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The seven most powerful questions great leaders ask their people…

During my career in management and consulting, I’ve been blessed with the opportunity to work with numerous entrepreneurs and managers.

Whilst many things were different, there were some commonalities – especially amongst the successful ones.

From over 20 years of experience, here are the seven most powerful questions great leaders ask of their people:

1. How are you?

Good managers care about their people – always!
Their primary concern is the human person, their welfare, their loved ones and their journey. Regardless of the number of people on the team or the time spent together, good managers invest in the relationship authentically.
They understand how each person performs, their modalities and their strengths.
Good managers are caring yet challenging coaches!

2. Where are you going?

Great leaders try to align the team’s mission with the individual’s aspirations. They do this from the start – at the recruiting stage.
When there is dissonance of purpose, no one wins.
What are your goals?
What drives you?
Is it Learning, Legacy, Voice, Choice, or Reward?

3. What would you do differently around here? How can we improve?

A question particularly pertinent to new staff about a week or fortnight after they’ve joined the organisation is to ask them what they would do differently. Whilst they still have a fresh and objective perspective but know enough about the organisation to provide valuable insight. Over the years, some of the greatest insights we’ve gained have been from new staff and their views.

4. What’s our aspirational Plan A and our bullet-proof Plan B?

One of Australia’s wealthiest entrepreneurs had a habit of asking me two questions: All things being equal, what would be our most courageous and aspirational goal? It was always accompanied by: what is our backup plan if we didn’t quite make it.
Once the risk was sufficiently contained, he would encourage the team to aim for the seemingly impossible.

5. What three things concern you the most right now?

Another successful entrepreneur I worked closely with used to consistently ask what were the most significant concerns his people were facing.
What three things occupy your mind or trouble you right now? Then he would say – let’s talk through them.
Asking someone what keeps them up at night is a great way to understand them and their contribution to the organisation.

6. Do you have any questions or need more information to do your job?

People perform to the best of their ability when they have all the necessary and available information to do so. The days of managers withholding information and knowledge as a way of exerting power are long gone. Great leaders share appropriate information as they take on the role of coach. They stand on the sidelines to encourage and support with knowledge and direction – when required or called upon.

7. What resources do you need to get things done?

Good managers don’t micromanage – instead, they empower. They let people work to their strengths and capitalise on their expertise. Rather than looking over their shoulder, they emancipate and get out of the way.
They focus on assisting and enabling performance. We call this execution empowerment!

The following two are not questions but are worth honorary mention.


When a good manager makes a mistake, s/he must have the humility to admit it, take full responsibility and rectify matters.
Admitting you were wrong is not a weakness. It requires a sense of self-awareness and honesty – something we’ve seen only in true leaders.


Authentic leaders also regularly try to understand what their people do well and provide authentic feedback and sincere gratitude as appropriate. They recognise efforts as well as results.
Being grateful and acknowledging contribution is a rare trait of a good manager.

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