In the hustle and grind of day-to-day work, one-on-one meetings can easily feel like a drain on your precious time. Far too often, these sessions come off as awkward, unnecessary, or downright painful—more of an obligation than a meaningful conversation. So, how can managers transform these dreaded check-ins into impactful, energizing, and genuinely valuable interactions?
In this post, I’ll look at five science-backed strategies to elevate your one-on-ones so they can lead to better productivity, more engagement, and stronger relationships.
Before we get to our strategies, though, I need to share my #1 rule for one-on-ones:
DON’T CANCEL
I put this in large all caps because I think it’s THAT important. (Can you tell I’m passionate about this?) One-on-one meetings are often the first thing to get canceled when time gets tight. But while skipping these meetings might seem like a time-saver (and let’s be honest, canceling recurring meetings feels pretty awesome sometimes), it means missing out on vital opportunities to build trust, align goals, and boost engagement.
Most importantly, canceling one-on-ones is a sign of disrespect. These meetings should be employee-led, so canceling sends a clear message that you don’t respect your employee’s time or agenda. Employees can end up feeling they’re not important – when the opposite is true. Your team is the most important, and you need them to keep moving forward.
If you must cancel, make sure to reschedule promptly or check in to see if they really have nothing pressing to discuss. Show them that their time and priorities matter to you.
But really, just don’t cancel.
Prepare – and align on expectations
While this should be a no-brainer, research shows less than one-half of employees and leaders prepare for one-to-ones with each other, and one in three employees have no say in their agenda. To avoid awkward, unproductive meetings, set clear, shared objectives from the outset.
One strategy is to divide the meeting time into sections: one for immediate concerns and another for long-term development. Communicate to your employees that these sessions are their time to seek feedback, share concerns, and discuss their career aspirations—not just a place for status updates, which can be handled elsewhere, via email or other channels. To set the tone, I often say something like, “This meeting is for you. I’m here to guide the conversation, but it’s your agenda. Bring the topics that matter to you, not just what you think I want to discuss.”
By clarifying the purpose and encouraging employees to take ownership of the agenda, you create a more meaningful and focused dialogue that benefits both of you–and doesn’t feel like a giant waste of time.
Meet more frequently
It might sound counterintuitive, but meeting more often can actually make one-on-ones more effective. Employees who meet at least weekly with their manager report feeling significantly more positive about these meetings compared to those who meet less often. In fact, weekly meetings can reduce anxiety by 20%, decrease dread by 17%, and increase feelings of job success by 12%.
Consistency is key to building ongoing support, growth, and alignment within your team. By establishing a regular rhythm for one-on-ones, you turn these meetings from dreaded obligations into a natural part of the workweek. Most importantly, meeting regularly allows for the ongoing investment in relationship-building (see below for my soap box on this!) Do your best to commit to a steady weekly or biweekly schedule instead of scrambling to fit meetings in when things get chaotic. Trust me, your team will appreciate the reliability, and you'll both benefit from those dependable check-ins.
Build rapport early and often
One-on-ones aren’t just about work—they’re about building relationships. Establishing rapport is crucial to engagement, especially when you’re still getting to know a new team member. Try starting with open-ended questions like, “What do you enjoy doing outside of work?” or “What’s your priority outside of work?” These questions help break the ice and show genuine interest in your employee’s well-being.
Get creative. Instead of the usual “How are you?” try, “How are you doing today on a scale from one to ten?” followed by, “Why are you a six today? How can I help you become a nine?” This provides concrete insights and shows that you care about their individual experiences.
Don’t be afraid to show a bit of your own vulnerability, too, when it feels right and authentic. Sharing a bit about your interests or challenges can make your team feel more comfortable opening up. This can be especially empowering for employees who don’t hold as much formal authority, helping to create a more balanced and trusting relationship. While taking the time to swap personal stories can seem like a sidebar, it’s an important one! Building an authentic connection not only fosters trust but also makes employees feel genuinely valued, paving the way for more productive and honest conversations.
Also, let’s be real: having a strong manager-employee relationship is vital when it’s crunch time. Asking for a favor, requesting a late night, or pushing for a tight deadline is easier when mutual respect and trust have already been established.
Keep it focused–these aren’t therapy sessions
While it’s important to allow employees to share their thoughts and concerns, one-on-ones shouldn’t devolve into therapy sessions. The goal is to foster growth, solve problems, and ensure alignment, not to vent endlessly about personal frustrations.
If the conversation starts to veer into venting, gently steer it back by asking, “How can I help with this?” or “What’s one thing we can do together to move forward?” This coaching approach addresses issues and sparks problem-solving without letting issues linger unresolved.
If personal issues arise, be empathetic but direct the employee to appropriate resources, such as an Employee Assistance Program (EAP). It’s crucial to maintain boundaries while still offering support.
This doesn’t mean your conversation needs to remain sterile or impersonal. Some of my biggest breakthroughs in building lasting, trusting relationships have happened when discussing highly personal matters, such as health or family. I firmly believe our personal and professional lives are deeply interconnected, and that getting to know your team members beyond their job descriptions allows you to support them better – because when one area of their life is out of balance, it inevitably affects their work. Just keep in mind that the aim is to create a safe space for productive dialogue, not to take on the role of a counselor.
Experiment as needed
One-size-fits-all doesn’t apply to one-on-ones. What works for one team member might not work for another. Don’t be afraid to experiment with different formats, agendas, and frequencies until you find what resonates best with each individual.
Years ago, I managed a team of four, and we each crafted our unique one-on-one format and frequency that suited our individual needs. Once we established these personalized meetings, they didn’t require more preparation from me – usually, they even needed less, and their effectiveness skyrocketed. No longer were we scrambling to cover everything in some sessions or awkwardly filling the time in others. Instead, each meeting became a meaningful, productive conversation tailored to each team member and something we all genuinely looked forward to!
Try incorporating new elements like a “wins and challenges” segment, where employees can share their successes and struggles. This can provide valuable talking points and shift the focus to actionable feedback and growth. It also allows for those who don’t naturally share their successes or struggles to have permission and space to do so.
Alternatively, vary the setting – sometimes a casual coffee chat can feel more relaxed and open than a formal office meeting. I’m personally a big fan of walking meetings to get the creative juices flowing while getting some steps in.
I also find the age-old parenting trick to be true: sometimes it’s easier to have challenging conversations while not staring each other down. Hence, a lot of car conversations with my teenager. Bonus – they can’t roll out of a moving car safely, but that’s a blog post for another day!
Flexibility and willingness to adapt are key to keeping one-on-ones fresh and engaging.
What about remote workers?
Managing remote or hybrid teams adds another layer of complexity, but one-on-ones can be just as effective in these settings. Remote one-on-ones foster connection and ensure team members feel included and supported.
Focus on your listening skills, the questions you ask, and the empathy you bring to the conversation. While video calls can be helpful to stay connected, it’s OK to mix things up! Sometimes, an audio-only meeting lets you focus more on the conversation – and don’t be afraid to take a call while walking. I love strolling around my yard while chatting and find the fresh air often brings about a deeper conversation.
Leverage collaborative tools to track discussions and action items. I love OneNote because it lets me revisit past conversations to resolve open concerns or follow up on progress. It also features a handy “parking lot” for non-urgent ideas.
We’ve all had that boss who emails every time a new thought pops up. Instead, jot them down in OneNote and bring them up during your next one-on-one. This simple step helps prevent overwhelming your team and keeps conversations focused and productive.
Pro tip: taking notes also allows you to capture important details like kids’ names and big life events so that you can reference them in the future! And consistency is still paramount – regular virtual check-ins help build trust and keep communication lines open, regardless of physical distance.
The bottom line
So, is it possible to turn your one-on-one meetings from dreaded obligations into conversations you and your team members look forward to? My personal experience suggests a resounding yes! By approaching these sessions with genuine curiosity and a commitment to your team’s growth, you can create meaningful connections that inspire and empower.
Embrace the opportunity to truly listen and support your employees, and you'll foster a culture of trust and engagement that elevates everyone involved. I challenge you to reimagine your one-on-ones this year. Your leadership and your team will thank you for it!
(And don’t forget rule #1 - don’t cancel!)
Interested in learning more about coaching and building human workplaces? Send me a note at Katherine@worksproutpartners.com. I look forward to hearing from you!
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