Embracing Difficult Conversations to Create an Honest Workplace

Being a good communicator requires more than the ability to captivate people and get your point across. It demands a level of awareness, an understanding of human nature and a good measure of self-confidence. These qualities are honed over time and through experience, but in more junior employees, cultivating and teaching them to embrace these qualities is not by any means standard in today’s workplace—it’s progressive.

As challenging as it can be to effectively communicate compelling subject matter, it’s twice as difficult to discuss tough subjects or have difficult conversations. Email and text afford people the ability to address difficult topics in a less personal way, which many people find easier and less confrontational.

I believe it’s critical to develop high-functioning individuals and teams.

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The trouble with communicating only via our devices is that electronic communication lacks nuance and emotion, which can give way to misunderstanding. When used, for example, to convey empathy or sympathy, messages can sound hollow. Similarly, when used to convey regret, as in an apology, messages are often inadequate and can even make things worse.

I recently wrote about the value of face to face communication, because I believe it strengthens relationships, promotes understanding and supports camaraderie among colleagues.

In a similar way, having difficult conversations in person, as opposed to online, gives participants a clearer sense of each other’s intentions, motives, feelings and emotions. It promotes understanding, which is arguably more difficult to read in electronic messages.

Practice Makes Perfect

Understanding the advantages of having difficult conversations in person is one thing, but exercising that knowledge and doing it is another entirely.

In addition to training staff how to write effectively and speak publicly with confidence, teaching and mentoring staff to effectively communicate, especially when covering difficult topics, is an essential part of eradicating silos and developing sustainable collaboration in the workplace.

Enrolling staff in online courses or bringing in subject matter experts can go a long way toward inspiring and promoting learning, but practicing the art of having difficult conversations and letting staff witness that process is more effective.

Role playing is one way to teach tactful, effective communication. Another is conversation mapping. In advance of a challenging interaction, encourage employees to follow these steps to map out the conversation:

  1. List the key points that will be discussed.
  2. For each key point, support your perspective with fact-based information.
  3. Write out your desired outcomes. Think through what will and will not be acceptable.
  4. Brainstorm potential curve balls. What could come up that might derail a meaningful discussion? Anticipating the unexpected and being well-prepared for the conversation will help build the confidence needed to successfully manage the interaction.

Mentoring staff and actively teaching them how to successfully navigate difficult conversations gives them the tools they need, but to make them feel completely comfortable deploying those tools, the workplace culture needs to support their actions.

Creating a Culture of Open Communication

As transparency in the workplace has become an integral component of many best practices, the focus on honest and open communication at all levels has become central to establishing positive morale, professional satisfaction and a nurturing, supportive work environment. Few people are innately good communicators, engaging in meaningful discussions with direct reports, peers and supervisors regardless of the subject matter. Many of us have to work at it and unfortunately few workplaces, especially in the nonprofit arena in which I serve, focus on training staff to handle hard topics.

Consequently, many of us struggle when faced with tackling a subject like poor work performance or misunderstandings between colleagues. The root of the stress these situations can create, is often vulnerability and insecurity.

To inspire and promote open, honest communication among teams, employers must first create a supportive environment where staff feel their supervisor has their back and will stand behind them.

I encourage staff to be vulnerable and admit to mistakes, to foster an environment where understanding, patience and acceptance become part of the culture. A lack of understanding creates suspicion, blame, finger-pointing and fear. Being vulnerable, especially at work, has been taboo for so long and getting teams to buy into the notion that it truly is OK to be human and to not have all the answers takes practice.

It also demands that people in leadership positions practice what they preach. Only when leaders begin to openly admit when they’re wrong, ask staff for help and project humility, will staff risk exhibiting the same level of honesty and vulnerability.

My Proposition: Encourage Kindness

Several months ago, to foster such an atmosphere, our department began to champion kindness. We started celebrating employees who went out of their way to be kind to others. As the head of the department, I encouraged our team to give one another the benefit of the doubt when they felt they had been slighted or when they were irritated by the actions of a peer. We also started openly talking about the power of vulnerability in the workplace and how acceptance of it can draw us closer. While these efforts have not induced radical change, they have inspired improvements.

I sincerely believe that creating an atmosphere of trust and support is a critical precursor to facilitating candid, clear, honest communication. Only when these elements are firmly in place will people be able to engage in hard-to-have conversations that create pathways to mutual understanding.


*A version of this article provided by Operation Smile originally appeared here. Operation Smile has provided hundreds of thousands of safe surgeries for those born with cleft lip and cleft palate. With more than three decades of expertise, Operation Smile creates solutions that deliver free surgery to people where it’s needed most. Learn more at operationsmile.org.

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Kendra E. Davenport

Kendra E. Davenport is chief development officer for Operation Smile, where she manages global development strategy, brand, marketing and public relations. She previously served as president of the Children of Fallen Patriots Foundation and vice president of institutional advancement and external affairs at Africare. Kendra has also supported development at Project HOPE, the Population Reference Bureau, International SeaKeepers Society, First Candle and the SIDS Alliance, and Morgan Memorial Goodwill Industries. She earned a Bachelor of Arts in English and Communications from Chestnut Hill College and is currently working toward an Executive Master of Policy Leadership from Georgetown University McCourt School of Public Policy. Additionally, she is CFRE International certified as a fundraising executive and volunteers her skills and expertise to assist the Loudoun County government, Leadership Roundtable and Georgetown University.

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