The laziest two questions in the conversation book are “What do you do for work?” and “how is work going?”.

It’s inevitable. You can flex your conversation muscle with your Awkward Silence questions, but many aren’t used to putting effort into conversation yet.

The conversation is often dull. Unfortunately most people are in a job that they don’t love. They do it to make an income and pay the bills. Reliving the work week when they have a social moment doesn’t make for thrilling conversation. And often you are as bored hearing their answer as they are giving it.

So when the dull work conversation comes up, sabotage it.

Try shaking up the work theme into questions that are a little more interesting, such as:

  1. “What should be the highest paid job in the world?”

  2. “What new types of job that don’t exist now will come along in the next 20 years?”

  3. “If you were an employer, what characteristics would you look for when interviewing someone for a job?”

  4. “Would you rather be with the man/woman of your dreams or have your dream job?”

  5. “Is it too late to change your career path?”

  6. “Do you put more effort into your career or your family?”

  7. “What would be the most boring job”

  8. “What do you think would be the easiest job to have?”

  9. “What volunteer work would you like to do?”

  10. “What job would you refuse to do no matter how well it paid?”

  11. “Is it always a bad idea to “hook up” with someone who you work with?”

  12. “Which jobs will be obsolete in 10 years?”

  13. “Why do billionaires continue to work?”

  14. “If you were the employer at your job, would you consider hiring someone who was blind or deaf?”

  15. “How long do you think you will stay in the career you are in?“

  16. “If you were so rich that your kids didn't ever have to work, would you let them live permanently from your money or encourage them to find a job?”

  17. “How would your personality be different if you never had to work?”

  18. “What is your favorite task at your job?”

  19. “What was your first job?”

  20. “Have you ever had to fire someone? If not, how would you do it?”

Work conversations tend to have no verve before they even start. Turn a dull conversation topic into a conversation that sparks a livelier discussion. It works.

Let’s talk.