4 Transformative Questions That Every Leader Should Ask Themselves – And Their Teams

June 4, 2019 Chris Pearse

3,271 views Dec 2, 2018, 02:10am

Chris Pearse Contributor I write about the realities and challenges of leadership.


Questions signal a vacuum of knowledge that demands to be filled. Just as Aristotle’s idiom ‘Nature abhors a vacuum’ applies to the physical world, so it applies to our cognitive worlds.

Questions are divergent – they open up possibilities and potentialities. Answers shut them down, filling the void.

Questions demand answers and their power to compel a response can be heard in any interview. Although the interviewee may well evade the question, or answer another of their choosing, rarely do they resort to silence.

Without questions, dialogue mutates into monologue; enquiry becomes instruction.

There are many different forms of questions but here we examine four questions that have the power to shift perspectives and to open minds to a larger reality:

How does that feel?

Usually associated with therapy, this question asks the listener to shift their attention from thinking to feeling. Many, including leaders in positions of great power and responsibility, are not in touch with their feelings and frequently respond to this question by describing what they are thinking. Yet, counter to popular belief, we do not make decisions – any decision – on the basis of thinking. All choices are feeling-based – bar none.

Antonio Damasio, in the early 1990s, demonstrated the pivotal role of feelings through the clinical study of brain lesions in patients unable to make good decisions because their emotions were impaired, but whose reason was otherwise unaffected.

Clearly, if feelings and emotions control decisions, we would all be well advised to get in touch with them and develop a sensitivity beyond the cursory and vague awareness that C21, Western business culture promotes. It is incumbent on leaders to do exactly that.

What is that like?

This is a question that often gets lost the first time it is asked and may need repetition with a firm insistence that it is not going away. But it has great power to compel the responder to dig deep for an answer. Its power comes through linking disparate events through common feeling and a realisation that how one feels is more substantial than the circumstances that appear to provoke it.

In their classic work Metaphors We Live By Lakoff and Johnson explain that metaphor (and its subset, simile) ‘…is a fundamental mechanism of mind, one that allows us to use what we know about our physical and social experience to provide understanding of countless other subjects.’

Shifting perception of an issue around the board table by invoking metaphor can have immediate impact:

When a company director was asked what his work situation was like, he replied: ‘It’s like I’m drowning and being stabbed simultaneously by two people.’ It turned out that he was referring to two fellow directors sat next to him. The shocking nature of this revelation prompted swift action which addressed and resolved much of the stress the director was suffering.

If your entire team resigned on Friday and changed their minds on Monday, who would you re-hire?

This question bypasses the subliminal barriers – it’s too difficult, it’ll get better, I don’t have time, it’s not fair – that often block us from taking action that we know is needed. Best asked without the team present, it can provide deep insight into the realities of teams at all levels, including boards. Frequently it catalyses immediate remedial action, as the absurdity of retaining non-performing staff becomes apparent. Even when the answer is ‘everyone’, pauses, body language and equivocation may be significant.

How will it fail?

This question needs asking as the point of action in the decision-making cycle approaches. Particularly with projects, initiatives and decisions that are apparently of benefit, and with a low risk profile, the team needs to embrace all the possible outcomes, including failure.

The key information here is not will it fail? (the answer to which is unknown) but, how will it fail? This forces the collective imagination to explore modes of failure, however remote, that will further mitigate risk, or even identify previously hidden risks that may be significant. Either way, the boundaries of thinking are expanded beyond their previous limits.

To summarise, these four questions – and there are many more –  exemplify how to break through the assumptions, unconscious biases and mindsets that constrain our mental worlds to our detriment, and that of our teams and organisations.

The art of asking questions has to be a primary focus of everyone in a leadership position.

I help leaders accelerate their development and impact through a deepened awareness of our inner dynamics – the belief systems and emotions that shape our leadership. Discover more here…

Chris Pearse

Chris Pearse Contributor

I am an Executive Coach to leaders across diverse sectors including FTSE100s and SMEs. I am also an Interim CEO.