Map Out Pivotal Moments



Updated August 22, 2022
Ask Me This Instead

You’re reading an excerpt of Ask Me This Instead: Flip the Interview to Land Your Dream Job, a book by Kendra Haberkorn. This powerful work is written by a veteran recruiter for job-seekers who want to find their dream job—not just the next job. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, worksheets and a question database, commentary and future updates, and a high-quality PDF download.

Your career, like a plot, is made up of a series of events. There are events of a more significant magnitude—new jobs and promotions, for example. Then there are those that may seem small, but that are, upon reflection, deeply meaningful and important—perhaps that first tough conversation with a direct report or turning a bad relationship around.

Though time facilitates a natural sequence and order of the events that take place, it may not always be the most compelling way to tell your story, specifically within the context of a particular role or period of time. The moments that are most relevant, impactful, and indicative of the journey you’ve been on as the protagonist might need to be put into a structure that will catch attention, build suspense (OK, probably more like interest in this scenario) and keep the reader curious and wondering about what they will read next.

Start to think about events, accomplishments, and activities that were important to you at the various stages and steps of your career and that would be interesting to the reader (like a recruiter assessing your potential, a hiring manager wondering if you’ve got the capabilities, or a future direct report trying to see if you’re someone they think they’ll learn a lot from).

To refresh your memory about events that are important to your plot, ask yourself the questions below. These questions are not only helpful for crafting your resume, but also for practicing your answers to interviewers’ questions.

  • What were specific, high-impact initiatives that you contributed to?

  • When did you take a bold or controversial stance?

  • When did you achieve something unexpected under tight deadlines, or despite other obstacles and constraints?

  • How did you change the outcome of a key decision or important project?

  • When have you changed someone’s perspective or challenged the status quo?

  • When did you lack confidence, but persevere and achieve the desired outcome?

  • If you were able to share your best work with a future colleague, what would you share?

  • What would others consider your greatest success, and would you highlight the same thing?

  • When has someone recognized you for an accomplishment, large or small?

  • When did you adapt to surprises or change successfully?

As you take this new lens, you might change whether or not you include a specific accomplishment and how you combine and sequence as part of a larger whole. You’ll start to see how the story comes together once you consider the relationship between the events, the characters who helped shape them, and the setting that influenced why things transpired the way they did. Your job is to thread all these points in time together so that they don’t come across as random occurrences but a strategically threaded and cohesive progression of discovery, growth, and impact.

This will help them move through your resume and keep reading to understand not just what you can do but more about your progression and your potential. Who you are is more than what you’ve done!

Include Tension and Conflict

The desire to move beyond and even forget particular conflicts we have throughout our careers is natural. However, conflict in your career, like the tension in a story, is where some of the most interesting and important moments occur. In fact, these moments often represent the catalyst for characters to transform. Being able to articulate how these tests impacted you will add depth, interest, and a dose of reality to your resume. Without realizing it, you’re also preparing for the interviews by thinking about the experiences that pushed you and those that you might want to avoid in the future. These memories can be helpful in building the list of questions you’ll ask certain interviewers.

Interpersonal conflictConsider a broader lens
Relationships that got off to a bad start that ultimately turned aroundExternal factors that shifted timelines, product design, or even internal operations
The dynamics in meetings during periods of stress or high stakesWhen a customer backed out of a deal or a colleague unexpectedly left the team
Trust, or rather the lack thereof, within a team or organizationHard moments, unexpected changes, or big surprises
Failure that led you to quit, change course, fire someoneTimes when you made a mistake or intentionally disrupted progress
The times you cried or lost your temperA moment or experience that was embarrassing
Tough conversationsA period when you were bored or unengaged in your work
New hire or new manager changing the status quoWhen you didn’t believe in the company, its product, or people
Moments that made you look for another roleLack of a feeling of belonging, being “othered,” or needing to assimilate

As you reflect, acknowledge the frustration, pain, and problems, and the context that surrounded them. Then, think about what positive growth, lesson, or change happened as a result. That is where the magic lies and what will be most helpful as you craft your resume, prepare to respond to interview questions, and evaluate if you’d encounter similar challenges in a new role.

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