Master the one-on-one meeting

By Dawn Wotapka

When it comes to leading others, the one-on-one meeting is an opportunity for managers to get to know their direct reports as individuals while gleaning the information needed to guide them in the short and long term. But not every manager receives an instruction manual on how to conduct these meetings. A few simple tips can help managers make the most out of the one-on-one for themselves and their direct reports.

David Almonte, CPA, CGMA, might love being a boss to 15 "rock stars," but he feels slightly nervous before the one-on-one meetings he holds with each of them.

For Almonte, a financial reporting and analysis senior manager with Amica Insurance in Rhode Island, the jitters are a good thing. They mean "that I truly care about why I am there and what I am doing," he said. "It is a reminder that the conversation I am about to have or give is meaningful to me."

When done right, these meetings can be an extremely rewarding aspect of management. "At the end of the day, the best part of my job is helping other individuals grow and succeed in their careers," said Almonte, a winner of the 2022 AICPA Outstanding Young CPA Award.

The benefits also ripple beyond you and your staffer. According to Cody Austin, CPA (Canada), an entrepreneur who wears several hats, including vice president of operations for Integrity Audit and Accounting Ltd., Calgary, Alberta, Canada, "Having great lines of communication creates a better, stronger team."

Unfortunately, not every manager receives training in how to conduct one-on-one meetings. Here's how to get started:

Make it recurring. Having an occasional meeting won't create the momentum needed for relationship building and guidance, so experts advise having weekly or biweekly meetings. Maureen Crawford Hentz, a Boston-based career coach and human resources professional, uses Wednesdays for meetings. Austin, meanwhile, blocks off 30 minutes on a day that works for both him and the employee. If the entire time isn't needed, that's fine, but "there's always something I can talk about with them for 15 minutes," he said.

Consider the environment. While many meetings are being conducted virtually, when it comes to the office, the setting matters, Almonte said. If the goal is an informal catch-up, consider a walking meeting or a conference room. For serious meetings, Almonte avoids sitting behind a desk to avoid a position of power. "Remove barriers in the room to create an open space for the other individual," he said.

Set an agenda. Be sure that both sides know what will be brought up in the meeting in advance, giving everyone a chance to prepare responses. Crawford Hentz suggested including an agenda — it doesn't need to be extremely detailed — in the meeting invitation. "Maybe you are an introverted thinker, or maybe your direct report is. Introverted thinking means that you need some time to process," she said. "You like to think about your reaction to something."

For Almonte, "a meeting without an agenda is like sailing without any directions."

Ask the right questions. If the employee is the type to open up, spend the first few minutes asking about how life is going outside of work, which will show that you're invested in the whole person. "I need to know what my team is doing. We might spend five minutes finding out what's going on — if their dog is sick, for example," Austin said. "We bring a lot of the things that affect us in our lives to work."

Then, transition into work-related inquiries. For Austin, examples include: "What's on your plate? How is it going? What roadblocks are you encountering?" Crawford Hentz likes to ask: "What part of your job are you loving?" and "What part is your least favorite part?"

Don't cancel. The manager should try not to cancel, Crawford Hentz said. If the direct report needs to cancel, he or she should check in before not attending the meeting, which keeps the line of communication open. "That way if you [the manager] have something you want to talk about, you can say, 'Let's just talk about this, and then we'll leave the other things for next week/month.' Or you can just say, 'I'm here if you need me.'"

End it well. Wind down the meeting by discussing the next meeting and any potential schedule conflicts, Crawford Hentz said. Then consider ending on a positive note. You don't want to pass out praise that isn't deserved, but employees need to be reminded that they — and their efforts — are appreciated. When warranted, "end with an observation of their work this week or an appreciation you have for them," she said.

Follow up. Always be sure to follow up on the topics discussed, Almonte said. "Ensure that the message was received, action steps are being followed, and allow for the opportunity for feedback and questions," he advised.

Practice what you preach. Be sure that you're following this advice with your leadership. "Communicating up the chain is just as important to my boss," Austin said. They discuss what's going on with Austin and what he's learning from direct reports, he said.

Start with these simple tips to get comfortable with one-on-one meetings. Managers who learn to successfully conduct one-on-one meetings, and practice what they preach, benefit themselves and their direct reports.

Caitlin Morin, CPA, a senior accountant who reports to Almonte, acknowledged getting nervous just like him. But she was quickly put at ease and gained valuable guidance.

"I not only left feeling that my ideas had been heard but also came away with concrete ways to develop my own skills, specifically when it comes to getting outside my comfort zone," she recalled. "These [weekly] meetings, as well as other one-on-one meetings, have been instrumental in my career growth and in building relationships with my higher-ups."

Dawn Wotapka is a freelance writer based in Georgia. To comment on this article or to suggest an idea for another article, contact Courtney Vien at

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