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Impactful Coaching Conversations

Last week, I wrote about the importance of transitioning your bosses to coaches. Clearly, the first step is to develop your managers to be good coaches which includes giving feedback effectively, listening well, coaching (rather than fixing or giving advice), and tapping into employees’ strengths. The second step to support boss to coach is to insert some coaching conversations into your culture.


5 Types of Impactful Coaching Conversations


#1 Roles and Responsibilities This is a foundational discussion which should be held once a year where the following takes place:

  • Establish expectations

  • Define what success looks like

  • Discuss how their job fits in with the team/organization

#2 One-on-Ones

One-on-ones or check-ins should be held with a frequency that probably differs based on the job role and the organization. Let’s face it – most managers kind of suck at making the most of their one-on-ones. It’s often, “update me on what’s going on” and “see ya next time.” Here is a loose agenda that I Iike for one-on-ones.

  • Opening – Connect, ask “What’s on your mind?”

  • Follow-up items from previous one-on-one including updates on projects/tasks

  • Ask – Biggest accomplishments since our last check-in? Where have you gotten stuck?

  • Two-way feedback

  • End with developing accountabilities on both ends

#3 Career coaching

These conversations help employees explore options and provide support to help them meet their career goals. Here are some questions that you could ask as part of career coaching.

  1. What are you most proud of?

  2. How are you using your strengths at work? How could you use them more?

  3. What tasks do you enjoy the most? What don’t you enjoy?

  4. What knowledge or skills do you need to get to the next level in your career?

  5. When you have reached the pinnacle of your career, what do you see yourself doing?

#4 Performance Conversations

Performance conversations are my personal preferred method of performance management. They are focused on celebrating successes, learning from setbacks, preparing for future achievements, and planning for development. The frequency of these conversations is ideally quarterly, but at least twice a year. If you haven’t ditched the traditional performance review process, it’s time to consider that. Research has shown that they are dreaded and not effective in increasing performance.


Here are some topics to consider including in performance conversations.

  • Purpose

  • Goals

  • Metrics

  • Development

  • Well-being

  • Values

#5 Stay Interviews

These are periodic one-on-one interviews that identify factors that drive an employee to stay or leave the organization. Stay interviews are Ideally conducted by the manager if it is a trusting relationship. Below are the top 5 questions to ask:

  1. What do you like the most about working here?

  2. What do you like least about working here?

  3. What would you like to learn?

  4. What motivates (or demotivates) you?

  5. How can I best support you?

Benefits of Coaching Conversations

You may be thinking, “Is this woman crazy? Our managers are busy as it is. They don’t have time for all of these conversations.” I’m not suggesting that you implement all five. Consider where you would get the most bang for your buck and what makes sense for your organization and move forward accordingly.


More frequent conversations of this nature will save time and energy spent on misguided work efforts, unproductive politics, and dealing with turnover.


Would you like more resources to help?

I have toolkits for one-ones, stay interviews and performance conversations available on my website!


Want to move towards a coaching culture? Ask me about my Boss to Coach program for managers and train the trainer option! Let's get started!





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