Four Critical Questions to Ask the Job Seekers You Coach

You’ve probably experienced the “ah ha” of being asked a question that set off a light bulb in your brain. The question likely pumped up your hope, or got you out of a funk, or led you to take action on what was most important to you. 4 Career Coaching Questions to Ask

The questions you ask your job seekers can shift them from stuck or stalled to unstoppable and successful. After teaching career coaching for more than a decade, I’ve noticed that there are four categories of questions that must be asked of the job seekers you coach:

  • What?
  • Why?
  • What If?
  • How To? 

These four types of questions uncover visioning, purpose, fears, and practical action steps. For example:


“What Questions” create self-awareness and step people into the future … into a space of possibility and designing what they really want from life and work. When they are in that space of “co-creating” with God, it’s easier to be optimistic and see solutions. Some “What questions” might sound like these:

  • If the Lord knocked on your door and offered you access to any influential people, all the time in the world, and the riches of heaven at your disposal, what would you choose to do with your days?
  • What would you love more of in your work? . . . and less of?
  • What’s the Lord placed in front of you right now . . . a challenge disguised as an opportunity, a need that needs met, a longing or inkling in your spirit?


“Why Questions” are the proverbial carrot—they are reminders of the motivations for goals and dreams. “Why questions” might sound like this:

  • What would be different? And what would that bring you? How might this connect with the final – “well done, good and faithful servant?”
  • Why would that be fulfilling?
  • How would that change your current circumstances?

What If?

“What If Questions” get at the root of fears and concerns that cause procrastination, excuses, limiting beliefs, or misguided and inefficient action. “What If Questions” might include:

  • What’s the Lord’s response to that question?
  • What’s the worst that can happen?
  • How would you lessen the risk of that happening?
  • If not now, when?
  • I get the sense you’re thinking, ‘Who am I to do this amazing thing?’ As a child of the King  ‘Who are you not to go for it?’
  • What’s the payoff for procrastinating?


“How Questions” involve processes, steps, timelines, and accountability. They  bring structure and support to the client’s action steps. For example:

  • What specifically will you do to move closer to your goal?
  • What are some other options for making that happen?
  • How many ___________ (informational interviews, target companies identified, etc.) would be the right number?
  • How will you know you’ve been successful in that step?
  • When do you want to be finished with that?
  • Who else needs to be involved to make it go smoothly? Or, whose cooperation do you need in this?
  • What will finishing that allow you to do next?

Experiment and have fun with these categorical questions. Try them out with your clients, as well as yourself when working toward your own goals!


Career Coach Certification Training

Christian careers author, Susan Whitcomb, and her organization The Academies | Career Coach Academy is offering its ICF-approved, 30-hour career coach certification training for those who want to help the thousands of unemployed/underemployed who are turning to career ministries for help. Call 877-659-3769 ext 1 for details.


  1. Thank you Susan for great coaching tips! Loved going through your training myself!

  2. Thanks, Brian! So grateful your ministry partners are making such a difference in jobseekers’ success.

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