With the fast pace of startup life, it is easy to avoid having those difficult conversations we know we should have – with our teams, our board, even our customers – but not having them can leave relationships stagnating or projects and performance waning. In this article, we dissect why we don’t have them and build a practical plan for how to have them in a way that generates an effective result.
What is the conversation that you’re not having within your business, but should be?
We’ve asked this question of hundreds of founders and startup leaders and regardless of stage or team size, not one has been short of at least one such conversation. For some it is an internal conversation – a team member or an SLT member. For others, it’s an external conversation – a board member, investor, partner or customer. We all have them, and it is usually holding us or our team back.
So coming back to the ‘crucial conversation’ that came to your mind:
- what would improve if you did have the conversation?
- what is the impact of not having it?
- and what holds you back from having it?
Dissecting why conversations get difficult
A lot sits behind why we don’t have these crucial conversations: Sometimes we fear the conversation (or response); sometimes we don’t want to ‘rock the boat’ in the relationship. It ultimately comes down to an anticipated difficulty in the conversation, but that can leave relationships stagnating or projects and performance waning.
So how do we break out of the cycle and move forward with our crucial conversations? By understanding our own reactions, and those of others, we can start to build understanding between you and them, and then find common ground – even if you’re starting from a place of conflict.
A helpful starting point is to understand your responses: The Thomas Kilman Instrument (TKI) is a helpful framework for considering your behaviours when you encounter (or anticipate) conflict. It plots your behaviour along two axes – your level of assertiveness and your level of cooperativeness in a conversation – giving us five modes:
It’s common for us to have a default. You may also find that your most common mode changes by person, context and even by how much you care about the topic of discussion (all normal!). Thinking about the conversation that you’re not having through the TKI lens can help build self-awareness: Which mode are you currently in regards this conversation? Which might you be in when having the conversation? And which mode do you anticipate the other person being in?
Bringing in the neuroscience can help us further understand the feelings and reactions that we’re having, as well as better understand the other person: When the emotional centre of the brain – your amygdala – perceives danger, it triggers a physiological reaction. The rational thinking part of your brain – the pre-frontal cortex (PFC) – gets shut down, and the body responds in a defensive way to the danger (fight, flight, freeze, fawn). Unfortunately, in modern times, this old part of our brain can anticipate an upcoming conversation as perceived danger and the resulting emotional and neurobiological reaction is often unhelpful to managing the conversation with calm, self-awareness and rational thinking.
It helps to tune into your stress-response signs – maybe it’s a clenched jaw, a tight tummy, or inability to focus – knowing your early-warning signs gives you the power to intervene. The metacognition and interoception skills we covered last month can help with this. Recognise how you’re feeling (naming it helps), focus on your breath to re-regulate the nervous system in the moment and then once the PFC is back online, start getting curious about how to approach the conversation effectively.
Connection builds bridges in any difficult conversation
What are you hoping to achieve with your crucial conversation (really!)? I can certainly think of instances where, despite how I dressed it up, I just wanted to ‘win’ or have my view heard. Yet what would be more productive is to identify the shared outcome – which considers the perspective of the other person too. Tuning into those initial reactions and calming the nervous system, allows you to step back and focus on this shared outcome and increases the likelihood of connecting over the conversation constructively.
Connection and curiosity underpin a constructive conversation, especially one that has the potential to become difficult, and both draw on the coaching skills that we practise in our FounderCircles. Genuinely connecting means both parties feel heard and understood, removing the need for emotional responses and increasing the likelihood of finding shared understanding. To connect, we start with listening – deeply listening (something we impatient founders often struggle to do!) – keeping in mind that the focus is not ‘listening to respond’ but ‘listening to understand’. From a biological perspective, it’s actually pretty hard to do this due to how we’re built as humans – but with focus it is possible to quieten the inner-chatter and tune into what the other person is really communicating.
Conversational frameworks to help have the conversation
From the foundation of understanding through listening, we can utilise the second half of the founder-coaching skillset – asking good questions: We ask questions all of the time, which much like listening can lull us into a habitual way of doing it. For difficult conversations, dialling up the intentionality can really aid a constructive result. A simple approach for this is to consider how you ask questions: To have solution-oriented, productive discussions – especially around tricky topics – we need solution-orientated questions, and they usually start with What, not Why. Why tends to create defensiveness, so swap them for questions that start with What instead, and this encourages others to think about the future.
The SING framework is a helpful tool for clearing the air – enabling you to explain your point of view and kick start a conversation to move forwards:
The tGROW framework can be used to guide a solution-focused conversation – enabling you to initiate a conversation around a topic with one or more people so that you can collaboratively move towards a shared solution or action plan.
Treat both frameworks as a structural guide for navigating a conversation, rather than a straight jacket. The best implementation of all coaching-style frameworks (which these are both based on) is to combine them with your deep listening skills so that you can respond fully to what is coming up in the conversation. The SING framework for example could be used as a starting point for a conversation – you share your perspective using the framework, then you endeavour to understand their perspective more too. This can then lead into a collaborative conversation to form a shared solution (which tGROW could also assist with).
Having these difficult conversations is undoubtedly part-art and part-science – like most aspects of leadership, given we’re working with humans – but by building self awareness, seeking to understand different perspectives and guiding the process with thoughtful questions, we can carefully craft a more productive result.
If you’re struggling with conflict, or navigating a tricky co-founder or professional relationship – our founder-relationships expert and mediate Sanja can help. Find out more here.
Other FounderFuel articles on a similar theme
A coaching approach for empowering others as a founder
Co-founder conflict and communication break-downs, how to manage it constructively
Keeping it together when you’re feeling the pinch – a founders’ guide to emotion-regulation








