5 Difficult Questions Every Leader Should Ask Themselves

What are the provocative and challenging questions all business leaders should ask themselves daily?

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What are the provocative and challenging questions all business leaders should ask themselves daily?


5 Difficult Questions Every Leader Should Ask Themselves

What are the provocative and challenging questions all business leaders should ask themselves daily?

Share this article

By definition asking ourselves the hard questions is not easy.  Difficult questions about our skill as a leader and visionary require a certain strength and diligence to answer honestly and usefully.

Running a business and leading teams can be hard, the greatest leaders strive to develop their self-awareness and maintain that discipline especially during the tough times, a continuous pursuit of betterment despite the challenges.

Asking yourself the questions that make you uncomfortable, that you’d rather ask tomorrow or you’d just rather not, period, are the hallmarks of great leaders.

1. What mistakes did I make and how can I learn from them?

Inevitably not every decision we make will be the right one. Admitting that we have made a mistake and holding our hands up can be hard. I know some extraordinary leaders who do this exceedingly well, their businesses move swiftly from crisis’s and the trust in leadership is palpably great.

There is a saying, ‘more people would learn from their mistakes if they weren’t so busy denying that they made them.’ These words are slightly uncomfortable making too but remember, everyone makes mistakes (even those who would have us believe they don’t). It's how you respond to them that defines you.


Mistakes can be painful, but they can also be good learning experiences

2. Did I help someone else succeed today?

Good leaders focus on the success of those around them as well as their own personal achievement, thereby building strength and capability in their people and ultimately the company or team too. I have a client for whom this is the first focal point of the day.

Ask yourself daily if you can help someone else succeed or provide someone with a new opportunity.   It doesn’t have to be a grand gesture, something as simple as discussing performance or progress with a colleague, or making an introduction.

3. Have I behaved in a way that increases trust?

Trust is one of the foundation stones of good leadership and identified through what you say, do, and of course how you make people feel. Does your behaviour enhance how much people trust you - or erode it?  While trust is a somewhat subjective concept, leadership trusting behaviours can be defined, measured, and improved upon.

In his book The Speed of Trust, Stephen M.R. Covey highlights that trusting behaviors that are culturally ingrained in the structures of some great companies have significantly better employee engagement.

4. Have I asked for constructive feedback; even the kind I don't want to hear?

Some leaders don't want to listen to the ideas, opinions, and constructive feedback of others. They operate in an ego-system, not an ecosystem. Unfortunately, if you've ever worked with this type of leader, you will know that it can be utterly exhausting.

A leader who is good at listening, does so actively, not reactively. Listening to understand (actively) means that you are more likely to find the facts instead of the perceived criticism. Leaders then respond accordingly, smoothing over any potential drama.

angry boss

Feedback should be constructive - and a two-way street

This is a skill to practice and master. If you find you can't shake off the urge to react, ask more questions, keep probing and keep asking until you get clarification. In turn this means you listen to understand, and you’ll gain so much more knowledge and information as an added bonus.

5. What am I willing to sacrifice?

Perhaps an odd question, however what are you genuinely willing to sacrifice in order to achieve your goals?  People who sacrifice an extra hour in bed to endure the hard effort of the gym or to exercise are the ones who get in good shape.

People who commit the long hours, sacrificing time with family and friends to learn, research, develop, achieve and navigate the nay-sayers and corporate politics, significantly up the potential stakes of success.

I recently had lunch with an Olympic gold medal winner, the family events, weddings, celebrations, time with friends or just a lazy Sunday that she sacrificed in order to purse her path would make many wince.

I’m not suggesting that you need to find more ‘grit’, it is the coping with the sacrifices along the way that is important.  Developing and honing the ability to bounce from disappointment in whatever form it takes.

At the core of all human behaviour, generally speaking, positive experience is easy to handle. It’s negative experience that we all, by definition, have some degree of trouble with. Therefore, what we get out of life is not determined by the goals we desire but by the difficult questions, situations and sacrifices we’re willing and able to take, to enable us to achieve those goals and dreams.

You can make the difference.

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5 Difficult Questions Every Leader Should Ask Themselves

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