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4 Questions That Help Build a Winning Leadership Team If delivering value every day is part of your organizational "menu," consider these four queries.

By Jeff Boss Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.


Building out a company is not for the faint of heart. Heck, the mere thought of accountability, risk and potential failure is enough to make some people want to curl into the fetal position and suck their thumbs.

Developing a product that appeals to the masses can be daunting, but ensuring its lifelong success is a whole other factor. Doing so is only sustainable if your leaders know how to "set sail" in the right direction and keep that sail inflated indefinitely.

How do you know if you have the right leaders? That depends on your process for selecting new applicants and the questions you're constantly asking to foster organizational improvement.

Related: 12 Things You Can Do Starting Today to Be a Better Leader

In the SEALs, whenever we were on patrol, there were three fundamental questions each operator would constantly ask himself:

  1. Is my gun up?
  2. Where would I go if we were contacted by the enemy?
  3. How can I support my buddy?

Of course, asking the same questions over and over for hours on end gets monotonous, so the occasional, "How am I going to beat the next level in HALO?" question would surreptitiously sneak in, too.

The takeaway here is this. What questions -- when asked repeatedly -- breed relevance and avoid obsolescence? In other words, what questions never get old, continue to foster growth, and directly apply to every situation?

If delivering value every day is part of your organizational "menu," consider these four questions to drive perpetual leadership development:

1. Who do we want to attain?

Notice the question isn't how will we retain, but who. Organizational fit is everything. Skills can be taught, will cannot. In assessing the right leaders for the right role, strengths are an obvious area to consider as well as areas for development.

More important, though, is the degree to which that person demonstrates curiosity in perpetual improvement and takes the necessary steps to implement change. Curiosity without action is akin to a goal without a plan -- it's just a dream.

Related: 3 Common Leadership Mistakes That Make a Miserable Company Culture

2. How will we train?

Sure, you can go the old death-by-PowerPoint route and watch eyelids flutter and heads bob and weave out of both boredom and exhaustion. Or, you can implement action training. Action training is just that -- live, in-the-moment training that builds muscle memory and helps inoculate against stress. When the metaphorical bullets are flying, you don't rise to the occasion, you fall to the level of your training.

Train hard. Train often.

3. What do we want to sustain?

We all have good and bad habits. Having a routine helps us feel more secure and in control because there's "structure" to guide us.

Organizations are no different, and when greater numbers of people comprise that habit, it's worth analyzing whether that habit is productive or not. After all, habits comprise behaviors that equate to dollars, which translates to cost. If there's a company habit that doesn't promote progress, ask yourself what you can do to remove it. If doing so is above your pay grade, then consider what you can do to improve it.

4. How will we retain our people?

If you've hired the right people then the question isn't who do we want to retain (because you already have them) but rather how will you make them stay?

Daniel Pink, in his bestselling book Drive: The Surprising Truth About What Motivates Us, posits the old carrot-and-stick approach of motivation is outdated. He argues that throwing more and more money at soon-to-be lost talent does nothing. Instead, he reveals three sources of motivation to resurrect employees from the trenches of company complacency: autonomy, purpose and mastery.

These are just sample questions with the intention to get you thinking about how to shape success. If you don't plan for success, somebody else will get there first.

Related: 7 Leadership Qualities of a True Champion

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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