The (5) W’s and (1) H: Career Coaching Edition

I’m lucky that part of my corporate day job includes career coaching. Not only am I able to talk with employees at all experience levels and in different business groups, I also get regular check-in with myself on my own career aspirations.

Across my coaching conversations, I find myself turning to those classic reporter’s questions, the (5) Ws and (1) H to understand why someone isn’t happy in their current role – and what might make them happier in a new job.

Asking these (6) questions uncovers what’s not working in a current role and where to look for something different. Vague answers require more reflection before action, but once someone can concisely answer these questions? Well, usually a next step on the career journey becomes much clearer!

  • Who does your work serve?
  • What are you learning in your current role?
  • When do you anticipate completing skill development in your current work?
  • Where do you see future opportunities to apply your new-found expertise?
  • Why did you chose this job, at this company, at this time?
  • How would someone who is great at this work show up every day?

Who: Research shows that being of service to others increases the chance of feeling happiness. If there is no “who” to your work, or it feels convoluted, insights into who benefits from your efforts may change how you feel about your work – without actually changing your work.

What: Happiness is an outcome of learning and intellectual curiosity. If you’re not learning, you’re not growing, and stagnation is never a desired end-state. If you feel you’ve reached the limits of learning in your current role, creative thinking about where to learn something new outside of work may increase an overall sense of satisfaction on the job.

When: Daniel Pink’s Autonomy, Mastery and Skill framework is a great tool to check in on what’s motivating you. Motivation comes from work that involves all three concepts, and knowing if your current role isn’t providing one of the three foundational needs for motivation is itself insightful in what to look for in a new assignment.

Where: If you can’t imagine a future where you might use a skill you are acquiring, you may be in the wrong role. It may be a loose connection to future aspirations, but what you’re choosing to do today should support the work you hope to be doing in the future.

Why: There’s no right answer to the why question. Getting food on the table, paying bills, maintaining health insurance… all valid answers to the “why this job?” question. So are opportunities for advancement, earning potential, and prestige. Knowing the why will help frame how your job fits into your overall life. If a job is a paycheck and not your identity, the emotions behind your work will be different.

How: Inspired by Cy Wakeman’s work, asking what someone great at your job would do – and then doing it! – is a great way to check in and see how you’re showing up every day. If you’re inspired to do what someone who would be great at your job might do, it may be time for a change.

What questions do you ask yourself before making a career move?
How do you know it’s time for a change?


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