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Mastering Difficult Conversations

Building an enduring company takes strong leadership and many tough conversations.

Building an enduring company takes strong leadership. As many of us know too well, the startup journey, even when it is up and to the right, is filled with many bumps and challenges along the way. The best leaders use those opportunities to continue to push themselves and grow. Nobody knows all the answers from the start - the key is to always seek the tools and skills to foster a strong team and culture.

The Female Founders Forum is one way in which Emergence helps to facilitate that evolution. At our most recent event, we were lucky enough to have Lucy Georgiades, an executive and leadership coach who works with high-growth companies like Stripe and Eventbrite, run a hands-on workshop for the room of women CEOs and entrepreneurs.

Below, we recapped the session to share how Lucy helped us understand the best way to have the inevitable “difficult conversation.”

Lucy, before we dive in, let’s start with some basics - what qualifies as a difficult conversation? Why do we view them as difficult?

A difficult conversation is one that you’re not particularly looking forward to, like giving someone feedback about their own or their team’s performance, having to tell someone you can’t give them what they want (budget, headcount, promotion, etc.), or addressing someone’s bad behavior. 

The main thing that makes them difficult is that emotions are in play. They are usually conversations that require a bit of planning since they are often quite important and there’s likely to be a difference of opinion. Humans want to be liked and that drive for acceptance and community makes difficult conversations particularly unappealing or painful to have. When emotions get involved we start to trigger the part of our brain - our amygdala - that controls our fight/flight/freeze responses. Research found when we trigger our amygdala, our executive functioning is impaired, so it becomes more difficult to think rationally, logically, clearly and empathetically. To help combat this, a little preparation goes a really long way.

    A few, if not all of us, are probably nodding our heads about now. So what can we do to make sure they go well?  

    My advice would be to spend 10 minutes at least preparing for the conversation. Ask yourself, what outcome do I want from this conversation? What outcome do I want for myself? What outcome do I want for the other person? Getting clear on your outcomes will help you stay focused in the moment and keep the conversation on track. Then ask yourself, if I really want this outcome, how do I want to show up / behave in the conversation? If you’re someone who tends to shut down when you feel anxious, then maybe you want to remember to be firm. If you’re someone who tends to get irate in conversations, then maybe you want to remember to be more calm or empathetic.

    I would take a minute to write out what you’re going to say as soon as you get into the room. Often a worrisome part is knowing exactly how you’re going to broach the conversation. Keep it high level. Something like, “I’d like to chat with you about our working relationship and a couple of ideas I have to make it better. Are you open to having that conversation with me?” When you get a yes from them then you can get into the details. This yes forms a kind of contract where the other person has agreed to listen.

    When it comes to organizing what you want to say, I give my clients my 4-Point Feedback Framework that’s rooted in Marshall B. Rosenberg’s Nonviolent Communication Model. Start with the facts. Talk about what you’ve noticed happening. Mention how you feel about what you’ve noticed (worried, concerned, surprised, etc.). Talk through the wider impact of those facts. What’s the cost of them to the individual, company or relationship? Lastly, ask a gentle question. This question is not a fix-it question, but more like, “So how do you see things?” or “What are your thoughts about what I just said?” Structuring what you want to say in this way keeps it simple, keeps your emotions separated and opens up a conversation about the actual problem rather than surface symptoms.

    Maybe the best way to explain this approach through a specific example?

    Let’s pretend I am annoyed because I keep getting interrupted in meetings by this one person and I want to address it with them. 

    Start by finding an appropriate time to approach them. I recommend a quiet, non-threatening location away from a crowd or anywhere people might be able to watch or listen. 

    Second, start the dialogue off by saying, “I’d like to have a conversation with you about the dynamic we have in our group meetings. Is that OK to talk about now?” If they agree, then now you have their verbal agreement to continue.

    Next, use the following 4-Point Feedback Framework:

    1. Open with the facts: Start the conversation by sticking to the facts to accurately convey the situation at hand. For example, "I’ve noticed that in the last three team meetings we’ve had, you’ve interrupted me talking at least twice." This puts the event or action into context of time and place. 
    2. Show your feelings: Next, add in how their actions made you feel. "I feel a little frustrated by this because..." and add in the background on why it made you feel that way. 
    3. Wider impact: They might not understand or agree with how it made you feel since feelings are subjective, so it is important to highlight how their actions had a wider impact on their team/performance/project, etc. For example, "I am not able to complete my thoughts on the project and it undermines my credibility in front of the rest of the team." 
    4. Follow-up with a gentle question: Confirm their understanding of the issue by asking a gentle question such as "How do you see this from your perspective?” When put like this the feedback is direct but non-judgemental. You are not accusing them of being disrespectful, but are letting them know that it needs to be addressed. 

    I am sure after reading this some of us might wish we had a do-over on a recent conversation. Can you apply this AFTER an unsuccessful difficult conversation?

    We all mess up difficult conversations from time to time, but leaning into fixing the mistakes rather than avoiding another conversation is what’s key. You can apply the framework again but I’d suggest starting with acknowledging that the last conversation didn’t go as you hoped it might, own up to any mistakes you made during the conversation, and say you’d like to have another go at resolving things or making your point again in a more constructive way.

    A lot of our audience are CEOs, how can they create a culture that supports this type of communication?

    This is a topic that I work on with my CEOs in depth regularly during our coaching sessions. We know that the major reason for projects and companies failing is the inability of its people to have difficult conversations in the right way at the right time. It’s so fundamental to a healthy organization that I‘d encourage any CEO to think how they can create a culture where it feels safe to have tough conversations with people, regardless of their seniority. It’s got to be modeled from the top.

    Creating a culture relies on people having the tools and training to feel more confident in bringing difficult things up, and the psychological safety to engage in the conversation without fear of reprimand or retaliation.


    If you are a female founder or CEO of an early stage start-up B2B start-up and want to participate in the Female Founders Forum, please email me at

    For those interested in learning more from Lucy, she is hosting a workshop on Elevate Leadership Fundamentals on February 11 from 9 to 5 p.m. in San Francisco. The techniques and frameworks taught are rooted in recent psychology and neuroscience research.

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