5 coaching questions that will help grow and retain employees

Leaders who are seeking ways to increase engagement and retention should call on these five open-ended, exploratory questions with their employees.

Coaching as a profession has become increasingly popular during the pandemic. So many people are balancing life in ways they never imagined possible and are in need of proven methods to help them become unstuck. Enter the coach! 

As a Certified Executive Coach, I have witnessed the power of this process first-hand. But coaching isn’t just impactful for the top levels of organizations; people leaders at all levels and functions can use coaching techniques and questions to grow, engage and retain their team members. 

The terms coaching and mentoring are often used synonymously; they are, however, quite different. Mentoring falls into the more traditional training realm, occurring when a seasoned expert shares insights, learnings and knowledge gained through experience. Mentoring includes specific guidance and even direction drawn from the mentor’s skills and background to drive the mentee’s growth and development. Leaders often believe their biggest value to employees resides in sharing the methods they have personally found successful. This certainly can work as part of development. However, each person and circumstance is unique, and what works for one person may fall flat for another.

Coaching, on the other hand, is described by Sir John Whitmore as: “unlocking a person’s potential to maximize their own performance. It is helping them learn rather than teaching them.”  Coaching allows the coachee to develop their own ideas and decide how to move forward, helping to reveal previously untapped sources of imagination, productivity and leadership. Because outcomes are rooted in actions and behaviors that are inherently authentic to the individual coachee, they are more likely to follow through, experience a sense of pride in their success, and achieve what they want. 

While both mentoring and coaching have their place in people leadership, coaching can help empower, engage and motivate employees to act on behalf of their own growth and development. I find the following five basic coaching questions to be impactful and easy to implement in most employee feedback conversations. 

1. What is going well, and how can you leverage this going forward?

This question works well for employees who are achieving a good measure of success but also those who are feeling stuck. It focuses attention on the positive and/or helps to reframe difficulty in a more positive light. For the employee who is already experiencing success, this question helps create a vision of the next opportunity for success, whether it is a project, a relationship or a promotion. Alternatively, this question can help an employee experiencing challenges to examine pieces of the problem where they are experiencing success and how to capitalize on them and imagine new ways forward. In either situation, this question helps to create positive momentum, which ultimately drives engagement as well as vision and desire to attain increasing levels of success. 

2. If you could move one obstacle out of your way, what possibilities could that reveal?

An employee who is having difficulty moving a project forward can particularly benefit from this coaching question. As a leader, it is hard to watch an employee struggle. Often, leaders feel compelled to identify and remove obstacles themselves but doing so can diminish the employee’s self-esteem and enable a sense of weakness or victimhood. This question empowers the employee to activate his understanding of inherent obstacles and see past them to the desired outcome. It creates a renewal of positive energy towards the goals and an urgency to remove or work through the obstacle(s). This can be a great skill and confidence builder; the employee learns how to effectively navigate the challenge on his own, experiences success doing so, and thereby feels more prepared and capable for the next challenge. 

3. Who can you look to for support? How could other people help you accomplish your goals?

This question can be harder for leaders to ask because we often like to consider ourselves the “hero” that employees look to for support and guidance. A primary goal of this coaching question is to boost the employee’s self-sufficiency and help them identify additional advocates and influencers. This question can be used in almost any circumstance, but I personally like to use this in succession and career conversations. In a recent career coaching discussion with an employee who desires the next step but there is not a clear path to what they want, I posed a similar question: “Who do you know who has created their own career path?” Almost immediately the employee named three people, and the future she had been struggling to envision came into clarity from there. After some discussion around how she can leverage those three people to find her own way, she feels more supported than if I had simply shared my ideas. Using this question can help retain your top talent, because employees will build their network of supporters beyond you, their leader. 

4. A year from now, what would you like to be different for you? The same?

This is a question about goals, dreams and fulfillment. This question can be used in almost any conversation, whether things are going well or not going well for the employee. In fact, this is a great question to ask repeatedly over time, as the answer will likely change as your employee explores their own thinking and becomes more empowered to come up with new ideas. Your employee will share things he finds most fulfilling, which can guide you with future work assignments that are more engaging and influence the way you lead. Be open-minded when you listen to what your employee wants to be different; these are the things that do not satisfy or motivate him. Following through on removing these unfulfilling things (as possible) can prove to be great for retention. 

5. Imagine having a chat with the wisest person you can think of (whether you know them or not), what would he suggest you do? (Or what would you tell your best friend in this situation?)

This is a great question when your employee is grappling with a difficult situation and you sense the employee knows the answer but is hesitating to say so or act on it. As a leader, you are probably biting your tongue because you want to give advice. This question literally puts your employee in the role of expert, by channeling the imagined expertise of someone he admires. Another way to phrase this is to imagine that he needs to give advice to a friend or colleague. Then ask an open-ended follow-up such as: How might that advice help you now? Your employee will make the connections he needs, even if it’s not the advice you would offer and will ultimately feel more empowered and accountable to act for himself. 

Some final tips for leaders who like to give advice

Leaders frequently feel like we should have answers. But employees grow and develop the most when they generate their own ideas and are empowered to take ownership for the follow-through. So here are a few final pieces of advice for my fellow leaders:

  • Stop talking: Remember, coaching it is not about solving your employees’ problems for them, it is about helping them examine their own ideas. You don’t have to be an expert; in fact, it is better if you allow them to learn how to become their own best resource.
  • Listen: It might be surprising what you learn from them that you can use yourself! 
  • Hold your advice: You will feel compelled to give advice, to be the expert. Also, sometimes employees outright ask for it. If the employee solicits your counsel, explain that you want to explore his ideas first; then if it’s still appropriate, share any additional thoughts you have. 

Unless your employee is clearly going down a wrong path that could hurt them organizationally or is lacking key information to determine the best way forward let him do most, if not all, of the talking. 

Leaders who are seeking ways to increase engagement and retention should call on these types of open-ended, exploratory questions with their employees. I have personally found these five simple questions to be impactful and easy to implement in many employee conversations. Any leader can use these in everyday situations – you do not need to be a certified coach to get results like one.