Coaching Tip – Have the “Tough” Conversation! 

 February 6, 2022

By  Tamara Davidson

This year I would like to share with you a coaching tip each month on a particular area which I come across often in my coaching sessions with clients. These coaching tips will by no means address all the nuances regarding the specific coaching topic, however, I hope to share some of the gold that I believe can, and will, make a difference for you in your life if you apply it to yourself. 


Have the "Tough" Conversation! 

Often clients come into coaching not wanting to, OR not knowing how to, have what they describe as “tough” or “difficult” conversations. This may be with their manager, team member, peers or even family members. This is often problematic for the client as these are the very kind of conversations that are required to address an issue, face a challenge, understand someone, or be understood. These conversations can make you highly effective in your communication and can develop deep and intimate relationships with others.

What do clients often classify as “tough” or “difficult” conversations? 

  • Addressing a problematic behaviour with a direct report.
  • Giving honest and direct feedback to a manager.
  • Speaking one’s truth, sharing one’s voice with peers or colleagues.
  • Addressing conflict in intimate relationships.

Throughout my coaching sessions with hundreds of clients over the years, common themes start to emerge in a person’s thinking strategy regarding how they approach or avoid these kinds of conversations. Below is a checklist for your own self-inquiry, if you find these kinds of conversations difficult to have… 


How are you framing this conversation?

The way you “frame” a conversation will often produce the experience of that conversation. A frame of reference is a way we think or believe about a thing. E.g. If I am convinced that the conversation I’m about to have is going to be “tough” or “difficult” then am I setting myself up to have this experience? 

Coaching Questions: 

  • Are the frames you’re holding about this conversation serving you?
  • How could you re-frame this conversation? If it is not a “tough” or “difficult” conversation, then what else could it be? Just a conversation? or what about; A "truthful" conversation, a "real" conversation? A "productive" or "necessary" conversation? A "compassionate" conversation? 

Changing the way you frame the conversation with yourself and others will dramatically change the way you experience it. 


Have you "tabooed" these kinds of conversations?

Often clients have unconsciously “tabooed” having this kind of conversation – a version of this that I hear often is “I can’t say that, can I?” Taboo-ing, prohibiting or imposing semantic limits on oneself and others using the word "can't" presupposes that there is some law or rule that constrains us from doing something. This limits ideas about what’s possible for us. It stunt’s ideas of human potential, and it impairs our ability to dream and to take risks. 

Coaching Questions: 

  • Who says that you can’t have this kind of conversation?
  • What stops you from having this kind of conversation?
  • Do you have permission to have this kind of conversation?
  • What would it sound like, look like, feel like if you did? 

Using possibility thinking allows us to question these rules and constraints which we’ve often unconsciously put on ourselves and others. We can then explore the entirety of what’s possible for us.


Do you tend to avoid conflict?

Are you fearful of having these kinds of conversations? Do you tend to choose comfort rather than disrupting the status quo? Many personality types tend to avoid what they consider “tough” conversations through their fear of conflict. And yet, often not having these conversations is what creates even more conflict. And whilst some people may think they are avoiding external conflict by not having these kinds of conversations, they often cannot avoid the inner conflict which occurs from not speaking up and speaking their truth. So, the very thing a person is trying to avoid is exactly what they manifest in themselves. 

  • What do you believe about conflict? Are these beliefs serving you to be at your best? 
  • What are some of the positive outcomes of conflict?
  • Is it possible that by not having the conversation that you are also creating conflict?
  • How could you re-frame conflict? What else could it be?  

Understanding your own relationship to conflict and the strategies you run regarding how you deal with conflict can be powerful and transformative. This is where the Enneagram is at its best. Working with a typology lens like the Enneagram, can allow you to deeply understand your core motivations in relation to things like conflict, which can facilitate great flexibility in how you show up in the face of conflict.  


Bonus Tip

I think it important to mention the role that Intention plays in having these kinds of conversations. Having an intention or desired outcome in mind when having these kinds of conversations can provide clarity and focus as you communicate. E.g. If you are having a conversation with a direct report about a problematic behaviour they are displaying, and your intention is to bring awareness to the behaviour and facilitate this person to change this behaviour, then this informs the what and the how of your conversation. It keeps you on track to only communicate in ways that are going to help you achieve your desired outcome or intention. 

  • What is your intention in having this conversation?  
  • What do you hope to achieve by having this conversation? 
  • Is the way you are communicating facilitating your intention or desired outcome? 
  • If not, what do you need to change / alter in your approach?   


It has been my own personal experience in my personal and professional life, and as a coach, witnessing my clients stepping into these kinds of conversations, that having a real, truthful, heartfelt, and compassionate conversation is often the very approach that; resolves issues or challenges, clarifies understanding in communication, deeply connects people, avoids further conflict, and facilitates a person’s highest and best. 

Yes, it may feel clunky at first and can take practice to feel confident in having these kinds of conversations, however, the beginning of every journey, starts with a single step. There are also many skills that can be learned to become masterful at these kinds of conversations, which is where a Meta-Coach can help! 

So, my offer is this - have the tough conversation, practice getting real with others, challenge your beliefs about these kinds of conversations and about conflict. Yes, there can often be a cost or consequence involved in having these kinds of conversations, however, do not kid yourself, there is often a cost or consequence, sometimes greater, in not having them. So, choose your cost wisely. 

If after you’ve asked yourself these coaching questions above you still feel there are particular block’s getting in your way of having these kinds of conversations, then schedule a coaching session with a Meta-Coach to unlock your potential in having these kinds of conversations. 

I would love to hear your experiences and comments below…  

Tamara Davidson

Tamara Davidson is an Executive Coach, Trainer and a Managing Director of Modo Coaching and Training, with over 20 years of experience leading large organisations. Tamara is a certified Meta-Coach, Master NLP practitioner and experienced Enneagram facilitator, and her passion is to facilitate people to discover and actualise their highest potentials in their personal and professional lives.

Tamara Davidson

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