7 killer questions that fundamentally shift a conversation

Throughout my career as a facilitator and coach I’ve stumbled across a handful of really great questions to have in the ‘kit bag’.  A great question at just the right moment can help individuals or groups generate insight and bring about a fundamental shift in a conversation.  Some you’ll likely be familiar with, while others might be new and worthwhile adding to your kit bag for when the moment is right!

What do you mean by that?

Conversations are often peppered with generalisations, untested statements and value-laden language…‘the management team is providing nodirection on this’; ‘the team is in bad place at the moment’; ‘Fred is a difficult person to deal with’.  If these types of statements are not explored, it can lead to less than useful, and sometimes damaging, conclusions and consequent actions.  This question, asked with the right intonation, can be a non-confronting way of getting people to explain their thinking without feeling that they are being challenged.  It often has the impact of helping people clarifying their own thinking in the moment, including assumptions and judgments they may be making, as they respond to the question – in essence a forced reflection.  It can be used effectively in both a group setting or in one-on-one conversations.

How did you reach that view?

Similar to the question above, however it is most useful where it is clear that someone has expressed a view or an opinion on an issue, often prefixed by the phrase I think‘the problem lies with the organisation’s culture’; ‘we need to implement a staff incentive scheme’; ‘it’s clearly a personality clash’.  In the fast moving dynamics of conversations these statements of opinion inadvertently, and very quickly, can be accepted as facts and are then acted on as such!  Alternatively an opinion might challenged by someone who expresses a different opinion.  This can often lead to defensive routines as individuals seek to win the argument through having their opinion prevail!  In both types of scenarios a very powerful question to ask is how did you reach that view?  The intent of the question is to move from opinion to the underlying facts (the directly observable data) of the situation to enable an exploration of alternative interpretations of those facts.  The question is non-confrontational and can be very powerful in taking a conversation into a productive zone.

What are you trying to achieve?

An oldie but a goodie!  Nothing new in this question, but often it’s not asked when it should.  It is very easy for people to get lost in a process conversation about what action should be taken – we should do this, we should do that…but to what end?  Again it is easy for people to get into a win-lose debate with each other.  For instance I often see it when discussing an agenda for a proposed meeting or workshop, where, when going around in circles, the simple asking of the question What are we trying to achieve here? stops people in their tracks, raises their thinking to a higher level and enables them to think in terms of cause and effect – what actions are necessary to have the impact we desire.  In some ways it represents the essence of strategic thinking and ability to focus on what’s important.  Again, this is often a real circuit-breaker of a question.

Upon what assumptions is that based?

Imagine a scenario where a proposal for a particular organisational initiative is being put forward to a senior group.  While there may be a swirl of opinions as to the merits of the idea, the really hard question about the assumptions – the underpinning beliefs about cause and effect – upon which the initiative is based is rarely explored.  This question steers the conversation away from an opinion-fest about the merits of the idea/initiative itself and allows a deeper conversation about the underpinnings of the idea/initiative.  In doing so, it builds a consciousness and deeper understanding of the likely success of otherwise of the initiative.  Equally it provides a very sound basis for learning and reflection during/post implementation – what assumptions turned out to not be true?  If I were a CEO it would be one of the most fundamental questions I would have in my kitbag!

Would you be willing to engage in a conversation where you might change your mind?

You know that feeling where it seems some conversations are doomed from the start – you are keen to bring some one around to your point of view on an issue but you just sense that the person you are dealing with is likely to ‘dig in their heels’ through skillfully providing counter arguments to your suggestions.  It’s a win-lose game.  In such situations it can be beneficial to ‘call’ the game upfront with the question: Would you be willing to engage in a conversation where you might change your mind?  For a responder to answer ‘yes’ requires them to consciously and publicly state a willingness to entertain alternative views.  They will want to be seen to behave consistently with this stated commitment.  It doesn’t mean that they will change their mind, but the likelihood of a more open and exploratory conversation is greatly enhanced.  So, again, it’s another question that can fundamentally change the dynamics of a conversation.

What are the potential unintended consequences?

Individuals and groups can easily get caught up in the immediate objectives or outcomes they are trying to achieve such that they have little conscious regard for the impacts of actions, strategies, policies or initiatives may have on other things outside their immediate field of vision.  The asking of this question can move the thinking of individuals or groups to a more systemic level that can potentially uncover impacts that might not be considered.

How might person X* view this situation?

In some conversations it can be really powerful to access the perspectives of others. We all have a natural tendency to see situations or issues through the prism of our needs, values and assumptions.  The simple asking of the question: How might person X* view this situation? immediately asks the responder to put themselves into someone else’s shoes which helps them access a different perspective.  This very simple question can be extremely powerful in shifting thinking and opening up a whole new set of possibilities and options in the situation.

* Person X being anyone or any group that could be involved in the issue or even a respected person completely independent of the situation.