Effective One-on-One Meetings: 12 Experts Share Their How-to Tips

It’s not an overstatement to say that effective one-on-one meetings are critical to the overall success of your organization. One-on-one meetings keep communication lines between managers and employees open and increase employee engagement, both in individual roles and within the organization as a whole.

Ultimately, as a manager, conducting effective one-on-one meetings is not optional. If you want to ensure employees progress—and you do—then there are certain things you should and shouldn’t do during these meetups.

We reached out to experts for their insider tips on how to have effective one-on-one meetings. After getting over 100 genuinely good responses, we’ve pulled out the best advice and we’re passing it on to you.

What Makes a 1-on-1 Meeting Different?

A one-on-one meeting with a manager is different from other meetings because of its main purpose: to build a trusting relationship between the manager and the employee. In fact, this purpose essentially makes one-on-ones the most crucial kind of meeting you can conduct.

Brianna Inoa, an organizational psychologist, perhaps says it best:

“Making this time investment will enable the employee to tackle challenges more effectively on their own, help them see your commitment to their career growth, and embed development in your ongoing conversations.”

One-on-one meetings are much more than a simple formality, and each employee deserves an individualized approach, as Chelsea Cohen, co-founder of SoStocked, makes clear:

“You can’t have the same expectations out of a 1-on-1 meeting with every employee[;] in fact, you should expect the outcome to be different for each person. Everybody’s situations are different, so be wary of basing people off a checklist.”

Effective one-on-one meetings with a manager provide a unique opportunity to support employee growth. That’s because:

• They keep both parties informed on new developments.
• They help managers to stay aligned with and address their employees’ goals.
• They provide managers with constructive feedback from employees.

Brian Turner, CTO of ConvertBinary, highlights the importance of listening to employees:

“As much as the employee can benefit from you offering constructive criticism, feedback and goal-setting, it’s important to recognize that employees can offer guidance just as much as you can. This gives your employee a chance to share their feedback for the direction of the company, advise on how things could improve going forward, and feel a sense of empowerment in sharing their thoughts.”

What Are The Common Challenges of 1-on-1 Meetings with Managers?

It’s not uncommon for you as a manager to struggle with one-on-one meetings—even before they begin. One of the most common challenges is the fact that many employees (including senior managers!) believe meetings to be a waste of time.

Harvard Business Review surveyed senior managers across a variety of industries who said these negative things about meetings:

• They prevent them from finishing their own work
• Nothing gets accomplished
• The format doesn’t allow for deep thinking
• There are missed opportunities for creating team unity

These beliefs put meeting attendees in a poor frame of mind as the meeting begins and leaves them feeling unmotivated to contribute anything of value during their one-on-one time.

There are plenty of other obstacles as well. It’s wise to find out if you’re guilty of one or more five mistakes managers make during one-on-ones that make meetings even more challenging than they are already.

Andrew Winters, an attorney and co-founder of the law firm Cohen & Winters, helps to reframe how managers should prioritize one-on-ones:

“I prepare for a meeting with my employees as much as I would for any of my clients because their time is just as important.”

Another secret to having an effective one-on-one meeting comes from Michelle Devani, a relationship advice expert and founder of Love Davani. She tells managers:

“You are not there to instill fear in your employee. Share your success with them, praise their hard work and sacrifices, and encourage them to come up with new ideas”

What Are Good 1-on-1 Meeting Questions for Employees?

One-on-one meetings shouldn’t be a one-way street. While they provide an opportunity for managers to give feedback to employees, the real goal is to establish an open channel of communication in which employees and managers find alignment with their goals and expectations. Therefore, you want to make sure the questions you ask in one-on-one meetings are effective at helping the two of you achieve that outcome.

To accomplish this, Marc Lewis, general manager and executive editor at EcoWatch, reminds managers to ask open-ended questions, saying:

“[Asking open-ended questions] keeps the conversation going, avoids awkward silences, and makes the conversation less one-sided.”

Michelle Devani suggests two questions, which she asks her own employees in order to better understand where they may need help:

1. “How can I support you?”
2. “What problems did you solve this week?”

She believes these questions bring out the most pressing issues and reveal an employee’s priorities.

Holly G. Green, best-selling author and founder of The Human Factor, also suggested the following one-on-one meeting questions for employees:

• What is the most important thing you and I should be talking about?
• Can you describe the issue for me?
• How is this currently impacting you? Who or what else is being impacted?
• What else? (Ask this at least three times.)
• If nothing changes, what are the implications?
• How have you helped create the issue?
• When this is resolved, what difference will it make?
• What’s the most important first step you can take to begin to resolve this issue?
• What exactly are you committed to do and by when?
• When should I follow up with you?

Green also offers these additional one-on-one meeting questions for employees as a way “to shake things up”:

• What is currently impossible to do that, if it were possible, would change everything?
• What is the most important decision you are facing? What’s keeping you from making it?
• What topic are you hoping I won’t bring up?
• If you were hired to consult with our company, what would you have us do differently?
• What’s the most exciting thing you worked on in the past month?
• What great ideas do you have about your role?
• What is an area that, if you made an improvement, would give you and others the greatest return on time, energy, and dollars invested?

Just be careful how you present your questions, advises Nathan Grevo of Project Hatch:

“If you come across as negative or critical, your team member will probably shut down and not want to talk about anything. Be sure to stay positive and don’t speak down to them.”

How Can Managers Improve the Quality of 1-on-1 Meetings?

To improve the quality of one-on-one meetings, Maya Rotenbert, VP of marketing at Stoke Talent, advises her team not to take notes during personal meetings:

“Leaders can write down notes after the interview, but while they are talking to someone, they must give them their undivided attention.”

Kristaps Brencans, CMO at On the Map, reminds everyone to be considerate of each other’s time:

“It’s critical that the timing works for both of the people that are going to be in the meeting.…[W]ait for a time that both of the coworkers can make it to…rather than have to squeeze it into an already packed schedule.”

This allows for a more effective one-on-one meeting than one where you or your employee feel rushed, distracted, or uncomfortable.

One surprising tip for improving the quality of one-on-one meetings came from not one, but multiple experts. Brett Downes, founder of Haro Helpers, was one of the many who feel strongly about having outdoor “walk and talks.” He says they bring “a whole new freedom and relaxed atmosphere” to the sometimes tense or formal atmosphere of one-on-one meetings.

Walking outside together can break down hierarchical dynamics, encourage more open and honest discourse, and produce better results from your employees because they are actively engaged during the meeting. Lara Quie, founder of Lara Q Associates, agrees that walking side-by-side “is less confrontational than [sitting] face-to-face.”

Finally, one more way managers can improve the quality of one-on-one meetings is to implement performance management software. This tool encourages managers to guide employee performance improvement through action, without having to deal with the pain points of speculation and limited subjectivity. It also provides a method to track goals and feelings over time, so you can see if you’re making progress or addressing the same issues over and over.

By following the advice of these expert contributors, you’ll quickly find yourself having much more effective one-on-one meetings and more fully contributing to the overall success of your organization.