Most people are promoted into management because they’re great individual contributors. In a way, it’s the logical progression in one’s career path. Having been successful as an individual contributor, the hope is they’ll also be successful at leading and improving the performance of other individual contributors. But being a manager, as compared to being an individual contributor, requires a different skillset.

Some companies are great about training these new managers and helping them develop the skills they need to be successful. Sadly though, most companies don’t offer any training or mentorship, and new managers are left on their own to figure out right from wrong, good from bad. Those who used to be great individual contributors are now often subpar managers with disgruntled employees, and to no fault of their own.

What can make or break a manager, new or experienced, is the amount of trust that exists between them and their employees.

What can make or break a manager, new or experienced, is the amount of trust that exists between them and their employees. By being open, vulnerable, and honest with their employees, managers can establish the trust necessary to develop their skills and successfully lead a team. Furthermore, employees who trust their manager are more engaged, assume more responsibility, and look to move the entire company forward.

Personally, I’ve faced these problems. Of everything I’ve tried, I’ve found routinely meeting with an employee one-on-one to discuss how they’re feeling, what’s going well, what isn’t, and to get their pulse on how they’re doing and where we can improve is by far the best way to build trust. These meetings are about the employee and what they need or wish to discuss. The most organic conversations are the best, however much like a fire, a few sparks or questions to get the conversation started go a long way.

The most organic conversations are the best, however much like a fire, a few sparks or questions to get the conversation started go a long way.

Finding questions that work well within a one-on-one can be tricky though. Darby Frey, a long time friend and excellent manager, and I often find ourselves discussing the questions we ask during one-on-ones and the hidden perspectives they’d unlock. This has became a habit for us, and we’ve found by asking the right questions and having honest conversations we are able to build stronger trust and actively engage employees.

Introducing Lead Honestly

Lead Honestly

Darby and I know we’re not alone, and to share the questions we’ve found that lead to the most engaging one-on-one conversations, and to help managers become better leaders, we built Lead Honestly. The way it works is simple. Every Monday morning we email you five questions to ask your employees, along with one tangible management recommendation. In fact, let’s get started now.

Here are five questions to ask your employees in your next one-on-one:

  • What keeps you engaged?
  • What is your largest frustration?
  • What is something you would like to try?
  • Who deserves more recognition?
  • Where may I help you?

As for a management recommendation, we suggest:

For insight into someone’s thought process and interests, ask them to “please say that one more time.” Their answer will provide a new explanation with different context.

If you like these, sign up for Lead Honestly to get five new questions and one management recommendation every Monday.

In our experience, we’ve found a way of asking questions that isn’t interrogative while offering the most insight into how someone feels. This includes sticking to open ended questions, using follow-up questions to ask about specific emotions and reactions, and finding the story that provides the context to hold everything together. Furthermore, we’ve found using different questions during each one-on-one goes a long way to ensure each meeting provides value and isn’t the “same” as the last one.

Being a leader is challenging and incredibly rewarding work. Our goal is to help others become better leaders, and to lead honestly. We hope you’ll join us by signing up for Lead Honestly or sharing with your friends.

If you ever have any questions or feedback, we’d love to hear from you. Thanks!