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When to Take the Leap: Hiring the Less Obvious Choice

Posted by Lauren Kendall on April 22, 2019
Originally published on LinkedIn by Paul Manning (Managing Director, Software & Technology at The Bowdoin Group).

We’re living in a candidate-driven market, which means there are more jobs out there than candidates.  One of the ramifications of this kind of market is that landing the “ideal” candidate doesn’t always happen—there is simply too much competition.  In cases like these, the “underdog” (someone who lacks experience in the role you’re hiring for but has what it takes to be successful) may be the perfect fit.

If you’re like many of our clients, you may be thinking, “Why would I settle when I know who I’m looking for, and that person has proven success doing what I need?”  The truth of the matter is that sometimes the ideal hire you have in mind may not be who you actually need.  So how do you know when to take the leap and hire the less obvious choice?

Start with an Open Mind

If you’re heading into a search with an ideal candidate in mind, you may be starting the process down the wrong path.  Great searches happen when companies are willing to think about a role differently.  The best executive search partners must understand everything they can about your business—where it’s heading, what your challenges and opportunities are, what skills are already on your team, and more.  They bring outside perspective and clarity to shift your thinking based on market trends and what your business needs (which may be different from what you think you need).  What the market dictates and what your business objectives are don’t always align, so a great partner will pivot along the way to ensure you get the best possible candidate out there.

This was exactly the case for a salesperson that we placed into a sales leadership position.  He didn’t have leadership experience at the time, nor did he have the perfect experience in our client’s domain, but some roles (like sales for example) require skills that are more easily transferrable across domains.  What he did have was a passion for selling and a strong track record in that arena, a demonstrated knack for developing people, and a desire to move away from a transactional sale into an area with more complexity (which software represented).  The company decided to take the leap on this less obvious candidate and never looked back.  Today, he manages a 500-person team and $1B in revenue.  We’ve seen this happen time and time again with this kind of talent, and it’s thrilling to see their success.

Three Things to Test Before You Make the Leap

If you’re considering hiring the less obvious choice, make sure you have a strong sense for three things:

  1. KnowledgeHow deep does this candidate’s knowledge go in the areas you’re looking for? Ensure you have a methodology in place to test a candidate’s knowledge of specific domains—we use behavioral interviewing to identify what they’ve done versus what they’ve been involved in.  This goes beyond industry knowledge to “soft skills” this person will need in their new position—dealing with difficult people, negotiations, and getting buy-in, for example.  The less obvious candidate will likely have gaps in knowledge, but can those be filled with guidance?
  2. CapabilityHow capable are they of learning new things? Sounds simple, but there are plenty of candidates who are simply not coachable.  You’ll want to ensure you find someone who can prove that they have been successful taking on new challenges.  Be sure to push them on how they learned these things to give you a sense of what kind of support you’ll need to provide them.
  3. SupportHow willing/able is your company to support the candidate in any identified gaps? We’ve seen companies hire the less obvious choice and then provide little to no support to help them level up into their new position.  Sadly, this often ends with teams swearing off these kinds of candidates for good rather than internalizing the outcome.  Make sure that there are people on the team who can help guide this candidate and support them in filling any knowledge gaps.

Advice for the Underdogs out There 

If you’re a Director or VP who is looking to step into the C-suite, make sure you have the skills you’re going to need in your next role on your resume somewhere.  Successful underdogs gain these skills by taking on new projects and gaining valuable experience, whether that’s in their current role or through volunteering for a local organization.  And lastly, there will be more opportunities for advancement at high growth companies—are you working for one?

Have you had success hiring the less obvious choice?  Or were you once in this position?  Tell me in the comments.