The Art of Effective Career Coaching Using 5 Questions

The Art of Effective Career Coaching Using 5 Questions

Have you ever wondered what could happen if you truly understood what drives you or your team members at work? Shake things up on your approach to career coaching with five pivotal questions that uncover deep insights into personal motivations and emotional connections. This powerful framework is designed to not only clarify self-perception but also illuminate potential career paths and essential development areas for future success. We'll discuss real-life scenarios and offer practical advice on how to foster self-awareness without discouraging anyone. Find out these crucial actionable tips and strategies to elevate your career coaching conversations and help your team reach their full potential.


There are five great questions to ask somebody when you are doing career coaching, whether it's yourself or your team members. The first three are:

1) What do you love about your job?

2) What do you like about your job?

3) What do you dislike about your job?

You're going to get insight into people's wants and their emotional attachments, whether it be a present job or a future role. Gear the questions to either their present job or future role.

Option A: What do you love, like, and dislike about your present job?

Option B: What do you think you would love, like, and dislike about that future ideal role?

The other two questions are strength and opportunity. (Continue the article below the video.)

4) As it relates to your present job, where do you feel like you have strengths?

5) Where do you feel like you have opportunities to grow and improve?

You can also reframe these questions to be geared toward their future desired role.

Option A: As it relates to your present job, where do you feel like you have strengths? Where do you feel like you have opportunities to grow and improve?

Option B: What strengths do you feel like you have right now that relate to that future job? What opportunities do you feel like you need to improve to take that new job?

Recently I had someone share with me, "I had an employee list their strengths, and I was thinking to myself those weren't their strengths at all; those were their weaknesses. And I said so in our meeting. They don't see themselves clearly, like most people don't. What do I do in that situation?"

I told them it was simple. Now they had to coach in self-awareness. They had to change gears and ask questions about how they see themselves.

I asked the manager, "When you reacted to their list of strengths you viewed as their weaknesses, how did you react?" He said he was a little dismayed and admitted they likely saw that he was dismayed by their response.

"Do you think they wanted to continue the conversation?"

"Wow, good point. Probably not."

We all make mistakes sometimes, everyone. When we hear something we disagree with, we have an emotional reaction. We're human. I always go back to the concept of EAT Feedback: Embrace, Ask, and Tell. Here's what that exchange could look like:

"Oh, that's awesome, Joe, you see that as a strength. Let me ask you something. Could you give me a couple of examples and walk me through a few specifics where you feel like those strengths have manifested themselves? Then tell me about some things where you need to take those strengths to the next level."

Dive into that discussion. The person may not see those strengths or weaknesses as clearly as you, their leader. The point of a career conversation isn't about agreement; it's exploration.

Remember these five great questions: Love, Like, Dislike, Strengths, and Opportunity. This will start to flush out how people see themselves. Yet more importantly, it provides a direction of where they want to go and the path they need to take to get there.

SUPPLEMENTAL COACHING IDEAS FOR CAREER DEVELOPMENT PLANNING:

  1. Have the person create their own self-development plan focusing on what they need to do for their target promotional opportunity they want to seek, and have them create a communication strategy of what they're doing to pursue improvement to position themselves.
  2. Assign a mentor or have them ask someone who is good at their target role or skills to agree to be their mentor. This shows trust on your behalf as their leader and your willingness to help find someone who can invest in them.
  3. Read the following titles and have them journal after each chapter what they learned, what they learned about themselves, and what actions they're positively committed to doing moving forward: Talent Keepers by Christopher Mulligan & Craig Taylor, or Crucial Conversations by Kerry Patterson, or another title related to the area you are coaching to. Ask them to share their findings with you every few weeks.


Being approachable and coachable-- this is the real secret sauce to what's missing in workplace cultures and is needed most.

Watch the FREE Webinar with Tim Hagen today: Become Approachable & Coachable: The Secret Sauce to Workplace Success

Learn how to help coach individuals to become approachable and coachable. Teach them how to EAT feedback (Embrace, Ask, & Tell) to help them pursue their own development in positive and effective ways. Learn the top 10 tips for approachability and how to implement them in your coaching sphere.



Kamuzinzi Billykapo

Business Owner at Billykapo

1mo

Getting new friends and more connections and proving what am doing… I like it so much..it makes me hungry later in the night and transportation issues…

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Claire Golding

I help professionals rediscover their inner compass, ignite their spark, and navigate career transitions with clarity and confidence.

1mo
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Tiffany McMacken

Best-in-Class Learning & Development Leader ➞ Solutions to grow individuals & fuel overall performance

1mo

Thanks for sharing! Excellent questions!

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Neil Torino

Organizational and Business development consultant who ROCKS THE HOUSE!!

1mo

Thought provoking questions are useful only if the introspection of the individual answering them is truthful.

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Maurice Rondeau, MA CPTD®

Learning & Organizational Development Executive >>> Global Leader & Strategist >>> Passionate Practitioner

1mo

Thoughtful approach for self reflection and good options. Thanks for sharing this.

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