Tips & tricks on dealing with difficult conversations

We love to learn and get inspired by great leaders. We reached out to some of the leaders from our network to hear more about their experience dealing with difficult conversations. They shared with us their tips and tricks on how to deal with difficult conversations.

What we learned from Judith Jungmann

As CHRO at Beckers Group, Judith has many opportunities to experience difficult conversations. “The last one I had last week. I already knew it would be difficult, so I structured the points that I thought were relevant to mention beforehand, I also tried to think about which atmosphere I want to create (in that case a lighter tone to ease the situation as it was a conflict mediation) and then listen very carefully during the conversation and make sure everyone has room to mention their thoughts.”

For Judith, the key to best dealing with difficult conversations lie within three things:

  1. Preparing ahead of time and structuring your thoughts;
  2. Listening as generously as possible;
  3. Using humour to ease the atmosphere, if it makes sense.


On the other end, she recommends to avoid:

  1. Judging;
  2. Taking it personally;
  3. Shutting down the door to further conversations.


Unlike most people, Judith seems to actually enjoy and thrive on those difficult conversations. When we ask her, she replied: “I was a bit lucky: early in my career, I decided to like difficult conversations as the chance to learn something is much higher.” She also mentioned that one thing she wishes she knew earlier in her career was learning to speak about her own emotions.

What we learned from David Edwards

David is Head of Portfolio Growth at Techstars, which makes him a regular point of contact when it comes to queries and issues with different stakeholders such as founders, internal teams, and partners. For him, there are three clear “do’s” when it comes to difficult conversations :

  1. Be sincere and clear
  2. Don’t let emotion cloud your mind or influence your speech
  3. Stay on topic


When we asked him about the one thing he would have wanted to know early on in his career when it comes to difficult conversations, he said ”Having difficult conversations is part your job. To the best of your abilities, you have to communicate in a way that the other person accurately receives both your core message and tone.”

We were curious to know whether there was a conversation David wanted to have but was afraid to do so because it might be too difficult. He shared: “I don’t think this feeling every goes away, but with intentional and conscientious practice we can get better at not avoiding conversations, or worse handling them poorly, just because they will be difficult.”

What we learned from Johann Romefort

Johann is mentor, coach, and Founder of Systemic Ventures. Through his work, he has the opportunity to meet different founders with different personality types, and he cannot escape some hard conversations. “I tend to have regular difficult conversations, but more importantly to teach founders how to have difficult conversations themselves with their team. If we look at “The 5 Dysfunctions Of a Team”, a seminal book from Patrick Lencioni, “fear of conflict” ranks at the second place on the pyramid of dysfunctions, right after “lack of trust”.  Without trust first, it is generally difficult to have difficult conversations.” Johann recommends to first try to build a good foundation based on trust before getting into the most difficult conversations.

For Johann, coaching founders on how to have difficult conversations with their team means:

  1. Showing empathy and understanding: “During that part I might bring up personal story where I’ve experience a similar situation, once again to build trust through vulnerability.”
  2. Diving deeper into the difficult conversation: “I clearly express that action is needed and a conversation needs to happen as the status quo won’t lead to good outcome. At that point the person in front of me exhibits a high level of stress facing the fact.”
  3. Emphasizing on care and tools. “In this situation, care means being an advocate for courage and reassuring the person on their ability to actually have the conversation even if it is uncomfortable. Tools are about helping them with communication techniques to help them express what they have to say to relevant parties. Those techniques revolve on building trust, empathy, but also direct communication.”


Johann reminds us that not directly facing a difficult conversation won’t magically make it disappear. “More importantly, delaying a difficult conversation has a tendency to have ripple effects and create toxic environments where fake harmony becomes the norm. I’ve also noticed that the more we delay a difficult conversation, the more mental space it starts to take, and the worse we imagine the outcome to be. Difficult conversations are generally the most transformative. That is also where the true essence of leadership is revealed!”

Would you like to feel even stronger supported in your first leadership role? Katrin also offers a new product to support first-time leaders even better: The First-Time Leaders Community. It includes a self-paced video training, regular workshops and exchange with peers, and optional individual coaching sessions. Learn more and sign up today if you think you can benefit from it!

photo by Lucie Greiner