Reflect Before You Update

A former client reaches out for a résumé refresh. You helped her land her current position three years ago, and now she’s aiming for a more senior role in the same field, this time at a new company. At first glance, it seems straightforward: Add her current role to the top of the experience section, swap out a few keywords based on the job posting, capture a few accomplishments, polish the formatting, and send it back.

That’s the easy way, and nowhere near the best way to deliver real value. If you rely solely on the information your client provides, you may be working with weak raw materials. Instead, take this opportunity to 1) Recalibrate her entire go-to-market strategy for the next role, and 2) Position yourself as the career professional who helps clients stand out in a hyper-crowded market.

To do that, ask deeper, more revealing questions that uncover the kind of stories and metrics employers remember.

Dig deep into their update

• What problem(s) have you solved lately that no one else wanted to touch? Highlight the client’s initiative and willingness to take on challenges that others avoid (leadership + resilience). Example: “I took over a failing cross-department project no one wanted, streamlined communication, and delivered it two months early, saving $50K.”
• When was the last time you helped prevent a mistake, loss, or failure? Challenge the client to think about how they demonstrated value beyond just producing work. Example: “I caught a data error before it went to a client, avoiding a $10K refund and preserving the relationship.”
• How have you adapted to AI, automation, or new technology? Try to elevate the client’s bias for learning and future-readiness. Example: “I integrated AI-driven analytics into our reporting, reducing turnaround time by 40%.”
• What feedback have you gotten that changed how you work—for the better? This reveals coachability, self-awareness, and continuous improvement. Employers value people who evolve with input. Example: “A manager suggested I lead weekly check-ins; the change improved my team’s on-time delivery rate by 15%.”
• Have you made someone’s job easier, even if it wasn’t in your job description? Collaboration, empathy, and cross-functional support indicate a team player who goes above and beyond. Example: “I created a quick-reference guide for new hires that cut training time in half.”
• What systems, workflows, or tools did you help build, fix, or streamline? This often leads to a deeper discussion about operational and/or efficiency improvements that can be quantified for even stronger impact. Example: “I rebuilt the client intake process, reducing onboarding from five days to two.”
• Where have you failed, and what did you learn that made you better at your job? The ability to turn failure into growth is a story with universal appeal, especially for leaders. Authenticity is a weapon. Example: “A project I managed missed its launch deadline. I used the post-mortem to develop a risk checklist that’s now standard in our department.”

Check out their brand too

1. What do you want people to Google and find about you? This will help your client realize the importance of aligning her digital footprint with her professional brand.
2. Which skill(s) or accomplishment(s) have you outgrown—but still appear on the résumé? This is the time to trim outdated, irrelevant content and put the proper perspective on her current level and career goals. Plus, it can free up space for more recent and powerful content. If your client wants to showcase managerial skills, those early retail sales awards may be irrelevant. Replace them with leadership wins.
3. If your job were a superhero mission, what would your superpower be—and how would you describe your origin story? Identifying her unique strength and the backstory that shaped it helps craft a memorable personal brand. The answer to this question also makes great cover letter content. Example: “Superpower: connecting people to opportunities. Origin: I’ve been the go-to resource for career advice since college, turning that passion into a 15-year career.”

Instead of taking the easy way, use these questions to reshape the entire narrative. This is how you transform a résumé presentation as opposed to just updating it, and how you establish yourself as the professional who consistently helps clients land their next big role. Your ability to help clients get to the next level is directly tied to your ability to ask next-level questions, and to capture their stories in ways that are both powerful and remarkable….again and again and again.