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5 Questions Highly Successful Leaders Always Ask

Effective Leadership

Effective Leadership

Great leaders lead by asking questions. Here are 5 questions they consistently ask to deliver great results time and time again. 

In today’s global organizations, most employees are dealing with between 3 – 5 change efforts at any given time, of which 75% will fail. The lack of success of change management efforts can be directly traced to leadership’s failure to consult frontline and non-managerial employees. According to PeopleNRG, a Change Management Consulting firm, skepticism of any change effort among the rank and file runs about 77%, a clear signal it is time for leaders to alter the way they lead.


In the book Change Anything, the authors identified 6 influencers of behavior. Expanding on their findings combined with our interactions with leaders all over the world, I suggest all highly successful leaders share one practice in common. They consistently ask questions to guide their actions in order to significantly increase the probability of success. They don’t just ask any question. They consistently ask these 5 questions, and if you want to increase your success at leading in an ever changing globally connected business environment, you should ask these as well.


The “Accountability” Question

People become highly motivated to change their behavior for two reasons: pain or pleasure. It must be more painful to maintain the status quo or it must be more pleasurable to change. Without developing an effective strategy for holding people accountable to change, the status quo will reign.


The critical question every successful leader asks: What do I need to be doing to encourage and reinforce the change I desire in my people?


The “Ability” Question

In almost every case, to change behavior requires the acquisition of new skills or knowledge. Highly successful leaders know this, and they always ensure their people are provided access to the information required in order to achieve success.


The critical question every successful leader asks: What skills and knowledge does each affected employee need in order to change, and what do I need to do to ensure they get it?


The “Culture” Question

We are creatures of habits, and the collective habits of a group of people form the routines by which work is done. Combine all of the routines within any organization, and you now have the organization’s culture. It is often described as “the way we do things around here”. Highly successful leaders know they must attack the status quo (the way we do things around here) because habits are extremely difficult to change. Great leaders know they must identify the true influencers inside their organization and utilize their power to drive transformation.


The critical question every successful leader asks: How can we effectively deploy the influencers of change to drive the transformation throughout the organization?


The “Incentives and Rewards” Question

Often times, the incentives and rewards used to motivate people to change are insufficient. All you have to do is ask how many employees have received praise in the last 7 days. As the Gallup organization’s research shows, the number is consistently very low. In fact, many managers don’t know what motivates their employees. Effective leaders ask one question that focuses their efforts and attention in the right direction:


The critical question every successful leader asks: What do I need to do to ensure the incentives we use are immediate and are rewarding the right behaviors?


The “Marketing Desired Outcomes” Question

Advertisers know they must constantly repeat messages in order to motivate people to buy their products. Highly effective leaders are brilliant advertisers as well, and they demonstrate their prowess most effectively during change initiatives. They know they need to pepper their work environment with examples of what success looks like. As a result, their action is consistently predictable because they ask the same question.


The critical question every successful leader asks: What visual reminders can we place throughout the work environment to remind people of the outcomes we desire?


By asking these 5 questions, you will be able to define the actions necessary for implementing an extremely powerful and very effective change management strategy. Success does not come over night, but it will come with time, practice, and commitment so start thinking your way to success today just as highly effective leaders do every day.


If you are seeking to significantly improve your leadership effectiveness or the effectiveness of your team, email me today at and check out the rest of my website for more tips and strategies for success.



Great questions for Leaders to ask. We would like to suggest the meta question all great Leaders ask is “Why”? By articulating Why an organisation does what it does and ensuring employees and stakeholders connect with that Why during successful times and lean times is what drives purposeful and transformational change e.g Apple, Zappos, Martin Luther King

Simon Sinek’s book Start With Why is a great resource. See his insightful TED talk here

I absolutely agree with you! As you stated, highly successful leaders always ask “Why”, and that simple question creates so much momentum when asked in the right way. Unfortunately, when many leaders ask “why”, they ask it at the wrong time or only during difficult conversations (such as when discussing / assessing failure or giving constructive feedback). And that makes the “Why” question come across as accusatory or blame focused. When asked in the proper manner using appropriate body language, the “Why” question is the ultimate question. Simon’s book and his TED talk are excellent resources, and I sincerely appreciate your great comments. Please continue to share on past and future articles!

Best Regards,