Many people feel uncomfortable talking about themselves and their wins. You might find it particularly challenging to identify your career accomplishments if it’s been 5, 10, or 20+ years since you last updated your resume or interviewed for a job.
Keep reading to uncover why you might downplay your achievements, how to get better at owning your successes, and 40+ questions that will help you identify your biggest career wins.
Why Do I Downplay My Achievements?
As a career coach to tech executives, a major phenomenon I see is talented individuals downplaying their achievements and skills.
One reason you might downplay your achievements is that you were brought up in a culture that said your work should speak for itself.
Here’s the truth: Accomplishments can’t speak for themselves. If you’re looking for a job, you need to learn how to talk about yourself and your career wins.
Another common reason you might downplay your achievements is because you believe they were due to luck, rather than talent or effort, so you don’t think you deserve credit. To that I say, if you did it, you deserve to take credit for it.
Why Don’t I Recognize My Accomplishments?
Now, what happens if you simply don’t recognize your accomplishments? It’s common to not recognize your own successes, particularly when you’re great at what you do.
You can begin to identify your accomplishments by turning to your workplace evaluations and LinkedIn recommendations to see what managers and colleagues have said about you and your performance.
You can get also better at recognizing your accomplishments by practicing internalizing those wins you do notice. While easier said than done, take time to really honor and celebrate each career victory, rather than quickly moving on to the next one.
How To Identify Your Career Wins: 40+ Questions To Identify Your Career Accomplishments
In the following section, I share 40+ questions to ask yourself to identify your career accomplishments.
As you reflect on how you would answer the following questions, try to get as specific as possible with descriptive stories, examples, and results.
When possible, be sure to include relevant numbers and percentages, and if you don’t have the answer to a question, that is OK, just move on to the next one. The goal is to practice identifying and internalizing your career wins.
Questions To Identify Your Leadership Accomplishments
- When have you served in a leadership capacity?
- What projects have you led or supported?
- When have you taken on responsibilities that were beyond your day-to-day duties?
- What partnerships have you developed?
- How have you demonstrated flexibility?
- What challenges have you addressed?

Questions To Identify Your Operational Accomplishments
- What new systems and procedures have you implemented?
- What processes have you improved?
- Where have you saved your organization time?
- How have you improved quality, customer service, or other metrics that are important to your organization?

Questions To Identify Your Financial Accomplishments
- How much revenue have you generated for your organization?
- How have you saved your organization money?
- How have you saved your organization resources other than money?
- When have you delivered a project under budget?

Questions To Identify Your Human Resources Accomplishments
- What has been your involvement in hiring decisions?
- When have you trained and coached colleagues?
- How have you empowered colleagues to reach new heights?
- When have you mentored new hires and emerging leaders?
- How have you influenced people you did not manage?

Questions To Identify Your Culture Accomplishments
- What conflicts have you resolved?
- What steps have you taken to improve your workplace culture?
- How have you strengthened communication within your organization?
- How have you improved collaboration within your organization?
- How have you supported a culture of inclusion and belonging?
- In what ways have you made your workplace better?

Questions To Identify Your Professional Development Accomplishments
- What education, certification, and advanced training have you obtained?
- What courses have you completed?
- Where have you delivered speaking engagements?
- Where have your words been published?
- What board and volunteer positions have you held?
- What awards, honors, and recognition have you received?

Additional Questions To Identify Your Career Accomplishments
- Why did your organization originally hire you?
- What goals have you met or exceeded since joining your organization?
- What sets you apart from your peers?
- How have you outperformed your peers?
- What kind words have you received from clients and colleagues?
- When have you made your manager look good?
- What positive remarks have you received on your performance evaluations?
- What positive feedback have you received during one-on-one meetings with direct reports and supervisors?
- What are you most proud of from your career?
- My favorite question: If your organization was conducting a reduction in force, how would you convince them that they should keep you over your peers?


How To Decide Which Accomplishments To Include On Your Resume
Now that you have a list of your top career accomplishments, choose which ones to include in your resume. Use a target job posting to guide you, and highlight the accomplishments that are most closely aligned with the qualifications outlined in the job posting. Doing so will help a recruiter understand the value of your transferable skills.
But don’t stop there. Also include accomplishments that set you apart from other job seekers. In other words, share stories, examples, and results that help showcase your fabulousness. This will allow you to stand out in the saturated job market and increase your chances of landing an interview.
How To Get Better At Talking About Your Accomplishments
Getting comfortable sharing your accomplishments takes practice, particularly if it’s something you’re not used to or if you were raised not to talk about yourself.
Consider developing a daily or weekly practice of documenting and speaking your accomplishments aloud. Over time, you’ll get more comfortable and confident sharing about yourself and your career wins. You’ve got this!







