Blend These 7 Personality Types When Building Your Executive Team Strong leaders thrive when their top people challenge assumptions and ask the uncomfortable questions.

By Jeff Boss

entrepreneur daily

Opinions expressed by Entrepreneur contributors are their own.

While the popular contention that "there are no stupid questions" is nice to hear (especially after asking a stupid question), it's not exactly true. Let's face it. We've all heard plenty (and I mean a lot) of dumb questions, and unfortunately, they typically come from dumb people who are not necessarily "terrible at life" but perhaps just suffering a momentary lapse in brain activity (I know I have).

If you look at what effective (read smart) leaders do, they surround themselves with people smarter than themselves. They must, because if they don't then they won't grow as leaders and growth is a defining characteristic of leadership. Smart leaders are humble enough to know that they don't know everything, so they rely upon subject matter experts who do. In fact, a recent survey by HBR shows that those leaders who underrated themselves compared to those who overrated themselves were considered by others to be more effective leaders.

To elevate your level of "smart" and grow as a person and a leader, here are seven types of people who will help you "C" new perspectives:

1. Contrary.

These are people who like to head left when everyone else goes right. They challenge the status quo because they're not satisfied with what is "acceptable." They're always looking to redefine what "right" looks like and in doing so, challenge your thinking, too.

Related: 7 Telltale Signs of a Weak Leader

2. Curious.

Ever been around somebody who asks questions incessantly, almost as if they're writing your biography? Curiosity is the pathway toward greater insight and self-reflection. I admit, I get annoyed by people asking question after question (which is pretty ironic being an executive coach), but it's only because they beat me to the punch.

3. Critical.

Being under the social microscope is no fun. It's much easier to work with easy going, praiseworthy people who don't challenge your every comment. However, such wallflowers don't challenge your thinking, either. While being harsh or caustic is about as welcoming as a box of dead roses, criticism is an effective way to boost self-awareness. After all, nobody likes being "that guy" or girl.

4. Candid.

Along similar lines of criticism exists candor. It takes courage to speak your mind and if you don't, then how do you define your relational value as a leader? A friend? A coworker? A sibling? You may not like hearing how your breath is strong enough to melt plastic, or how your last presentation was a five out of ten on the scale of "awesome," but candid coworkers will tell you regardless, affording you the opportunity for reflection and growth (and a breath mint).

Related: 4 Ways to Get Truly Honest Feedback From Employees

5. Competitive.

A little competition never hurt anyone. In fact, it's the basis of entrepreneurship. Without competitors to challenge your strategies, goals, products or services, chances are that complacency would settle in way too soon. Surrounding yourself with competitive people will draw out the best in you as they call for 100 percent every day.

6. Confidant.

A confidant is somebody you admire, somebody who models what "right" looks like and somebody whom you hold in high regard. Leaders especially need confidants. Leadership gets lonely without someone to bounce ideas off of or share feedback. Confidants provide that space in which leaders can share their insights and gain perspective.

7. Collaborative.

On the introvert/extrovert scale, extroverts tend to be more collaborative because they gain energy from interacting with others. Conversely, it's not that introverts don't enjoy talking with others, they just gain their energy from solitude. No matter where on the spectrum you're at, there's always something to gain from people who are willing to collaborate and share ideas with you. After all, everybody is smarter than anybody.

If you want to optimize your personal effectiveness, surround yourself with like-minded and dissimilar people. It's only when you know both sides of the story that you draw the most effective conclusion.

Related: The Future of Collaborative Business

Jeff Boss

Leadership Team Coach, Author, Speaker

Jeff Boss is the author of two books, team leadership coach and former 13-year Navy SEAL where his top awards included four Bronze Stars with valor and two Purple Hearts. Visit him online at

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