Diagnose or Die! Managing Difficult Conversations
Published on: 09/07/2026
Issues Covered:
Article Authors The main content of this article was provided by the following authors.
Luke Monahan Founding Partner, Dynamic Partners
Luke Monahan Founding Partner, Dynamic Partners
Luke Monahan

Luke has consulted for organisations in all parts of Ireland and on four continents. He has specialisations in change management, leadership excellence, strategy development, resilience, conflict and facilitation, also in mentoring and coaching leaders, boards and senior management teams.
He has carried out extensive research into the culture of organisations and how to effect positive change throughout an organisation. He has a long track record in professional development and training as well as a frequent speaker at conferences nationally and internationally.

In one instance recently, a key leader in a difficult scenario said, ‘…up until now I had hoped against hope that a solution I could live with would emerge from the fog! What in fact happened was a 10 tonne truck emerged from that fog and nearly flattened me!’  

I so miss House – one of the breed of high quality US drama on our TV’s. Hugh Laurie played this near insane doctor whose skill was to diagnose – a diagnostician. He cared about little else only about wondering if all the right questions were being asked. Had the truth come out…what symptoms are we missing…what do we not want to find…and why are we avoiding the reality… Only then would he proscribe – the right diagnosis was everything. Dealing with it.

I have discovered how much I enjoy the business of diagnosis in difficult issues. A close friend asked me which aspect of my work I enjoy most…after long thought my answer was the following: ‘…it’s when it’s tough, when the usual answers don’t work, when there isn’t an off the shelf approach to take. I just soak that stuff up!’ Apart from any masochistic dimension to my personality, I believe in the importance of dealing with challenges rather than passing on them. We all know instinctively that these challenges will wait for us, will probably escalate, will probably drain us even further if we continue to placate or avoid.  

Whatever the challenge it is so important to develop the skill of critical diagnosis. The detachment, honesty and courage needed to ask and answer the critical questions are essential. Of course, how can we be sure that we are asking and credibly answering those questions? 

I often say to leaders I am supporting through a difficult challenge that you need three resources: 

A critical friend – one who will ask the searching questions, who will challenge your assumptions, your narratives around the issues. 

Unconditional support – the person who is just there for you, to let you vent, to let you get it wrong but get going again.

Expertise – the necessary people with the skillset and experience needed to resource you through the challenge or crisis. 

Be very careful not to mix and match the above as in general it is far better to have distinctive people for each of these core roles.  

I have developed a framework I call Breakthrough Conversations. The aim is to upskill leaders to engage in conversations where what is core is addressed with a mindset of courage, curiosity and constructiveness so that less of these  important conversations are avoided and less of them cave in for peace sake. There is no magic formula but rather a building of confidence, a deployment of good judgement and the use of a few human relating skills that make the difference. One of these key skills is that of asking questions about the potential conversation – the diagnosis dimension.  
 

  • What am I looking for from this conversation? 
     
  • If this conversation was to be effective, what would that look like? 
     
  • What are the key points I really want to have heard? 
     
  • What can I do to ensure the other is heard, that their view is appreciated? 
     
  • What do I do if it gets very negative, destructive? 
     
  • When would I bring the conversation to an end, what next steps would I have in mind to not close down the issues completely? 
     
  • What is going to be different about this conversation to others I have had with this person/group? 
     
  • What changes do I need to make to credibly communicate I want to make constructive progress? 
     
  • Where and when should the conversation happen to give it its best chance of success? 
     
  • What am I afraid might happen in this conversation that I need to prepare for? 
     

There are just some of the questions that you can ask yourself in preparation for a significant conversation – a breakthrough conversation - and to carry out a credible diagnosis of the situation – and you don’t have to be a near insane doctor to get the right result! 

Dynamic Partners

13 Carriglea View
Firhouse
Dublin 24 
T: +353 15649626 
E: info@dynamicpartners.ie
Website: www.dynamicpartners.ie

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Disclaimer The information in this article is provided as part of Legal Island's Employment Law Hub. We regret we are not able to respond to requests for specific legal or HR queries and recommend that professional advice is obtained before relying on information supplied anywhere within this article. This article is correct at 09/07/2026
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