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How to Have Difficult Conversations

Disclaimer: The views and opinions expressed in this article are those of the authors and may not reflect the perspectives of IIBA.
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Awkward silences. Sweaty palms. Nervous glances. Most of us have been there.

Difficult conversations can send shivers down our spines and strike fear into the hearts of even the most accomplished communicators. But with a little preparation, the right attitude, and good timing, you can turn difficult conversations into opportunities for growth and stronger relationships.

In the latest episode of Business Analysis Live, agile analyst and scrum master extraordinaire Mindy Bohannon joins Scott Bennett and Susan Moore to uncover the secrets for mastering the toughest of talks.

Get ready to transform anxiety into confidence and uncertainty into clarity, as we dive deep into the art of navigating challenging conversations.

Preparation Is Key

Difficult conversations are part of life, both personally and professionally. Whether it's addressing a performance issue with a team member or negotiating a difficult contract, they can be uncomfortable and challenging. And while it’s tempting to view them as extremely unpleasant tasks that are best avoided, they’re actually rather positive in the long run.

With adequate preparation, you can navigate them more effectively and achieve positive outcomes. Your first step is to consider the purpose and objectives of the conversation. Are you trying to solve a problem and create something new? Or are you being forced to confront a colleague? Understanding the purpose and objectives will help guide the conversation and ensure it stays focused on the desired outcome.

Next, put yourself in the other person’s shoes and try to understand their concerns. This can help you approach the conversation in a more empathetic and constructive way. It’s especially important when dealing with people in positions of authority or when addressing performance issues.

Once that’s done, it’s crucial to gather the necessary information and conduct root cause, document, and interview analyses beforehand. That way you’ll have relevant facts and data to support your points, demonstrating preparedness and credibility.

While it's normal to feel anxious or defensive, strive to remain calm and composed during difficult conversations. Techniques like deep breathing can help maintain focus and control. Prepare to manage emotional reactions by having a plan in place, such as taking breaks or using calming techniques.

Keep in mind that difficult conversations aren't always confrontational—often they simply involve admitting limitations or unmet expectations. Addressing feelings of guilt or disappointment with respect and empathy can foster a positive and productive conversation.

As Winston Churchill once famously said, “Never let a good crisis go to waste.”

Document the Evidence

Documenting evidence, or CYB (Covering Your Butt) as it's more commonly known, is a related practice that involves recording the conversation and summarizing it in an email or other written form.

It serves multiple purposes. For one, it establishes a clear record of agreements and discussions, which is crucial for resolving disputes and preventing misunderstandings. With a written record, individuals can refer to it, ensuring accurate representation of perspectives and preventing conflicts.

Second, documentation fosters trust and credibility within teams and organizations. It demonstrates a commitment to transparency and accountability, showing that input and concerns are valued. This provides team members with confidence since they’ll know their voices are being heard and their contributions acknowledged.

This practice also helps in the recovery process after challenging discussions as it acknowledges the intensity of conversations, allowing individuals to express gratitude and find closure. Sharing notes ensures clarity on decisions made, providing a basis for follow-up actions and discussions.

The short version? Documented conversations enhance credibility and trust, crucial for building and maintaining relationships internally and externally.

Timing Is Everything

As with most things, timing is important here. While tempting, delaying a difficult conversation will only make things worse. Addressing the issue promptly allows for immediate resolution, preventing further escalation and facilitating productive problem-solving.

It also allows you to prepare better for a successful outcome. Gathering relevant information and reflecting on the issue beforehand increases the chances of a positive resolution and enhances communication and problem-solving during the discussion.

As mentioned in the preparation section, you should again consider the audience and their perspectives when it comes to timing. Assess who needs to be present and create a conducive environment for open communication. This will ensure that all perspectives are heard, and it leads to a more comprehensive and effective conversation.

Don’t Put It Off

Like the importance of timely discussions, procrastination can have some negative consequences. Delays can escalate tensions, fuel rumours, and even exacerbate existing issues, making them appear worse than they are.

Trust us. Amplifying negative thoughts and fears until they spiral out of control isn’t a path you want to go down. Instead, approach difficult discussions with kindness and understanding, fostering empathy and compassion in your interactions.

Despite the initial hurdles that come with it, addressing conversations promptly is key for long-term positivity. Confront issues head-on, aiming for outcomes characterized by kindness while keeping personal emotions separate from professional dynamics.

Timely communication is paramount. Avoid the pitfalls of postponing discussions and reap the rewards of addressing them promptly—enhancing relationships, honing problem-solving skills, and improving overall communication effectiveness.

Hungry for more insights? Dive into the full conversation and mark your calendar for our next discussion in two weeks. For questions or comments, connect with us via email at

Until next time!

Explore fresh and candid conversations on a wide array of business analysis topics with the Business Analysis Live podcast.

About the Authors
Susan Moore

Susan A. Moore, Community Engagement Manager, IIBA

Scott Bennett

Scott Bennett, Manager, Business Analysis, IIBA

We host Business Analysis Live to discuss business analysis topics and answer questions from our live audience.  We have a backlog of upcoming topics and we’re happy to take suggestions. Add a comment to one of our videos to suggest a topic you would like us to cover in an upcoming episode!


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