More Than Small Talk: How to Have Effective One-on-Ones

Tech teams are used to tackling challenging questions, but sometimes “how are you?” is the toughest of all. Here’s how check-ins establish trust and boost wins.
Sunny Betz
July 13, 2021
Updated: July 14, 2021
Sunny Betz
July 13, 2021
Updated: July 14, 2021

If you’re a manager, you’re likely no stranger to a packed to-do list. You have a seemingly endless number of meetings to attend and responsibilities to delegate, and on top of it all, you have a team of employees looking to you for guidance — each of them with different communication styles, needs and goals.

Making sure that your teammates feel supported can be the hardest part of any manager’s job, but putting employees front and center is essential to running a high-performing team. Communication is everything if you want to get it right, and scheduling a check-in meeting is a good place to start.

The central purpose of a check-in meeting is to strengthen the relationship between employee and manager, helping both parties feel more comfortable with each other and able to work better together. What makes a one-on-one or check-in different from other meetings is that in a check-in, the employee should steer the conversation, rather than the manager. 

5 Questions to Ask in Your First One-On-One

  • How do you prefer to communicate with your manager? 
  • What projects do you most enjoy?
  • How often would you like to meet?
  • Where would you like to see yourself in six months?
  • What do you find most challenging about your role?

Employees can use check-ins as an opportunity to bring up workplace issues, ask for help with tasks or discuss their professional development goals. Managers can then take action on that feedback and help their employees move closer to their aspirations, or make improvements to help them be more productive and fulfilled. Ultimately, effective one-on-one meetings lay the foundation for managers to become mentors for their employees.

Drew Kutcharian, cofounder and CTO of Los Angeles-based marketing analytics company DISQO, said that regularly scheduling check-ins with his employees has helped him immensely as a technology leader.

“I personally have used one-on-ones during my career to ensure that all my team members have a clear direction and a sense of purpose, and that I was able to support them through the challenges,” he said. 

Work concerns do usually take center stage, but Kutcharian said check-ins have been successful because they give him a chance to connect with people on a more personal level. In his experience, if managers let that personal connection slip to the wayside too often, the work itself will suffer. In order to build trust and maintain a lasting connection, you’ll need to embrace small talk and make an effort to really get to know your employees.

“The stronger that trust, the safer the participants feel, the better they can address even the most sensitive topics and challenges,” Kutcharian said.

 

Ask Lots of Questions

Every employee prefers to be managed differently, so you should never assume that you’ll be able to manage someone effectively without asking for their input. Whenever you onboard a new employee, you need to take the time to learn about who they are, how they like to be managed, their communication style and what their career goals are. The time investment will go a long way toward establishing a lasting bond with your employees.

“Everyone is looking for different things,” said Mike Jahn, engineering manager at Chicago-based childcare tech platform Sittercity. “[Knowing that], you can tailor your relationship to make sure they have a successful career.”

“The goal of these questions is to enhance the team member's self-awareness so they can help shape a vision for their career and future.”

When you ask detailed clarifying questions about your employees’ preferences, you’ll get a clearer picture of how to serve them — but you will also push them to do some self reflection. Some good questions to test out: How do you prefer to communicate with your manager? What projects do you least enjoy? How often do you like to meet with your managers? 

“The goal of these questions is to enhance the team member's self-awareness so they can help shape a vision for their career and future,” said Kutcharian.

More Leadership TipsRelax Your Grip: How to Avoid Micromanaging

 

Help Set Goals

What differentiates a one-on-one from a casual chat is the structure — you should be using your time in one-on-ones to proactively set goals for your employee and yourself. When it comes to goal setting, help your report get as detailed as possible, and find out what you can do to help them get there. 

“I usually will try to figure out where they are trying to get in the short term, and what they want in the long term,” said Jahn. “We can differentiate what they can do in six months and what will help them a couple years from now.”

Instead of setting vague objectives without a plan to achieve them, create a definite roadmap with action items that both of you can work toward. Use your check-in time to hold each other accountable to those action items and to each other. Don’t shoulder all the responsibility for supporting your report’s growth, but make sure that you’re doing your part to help them get to where they want to go.

 

Keep a Good Record

Lisa Kalscheur, CMO at the Dallas-based cloud commerce company Kibo Commerce, maintains a sense of accountability during her check-ins by keeping meticulous records. “I take real-time notes throughout the week on each of my reports so that I am ready to come to our meetings with actionable insights,” she said. “This allows me to share specific feedback during our one-on-ones to help improve their team management, communication and other skills.”

“You should also encourage your employees to freely add any relevant topics to the talking points list to ensure the conversation is not lopsided.”

Taking a lot of notes helps you avoid repetitive conversations and will help you maximize your meeting time by addressing the most pressing matters first. You should absolutely keep track of what you discuss in each check-in, but the method by which you do so can be up to you. Jahn uses a software program called Know Your Team that allows him to organize his notes from one-on-ones with each of his reports, as well as providing him with reminders to come up with topics for upcoming meetings. Kutcharian, on the other hand, prefers to use a shared digital document that both he and his employees can edit. This helps him make sure that everyone’s concerns get addressed and nothing falls through the cracks.

“You should also encourage your employees to freely add any relevant topics to the talking points list to ensure the conversation is not lopsided,” he said.

More Leadership Reading9 Mentors Reveal the Questions They’re Eager to Answer

 

Figure Out What’s Working and Fix What Isn’t

Having a reliable structure for your one-on-one meetings helps, but don’t set anything in stone. As your employees grow and change over time, so will their needs — don’t be surprised if they begin asking you to switch things up down the line. In fact, anticipate that by asking for feedback regularly and often. If you’re the one to initiate the conversation, your employees will be more likely to voice their ideas.

“An employee might be thinking about what they want to change, but may not want to bring it up during a one-on-one,” said Jahn. “Every few months or so I ask my employees ‘Hey, is this working for us? Is there anything we should do differently?’”

“The way you want to be managed is not necessarily the way someone you manage wants to be managed.”

If their feedback isn’t entirely glowing, try not to take it personally. Instead, work with your employee to figure out alternatives that work better for them. Be flexible, instead of using a cookie-cutter approach to managing everyone on your team. 

“The way you want to be managed is not necessarily the way someone you manage wants to be managed,” Jahn said. 

 

Keep Learning

Yes, you should center check-ins on your employees, but that doesn’t mean you can’t get just as much out of them. One-on-ones are learning opportunities for managers as well, and can teach you a lot about who you are and how you work best.

“One-on-ones are also a great opportunity for managers to build and refine their own coaching skills, practice active listening and enhance their overall leadership ability and impact,” said Kutcharian. 

“It’s okay for someone to make a mistake and learn from it. Don't dip your hands in too many things.”

Do some reading on management techniques for one-on-ones, or have conversations with fellow managers about how they approach check-ins and what makes sense for them. Test out some of your newfound skills or knowledge in your next one-on-one, and take notes on what works and what doesn’t. Above all else, be easy on yourself, especially if you’re new to management. While many people move into management roles without specific training, that doesn’t mean leadership skills are intuitive. Be prepared to learn a lot, and don’t overburden yourself.

“It’s OK for someone to make a mistake and learn from it,” Jahn said. “Don't dip your hands in too many things.”

More Leadership Tips5 Ways to Make Daily Check-Ins More Effective for Developers

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