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From difficult to transformative – the art of handling those hard-to-have conversations

20 Nov 2019 | Barbara Bassa Barbara Bassa, Advance HE Senior Leadership Development Adviser, points the way to conversations that build strong relationships and improve organisational performance.

When I talk to leaders in the higher education sector about some key challenges that they face when leading teams, managing individuals or influencing internal and external stakeholders, inevitably, they mention ’difficult conversations’. And the issue seems to trouble leaders at every level, whatever their experience.

What is a “difficult conversation”?

Typically, leaders describe a conversation difficult when they find it personally challenging: the conversation which they perceive can have a negative impact on them personally, their relationships, or on their organisation; the conversation which brings a sense of awkwardness, anticipation, heaviness or high emotional charge. Examples of difficult conversations mentioned by the leaders that I spoke with include: challenging senior colleagues about their research outputs, addressing attitudes to work, admitting mistakes or not knowing, managing performance, telling someone that they have lost their job, announcing a restructure, encouraging staff to work together following a merger, talking to a colleague in bereavement, talking to a student with mental health issues…

Of course, a difficult topic for one person may be easier for another and the same or similar conversation with one member of staff could be more challenging with a different colleague.

Why is it difficult?

Conversation is the most common tool in human interactions. In her book Fierce Conversations, Susan Scott argues that ‘the conversation is the relationship’. We build relationships through conversations. Anything that we have ever achieved has it basis in conversations. So why is it difficult? As social creatures we have a desire to belong, to be accepted and appreciated. We have learnt early in life that saying things which are challenging may upset the status quo. And we are afraid that we may damage relationships and put ourselves in an unfavourable position as a result. Moreover, we may have previous experiences when a conversation did not go well and we don’t want to repeat the scenario. Or, we may have some deeply rooted triggers related to a particular topic which we are worried would irritate unhealed wounds. However, avoiding conversations doesn’t mean that issues go away! They fester, they grow, they play on our minds, they become bigger than they were initially, and then a problem could become insurmountable. I would argue that we may make ‘the conversation’ more difficult by our perception or attitude towards the issue; the issue is neutral. Calling these conversations ‘difficult’, even though they may not be easy, is not helpful. When we call something ‘difficult’, straight away it puts a label on it and, consciously or subconsciously, we are tempted to avoid it. So how about calling these conversations ‘transformative’?

Transformative conversations - why is it worth having them?

I cannot remember how many times I have heard from participants, who use the ‘transformative conversations’ principles and techniques, saying: ‘it was not as bad as I’d thought it would be’. Actually, when we summon the courage to talk openly with another person, they usually feel relieved. They knew something was wrong but they did not know what. There is power in naming an elephant in the room…after all, it takes more energy trying to hide it.

We invest so much energy holding onto a problem: thinking about it, playing different scenarios in our minds over and over again, talking about it, possibly pretending it does not exist. It’s like a burden that we carry, and having a conversation releases all this stored energy towards finding solutions. Having transformative conversations is a foundation for building strong relationships, motivating teams, improving organisational performance, establishing sound personal boundaries, negotiating contracts, creating healthy working environments, being effective and fulfilled, etc.

How to prepare for the conversation?

There are many techniques and tools to help in preparing for a transformative conversation. Usually in my facilitation, I guide the participants through a preparation process and allow time for ‘real play’ and feedback. For now, I am going to concentrate on the elements which I see as the most crucial for success.

  • Intention Firstly, be very clear about why you want to have the conversation. What is your intended outcome? For example, is it to improve the relationship, or to create a stronger team morale, or to improve performance? How is having this conversation going to benefit the other party? They will be more inclined to engage in the process if it is driven by mutual benefits. It’s important that you state the intention to the other party and keep coming back to it during the conversation. It will help you ensure that you stay on track.
  • Creating the container: Before you start the conversation, think about how you can create a ‘container’ for it. By ‘container', I mean physical and non-physical aspects that contribute to the atmosphere of the interactions, helping to make it safe, respectful and comfortable. For example, think about the timing, the location and privacy. How are you going to start it? How would you position yourself in the room? What language may be useful or not?

  • Embracing vulnerability: Talking about tough topics takes courage. It is natural to feel nervous. The courage comes with the ability to feel the fear and act in spite of it. Stepping up and initiating a challenging conversation is in itself an act of leadership. It is important to acknowledge your emotions about it and deal with them appropriately. We want to enter the conversation authentically, perhaps stating how we feel, but without emotional charge, so that we can stay factual and without risking losing balance. 

    A truly transformative conversation is the one whose outcome cannot be pre-determined. We enter unknown territory and we cannot predict what we are going to encounter in the process; and, again, that takes courage.

  • Truly listening: Conversation is a two-way process. If you want to achieve transformative results, you have to be prepared to listen and perhaps admit that you were wrong. It may be that your perception of the challenge was distorted or your view was biased, or you have not considered other aspects of the problem…You will have to listen to what is being said and what is not being said. Consider the emotions in the conversation.  What are the unspoken motivations? What wants to emerge through the conversation? Truly listening is particularly important if the person feels frightened, upset or defensive. Words are often just the first layer of communication. What we really want to find out is the motivation behind the words. What are they really saying?

  • Knowing your triggers: When entering a tough conversation, it is good to know your triggers. Which of your buttons are likely to be pushed? It may be when someone starts crying or saying ‘it was not me’, or blaming and shaming… we all have triggers. How do you react when your buttons are pushed? Do you get angry, defensive or withdrawn? How can you make sure that your trigger will not impact the conversation? What strategies can you use? Maybe you can breathe or pause the exchange? Remember the intention for the conversation.
  • Being authentic, speaking from the heart: Have you ever been a part of a conversation that was ‘done’ to you, that was staged, or every word of it planned? Engaging in a transformative conversation is different. You need to be honest and authentic. Only when you speak from the heart, you will be able to open the flow of the conversation and invite the other person to speak genuinely…

We all need to have more transformative conversations to create more meaningful workplaces, more connected societies and more sustainable environments. Having conversations takes energy. If we need to have them, let’s talk about things that matter!

What do we need to talk about right now?


Barbara Bassa is a Senior Leadership Development Adviser at Advance HE and Director of the Senior Women's Leadership Development Programme and our new Transformative Conversations Programme. She is an accredited Fierce Conversations® facilitator and a Senior Fellow.

Barbara holds an MSc in Organisational Development from Sheffield Business School, MSc in Business, postgraduate diplomas in Social Communication and Human Resource Management.

Barbara has worked extensively in the higher education sector, particularly with senior leaders and executive teams facilitating programmes aimed at developing organisational effectiveness and leadership behaviours. She has also worked with leaders and executive teams in the NHS, government bodies, housing associations, pharmaceutical and cosmetic companies, manufacturing, banking, insurance, aviation and IT sectors, in the UK and internationally.


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