Jake Manuel
Marketing Project Manager
January 8, 2021


How to Have More Conversations at Work that Count

When do you usually see your employees?

Is it only during that time for performance appraisal where your employees get to hear your thoughts about their performance for the first time in months?

Did you know that conversations done only during the employee’s yearly performance reviews result in high anxiety levels in employees?

This pattern creates a negative, if not frightful, experience between manager-employee conversations. Do you know if when you call your direct reports, the first question running through their minds is, “What did I do wrong this time?”

This is not the culture you want to have in your company.

You want a culture where employees get to maximize their potential and are busy being awesome at what they do best. Because when they are busy being awesome, that means you’re all busy making your customers and your company happy.

What’s one way to attain that?

Make coaching conversations a consistent part of your team’s workweek.

Benefits Of Using Coaching Conversations

As I shared the downside of not having coaching conversations as part of the company culture, let me share with you the benefits of using coaching conversations to grow your company by building up your team.

How do you turn the rod of your ship as your company pursues a new destination?

It happens – the company’s priorities change all of a sudden. It is easier to redirect everyone’s effort to meet new and revised goals when regular coaching conversations happen and are done more than once a year.

When is the best time to give your feedback after something happens?

Little children learn the lesson of their action if explained immediately after the event. The same goes for employees. Immediate feedback is best appreciated and understood if provided right away – not after weeks or months have passed.

Do you want your employees to not hesitate to ask for your help?

They are more likely to reach out to you for guidance if there are more consistent and informal coaching conversations happening outside of performance reviews.


Your Go-To Guide for Asking Executive Coach Vendors The Right Questions

Types of Coaching Conversations

According to Harvard Business Review, there are two types of coaching conversations that can happen:

Type #1: Calendar-Driven Coaching

Here’s how it looks like at a glance:

  • When: Specific time and date scheduled beforehand
  • How: Formal and structured; sit-down setup
  • Coverage: Work done over time, not a single specific event
  • Who: Initiated and controlled by the manager

This type of coaching should be clear to the employee as constructive feedback sessions.

For this session to be successful, make this event a “joint” one as you work with your employee.

Don’t dominate the session.

A week or two before the meeting, ask your “joint partner” to send you a list of topics that he or she wants to include in your upcoming coaching session.

Type #2: Event-Driven Coaching

Here’s how it looks like at a glance:

  • When: Whenever needed; “teachable moment”
  • How: Informal; part of the regular workweek.
  • Coverage: A particular incident
  • Who: Initiated by either the manager or the employee

This type of coaching doesn’t feel like a feedback session because it’s casual and spontaneous.

You can even do this right after a meeting. Process your team member as you both walk down the hall.

After saying his or her piece, make sure to give your own thoughts and insights and make sure that the takeaway is clear in your conversation.

Whichever type of coaching session you do, the best structure is the one called AAR or after-action review. To adopt this approach in the business context, remember to ask these key questions:

  • What was supposed to happen?
  • What did happen?
  • What worked?
  • What didn’t work?
  • How to improve next time?

How to Have Coaching Conversations at Work

There are many techniques on how to have great coaching conversations. For now, here are three tips to jumpstart your learning.

#1: Be crystal clear.

If you want to commend your direct report, think about the employee’s specific traits that contributed to the company’s success.

The same goes for correcting and suggesting changes. If you notice that your direct report lacks self-confidence, don’t simply imply the obvious. Be specific about your observations. You can say, “Your posture and eye contact show that you lack confidence in your expertise. Let’s discuss that.”

#2: Be compassionate.

Show that you’re human and not all-knowing.

Meet your coachee at his or her level.

Remember, the coaching conversations are to benefit them, not you.

If it’s any help, put yourself in their shoes and think about how you want your superior to talk to you during your one-on-ones.

You can also show compassion to yourself by learning to forgive yourself and taking it easy as you learn how to effectively create coaching conversation questions. And if it would help your coachee open up, you can even show your vulnerability by sharing that you’re also learning as you go.

#3: Be curious.

Your own biased views on things make it difficult to stay focused on your coachee and their learning.

Curiosity allows you to put those biases aside as you listen more actively and open yourself up to new insights and new ways of things. This curiosity will even lead you and your team to collaborative solutions where everyone – your team, you, and the company – is happy.

One of the best ways to show your curiosity during coaching conversations is by asking some of the AAR questions mentioned above.

What worked?

What didn’t work?

How do you think you could do better next time?

To Summarize

Keep these three things in mind when you’re having coaching conversations regardless of the when and where of your discussions.

  1. Listen actively. Listen to understand. Don’t listen to “respond.”
  2. Ask probing questions. Ask powerful questions to uncover insights your team member is not aware he or she has.
  3. Do not “fix.” This is about your team member learning and discovering himself and not about you showing how capable and knowledgeable you are.

Whether it’s a planned conversation or an impromptu one, learning coaching conversation questions and applying them in your work routine certainly build trust, create a safe environment, and encourage employee engagement and transparency.

And when good chemistry and relationships are built among colleagues, expect productivity from your employees as well as a company culture that is envied by your others.

Churchill Leadership Group is a seasoned and trusted partner for building the soft skills your leaders need. Learn more about our Leader as Great Coach program, where leaders at all levels in your organization develop coaching capabilities, like asking powerful questions, that enable better conversations for more growth and productivity across your organization.

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About Jake

Jake has a Bachelor’s Degree in Political Science and is currently working towards completing his Juris Doctor Degree. As an educator, he has a passion for teaching and learning. Between work and law school, he enjoys taking online courses such as Fundamentals of Project Planning and Management, Entrepreneurial Strategic Management, and International Organizations Management. He also volunteers his time for community outreach and education programs for local and international organizations.


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