Tips for Courageous Leaders to Have More Effective One on One Meetings

One of the most important skills for leaders is the ability to coach their employees. Coaching is a tool for leaders to help others discover their own strengths, passions, and potential. It’s not about fixing problems but creating opportunities for learning and growth.

But how do you coach your employees effectively? How do you maximize your 1:1 meetings, which are frequently the only opportunities you have to engage them more deeply? How do you provide a secure and safe environment where they may discuss their problems, goals, and feedback?

Here are some of my own learnings from two of my favorite books on coaching and leadership -- “The Coaching Habit” by Michael Bungay Stanier and “Dare to Lead” by Brene Brown. I hope these will help you run most useful 1:1 meetings, empowering your employees and yourself to be more courageous, authentic, and engaged.

Tip #1: Ask more, tell less

Curiosity is key: Both Stanier and Brown emphasize that one of the most important qualities you can bring to a one-on-one meeting is curiosity. You should aim to listen well, ask thoughtful questions, and explore the other person's perspective rather than telling them what to do.

One of the biggest mistakes that leaders make when coaching their employees is that they talk too much and listen too little. I've made this mistake myself plenty of times. As leaders, we may sometimes assume we know what the employee needs, wants, or thinks, and then offer advice, solutions, or opinions too quickly, without really understanding the situation or the person. This is not only ineffective, but can accidentally send the message that you don’t trust your employee’s judgment, creativity, or agency. It also robs them of the opportunity to learn from their own experience, to develop their own skills, and to own their own outcomes.

Instead of telling your employees what to do, ask them more questions. Questions that are open-ended, curious, and empowering. Questions that invite them to reflect, explore, and discover. Questions that challenge them to think deeper, broader, and higher.

In “The Coaching Habit”, Michael Bungay Stanier offers seven powerful questions that you can use in your 1:1 meetings to coach your employees effectively. These are:

• “What’s on your mind?” This is the kickstart question that opens up the conversation and lets the employee choose what to focus on. It shows that you care about what matters to them and that you are ready to listen.
• “And what else?” This is the AWE question that helps you dig deeper and uncover more information, insights, or emotions. It shows that you are not satisfied with the first answer and that you want to explore further.
• “What’s the real challenge here for you?” This is the focus question that helps you narrow down the issue and identify the root cause. It shows that you are not interested in superficial symptoms or distractions, but in the core problem that needs to be solved.
• “What do you want?” This is the foundation question that helps you clarify the desired outcome and the motivation behind it. It shows that you are not imposing your own agenda or expectations, but supporting the employee’s goals and aspirations.
• “How can I help?” This is the lazy question that helps you avoid jumping into action mode and instead offer the right kind of support. It shows that you are not taking over the responsibility or the credit, but empowering the employee to take the lead and ask for what they need.
• “If you’re saying yes to this, what are you saying no to?” This is the strategic question that helps you evaluate the trade-offs and the consequences of the decision. It shows that you are not ignoring the reality or complexity, but helping the employee think through the implications and the alternatives.
• “What was most useful for you?” This is the learning question that helps you close the conversation and reinforce the key takeaways. It shows that you are not just moving on to the next thing, but reflecting on the value and the impact of the coaching session.

These questions are not meant to be used in a rigid or sequential order, but rather as a flexible and adaptable guide that you can adjust to the context and the person. The key is to ask them with genuine curiosity and empathy, and to listen attentively and respectfully to the answers.

Tip #2: Be vulnerable, not perfect

Another common mistake that leaders make when coaching their employees is that they try to appear perfect, confident, and in control. They hide their own doubts, fears, or mistakes, and they pretend to have all the answers, all the time. This is not only unrealistic, but also harmful. It creates a culture of perfectionism, where people are afraid to take risks, to make mistakes, or to ask for help. It also creates a distance between you and your employees, where they don’t feel comfortable or safe to be themselves, to share their struggles, or to give you honest feedback.

Instead of trying to be perfect, be vulnerable. Vulnerability is not a weakness, but a strength. It is the courage to show up and be seen, to admit that you don’t know everything, and to ask for help when you need it.

 In “Dare to Lead”, Brene Brown defines vulnerability as “the emotion we experience during times of uncertainty, risk, and emotional exposure.”  She shares four skill sets that you can use to cultivate vulnerability and lead with courage. These are:

• Rumbling with vulnerability. This is the skill of embracing vulnerability as a source of learning and growth, rather than avoiding or suppressing it. It involves recognizing and naming your emotions, being curious about your stories, and challenging your assumptions.
• Living into our values. This is the skill of aligning your actions with your beliefs, and holding yourself and others accountable to them. It involves clarifying what matters to you, making intentional choices, and practicing integrity.
• Braving trust. This is the skill of building and maintaining trusting relationships with yourself and others. It involves honoring the seven elements of trust: boundaries, reliability, accountability, vault, integrity, non-judgment, and generosity.
• Learning to rise. This is the skill of recovering and growing from setbacks, failures, or disappointments. It involves reckoning with your emotions, rumbling with your stories, and revolutionizing your learnings.

These skills are not only useful for yourself, but also for your employees. By being vulnerable, you model the behavior that you want to see in them, and you create a culture of courage, where people can show up as their whole selves, take smart risks, learn from their mistakes, and support each other.

Tip #3: Give feedback, not criticism

One of the most challenging aspects of coaching your employees is giving them feedback. Feedback is essential for their development and performance, but it can also be difficult to deliver and receive. Many leaders avoid giving feedback, or give it in a way that is vague, harsh, or unhelpful. In a desire to not offend or hurt feelings, leaders can sometimes sugar coat messages so much that they can lose their impact or meaning. This is not only a missed opportunity, but also a disservice. It deprives your employees of the chance to improve, to grow, and to achieve their potential. It also erodes your credibility, your trust, and your relationship with them.

Feedback is not criticism, but guidance. It is not about judging, blaming, or shaming, but about helping, supporting, and encouraging.

At Microsoft, we talk about "speaking truth with care." It’s the art of having difficult conversations in a way that is clear, while also being empathetic. In “Dare to Lead”, Brown shares a simple framework that you can use to give feedback effectively and compassionately. It is called the SBI model, which stands for:

• Situation. This is where you describe the specific context and behavior that you observed, without making any interpretations or assumptions. For example, “Yesterday, during the team meeting, you interrupted me several times while I was presenting the project update.”
• Behavior. This is where you describe the impact of the behavior, both on yourself and on others, using “I” statements and expressing your feelings. For example, “I felt frustrated and disrespected, and I noticed that other team members looked annoyed and distracted.”
• Impact. This is where you describe the desired behavior and outcome, and invite the employee to share their perspective and collaborate on a solution. For example, “I would appreciate it if you could wait until I finish speaking before you share your comments or questions. This way, we can have a more productive and respectful conversation. What do you think?”

This framework is not only useful for giving feedback, but also for receiving it. By using the SBI model, you can ask for feedback from your employees, and listen to it with curiosity and openness, rather than defensiveness or resistance.

Coaching your employees is one of the most rewarding and impactful things you can do as a leader. When implemented consistently, these tips can make your one-on-one meetings transformative for both you and your employees.