Create A Workplace Where Difficult Conversations Are Appreciated

Tackle Difficult Conversation Head-On to Bolster Teamwork


I often find myself being sought out for advice on handling interpersonal challenges in the workplace. One common observation I've made is that when I ask individuals if they've directly addressed the issue with their colleague, the response is frequently "no".

While it's understandable that difficult conversations can be uncomfortable, avoiding them only allows issues to persist and worsen. It's important to muster the courage and honesty to address these matters openly and directly.

Establishing a workplace culture that values and encourages candid dialogue is a collective responsibility. Only by fostering an environment of mutual respect and transparency can teams effectively address conflicts and bolster teamwork.

Recognize Imperfections in the Workplace

As leaders, we often strive to cultivate positive work environments. While this is an admirable goal, it's essential to acknowledge that challenges, underperformance, and shortcomings in work quality are inevitable occurrences. While fostering positivity is crucial, it shouldn't come at the expense of avoiding tough conversations.

Confronting difficult discussions head-on is fundamental to fostering the healthiest workplace cultures. Addressing challenges promptly prevents them from escalating and affecting the entire team. Rather than striving to maintain an illusion of perfection, it's more effective to accept that obstacles will arise and be prepared to address them proactively as they emerge.


Do not confuse difficult conversations with negativity or perceive them as confrontational. Instead, recognize their importance in creating and maintaining a positive and cohesive workplace.
— John Fildes

Prepare for Resistance

When approaching challenging conversations, it's important to anticipate resistance. People often react instinctively by either engaging in arguments or withdrawing altogether. Understanding these reactions in advance equips you to handle them more effectively when they occur.

In the face of arguments, maintaining a calm and factual demeanor can defuse tensions. Facts are hard to dispute, so sticking to them helps to mitigate emotional reactions and keeps the discussion centered on objective aspects.

Similarly, when encountering silence, defensiveness, or dismissal, a straightforward approach rooted in fact is most effective. Start by gently prompting acknowledgment of the situation and gradually encourage further dialogue. Creating a safe and relaxed atmosphere is essential to fostering openness and progress in conversation.

Resolve Matters and Move Forward

The aim of confronting difficult situations is to find a resolution. It's crucial that your conversation is constructive and ends with both parties agreeing on a way forward. Before diving in, be clear about the outcome you hope to achieve and stay focused on it throughout the discussion.

Equally important is bringing closure to the conversation and shifting your attention afterward. Continuously dwelling on the discussion can reignite tensions and prolong the problem. Sharing the details of the conversation with others may lead to gossip and could potentially embarrass those involved. Instead of lingering on the topic, it's crucial to promptly transition and redirect your focus to other pressing matters. This ensures that the positive results achieved in the discussion are upheld, allowing everyone to move forward effectively.

In Conclusion

Do not confuse difficult conversations with negativity or perceive them as confrontational. Instead, recognize their importance in creating and maintaining a positive and cohesive workplace. Embrace the opportunity to initiate these discussions when necessary and be open and willing to engage in them when approached by others.

Building a culture that values and respects difficult conversations is a shared responsibility. Lead by example and encourage others to do the same. By fostering such an environment, you will contribute to a workplace that is more positive, interconnected, and grounded in trust and respect for one another.

About John Fildes

I grow the top line by connecting marketing to business strategy. By leveraging powerful positioning, content marketing, and client insights, I help organizations drive qualitative and quantitative results at scale.

I've built an amazing network of incredibly talented people over the years. What I've appreciated most is those who have invested in me, mentored me, and helped me become the talented professional I am today. I pay it forward by doing the same for other high performing professionals and entrepreneurs.

Learn More: Marketing Leader | Adept Entrepreneur | People Developer


All views are my own and not those of my current or prior employers.


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