The 5 Powerful Questions All Strong Leaders Must Ask

is the best?

Is it Bezos’s ability to adapt and change on a dime? Is it Buffet’s long-term persistence? Or maybe it’s Branson’s charisma? And what about transactional, situational, or transformational leadership? — WHICH is best?

Leadership studies across industries give different answers and no clarity on what leadership quality is best. In addition I think you’d agree it’s clear that Bezos, Buffet, and Branson are ALL successful leaders, yet they ALL have wildly different leadership styles and methods.  Furthermore, I bet you also from your experience have had great leaders who have had opposing views, qualities, and styles. So what gives, who’s right, which style or quality of leadership is best?

The fact is, there isn’t any single best style or quality of great leadership. So my humble suggestion is to stop looking for the best leadership quality or style and instead start focusing on the single thread that unites all great leaders past, present, and future. The thread and the common denominator of leadership strength.

OR said different, no matter how gifted the leadership style or flawless the strategy, it’s all worthless without a strong leader to carry it through to fruition. And from my study and direct experience, strong leadership always starts at home. Because the truth is, leadership starts with YOU. You are the foundation, and everything else rises or fall based on the strength of YOUR foundation.

So let’s inspect your foundation. Let’s question its resolve and directly poke and prod so that you can strengthen yourself and by direct affect your capacity to lead. And all it takes is getting in the habit of asking yourself:

The 5 Powerful Questions All Strong Leaders Must Ask

What tomorrow is worth fighting for today?

Our strength as leaders is ultimately rooted in the importance of our mission. So one of the first questions I ask clients is, why?

• Why does it f#cking matter?
• Why are you here?
• Why not give up and settle, wouldn’t that be easier?

Conversations like these provoke something in leaders. It forces them to defend the importance of their mission. And once backed into a corner, it can get heated (which is a good thing).

For example, I once had a client who seemed disconnected from her purpose. She was a ball of complaints and excuses. So I told her, it sounds like you have microwaveable goals. I told her that her mission was weak and not worth defending, so she should just quit. But she was so disconnected that I still wasn’t getting through. So I kept the pressure on. I kept interrupting her excuses with:

Ding your meal is ready…
Ding your microwaveable mission is ready…
Ding, ding, ding…

Eventually, it struck a nerve, and she said, “my mission is worth fighting for, it’s not some damn microwaveable dinner.” I said, “prove it.” In that instance, she came to life and went into precise detail why her mission was worth fighting for. But more important than details, I finally felt her passion. It was now clear she had something worth fighting for today.

Connecting to your leadership WHY is basic performance psychology and easy to do. However, the BIG challenge is remembering to do it, especially when dealing with significant challenges, pressures, and balancing competing needs.

That’s why in our rise of a leader program we use this question first thing in the morning. It’s a quick and easy way to connect to your WHY. So every day ask yourself: What tomorrow is worth me fighting for today? If that doesn’t work – just keep repeating – ding, ding, ding.

What would I do differently, if I took 100% responsibility for what happened next?

This question is empowering for a couple of reasons. First, it brings leaders back to accountability. Accountability is important because, without it, there isn’t any real leadership power.

Second, this question doesn’t just point the finger back at leaders. It also presumes that with accountability must come the power to do something different and thereby the ability to get different results.

Most leaders already have enough personal accountability. The secret is not just to feel accountable but to also feel able. As in, I know I can deliver what I’m responsible for delivering.  

Have you felt this way before, where you’re responsible for a result, but don’t know how you’ll get it done? Then you know that when accountability doesn’t meet ability, it creates mounting frustration and pressure.

Over time, we have two choices when dealing with this. First, develop the ability and find a way (this is hard to do real time). Or our out of frustration we eventually decrease levels of personal accountability. When this happens, we will begin looking for something outside of us to blame. Have you done this? I know I have.

The path of blame is much easier and why we see weak leaders running around with their finger sticking out. To avoid being that guy, you need accountability and ability to line up. One of the quickest and most effective hacks to help you to do this, is to ask daily: What would I do differently, If I took 100% responsibility for what happens next?

What could I let go of right now and be better for it?

I love this question because it subtly points out a lack of focus without outright saying “hey, you’re not focused.”

Here’s how I define leadership focus: the ability to be subservient to purpose over preference. Or said different, leadership focus means having the courage to drop anything, not in direct service of the mission.

Said this way, we all could stand to be a little more focused. Because isn’t it true that we all have things lingering in our business and life that have well passed their expiration date?

That’s why this question is so compelling. It helps leaders find the spoiled and moldy cheese in the back of the fridge. But just as important, this question also helps leaders create the resolve to throw away what they find.

If you want to be a strong leader you have to focus on the essential. That means being subservient to purpose and results and not preferences and feelings. This backdoor question will help you do this. So ask yourself daily: What can I let go of right now and be better for it?

Note: this question if honestly approached can bring about many different emotions. For example, you might experience hysterical laughter, like “what was I thinking, I should have thrown that away years ago.” On the other end of the spectrum, you may experience a vehement defense of your preferences. There will be some emotional excuse hidden by clever rationalizations. That’s why I often recommend a non-biased partner to help with this power question.

What affordable risk can I take today to capture opportunity right now?

On the surface, this power question may look like simple risk/reward analysis (affordable risk vs. opportunity gained). And it is, but with a hidden gem. That gem is the emphasis on action, speed, and active experimentation. Let me explain why this is important.

Remember, great leadership always comes back to results. And in the context of our fast paced modern world, results comes back to speed and innovation. Meaning, leaders that can quickly leverage opportunity, are those that win.

That’s why this question is so powerful; It reorganizes long-term goals into active areas of focused effort today. It’s important to note this isn’t blind effort, it’s strategic effort around measurable results.

I consider this not only a strategic advantage but also a characteristic of strong leadership. That’s because questions like these, instead of alleviating pressure often creates more pressure. That’s good because it’s pressure for results, not complexity, over thinking, and useless things like endless meetings and whiteboard sessions.

With the pressure of results, you must remain strong to keep a consistent eye on outcomes. To do this ask yourself: What affordable risk can I take today to capture opportunity right now?

Note: use this question in your next meeting if you’re looking for an immediate spark around results. At rise of a leader, we use this question to drive the 30 Day R.O.I. phase. The goal of this phase is to help leaders make a measurable return on investment within 30 days. And we’re serious about this idea. If leaders and their teams don’t get immediate results, they are dismissed and refunded. Dismissal rarely happens because we use questions like these to create focused targets and discipline action around them. 

Are you who you say you are?

This power question can feel self-defeating, because if we’re honest the answer would be HELL NO — we are not who we say we are — or who they believe us to be. At least not yet!

That’s because there’s always a healthy gap between what we show the world and what we encounter on the inside. Think of what we project to the world as a social media timeline. On our timeline, we don’t post our weak points. Instead, we put forward our best foot. It’s like a highlight reel of “I’m awesome, look at me.”

In real life, when the camera stops rolling we are human and thus experience, fear, worry, anger, grief, and everything in-between. That’s the private gap that most people can’t see within us.

As leaders, our gap may be huge because we try so damn hard not to show the chinks in our armor. And that’s fine because leaders can’t panic when everyone else is.

But what’s not ok, is to hide from the gap and to pretend it doesn’t exist. Weak leaders do this. They spend lots of time, energy, and effort trying to convince themselves and others that the gap doesn’t exist. This is a big mistake because:

Strong leaders live more by the Latin Esse Quam Videri:

To BE rather than to SEEM

That’s why we built rise of a leader to be a Living Leadership program. It’s not about what you learn about leadership it’s about how you LIVE leadership. Because it’s in living it, becoming it, and being it that you are sure to become a better leader. And part of that process is NOT to run from your gap but to instead aggressively attack it. 

Because I guarantee ALL great leaders attack their gap just like a great ball player attacks the rim. They do this because inside their gap lives their biggest fears. The fear of failure, the fear of letting others down, the fear of not reaching their potential.

So quit it, if your instinct is to say something like “I’m not motivated by fear.” Bullshit, you are, or you’re not an effective leader. Fear is just another fuel, not a condemnation of who you are. Besides if you don’t have a healthy fear of leading, then you think too highly of yourself and too little of your mission and the people you have the great honor of leading. If part of you resists this idea, I suggest you do some soul searching because a combination of three things is in the way of you being a great leader.

• Ego: you think too highly of yourself, and eventually it will cost you and those you love and lead.
• Mission: it’s too small, it’s not important enough to drive you past comfort. And if you are not driven, there is no way to reach your highest potential (period).
• People: you don’t care deep enough about them and your outcomes. If you did, you’d feel the weight and pressure of that responsibility.

With a healthy fear and modest gap, you’ll desperately want to find a way to ‘actually’ be all that your people need you to be. Call this the daily burden of being a great leader. It’s the daily work to close your gap and meet a higher standard.

Last point on this. The work to close your gap isn’t glamorous. It happens when no one is watching, and the stands are empty. That’s why it’s hard to do. There are no likes, applause, or anyone to convince but ourselves. But it’s this gap work that differentiates and ultimately allows great leaders to come through in the clutch.

So ask yourself daily: Am I Who I Say I Am?
Then listen intently and dedicate yourself to attacking the gap.

Your Path to Better Leadership Results

You should ask yourself these power questions on a daily basis. Preferably at night and in the morning. To help organize your time and to get the most out it, I suggest you use the Live It Up and Live It Down Strategy. Here’s how it works.

Good leaders know their values while great leaders pursue their values. Meaning, it’s up to you to not only know what you value but also to actively pursue your values. When you do this you move beyond mental masturbation and into the realm of LIVING It. You are in fact becoming that which you value and pursue. For example: let’s consider the Live It Up Strategy for your first power question.

What tomorrow is worth me fighting for today?

1. Ask the question. Try to mentally and emotionally connect to your WHY. (next)
2. Apply The Live It Up Strategy: ask – how will I fight for my why today?

This is a powerful question because it turns your thought into a series of actions. You’ll know you’ve done this right because you’ll see clearly HOW YOU’LL LIVE IT TODAY. Every word in that sentence is relevant to The Live It Up Strategy.

• How (as in the actions and steps)
• You (it’s your responsibility to create the opportunity)
• Live It (you’re on the hook for doing, thinking doesn’t count)
• Today (not tomorrow, next week, but today)

If you activate the Live It Up Strategy in the AM then all day you’ll pursue your values and create opportunities to Live them. Again, good leaders know their values, while great leaders pursue their values.

So you’ve gone into the world and actively Lived It. Now it’s time to see how you’ve done. So each evening you measure yourself based on your values and how you’ve Lived up to them. A handy acronym we use for the Live It Down Strategy is it’s time to get RAW.

• R: recognize how you’ve lived it up today (+ positives, wins, victories)
• A: acknowledge how things could be better (- negatives, losses, lessons)
• W: what work will you do tomorrow (learn/grow, rededicate yourself, quickly game plan for tomorrow)

Again, let’s apply this to the first power question.

What tomorrow is worth me fighting for today? 

1. Recognize (+) how and where did I fight for my why today? (recall specific instances, count the specific examples)
2. Acknowledge (-) how could I have done better?
3. Work (=) how will I improve my fight tomorrow?

A couple of notes on the RAW Review. It’s best done just before bed. However, if you can’t do this exercise and THEN let go after 5-10 minutes do it just before leaving the office.

Also, don’t be an extremist. I find many leaders lean toward beating themselves up or the opposite giving themselves standing ovations. Neither will serve you here. I want you to simply find real positives to build on, real negatives or opportunities to fix, and 1-3 things to work on for the next day. That’s It!

This process takes about 5-10 minutes and can dramatically improve the quality of not just your leadership but also your life. I’ve witnessed this not only in myself but with clients, family, and friends. Bottom line, powerful questions through the Live It Up and Live It Down strategy flat out work. It’s a highly efficient way of creating an active connection to becoming and not just seeming to be.

Because remember, The Strongest Leaders  ______It!
I hope you said LIVE!

    1.    What tomorrow is worth me fighting for today?

    2.    What would I do differently, if I took 100% responsibility for what happens next?

    3.    What could I let go of right now and be better for it?

    4.    What affordable risk can I take today to capture opportunity right now?

    5.    Am I who I say I am (or who they believe e me to be)?

P.S. these 5 Power Questions are a great start to becoming a stronger leader. To take things to the next level, check out our rise of a leader program. It was specifically designed to build strong leaders who Live It!