Top 10 Practices to Implement in Coaching Conversations

Coaching conversations are a critical component of leadership.  According to ‘The Power of People Skills’ the top goals of a leader are to:

  1. Find the best people for the team
  2. Tell them what to do to win in their role
  3. Let them know how they’re doing and coach them on a regular basis

What is a Coaching Leadership Style?

 A coaching leadership style is, ‘Unlocking a person’s potential to maximize their own performance. It is helping them to learn rather than teaching them.’[1] Unlocking potential is not done in an authoritarian way, instead characteristics of a coaching leadership style include:

  1. Asking questions to produce insight
  2. Empowering the person by allowing them to figure out solutions to challenges
  3. Supporting the individual to achieve their desired outcome

Coaching takes more time, patience and skill than giving advice, but it ends up being more beneficial for both parties.

Why should I coach employees?

 When coaching conversations are done correctly, they produces insight (‘aha’ moments) and creativity. This is important because the brain requires insight to make lasting, transformational change.[2] In fact, when some people experience an ‘aha’ moment there is an influx of dopamine into the reward center in their brain. This is the same area of the brain that responds when a person takes a drug or a bite of good food and it produces motivation in problem solving activities. The person then repeats the behaviors to receive the reward again[3].

In other words:

When your employee comes to you with a challenge and you can coach them to produce an insight, they’ll feel great while problem solving, their habits will change and your business will benefit.

The coaching management style takes time to learn, but once mastered it gives you the approach needed to develop and engage your employees on a deeper and more transformative level.

As a certified coach, I recommend these 10 practical ways to create more insight in your day-to-day coaching conversations:

Ask, ‘What Else?’

The majority of us are spinning our wheels finding solutions to the wrong problems. Why? Rarely is the first issue presented the most meaningful to address.[4] Get into a practice of asking, ‘What else?’

Coaching style of leadership example:

Suzy is your employee and she comes to you and says, “I can’t seem to figure out how to make these sales calls!”  Time for some coaching conversations.

You say, “I can hear that you’re trying to figure out how to make sales calls, what else is going on?’

Ask mostly ‘What’ Questions:

In a coaching conversation, ‘What’ is open-ended and non-judgmental. You are less likely to ‘lead’ your employee into the solution (reducing insight) by asking, ‘Have you thought of?’ And you are much less likely to judge them by asking ‘Why’ questions.

Coach the ‘Person’

Have you ever heard an employee talking about their problem and thought, ‘This is so simple to figure out!’ You’re right. The tactical challenge presented is usually very simple because it is the ‘what’ of their problem. Instead, listen for emotional words, because they represent the ‘who’ of the person versus the ‘what’ they’re trying to solve.  Coaching the person is a critical part of a great coaching conversation.

Coaching style of leadership example:

Suzy tells you, “I don’t feel comfortable with the sales pitch.”

The ‘what’ is the sales pitch, the ‘who’ is feeling comfortable. If you address the pitch but not feeling comfortable, Suzy still won’t make calls.

Stay curious

We all know through personality assessments like DISC and real-world experience that each person has a unique way of looking at the world through their own personality, environment and set of beliefs. Ask about any words or concepts that can be interpreted differently. Your intent is to understand their way of thinking about the situation.

Coaching style of leadership example:

You ask, “What does feeling comfortable mean to you?”

Suzy says, “Feeling comfortable means I don’t have any hesitation making the pitch. I have all the details and I don’t have a heightened anxiety leading up to the call.”

In your coaching conversations, ask what’s been getting in the way of finding a solution themselves

This prompts deeper reflection.

Coaching style of leadership example:

You ask, ‘What’s been getting in the way of you addressing this on your own?’

Suzy responds, ‘I can write the pitch differently and research it more, but I feel really uncomfortable talking to new people.’’

  1. Know the Outcome: Ask what outcome they are looking for by talking to you. Are they looking for a to-do list, an action plan, a new perspective? Knowing this will set expectations with a true north and will reduce the likelihood of you assuming what they need.

Coaching style of leadership example:

You ask, “What are you wanting to walk away with from our conversation today?”

Suzy says, “I’d like a plan to feel more comfortable talking to new people.”

  1. Don’t try to fix it: This is the hardest one! 9 times out of 10 people don’t want your unsolicited advice and more often than not, it’s not very good (especially if you’re solving the wrong problem!)[5] Your objective is to keep asking about their ways of thinking and work towards their desired outcome without being attached to what you think they should do.

Coaching style of leadership example:

Knowing that Suzy feels uncomfortable talking to new people, instead of telling her, “You should join Toastmasters!”

Ask, “What is important to you about feeling comfortable?” or, “What specifically makes you feel uncomfortable when you’re talking to new people?”

Outcomes versus stories

  1. Avoid getting stuck in a story: We’ve all had it where we’re suddenly in the depths of a story that we didn’t anticipate and desperately want to get out. Stories get into unnecessary details, waste time and are better suited for a therapy session. Keep your conversation focused on the person, stay out of the past and keep them moving forward to the outcome they’re seeking.

Coaching style of leadership example:

Suzy says, “I think this stems from my first day in a new high school 20 years ago. I was talking to new people and my teacher totally embarrassed me.”

Don’t take the bait!

You say, “I can hear that you had an embarrassing experience in high school and it sounds like that impacted you. What would make this a comfortable experience for you now?”

This is critical to having effective coaching conversations.

Ask what they’re learning through your coaching conversations

I love this question because often there are deep internal thoughts that aren’t apparent on the outside as you’re coaching. This is where insight can be found (the ‘who’) and the solution to their challenge (the ‘what’) becomes clear.

Coaching style of leadership example:

You ask, “What are you learning about yourself as you talk through this?”

Suzy says, “I’ve realized that I’ve been making excuses and it’s been hindering my personal and professional growth. I am ready to take the next step to overcome this!”

Make an Action Plan

After great coaching conversations, you’ve figured out what obstacle was hindering the employee’s progress.  Now, make an action plan using SMART Goals:

Specific – what exactly will they do to address it? Suzy is going to attend a bootcamp at the Business Hub to increase her confidence.

Measurable – what will be looked at to ensure progress is being made? Right now, she is at a 2/10 for comfort and would like to be at 7/10 by the completion of the bootcamp.

Attainable – can they do this within a reasonable time frame? Yes, the bootcamp is next month.

Relevant – Is it something that aligns with their method of operating and values? Yes.

Time based – set a date to achieve and touch base. Touch base next week and complete next month.

Lastly, always ask how you can support.

If you’re not already implementing the Coach & Connect form on a regular basis, I encourage you to use this as a template in addition to the regular informal coaching you are giving employees using the tips above.


[1] Whitmore, J. (2017). Coaching for Performance Fifth Edition: The Principles and Practice of Coaching and Leadership UPDATED 25TH ANNIVERSARY EDITION (5th ed.). Nicholas Brealey.

[2] How Brain-Based Coaching Drives Lasting Change. (2019, August 14). UC Davis Continuing and Professional Education.

[3] Newman, T. (2018, April 30). What happens in the brain during a “eureka!” moment? Medical News Today.

[4] Stanier, B. M. (2020). The Advice Trap: Be Humble, Stay Curious & Change the Way You Lead Forever. Page Two.


[5] Martin, S. L. (2020, February 28). It’s Time to Stop Giving Unsolicited Advice. Psych Central.




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