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It’s wishful thinking to imagine difficult conversations will never arise in the workplace. As inevitable as it is uncomfortable, you’ll likely have to initiate a challenging conversation with a colleague sooner or later. Whether dealing with differing opinions, navigating sensitive topics, or addressing conflict, finding the right way to approach this tough task will help you improve the likelihood of a successful outcome.

When Are Challenging Conversations Necessary?

As much as you may try to avoid getting stuck in a difficult conversation, many issues within the workplace will not dissipate if they’re not addressed. Still, simply ignoring the problem at hand is the way that 53% of employees choose to handle a “toxic” situation. Only 24% of employees would choose to address the situation directly. Avoiding a challenging conversation can prolong the problem, lower team morale, and hurt business productivity.

For context, let’s imagine a scenario warranting a difficult workplace conversation. You and a colleague may share responsibilities–whether that’s managing client communication, handling administrative tasks, or producing certain deliverables–but you find them delegating tasks to you. Maybe they’ve started to hand off client onboarding, report generation, or other tasks they also should be managing. As your workload increases, finding the right way to discuss this imbalance with your colleague can help you remedy the situation and come to a mutually agreeable resolution. Without the right communication skills, you could be among the 49.7% of individuals who don’t report a positive outcome, such as increased stress levels, resentment towards your colleague, or lowered performance as you struggle to get all the tasks done.

Preparing For a Successful Conversation

Challenging conversations are difficult for a reason, but taking the time to prepare can help you effectively communicate your point of view without sounding accusatory or aggressive. Here are a few steps you can take to make the conversation productive and successful:

1. Determine Your Talking Points: Start by jotting down the key points you’re looking to communicate with your colleague. This can help guide the conversation, but remember, you don’t need to prepare a script. While you can try to predict what your colleague might say, the real-life conversation may not go as planned. Instead, approach the conversation with a flexible mindset and have a variety of potential responses ready to go. This will help you maintain a forward momentum throughout the discussion.
2. Focus On The Facts: Many workplace issues can stir negative feelings and strong emotions. While you want to convey to your colleague how the issue is affecting you, you’ll also want to focus on the facts of the situation. By focusing on the facts, you can help to separate what might be assumptions from the truth. Armed with facts, this can help you support your argument and avoid making the matter too personal.
3. Seek Understanding Over Agreement: When dealing with some challenging situations, it can be difficult to see eye-to-eye. Many workplace conflicts stem from misunderstandings, so establishing a mutual understanding between two individuals can ensure you’re not missing out on vital information. During the conversation, ensure your colleague feels heard and has the chance to express their perspective as well.
4. Work Together to Find a Solution: These conversations are not about who’s right and who’s wrong. If your conversation has been successful and productive, it should result in actionable steps you and your colleague can take together to resolve the issue. You can also seek to agree on a timeframe for a follow-up meeting to revisit the situation and ensure everyone is on the same page.

Difficult Conversations Pay Off

Even with the best preparation, tough conversations will never be fun. Still, they can have a significant, positive impact on colleagues and the larger organization. These benefits can include:

● Strengthening workplace relationships and fostering an environment of trust
● Clearing up misunderstandings or misconceptions
● Reducing workplace stress by de-escalating issues
● Improving productivity and collaboration by removing roadblocks
● Enhancing communication skills

Thus, individuals within an organization need to identify when there is an opportunity for them to address issues with a challenging conversation. Not only will they be able to seek a better outcome for themselves, but these colleagues can also drive valuable change within the organization.

For leaders who are unsure where to start tackling their team’s issues, Connect the Dots can help teams develop new tools to engage and be productive with their teammates.

Contact us to learn more about our team development and performance solutions.

As leaders continue to navigate an organizational landscape of virtual, hybrid, and in-person work, they need new competencies to foster connection of their teams and employees.

Employees who feel undervalued or disconnected have been leaving organizations far more frequently in the past two years, and it is up to leaders to reverse this trend. In April 2022, we sat down with CHROs to discuss these ongoing challenges and best practices to address them. Following is a summary of our discussion.

Discussion Points

• Leaders are focused on how to protect their culture when everyone is working in different places, as well as how to evolve their culture to meet the current state.
• The philosophy of the leadership team is a key driver of the decision to use a virtual, hybrid, or all-in approach. Participant CHRO organizations were in very different places with regard to “return to office” following the pandemic.
• Leaders may be in denial that employees are feeling disconnected. If productivity remains high despite higher-than-average turnover, leaders may not see the link between connectivity and turnover.

• Some employees are very interested in in-person work, while others expressed dissatisfaction about returning to the office.
• Employees want more empathy from their managers—not just asking about their weekends, but truly showing they care for employees at a deeper level. In particular, Gen Z employees’ workplace satisfaction depends on feeling valued and heard.
• Many leaders need additional development in their situational leadership ability.

• Regular listening groups or informal Q&A sessions make a big difference in employee engagement.
• Feedback surveys are especially fruitful when they are followed-up by discussing the results with employees, identifying action items, and the leaders being transparent about the changes made.
• Work teams also benefit from weekly wrap-up meetings to share accomplishments, feedback, recognition, etc. in a more casual and informal format

Need additional support?

As your leaders continue to stretch themselves to navigate new and challenging dynamics, coaching support can help them do so more effectively. CTD’s on-target® and quickconnect® coaching models give you the flexibility to invest in targeted coaching at any level.  Effective onboarding is another tool for organizations who want to differentiate themselves as an employer. Check out our solutions for leadership and all-employee onboarding that provide a branded, customized experience for your new hires. We welcome the opportunity to talk with you about your specific leadership development needs and a custom solution. 

George Bernard Shaw said it best in his quotation about communication: “The biggest problem in communication is the illusion that it has taken place.”

The numbers are sobering:

• 86% of senior executives, managers and junior staff at U.S. companies who report experiencing communication breakdowns that lead to reduced productivity, missed deadlines, and sales deals that don’t close, according to research from The Economist Intelligence Unit.
• 63% of U.S. employees in 2019 who have wanted to quit their jobs because ineffective communication has gotten in the way of doing their work, almost double from 2018 (33 percent), according to a Dynamic Signal study.

So, what can organization and individual leaders do to address these significant gaps?

Communicate clearly and often to reduce the opportunities for frustration, disengagement, and performance challenges.

As we continue to adjust to our new work environments, employees are looking to their leaders for clarity even more than usual.  Although leaders do not have all of the answers and are dealing with their own questions, establishing a regular cadence for communicating priorities and expectations and providing feedback is important.  And, because most of our communication will be done virtually, by phone and email, taking the time to be deliberately clear is critical.

Establish (or re-establish) a regular meeting cadence with your team and each individual

• Continue staff and one-on-one meetings.
• Send meeting agendas, keeping the scope tight and relevant.
• Establish expectations for participation.
• Include time to recognize team members’ well-being
• Ask your team for feedback on the cadence – what’s working? What could be better?

Make yourself available to your team

• Let your team know the best ways to communicate with you during this time.
• Reinforce and “apply” organizational communication and policies to increase understanding and compliance.
• Appropriately share how you are feeling about and managing the situation.

Be aware of assumptions: They will throw you off track every time!

• Be specific about your expectations: “As soon as possible” may mean tomorrow to you, and next week to your team member.
• Keep the basic communication model in mind: As information is exchanged between the sender and receiver, there may be a disconnect between what is intended and what is understood—particularly when you are using a different medium than usual (e.g., email vs. face-to-face).

By not underestimating the power and impact of simple, clear and consistent communication, leaders and organizations will see the payback both immediately and over time.  Regardless of the economic picture, market landscape or political environment, effective communication is a foundational component of a healthy and thriving organization.