Skip to navigation
Leadership asking questions for employee engagement
5 Min Read

5 One-on-One Questions to ask Employees Weekly

User Default Avatar
Guest Post

What makes a great coach? 

This age-old question has generated many different theories over the years; even researchers have joined the conversation and taken their shot at solving it. Although there isn’t one single

trait that makes an effective manager, one common skill shared among them is mastery in the art of asking questions.

At 15Five, we’ve found that when you get into a regular cadence of asking your people the right one on one questions, it allows you to proactively uncover issues before they manifest, helps your employees to grow and develop at a quicker rate, and you’ll get to the heart of what’s most important with every conversation, especially during 1-on-1s.

Becoming the best coach you can be is a lifelong practice. Here are five 1-on-1 questions to ask employees every week to jumpstart your journey and help lead your people to greatness.

1. What’s going well in your role? Any wins this week?

This is always a great place to start. Never miss an opportunity to let your employees celebrate and even brag a little about all the things that are going well in their role. This also includes the small wins that often get overlooked because they aren’t related to top priorities. As a bonus, you’ll get a better understanding of where their strengths lie so you can plan more opportunities to expand on them in the future.

Another way you can increase the amount of employee recognition shared between employees is through virtual High Fives. This feature within 15Five makes it easy for employees, managers, and leaders to send appreciation to one another in a more meaningful way.

2. What challenges are you facing?

Too often, people feel the only way to approach problems is to react to them once they’ve settled in. Ask your people what challenges they’re facing so you can take proactive measures to prevent them before they grow to an unruly point. This is also an opportunity to practice building a psychologically safe space for them to share their issues. If employees can let go of the fear of how their challenges will be received, they are more likely to let you in.

3. How are you feeling? What’s the morale around you?

The idea that feelings should be separated from work is an outdated principle, and frankly, impossible to achieve. Life doesn’t pause during the 40+ hours in the workday, so it’s important to understand how your people are really doing. Plus, helping your employees learn to articulate their emotions can lead to healthier relationships, greater wellbeing, and better resilience in and out of work. 

During 1-on-1 meetings with your employees, don’t forget to share your feelings as well. Research by Harvard Business School professor Jeff Polzer shows the process of building trust starts with vulnerability. Sharing your emotions with employees can help create a safe environment for your people to be honest.

4. On a scale of 1-10, how fulfilled are you? Why?

The research of positive psychology is clear: employee satisfaction is a precursor to success and accomplishment, not the other way around.  When your people feel fulfilled, they not only come up with better solutions, but their satisfaction also helps to build a culture of high performance and low turnover. Continuously asking this question will help you understand their engagement levels and send the message that they’re valued beyond their performance.

5. Ask for feedback on ways you can become a better leader

Feedback isn’t a comfortable thing to give or receive, especially when it’s unsolicited. That’s why the most valuable feedback is the kind you ask for. It can reveal what you’re currently doing well as a manager and which behaviors you can work on to become a better coach. Asking this question can also serve as a model and encourage your people to feel comfortable asking for their own feedback.

“Asking for feedback is a surprisingly powerful approach to self-development, especially when it’s part of basic performance management. It can even be considered a deliverable—the last step of a project. Regardless, requested feedback allows teams to demonstrate the care that everyone needs to feel engaged,” according to Gallup.

A lot can happen in an eight hour day, and especially over the course of an entire week, so don’t let these important discussions fall through the cracks. Asking each of these five questions on a weekly basis will help give your employees a voice, open the door for valuable conversations, and advance your path to question mastery.

David Hassell, CEO of 15Five

David Hassell is a business columnist, speaker, and serial entrepreneur who believes that when leaders institute cultural practices that support each person in being and becoming their best self, high performance and uncommon loyalty naturally result. As co-founder and CEO of 15Five, David created the science-inspired Best-Self Management methodology that helps leaders and managers address the hidden factors that stimulate sustainable growth and development – things like intrinsic motivation, strengths, and psychological safety. David has been featured in The Wall Street Journal, Inc., Entrepreneur, Fast Company, and Wired. Follow him on Twitter @dhassell.

Image credit: Shutterstock