Asking Job Candidates the $50m Question

03/13/2015 06:22 pm ET | Updated May 13, 2015

Last week, Reid Hoffman, the chairman and co-founder of LinkedIn, told attendees at The WorldPost's Future of Work Conference that he asks every candidate pursuing a position at his company what job they want after LinkedIn. It's a great question, one that most companies don't ask. As Reid points out, at a minimum it establishes trust, because odds are that employees won't stay at any job for their entire career.

There's another question I like to ask candidates:

What would you do with your career if you had $50m in the bank?

What I'm really asking is what they would do with their time if money wasn't an issue. Would they coach high school basketball? If so, they likely value teaching and mentoring. Would they sail around the world solo for two years? If so, that says something different.

Almost everyone stumbles for a minute. There's no right answer. Some start fishing for what they think we might want to hear. Eventually we start having a real conversation.

This conversation may seem difficult or risky. The employee hasn't started yet and we're already talking about what they would do if they didn't have to work, or left.

Identifying values and goals early on is crucial. The question is how to effectively identify them - especially given that most interviews are thirty minutes. I've found that open questions like Reid's and mine are some of the most effective ways to identify values and goals in such a short period of time.

And it's important that these conversations do not end with the interview process. People learn throughout their career and their goals change. Managers should have these conversations thoughtfully - with candidates, direct reports, and other managers - over the course of many years to create a values-driven organization that understands its people and prepares itself for continued success and growth.

That said, the "what's next" conversation is not one that every manager can handle. It takes time to be able to have this discussion without, for example, sounding like you want the employee to leave.

I recently had a series of discussions with employees at my company to learn what they valued most about working here. One of the things mentioned over and over was that they felt like working at GLG (Gerson Lehrman Group) gave them valuable experience and connections for future opportunities in their career. But employees also said they didn't always feel comfortable talking to their bosses about opportunities outside of our company. That seemed like a disconnect.

Our management team met to review the takeaways from these conversations. There was disagreement about whether or not it was wise to ask about future careers goals and the $50m question, whether with candidates or current employees. Half the team felt it was risky to position GLG as a strong stepping-stone. They didn't want us to seem like we want people to leave.

So we dug deeper. What did employees think of the best managers, the ones with the best performing teams and the highest employee retention? No surprise, those managers all had explicit conversations with employees about their goals beyond GLG, both personal and professional.

Conversations about values and goals are important at every organization. At my company, they're essential. As a global professional learning platform, our success depends on each of our 1,000 employees exercising curiosity, courage, and a love of learning. We need to discern those values in the interview process, but we also need to continue those conversations so we can keep our best people learning.

These questions about the future, and others that develop shared goals and values, help create a better and more cohesive organization where the question often becomes, how we can succeed together.