I attended a small job fair recently for mid-career professionals studying at a top Bay Area graduate school. I was impressed by the résumés — an array of engineering and design experiences at brand-name technology firms.
Yet, more often than not when candidates shared their stories, I struggled to contain a yawn. They engaged in formulaic narration, recounting past jobs and current graduate work, and telling me one after another how qualified they were.
Face the Future, not the Past, During a Job Search
The reason so many people struggle during a job search is deceptively simple: one party (you, the applicant) talks significantly about the past, while the other (your prospective employer) is focused more on the future. An applicant dwelling too much on past experiences and projects, even when asked about them, falls into an interviewer’s trap. Far better would be to remember the following mantra:
The most inspiring job applicants talk from the past toward the future.
Your entire presentation of self should be forward-looking. Your résumé should look as if it belongs to someone already in the job for which you’re applying. Downplay current and past roles, an approach which may seem self-defeating but in fact is quite liberating given that those are jobs you no longer have or want.
Take, for example, an assistant director of educational technology, whose résumé I recently reviewed. He had excellent work experience: three jobs each lasting five-plus years with no gaps in between. Yet, he has been unable to land a director role.
Unfortunately, his résumé dedicated two-thirds of a page — fifteen bullet points plus an additional paragraph of text — to his current job and the technology systems he administers. As a result, most prospective employers have inferred that he’s exactly where he should be: “Always the assistant director, never the director.” He is in the weeds, not the clouds: an excellent technologist, but an unproven leader.
Fixing a static document is one thing. Talking about yourself is quite another. How do you articulate a compelling, forward-facing vision when you’re constantly discussing past accomplishments?
Storytelling Your Past to Paint Your Future
It turns out that you can have your cake and eat it, too. You can talk about the past, but in the context of future decision-making. You can give insights about yourself both personally and professionally. But as the old adage says: Show, don’t tell.
The trick is to construct elegant analogies regarding parallel experiences of your life or career that simultaneously shed light on your managerial framework. This ability to distill complex subjects into bite-sized insights is exactly what good educational technology leaders do. Thus, if you show this skill, employers will take notice. You will instill confidence in a hiring manager who seeks a director able to translate both technical schema to a design team, and user scenarios to an engineering team.
Try to find an artful insight or construct within a discipline about which you are passionate and authoritative, and apply it directly to your line of work at a strategic level. Use this theme multiple times when talking about your past projects, each time pivoting toward a managerial framework.
Here is my own example that I often share when coaching aspiring executives:
I am a jazz pianist. When I reflect on the transformation of the ed tech industry, it reminds me of a classical ensemble shifting to jazz. Several decades ago, technology required everyone to follow the same script — akin to classical musicians dutifully playing the notes on a page. Now, ed tech offers far more choices and the freedom to experiment and improvise.
However, just as jazz musicians need to agree on a musical framework — a song — lest their sound become a cacophony, an organization must come to some consensus on its technology strategy. Otherwise, the learning (in a school) or the development (in a tech company) will be drowned out by an overwhelming cacophony of tools, systems, and data.
With this story, I can now paint my managerial framework to a prospective employer. As a director, I would value improvisation and iteration, not rigid over-planning — akin to Agile project management. I could discuss major initiatives I led to support disparate stakeholders, and analogize my future role as director to that of a bandleader. My simple musical metaphor acts as a bridge between my past experiences, my career ambitions, and my prospective employer’s current needs.
The bonus of sharing this kind of story is that candidates can construct through lines across disparate work experiences. Dancers, geologists, social workers, and even lawyers have all told me that their biggest hurdle in cracking the ed tech industry is explaining a seemingly “meandering” career path. I tell them all: Don’t run away from your past. Rather, celebrate it and leverage a unique set of learning experiences. Build your own metaphorical bridge from your past to your future, and it just might become your personal highway to the job you’ve always wanted.
