50 ESL Discussion Questions About Work, Money, and Success

Work and money are topics every adult ESL student can talk about - and wants to. Whether they're studying English for career advancement, preparing for a job interview, or just navigating life in a new country, these conversations are directly relevant to their lives.

That relevance is what makes them such effective speaking practice. Students aren't performing language exercises - they're discussing things they've genuinely thought about.

Here are 50 discussion questions organised by CEFR level, designed for pair work. YapYapGo is a free classroom speaking practice tool for ESL teachers that includes work and careers as one of its discussion topic categories, with questions matched to age group and CEFR level. But these work just as well projected on a board. For more on how to structure pair discussions, see our post on reducing teacher talking time.

A2 Elementary (questions 1–10)

1. What is your job? Do you like it?
2. What did you want to be when you were a child?
3. Do you prefer working in a team or alone?
4. What time do you start and finish work?
5. Do you spend money carefully or do you buy things quickly?
6. What is the best job in the world? Why?
7. Would you like to work in another country?
8. Do you save money? What are you saving for?
9. What is more important - a good salary or a job you enjoy?
10. Have you ever had a really bad day at work? What happened?

B1 Intermediate (questions 11–25)

1. What qualities make a good boss?
2. How has the way people work changed in recent years?
3. Would you take a pay cut to do a job you love?
4. Do you think university is necessary for a successful career?
5. How do you feel about working overtime?
6. What is the most stressful job you can think of?
7. Should everyone learn about money management at school?
8. How important is work-life balance to you?
9. What would you do if you won a large amount of money?
10. Do you think your generation has better or worse job prospects than your parents' generation?
11. How do you define success?
12. Would you prefer to work for a big company or a small one?
13. Do you think people should retire early if they can afford to?
14. How has technology changed the way you work or study?
15. Is it better to be an employee or to run your own business?

Tool tip: YapYapGo's Topic Discussion mode serves work and career questions at the right level for your students, with automatic pair shuffling between rounds. The question bank tracks what each class has discussed so conversations stay fresh.

B2 Upper-Intermediate (questions 26–40)

1. To what extent does money buy happiness?
2. Should there be a maximum salary - a cap on how much anyone can earn?
3. How has remote working changed workplace culture for better or worse?
4. Is the gig economy empowering workers or exploiting them?
5. Should unpaid internships be illegal?
6. How do you think AI will change the job market in the next ten years?
7. Is it ethical for companies to monitor employees' productivity digitally?
8. What role should governments play in reducing income inequality?
9. How important is job loyalty in 2026 - should people stay with one company or move frequently?
10. Do you think a four-day working week would benefit society?
11. How does your country's attitude to work differ from other cultures you know about?
12. Should companies be required to publish salary ranges for all positions?
13. Is entrepreneurship overrated as a career path?
14. How has social media changed the way people find jobs?
15. What would happen to society if nobody had to work?

C1 Advanced (questions 41–50)

1. "Hard work leads to success" - to what extent is this a myth that ignores systemic advantages and disadvantages?
2. How does the financialisation of everyday life - from housing to education - affect people's relationship with work?
3. Is the concept of "career" becoming obsolete in an economy that increasingly rewards flexibility over specialisation?
4. To what extent should a society's wealth be measured by GDP versus wellbeing indicators?
5. How does the intersection of gender, race, and class shape people's experience of work?
6. Is universal basic income an inevitable response to automation, or a dangerous disincentive to work?
7. "The purpose of work is not just economic - it provides meaning, structure, and identity." How far do you agree?
8. How should we ethically navigate the tension between economic growth and environmental sustainability in our career choices?
9. Is the rise of "hustle culture" a symptom of economic insecurity or a genuine shift in values?
10. If you could redesign the global economic system to be fairer, what would you change first?

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Free tools for your next lesson

• Topic Generator - Random conversation questions by category
• Debate Timer - Two-sided timer for structured debates
• Student Picker - Pick random students with a slot-machine animation

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Sources:

• Long, M. (1996). The Role of the Linguistic Environment in Second Language Acquisition. Handbook of Second Language Acquisition.
• Storch, N. & Aldosari, A. (2013). Pairing Learners in Pair Work Activity. Language Teaching Research.