know they can wait until the one-on-one.”

• “Establishing a consistent one-to-one meeting schedule is a critical tool to improving time management,” argues productivity expert Dave Crenshaw.

• “The fundamental reason the one-on-one exists is to give a platform to the direct report to allow them to communicate to you,” say Michael Auzenne and Mark Horstman on the Managers Tools podcast. “In order to effectively develop relationships with our directs, we’ve got to spend time communicating about things that are important to them.”

And while it’s clear that 1:1s are the best way to motivate your team members, build trust, solve problems, and help your staff grow and flourish – what if you just don’t have time? No, this isn’t a trick question, and no the tongue-in-cheek answer is not “find the time!” 

Although it’s true that experts and tenured managers generally recommend 1:1 meetings occur on a weekly basis for approximately 30 minutes, many managers report that they struggle to fit these meetings into their already busy calendars – and that’s not the only problem it seems. 

Common struggles and key challenges of one-on-ones

Readers of the Manager TLDR Newsletter and other managers looking to have effective 1:1 meetings have shared some of the following key challenges:

• Often 1:1s are awkward or feel forced, and sometimes there just isn’t anything of value to discuss 
• Fitting in 1:1s with a large team and no middle managers seems impossible 
• Meetings often turn into a gossip or complaining session
• Often the content discussed in 1:1s gets lost or is very repetitive week to week 
• 1:1s are frequently rescheduled, canceled or skipped
• Direct reports often come to 1:1s unprepared 

If you’re struggling with any of these issues as a manager, you should check out Fellow’s definitive guide to one-on-one meetings, which is chock-full of practical tips and advice from some of the world’s best leaders. 

But if this guide is on your reading list and you just haven’t gotten to it yet, don’t worry – below are 8 practical and useful tips for managers trying to make the most out of 1:1s. 

8 tips for managers struggling with one-on-ones

• Schedule 1:1s as recurring meetings
• Say no to non-essential meetings
• Use a template and maintain a set of notes
• Assess meeting frequency
• Assess meeting format
• Ask questions
• Hold office hours
• Talk about life instead

1 Schedule 1:1s as recurring meetings

Using your calendar to permanently carve out recurring time slots for 1:1s is one of the best ways to ensure they happen consistently. Also known as “time blocking,” saving space in your calendar for important meetings and tasks not only is a great time-management trick, but it ensures you prioritize the most important tasks and meetings before your calendar fills up with other obligations.  

2 Say no to non-essential meetings and busy-work

No one likes to say “no,” but as a manager, it’s a big part of your job, and protecting your time is vital. Practice recognizing non-essential meetings or busy-work by asking yourself these questions:

• Do I need to be in this meeting? 
• What are my contributions likely to be in this meeting? 
• Am I (or my team) likely to have action items from this meeting? 
• Is there an agenda? (This is HUGE! No agenda = no attenda!)
• Could this meeting be a quick stand-up or even an email?
• Does this work need to be accomplished immediately? 
• How does this work connect to the company’s overarching goals? 
• Can this work be completed at a later time with little or no effect on the overall outcome?

3 Use a template and maintain a set of notes for 1:1s – do not just wing it

Despite the fact that 1:1s are known as “the employee’s meeting,” it’s still a good idea to use a template, have an agenda, and maintain a set of notes and action items for these meetings. 

Fellow’s one-on-one meeting templates help keep both managers and employees on track, allow for collaborative agendas, action item tracking, and feedback. 

Not only does using a template or software help keep both the employee and the manager accountable, but it also helps focus meetings and limits opportunities for gossip or lengthy complaining sessions. It also helps direct reports think ahead, plan for the meetings, and come prepared. 

Not ready for software or online tools? No problem – for years I maintained an old-school pen-and-paper method. All my employees had a file in a locked cabinet and all of our 1:1 notes and action items from our sessions were in those folders. Action items of course made their way onto individual task lists and plans, and I reviewed past notes in advance of future sessions. Choose a method that suits your style and needs. 

4 Assess meeting frequency

Admittedly, in my early days as a manager, I didn’t follow the best practice of having 1:1s on a weekly basis – I actually had them monthly for 90 minutes (gasp!). 

In all seriousness though, this frequency worked for me for a number of years and my employees were happy, why? Well, they were all tenured employees, we were a small team, we had weekly staff meetings, and we worked collaboratively in a culture where we could share openly and have quick touch-base sessions whenever we wanted. As we grew and introduced more junior employees and roles to our team, 1:1s became more frequent for everyone, but particularly for new employees. 

As a manager, it is important to assess what works best for you and your employees and choose a cadence that takes into consideration role, tenure, project management, and employee growth. 

5 Assess meeting format

If you feel like your 1:1s are repetitive or are getting a bit stale, there’s a good chance that it’s not the meeting per se, but the format. 

The 90/10 format has always been my preference – where employees come to the table with 90 percent of the agenda items and I bring forward 10 percent. This format allows for flexibility while also ensuring that the manager doesn’t accidentally take over or monopolize the meeting. 

Other popular formats – including formats used at Fellow – are the chronological format where challenges and wins from last week and this week are discussed while also looking ahead to next week; and the key priorities format, which reviews a series of priority areas including team dynamics, feedback, and career development. 

6 Ask questions

Another way to avoid repetitive and stale 1:1 meetings is to come prepared with a few questions for your direct reports. My favourites are those that spark discussions about challenges or future growth opportunities such as: 

• Is there anything right now that is slowing you down or blocking you?
• What are some challenges you’ve faced recently? How can we work them out together?
• What work are you doing here that is most in line with your long term goals?
• Have any of your goals changed since the last time we talked about this?
• Are there any new ideas you’d like to discuss with me/the team?

7 Hold office hours

Now for managers who are managing large teams or who are short on middle managers, weekly 1:1s might just not be realistic. My advice: choose quality over quantity. Excellent 1:1s every second week are better than rushed and unproductive weekly 1:1s. 

To fill the gap in the off week, consider holding “office hours” for your direct reports, and specifically for those that want to schedule additional time with you. Scheduling office hours signals you are serious about 1:1 time, and this method is more helpful for employees than the often used come-by-anytime-my-door-is-always-open method. Employees know their bosses are busy and that time is valuable, and as such, they might be reluctant to pop by or interrupt you. Holding office hours ensures you give time and space to your employees should they need it.  

8 Skip the work stuff and talk about life instead

Sometimes work does indeed have its lulls and work-life gets a bit dull. This does not mean however that 1:1 meetings should be skipped or halted until things pick up. When work is slow, 1:1 meetings are a great way to connect personally with your employee, get to know them a bit more, and continue building a culture of trust and compassion. 

If you and your employee find your 1:1 agenda lacking, suggest going for a walk and catching up on some topics that fall outside of traditional “work” but impact work-life nonetheless. My favourite questions are:

• How are you feeling about work-life balance these days? 
• Are there any books you’re reading or podcasts you’re listening to that are inspiring you?
• Are you planning an upcoming trip or vacation? What can I do to help you have a worry-free time away?
• What’s new and exciting outside of work these days? 

A final word of advice

When I first became a boss (and every day after that!) I told myself that I had three main goals: 

1. Grow my company
2. Grow myself
3. Grow my team. 

This became my mantra. Everything I did as a manager somehow connected back to one of these three goals. 

Having effective 1:1s actually hits all three of these goals – it helps your team members grow and flourish in their positions, while also teaching them the necessary 1:1-meeting skills for when they become managers themselves. It helps you grow and develop as a manager and leader, and it helps you better understand how to manage multiple work styles and personalities. And finally, it helps your employees be more efficient and effective thereby positively impacting the company overall. Win-win-win! 

At the end of the day, making time for 1:1s and finding the right content to discuss can be a challenge, yes, but it’s one of those tasks where the benefits always outweigh the cost, and it’s definitely worth the extra effort.