28 One-on-One Meeting Questions to Improve Communication in the Workplace

When successful, one-on-one meetings contribute to development opportunities for employees, building trust, and fostering important communication. So, we came up with “The List” of great one-on-one meeting questions.We have something for every situation. Some are best for pre-meeting questionnaires and others for the actual meeting. All of them are best kept in your back pocket for the right moment. If you want an easy way to improve the effectiveness of your one-on-one meeting questions, bookmark this page to use it as a quick reference guide from week to week
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Communication: the great conflict mitigator and relationship builder. And one of the best communication methods in the workplace? The one-on-one meeting. One-on-ones are the key component of successful communication with the best being those that are 90% focused on the employee.

Culture questions

Ask these questions to keep your finger on the pulse of actual team dynamics and company culture from your employees’ perspectives.
  1. Are you happy working here?
  2. Who do you admire within the company and why?
  3. Who has really been kicking ass lately?
  4. What do you like about working here? What’s not fun about working here?
  5. If we could improve in any way, how would we do it?
  6. What’s the number one problem within our organization? Why?
  7. If you were me, what changes would you make?
  8. What’s the biggest opportunity we’re missing out on?
  9. What are we not doing that we should be doing?
  10. Is there anything that’s slowing you down from getting your work done?

Personal productivity questions

These questions can be great for encouraging employees to speak up about some of the tougher issues that may need to be addressed for more productive day-to-day collaboration.
  1. What are your long-term goals?
  2. How can I make your days more fulfilling?
  3. What can I be doing better to help you in your job?
  4. Are there any obstacles I can remove for you?
  5. What do you like most about your job today?
  6. What do you like the least?
  7. Where do you see your career in the next (2/5/10) years?
  8. What work are you doing here that you feel is most in line with your long-term goals?
  9. What’s one thing about your job that, if we fixed, would make you never want to leave?
  10. What would you like to learn more about this year?
  11. What are you most excited about?
  12. What are you most worried about?

Work-life questions

Sprinkling in a few casual, personalized questions can help spur important discussions around the topic of how work fits into your employees’ overall lives—and what you can do to ensure it’s a welcomed, enjoyable part of each week.
  1. How is your family?
  2. How was your weekend?
  3. How are you planning to balance work and personal life this year?
  4. What are you doing for yourself outside of work?
  5. Is there anything you’d like to be doing on your own time to relieve stress that you’re not getting to? How can I help you achieve those personal goals?
  6. What does your ideal weekday look like?

Free Downloads for One-on-One Meetings

We’ve put together these free resources to help you prepare for your next one-on-one meeting. For tips on how to run a successful meeting, please feel free to view our guide.

One-on-One Meeting Questions Poster

Add these one-on-one meeting questions to your Jell check-ins, either in the App or Online and you won’t have to remember them for future meetings. You’ll also be able to keep track of the answers and be prepared with the best culture and productivity-based one-on-one meeting questions.   

One-on-One eBook

In this free eBook, you’ll learn how one-on-one meetings help you build a successful employee-manager relationship and prevent workplace conflict (that we all want to avoid).One-on-One Meetings - Free eBookWe’ve even included a few quotes from managers with years of experience. Get more from your one-on-one’s, grab a copy of our guide today.

The Benefits of One-on-One Meetings

One-on-One meetings vary from business to business, manager to manager, and employee to employee. While approaches are different, the goal remains the same–to improve communication throughout an organization. One-on-one meetingsone on one meeting benefitsImprove employee performance: Ever worked in a workplace where you didn’t know how well you were performing? Conversely, ever work in an environment where there was too much communication and you just wanted to be left alone? There’s a delicate feedback balance, but the consensus is that regular weekly or bi-weekly check-ins allow managers to stay apprised of employee performance and productivity.Build trust: Schools use the metaphor “safe space” as a description of a classroom environment allowing students to feel secure to take risks, express views, and express themselves. This is translatable for the business world. It’s every manager’s duty to create a safe space for their employees. When your employees feel trusted at work, they’re more likely to take risks and perform at a higher level. Employees with a good managerial relationship may open up about issues impacting their professional performance, and when addressed properly, improves employee morale, loyalty, and Only 12% of employees leave companies due to salary, which means money isn’t everything, but building trust is.Propel professional development: 87% of millennials value growth and professional development opportunities in the workplace, more than any other generation before them. What better way to discuss professional growth than in a one-on-one meeting? Managers, really use this time to discuss your employee’s personal life, career aspirations, interests (outside of work!), and personal projects. Really show your employees you care about them. Showing interest in them as people increases their satisfaction in the workplace. After all, you want to keep your employees and not scare them away.Increase employee agility: One-on-one meetings give employees an opportunity to identify and address any blockers, challenges, and issues with their managers. When blockers are identified, teams can analyze and pivot their strategy, remaining agile and adapting to the changing needs of the business.  

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Tips to Improve Your One-on-One Meeting

It’s easy to go through the motions and hastily meet with each of your employees, but you want quality interactions. So, how can you better use the time you have? What do you need to ask? How can your meetings have a purpose? We recommend the following tips,one on one meetings

Just show up!

Woody Allen once said “80% of life is just showing up.” And he’s not wrong. Showing up means:
  • Setting one-on-ones at regular intervals
  • Avoiding excessing rescheduling or cancellations
  • Being fully present in the meeting
Block regular time for one-on-ones. This varies from company to company as every organization is built differently, but through trial and error you’ll develop a rhythm for your own and what works for you.Avoid cancelling or rescheduling. Look, things happen. It’s important to not reschedule too frequently or else your employees will view this as lack of respect for them and their time. And when you do show up, show up on time. Once again, showing up late rubs your employees the wrong way. If you don’t respect their time, why should they respect yours?Be fully present in the meeting. You expect your employees to give their undivided attention to you, they expect the same from you. Turn off your phone at the beginning of the meeting and block off the time on your schedule so your other employees know you are not to be interrupted at that time. In a distracted world, our attention is one of the most important gifts we can give our employees.

Have a plan

When you go into your one-on-ones, jot out a few notes for what you want to discuss during the meeting. Otherwise, your meeting may disintegrate into disorganized chaos.Consider sending questions ahead of time. This gives you an outline of your discussion and your employees an opportunity to think about them. Not everyone can think on the spot. Some need time to synthesize information and organize their thoughts before a meeting. It also provides a needed structure to the meeting and an opportunity to prepare exactly what you want to say.Let your employees set priorities. Your employees know the ins and outs of the business (and sometimes in more intimate detail than you do) because they live their job every day. Let your employees set the tone of the meeting and what they’d like to discuss. You can come prepared with questions but allow your employees to take the reins and share what they feel is a priority.Create actionable items. Perhaps one of the most important parts of the meeting: create actionable items. What do we mean by this? Document commitments and assign specific tasks for your employees to complete and improve upon in the next couple of weeks before their next check-in. Establish clear expectations so your employees know exactly what is expected of them in the upcoming weeks.

Take the opportunity to connect

It’s great to have an outline for your conversation, but you shouldn’t run through the motions like a dispassionate robot. Make sure to practice your one-on-one meeting questions in advance.Start positive. Take the first couple of minutes in the meeting to ask your employees how they’re doing, what they’re working on, what’s important to them in their world right now. Spending a few minutes to connect improves employee morale.Share your own feelings. Build trust by sharing your own feelings! Again, the idea is to create a safe space. If you are open to your employees, they’ll feel safe to share their own feelings. You don’t need to share your medical history, but it’s good to share a few things you’re working on, things important in your life right now, and challenges you’re facing as a manager.Close with gratitude. Always close by telling your employees how thankful you are for them. Think of one thing specific to them that you’re grateful for. For example, if you have an employee who always goes the extra mile when answering sales tickets, let them know, “Hey Taylor, I notice you’re always jumping in and helping with tickets when you notice your peers are getting overwhelmed–great job!” or “I’m grateful for your hard work and dedication to this company.”

Mistakes to Avoid

We’re all human so mistakes are inevitable. Casual check-ins don’t mean we should put any less effort into them. Avoid these behaviors that derail one-on-one meetings:one on one mistakes
  • Not having one-on-ones in the first place. Okay, so this is obvious, but one-on-ones are the best way to communicate with your employees on a regular basis. Put it on your schedule! Decide how often and when and keep a consistent schedule. When you know you’re going on vacation, reschedule for another week, but always get back on track.
  • Focusing on old problems instead of uncovering new ones. Don’t rehash old problems unless they’re relevant. Always look for problems affecting productivity and your employees’ jobs now and propose solutions.
  • Not asking employees for specific feedback. It’s easy to assume that because you’re the manager you know best, but often managers overlook problems that are clearly seen by employees. Always ask employees for suggestions on how to improve but keep them short and focused so they don’t derail into a workplace whine-fest.
  • Not listening. You should listen just as much as your employees. Stay engaged and ask great questions, and let your employees take the lead. Allowing your employees to lead provides them the opportunity to work out issues they are facing in the workplace, as well as growth aspirations, and personal and professional interests.
So, now that we’ve established the importance of one-on-one meetings, how about we go through some guiding questions to get you through your next meeting? We’ve labeled each section according to the subject matter so feel free to pick and choose which questions you want to use.

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