16 Questions That Leaders Should Ask During One-On-Ones

BY Jessica Helinski
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As a leader, you probably encourage your team to form authentic relationships with prospects and clients. But, do you take your own advice when it comes to your relationship with team members? Often, this vital part of leadership is overlooked. “The problem is that not all leaders are self-​aware, nor do they know how to develop an authentic relationship with their team to cultivate that much-​needed value,” writes Lance Baker for Medium​.com. Baker points out that this lack of rapport can have a negative impact not just on relationships but also on overall productivity.

Connect and Engage With Questions

Even if deep talks don’t come naturally, authentically engaging with others is a skill that can be improved upon. One way to do that is to ask questions. Not sure what to ask? Baker references Susan Scott who, in her book "Fierce Conversations: Achieving Success at Work and in Life One Conversation at a Time" shares a series of questions that are perfect for productive one-​on-​ones. Each of the 16 questions helps you connect and engage with each individual on a deeper-​than-​usual level. Here are the first five: 

1. What has become clear since last we met?

2. What is the area that, if you made an improvement, would give you and others the greatest return on time, energy, and dollars invested?

3. What is currently impossible to do that, if it were possible, would change everything?

4. What are you trying to make happen in the next three months?

5. What’s the most important decision you’re facing? What’s keeping you from making it?

Baker recommends not cramming every question into a single conversation, but rather spacing them out over various conversations. Adding one or two to each one-​on-​one can do wonders. “The great thing about a great question is that it does most of the work for you,” he writes. “Simply trading So, how are things going? with What do you wish you had more time to do? will give you a much more insightful answer.”

Take a look at all 16 questions and consider making them a part of your conversations with team members. Doing so will accomplish many things, from showing a genuine interest in your team to uncovering meaningful insights that can help you manage better.