Hiring Wisely: The Power of a Work Philosophy and Asking Applicants "Why?"


How often do you sit back and think about what you do, and how you do it?

In other words, do you have a philosophy behind doing a job?

It's a question you don't hear a lot, although sometimes it comes out in a job interview or during the recruitment process. But the fact is, it's really important to know just why people take a certain approach with their job because it tells you something about their thinking process and how they would move the job ahead.

The power of a job and work philosophy

I believe that you should have an overall philosophy about work and how you do particular jobs, so I wasn't surprised when I read that that Ben Chestnut, the CEO of the popular email marketing service MailChimp, thinks the same way.

Here’s what he told The New York Times' Adam Bryant in his latest Corner Office column:

When I interview ... I ask “why?” a lot. I want to see if they’re passionate enough to push back. I want to see if they have a philosophy behind what they do. I’ll just keep asking why, why, why until I get to their core philosophy on whatever it is that they’re passionate about.

I’m looking for that philosophy because I want someone to push me and make me better. I want people who are smarter than me, and who will push and fight for something they believe in while also respecting the values and unique nature of the company. We have to be creative in pushing our boundaries, but sticking to our values."

This is an interesting point: finding people who believe so much in their philosophy about work and a job that they would push back when questioned in an interview by a CEO who might possibly hire them. I wonder how often that happens -- or how many CEOs (or any other executive) would really, truly want to hire someone like that?

Is momentum something you keep an eye on?

I've interviewed and hired a lot of people, and in my experience, the tolerance level for people with a strong philosophy about what they do varies greatly. I can't tell you how many times I've seen candidates I thought were interesting because they were like this get kicked back and rejected because someone higher up the hiring chain thought the same qualities might make this person hard to manage.

Yes, many organizations say they want people like this -- until they're confronted with a person who has too many of these qualities for their taste.

In other words, be careful what you wish for.

But, MailChimp CEO Ben Chestnut had more to say about things other than hiring, leadership and management. Here are a couple that jumped out at me.

When asked, What are some leadership lessons?, here's what he said:

Never sacrifice momentum. I might know a better path, but if we’ve got a lot of momentum, if everyone’s united and they’re marching together and the path is OK, just go with the flow. I may eventually nudge them down a new path, but never stop the troops mid-march."

People in meeting

Two values: creativity and innovation

My take: This is a really interesting concept because momentum is incredibly important when you are trying to move ahead. When you have it, you feel you can push through anything, like George Patton and the Third Army mowing through Nazis in France. But, when you lose it or are struggling to get momentum back going again, you can feel like you aren't really accomplishing very much.

In my book, momentum is an underappreciated quality that more executives need to take seriously.

Ben Chestnut also weighed in on company values, and he had some interesting thoughts here as well. When asked, Did you go through the exercise of defining your company’s values?, here's what he said:

I asked all of our managers and senior managers to help me out with them, and we came up with three: creativity, humility and independence. The one that caused the most concern was the last one, independence.

It’s a hard thing for a manager to talk about independence when their job is to manage a team. But I don’t care if it’s hard. It’s a complicated concept, but you’re not going to be creative unless you’re recognized for your individuality.

In a team setting, we may be all working together to accomplish a goal, but if somebody has a concern, they need to be brave enough to stand up and say it. And other team members need to be humble enough to recognize this individual. If they have a creative idea, recognize them. We need fearlessness, because creativity leads to innovation."

The challenge in managing for creativity

My take: Far too many managers and leaders pay lip service to the concept of creativity. They talk about it in positive terms in the abstract, but they seem to think it's easily accessed, like tapping a keg for a glass of beer. When you get into a discussion about how terribly difficult it is to be creative, and how people need time and stimulus to think and make it happen, their eyes glaze over.

I wrote about this back in 2010, and here's the gist of what I said in What I've Learned About Managing Creative People:

I don’t know how they do it at Google, but I’ve managed writers, editors, graphic designers, photographers, artists, and other creative types and found the process comes down to one key element: putting people in the right environment to encourage creativity.

That’s the hardest thing for a lot of people in the business world to get their heads around, because there is not one single way that creative people work, nor is there any single path that leads to a new breakthrough or idea."

The fact that a CEO like Ben Chestnut is even talking about the need to recognize creativity is a huge and positive step ahead in my book, because way too many leaders either ignore it or don't really respect the process it takes to generate the creative juices that are the DNA of organizational innovation.

I was also struck by this, again: You never know where you will find great leadership advice. Although I tend to look at The New York Times' Corner Office column for hiring insights, it's full of great leadership thinking too. In fact, that may be even more valuable than the hiring takeaways,

In either case, it's usually worth a look.

Editor’s note: Checkster fuels the Talent Insider blog, and it can help you find out a lot more about job candidates with the Reference Checkup tool, and can help you better evaluate candidates and compare what your interviewers learn with the Interview Checkup.