Five Strategy Questions to Ask Today


Three Leadership Questions to Help You Better Lead Yourself

By May 26, 2015 No Comments

By Ben Sands – for additional insights and leadership resources, click here.

In a recent post, I asked readers to share some of their favorite “leadership” questions.

Specifically, what questions do you regularly ask to ensure that you spend your time, energy and resources in a way that maximizes both value in your life, and in the lives of others?

I was amazed by the response and will be sharing many of my favorites over the next few months.

Today, I want to start with questions related to self-awareness.

Why self-awareness?

Good question.

I start here because, in my experience, leadership is an evolution.

It is a skill – an ability to make great choices over time – that is shaped by our beliefs, our values and our experience.

The first milestone in that evolution is learning to lead yourself and the first step on the journey is self-awareness.


What does “leading yourself” mean?

It means holding yourself accountable to a personal set of values, beliefs and goals.

It means acting with integrity, when know one else is looking (or even cares).

“Leading self” is a three-part recipe.

Part 1 – Clarity. A deep knowledge about who you are (your values and beliefs) and what you want (your goals and objectives). In other words, self-awareness.

Part 2 – Integrity. Taking action (not just thinking about it) in a manner that is consistent with those beliefs and values.

Part 3 – Courage. The pre-requisite of integrity; a willingness to sacrifice your own personal well-being in order to act in a way that is true to your beliefs and values.

Your ability to achieve subsequent leadership milestones: learning to lead others and learning to lead an organization or community requires you to first be willing and able to lead yourself.

In that vein, here are a few questions that will help drive greater clarity and insight about who you are – and what you really want.

1. How would the world be different if you didn’t exist?

The reader that shared this question with me commented “it’s like the George Bailey question in “It’s A Wonderful Life.”

Bailey, if you recall from the film, fell upon hard times and came to believe that he didn’t matter; that no one would miss him if he were gone. Following some “angelic” intervention, he came to realize that he did in fact matter and that his very presence made the world a better place.

Like George Bailey, every leader may, at some point, ask: “Is this worth it? Does it matter? Do I matter?”

When you find yourself at such a crisis of confidence, use this question to help you regain your perspective, and your courage. Specifically, make a list of the many ways in which the world would be less well off if you didn’t exist and celebrate your impact.

Too often leaders obsess about the 5% that isn’t going well and ignore the 95% that is. Don’t do that. Keep George in mind whenever you’re feeling stretched thin.

2. What is something that’s true, that almost nobody agrees with you on?

This is a favorite interview question of PayPal founder, Peter Thiel.

This question, writes Thiel, tests for both “originality” and “courage” (i.e. will the persona being interviewed really share something that the interviewer/organization might not agree with them on?!).

But it is from this type of independent thinking, that great ideas are born.

One example: AirBnB.

Back in 2008, the founders of AirBnB were fresh college graduates with a radical idea: a homeowner would be willing to rent out a bedroom in her home to a person whom she had never met.

Honestly, I still can’t believe this worked – but of course it did! Today, the practice is rent out rooms is common and AirBnB is a multi-billion dollar company.

In some ways, Thiel’s interview question is the “litmus test” of leadership – a question that differentiates true leaders, from their closely related peers: managers.

In a world where everything is known and certain, managers make things happen – executing well within existing systems and processes.

In a world characterized by uncertainty, leaders make decisions – conceiving of the ideas, processes and systems we need to move forward.

No doubt this question is a hard one, but don’t dismiss it.

With time and focus you will begin to see your own original thinking emerge and, as a result, your leadership effectiveness improve.

3. What is life asking of me?

This question comes from columnist David Brooks who writes: “wonderful people are made not born…but [they] do not find their vocations by asking, what do I want from life? They ask, instead, what is life asking of me? How can I match my intrinsic talent with one of the world’s deep needs?”

What is life asking of you?

What are your responsibilities, your obligations, given the gifts you have been endowed with?

Like the question above, this is not an easy one to answer – but that is precisely why it’s so valuable. The leader that takes the time to better understand not just what they want to do, but what they are being called to do stands a better chance of finding the energy, motivation and will to make it happen.


A leader’s greatest contribution to her team or organization is her ability to help engineer a better decision, a better outcome, for all.

Ironically, your decision making acumen that benefits so many others, begins and ends with a heightened sense of self.

Your personal understanding of who you are, what you want and what you are being called to do, creates the firm foundation you need to take action and make decisions with confidence, even (and especially) during periods of great uncertainty.

What are you doing to help you drive a higher level of self-awareness today? How is affecting your leadership and decision-making ability?

Ben Sands

Author Ben Sands

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