My nine-year-old daughter and eight-year-old son have almost simultaneously become fascinated with baseball.  Perhaps it was the pair of regional playoff games we attended this past June for the College World Series.  Or maybe it was the makeshift whiffle ball field we recently erected in our tiny Bay Area backyard.

My daughter belts solid singles and doubles.  My son swings for power, sometimes striking out and sometimes blasting the ball over the roof.  Ever the competitor, my daughter recently became disheartened when she realized that her brother has hit multiple home runs while she has yet to do so once.

Our firm, Ed Tech Recruiting, runs retained searches for executive-level technology positions. Most final-round candidates fall into two buckets: those who hit singles — i.e., play it safe during interviews and performance tasks — and those who swing for the fences — i.e., take risks to show their bold and innovative sides.  No approach is right or wrong.  Rather, the situational needs of each employer most often determine which type of candidate will land the job. 

Two Case Studies

Two recent recruitments that we ran illustrate this point perfectly.

One search for a C-level technology position at a large organization yielded two distinct finalists.  A young slugger arrived in a hip outfit and winged most of his final round.  He wanted to show his improvisational, unscripted, and unconventional sides.  The more mature base hitter had done her research, dutifully prepared her presentations and handouts, and dressed the part of a traditional executive.

Some people were wowed by the slugger’s unorthodox approach (and even look) for a role that explicitly listed innovative leadership as a necessary qualification.  However, in the end the admin team recognized that they needed a proven executive with mainstream management skills — given that the priority for year one was steadying an underperforming department, not leading a new innovation charge.  The base hitter got the gig.

At another organization, the search also involved a C-level innovation position — and once again two distinct finalists.  The base hitter played it safe, particularly during a simulated cabinet meeting that he innocuously led as if he were trying to please everyone and offend no one.  The slugger was dynamic and bold, interacting with administrators like a talk-show host not afraid to broach controversial topics.  As it so happened, the board had just enacted a bold strategic plan designed to jump-start an aggressive growth campaign.  This time, the slugger got the gig.

Lessons for Future Candidates

So what does all this mean for future candidates?  On one level, know who you are, and work on both “hitting styles” if you cast a wide net during your search. Anyone who applies to enough positions will likely encounter at least one job at each end of the bold/play-it-safe spectrum. No sense getting caught looking at strike three when you could have done some advance scouting.

But that’s just it.  Behind every job opening is a unique story, so you need to do your research. Is the organization going through a major pivot, in search of an audacious leader to ignite a spark?  Or does the organization have more traditional problems to solve, with otherwise healthy financial indicators and a risk-averse management team?

These are the kinds of topics to explore during your first- and second-round phone screens when interviewers give you a chance to ask questions. Don’t be afraid to probe. Try to piece together the backstory, rather than asking the all-too-familiar question, “What are the next steps in the hiring process?” You’ll gain not only invaluable insight but also a competitive advantage — by showing yourself to be a sophisticated candidate who recognizes that no two job opportunities are alike.

Indeed, the title of the position often belies the true needs of an organization.  For example, many titles include the word “innovation” — director of innovation, chief innovation officer — but that doesn’t mean that only sluggers need apply, or that a slugger will even get the job.  Innovation could be a code word for: “We don’t like our current strategy, so we need a fresh start.  But we want to fix things gradually rather than abandon everything we’re doing.”

As the summer winds down and the fall hiring season opens up, candidates and employers alike would be wise to prepare early for a competitive job market.  Like an October playoff baseball game, you never know how an executive-level hiring search will turn out until the very end.

Gabriel Lucas is principal of Ed Tech Recruiting, an international firm helping educational organizations hire for senior technology administrators. He is a former educator and director of technology.