Career Oriented Questions

Stories Of Software Engineering Leaders

We are attempting to capture the stories and journeys of men and women who are making significant impact in the software industry. The purpose is to inspire young software engineers to see that are many paths for their careers and how they might move forward and eventually grow their impact wherever they work.

Our goal is to publish the same number of interviews with women and men because we care about diversity and inclusion in technology.

Who Will We Interview?

Tony Tam will interview directors, VPs, Product Managers, software engineers who have reached the level of principal, distinguished, and fellow who are making significant impact to their organizations.

Via Audio

  • Interviews will be 30 minutes long
  • The audio will be recorded and transcribed using the software Descript

Via Email

  • The interviewee may answer the questions via email and shared with

Final Edits and Ownership

  • The transcription will be edited by Tony Tam and will be approved by the interviewee
  • The final clean up will be done by the editorial team
  • All interview content is under full control of the interviewee and can be taken down at their full discretion.


Any of the questions can be skipped or replaced.
(A copy of these questions is on Google Docs for you to make a copy to email back )

0. How do you know Tony Tam, if you don’t know him personally, how did he make a connection with you for this interview?

1. Where do you currently work and what is your current role within the company? What scope of impact do you have within your organization?

2. Could you give us a history of your career path that led to where you are now? During this journey, where did you have the most significant growth/learning and why do you think that was the case?

3. What does a typical day at work look like for you and how do you stay on top of everything that is asked of you? What surprises you the most about where you spend your time?

4. Do you have productivity tips that you believe helps you? ie. meditation, planning apps, journals, exercise.

5. Who was the best manager you’ve ever had and why?

6. Which team was the best team you were on and why?

7. Which project are you the most proud of and why?

8. Who has helped / mentored you and has made the biggest impact on your career? What did you learn from this person that you still carry with you to this day?

9. How do you prepare for meetings that you are invited to and how do you successfully run meetings? What patterns of behavior do you wish junior engineers would do more of? Less of during, before and after meetings?

10. If a software engineer (senior, staff, principal) came to you and asked for advice on increasing their impact and getting promoted, what would you say to them?

11.What advice would you give to a smart, driven engineer zero to three years out of college? What advice should they ignore?

12. What blogs, newsletters, github repos, podcasts, conferences websites do you regularly read/attend in order to stay ahead of the changing landscape?

13. Thinking back on your career, what do you think has helped you personally grow your impact in the various stages of your career?

14. Do you have any advice on how to effectively mentor someone through their career? What does a successful mentor / mentee relationship look like? Do you think an engineer should ask their manager to be their mentor? Why/why not?

15. Is there anything that hasn’t been mentioned that you think is relevant to helping other engineers increase their impact? If so, what?

16. Was there any particular turning point or decision in your career that changed the trajectory of your career path? Tell us more about that.

17. In your experience, have you ever been faced with a situation in which you noticed certain things you were doing overshadowed the impact you had made or the good things you’ve done? Have you notice what mistakes other people have made which prevented them from increasing their impact in an organization?

18. What do you wish your younger self 20 years ago would have done more of, would have known more about?

19. What is one aspect for your current role that you absolutely did not expect?

The following questions are from Tim Ferriss’ book Tribe Of Mentors.

20. In the last 5 years, have you adopted any habits or rituals that make you more impactful?

21. If you could have a gigantic billboard anywhere with anything on it — metaphorically speaking, getting a message out to millions or billions — what would it say and why? It could be a few words or a paragraph. (If helpful, it can be someone else’s quote: Are there any quotes you think of often or live your life by?)

22. What is one of the best or most worthwhile investments you’ve ever made? (Could be an investment of money, time, energy, etc.)

23. In the last five years, what new belief, behavior, or habit has most improved your life?

24. In the last five years, what have you become better at saying no to (distractions, invitations, etc.)? What new realizations and/or approaches helped? Any other tips?

25. When you feel overwhelmed or unfocused, or have lost your focus temporarily, what do you do? (If helpful: What questions do you ask yourself?)

26. What is the book (or books) you’ve given most as a gift, and why? Or what are one to three books that have greatly influenced your life?

27. Who else should I interview? And could you make an introduction?

Meta Question:

What questions should I have asked you, that I didn’t ask; and which questions do you think should be removed or changed? What is your answer to the question that I didn’t ask?

Meta Questions from other interviewees (no need to answer these)

M. What lesson learned from your past experience that you either will emphasis/encourage or avoid? (Herri Gunawan)

See Also

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