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Navigating Difficult Conversations

March 10, 2025

By Andrea Beth Levy, CPA, CFE, CGMA, MBA

As trusted advisors, CPAs are expected to provide accurate, timely and valuable information. In conversations, we’re expected to show up as knowledgeable, accurate, confident and reliable, while simultaneously solving problems in real time. It can feel like rapid responses are required where the stakes are high. There’s a lot of pressure; the work is fast, and communication is everything. So, how do we navigate and resolve difficult conversations when we encounter them? 


What makes conversations difficult?

Solving difficult problems quickly with substantial implications to your workload and ethical requirements can be challenging. This may include requests to override compliance, disregard internal controls, neglect ethical rules or achieve incredible goals without appropriate resources.

Conversations can move in a different direction unexpectedly or become aggressive during the process of unfolding important or heated internal conflict. It can feel personal when another person is criticizing your hard work or directly impacting your workload. This can create an internal fire drill response.

It may take tremendous effort to not react when conversations feel high stakes. Everyone can be defensive at times, and it is especially common in difficult conversations. Most people’s reaction to feeling defensive is to start acting defensive, such as grandstanding, interrupting the speaker or firing continuous questions about multiple topics all at once. This can escalate the situation and make it increasingly challenging to stay calm and have a productive conversation.

What’s the first step to moving toward a resolution?

Noticing a conversation has taken a turn and become difficult may be crucial to initially reducing cognitive load and improving social emotions. This internal shift allows a move into an observer role instead of being directly pulled into a whirlwind of effort. One tactic to create this shift is to consciously slow your breathing down or silently count in your head.

Three Positive Outcomes to a Difficult Conversation

When working through a hard conversation, there are three possible outcomes: developing an understanding, a plan or a solution. 
The first positive outcome is an increased understanding between both parties.

Developing a new awareness about another person’s experience is realistic, but it takes a great deal of patience. Ideally, a difficult conversation happens in a calm moment, not because circumstances have forced the conversation to occur. Either way, there is no more productive and efficient activity than aggressively listening.

This requires suspending your own personal responses and emotions to what you’re hearing, holding them off to the side while the other person describes their experience, even when it’s most uncomfortable. When it gets hard to listen, it’s a cue to listen more. This can feel like you’re listening to the other person speak in circles, but if you can stay listening, and wait to speak, it will build trust.

Per Adar Cohen, “Every minute that you keep listening is an investment to your own payout in the end.” One crucial element of active listening is asking open-ended questions to stay curious, not litigious. An open-ended question invites the other person to describe their experiences, without being set up to litigate or blame during the conversation. The idea is to open the door even a little bit wider for the other person to describe their experience further.

The second positive outcome is a plan or roadmap to the big solution.

Creating a plan is great to aim for, but it might be hard to achieve without appropriate support. Keep in mind, we can’t always resolve a difficult conversation at once. Fatigue and blood sugar reduction sets in, resulting in diminishing margins of return; we may not be at our best even when the biggest part of the conversation is right around the corner. Instead, suggest revisiting the conversation after both parties have time to rest, so the conversation is fresh.

The third positive outcome is of course a solution. Finding a solution is the single highest form of achievement and remains a resounding win where the conflict is washed away and there are only blue skies ahead. However, a solution is the most difficult to achieve without a plan or understanding first. Typically, when folks engage in difficult conversations, they are looking for the big win. There’s a temptation to achieve a big solution without coming to an understanding or a  plan first.

However, there are times when we are working with team members who do not exhibit mutual respect or support. These difficult conversations can become even more tricky to navigate. Examples of these common experiences include unreasonable job demands, personal insults, being blamed for mistakes of others or an industry trend. In those instances, the best approach may be to create boundaries and requests. With this tactic, be acutely aware of your tone. It’s easy to show up as snide or snarky when feeling under attack. According to Dr. Craig Malkin, “Instead of challenging the behavior directly, question its relevance to successfully completing the task.” Below are examples of challenges and questions you could ask to respond.

  • Challenge: Your supervisor questions the quality of your work product and then shifts into questions about whether you have what it takes to be a success at work.
    Response: “Can you help me understand how this helps me with the problems you see? What is it that you want changed?”
  • Challenge: Your colleague blames you for the issues on the current project.
    Response: “Can you help me understand how this helps our project move forward? I’m not sure what it is that you’re asking for?”
  • Challenge: Your supervisor implies your work does not meet expectations but provides no specific examples – even after being asked for an example.
    Response: “You seem to be more anxious about the success of the project today. Have you heard something that has you worried?” or “What’s raising all these concerns for you right now? Has something shaken your confidence?"

In closing, for those of us who like to prepare for difficult conversations, consider four important questions:

  • What is my perspective?
  • What do you think is the other person’s perspective?
  • What is one thing we both agree upon?
  • What is my goal for this conversation?

Andrea Beth Levy, CPA, CFE, CGMA, MBA is the head of finance & operations with the Greater Phoenix Chamber. Levy currently serves as the Arizona CPA Foundation for Education & Innovation Chair and is an audit committee member of the Institute of Internal Auditors Phoenix Chapter. You can connect with her at linkedin.com/in/andrealevyfinance/.

References:

“10 ways to stay calm in difficult conversations” by Nick Wignall
“Difficult Conversations with Dr. Adar Cohen” by Nick Wignall, Minds and Mics Podcast
“Rethinking Narcissism” by Dr. Craig Malkin
“This is why we avoid difficult conversations” by Kaja Perina, Psychology Today