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The 7 Coaching Questions That Actually Help Career Clarity

By , founder, U.S. Air Force veteranPublished

The short answer

The questions that help career clarity ask about real moments, not dream jobs: when you lost track of time, what people ask you for, what you would refuse to put up with, what you would give up for something else, and what you could test in two weeks. Clarity comes from answers you can check against real work.

Launch League's take

The trade-off test

A value only counts if you would give something up for it. Everyone says they want good pay, freedom and meaningful work. The useful answer is which one you would sacrifice when they collide, because in almost every real job they do.

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Why most career questions don't produce clarity

“What do you want to be?” and “What are you passionate about?” are the two most common career questions adults ask teenagers, and they are the two least useful. Both ask for a conclusion before there is any evidence. A 16-year-old answers with a job they have seen on a screen, or with a shrug, and neither tells you anything.

I coached high school basketball for close to fifteen years. Nobody improves a jump shot by being asked whether they feel like a shooter. You watch what actually happens, then adjust. Career questions should work the same way: ask about what happened, and let the conclusion show up later.

The 7 coaching questions that actually help career clarity

These are the seven I would put to any teenager, in this order. Each one is answered with a story or an example, not a job title. If the answer comes back as a title, ask for the moment behind it.

  • 1. When did you last lose track of time doing something that wasn't a screen?
  • 2. What do people already come to you for: friends, family, teammates, a boss?
  • 3. Think of a day that left you completely drained. What exactly were you doing?
  • 4. If two jobs paid exactly the same, what would make you choose one over the other?
  • 5. What problem, in your school, your town or the wider world, bothers you enough that you would spend your working life near it?
  • 6. Whose working day have you seen up close that you would actually want, and which part of it?
  • 7. What is one thing you could do in the next two weeks to test your best guess?

What each question is listening for

Questions 1 and 2 find energy and strengths. Losing track of time is the most honest signal of interest there is, and what other people come to you for is usually a strength you undervalue because it comes easily. Question 3 finds the deal-breakers, which matter as much as the attractions. Plenty of people pick a career for what they like about it and quit it over the one thing they hate.

Question 4 is values, and it uses the trade-off test. Pay is held equal on purpose, so the answer has to be something else: the people, the schedule, being outdoors, being trusted to work alone. Question 5 is the why. Question 6 moves from abstract to real, because wanting a particular person's day is much more specific than wanting a field. Question 7 turns the whole conversation into an action, which is the only thing that produces more clarity.

Finding your 'why': career coaching questions that matter

A why is not a passion. Most teenagers don't have one burning passion, and telling them to find it makes them feel broken. A more useful why is a problem you want to be near. “I want old people in my town to not be lonely.” “I want things to work properly.” “I want my family to never have to worry about money the way we did.” Those are all real whys, and each one points toward many careers, not one.

That last example matters. A why does not have to be noble. Security is a legitimate reason to choose work, and a teenager who says so has given you more honest information than one who says they want to change the world. Write the why down in the teenager's own words. It will be the tie-breaker later when two options look equally good.

The role of values in career selection

Values are what is important to you in a job, separate from what you are interested in. The psychologists Dawis and Lofquist, in their Theory of Work Adjustment, grouped the many things people need from work into six broad values: achievement, independence, recognition, relationships, support and working conditions. Their research linked a match between a person's values and the job to how satisfied workers are and how well they perform. The six make a good checklist for a family conversation.

Here is how I use them. Read the six aloud and ask the teenager to rank them. Then apply the trade-off test to the top two: would you take a job with less independence for better working conditions? Less recognition for better relationships with the people around you? The ranking that survives those questions is the one to trust. When a career looks attractive on paper but fails the top value, that is usually the career a person leaves within a few years.

How to ask these so you get real answers

Parents, a few things that work. Ask one question at a time, not all seven in a sitting. Car rides and dishes work better than sitting across a table. Don't react to the answer with a job suggestion; just say “tell me more” and write it down later. And accept “I don't know” the first time. Come back to the same question a week later and the answer is usually better.

If your teenager will answer these questions for a stranger and not for you, that is extremely common and not a failure on your part. It is one of the best reasons to bring in an outside coach.

Take the answers to the Individual Pathways Plan review

Ontario students in Grades 7 to 12 keep an Individual Pathways Plan, and schools must have a process for reviewing and revising it at least twice a year with a parent, guardian or teacher. The plan is built around four questions: who am I, what are my opportunities, who do I want to become, and what is my plan for achieving my goals.

The seven questions above feed straight into the first three. A teenager who arrives at the review with written answers gets a far better conversation with their guidance counsellor than one who arrives cold.

How to figure out what career fits youCareer coaching for teens

Questions

Quick answers

Can I use these questions with an adult changing careers?
Yes, with one change: for question 6, think about colleagues and people in your industry rather than family friends. Adults also tend to have more receipts to draw on, which makes questions 1 to 3 faster to answer.
What if the answers point in completely different directions?
That is normal and useful. It usually means there are two or three career families worth testing, not one. Use question 7 on each of them and let the tests decide, rather than forcing a choice from the answers alone.
How often should we go through the questions?
Once properly, then again after any big new experience: a first job, a summer program, a tough semester. Comparing old answers with new ones shows what is stable about a person and what was just a phase.
Is it a problem if my teenager's top value is money?
No. It is an honest answer and a common one. Apply the trade-off test: what would they give up for more money, such as time, location or comfort? The answer separates someone who wants security from someone who wants to get rich, and those lead to quite different careers.