Exploring the art of communication within teams can be daunting, but this article breaks down real-life strategies for navigating difficult conversations about team performance. It provides actionable insights from seasoned experts, ensuring that each discussion is an opportunity for growth and clarity. With a focus on practical advice, the piece transforms complex challenges into manageable solutions.
- Scheduled Private Conversation During Software Transition
- Addressed Feedback Resistance With Growth Focus
- Set Clear Expectations For Over-Reliance Issue
- Delegated Tasks To Improve Project Management
- Implemented Task-Prioritization System For Efficiency
- Focused On Coaching To Improve Deal Closures
- Supportive Conversation To Address Subpar Work
- Balanced Accountability And Empathy For Improvement
- Used Open Communication And Empathy
- Curiosity Led To Solutions For Missed Deadlines
- Encouraged Feedback As Collaboration
- Balanced Honesty And Support For Inconsistent Work
- Opened Honest Dialogue About Workload
- Empathy And Clarity Improved Missed Deadlines
- Encouraged Data-Driven Insights Over Intuition
- Curiosity And Restructuring Addressed Burnout
Scheduled Private Conversation During Software Transition
During a company-wide software transition, I encountered a team member who strongly resisted adapting to the new system, which began to slow down progress and affect the team’s overall productivity. Recognizing the urgency of the situation, I scheduled a private conversation with them, ensuring the environment was open and non-confrontational. I started by acknowledging their frustration and giving them space to share their concerns, which I listened to attentively without interrupting. They expressed confusion, discomfort with the unfamiliar interface, and anxiety about their ability to keep up with the changes. I validated their feelings, assuring them that their concerns were both understandable and important, but I also addressed the broader impact their resistance was having on the team’s workflow and project deadlines. I made it clear that their contributions were valuable but that their adaptation was critical to the team’s success.
Rather than simply insisting on compliance, I shifted the conversation toward solutions. I asked them directly what type of support would help them feel more comfortable with the new system. Together, we agreed to arrange additional, personalized training sessions to address their challenges and boost their confidence. To further empower them, I offered them the opportunity to serve as a peer mentor once they gained proficiency, which not only provided a leadership opportunity but also reframed their role in the transition from a participant to an influencer. Over time, they became more confident and proactive, and their perspective shifted from resistance to engagement. The outcome was a smoother transition for the entire team and a more motivated, invested team member, reinforcing my belief that involving people in solutions fosters ownership and accelerates change.
Sean Smith
CEO & Ex Head of HR, Alpas Wellness
Addressed Feedback Resistance With Growth Focus
A skilled team member, known for their expertise, frequently dismissed feedback from peers and supervisors, creating friction within the team. Despite their strong performance, their unwillingness to accept constructive criticism was hindering collaboration and slowing progress on projects. Recognizing the impact this behavior had on team morale and productivity, I decided to address the issue directly but with a focus on growth rather than criticism. I scheduled a private meeting and began the conversation by acknowledging their strengths and contributions to the team. I emphasized that my intention was not to criticize their abilities but to help them reach their full potential as a leader and contributor.
Next, I provided specific examples of instances where their approach had fallen short, illustrating how their resistance to feedback had caused delays and misunderstandings within the team. I avoided making the conversation personal and instead framed it around the impact on team dynamics and outcomes. To encourage self-reflection, I asked them how they thought incorporating feedback could improve their leadership skills and contribute to overall team success. I also shared my own experiences with receiving feedback and how it had shaped my professional growth, modeling vulnerability and a growth mindset.
The conversation was initially met with defensiveness, but by remaining calm, patient, and solution-oriented, I gradually broke through their resistance. We agreed on a plan for implementing feedback more proactively, including regular check-ins to review progress. Over time, I observed a notable shift in their behavior; they became more receptive during team discussions and began soliciting input from peers. Team collaboration and morale improved, and they ultimately emerged as a more respected and well-rounded leader. This experience reinforced that feedback is most effective when framed as a tool for professional development and growth, not correction or judgment.
Joshua Zeises
CEO & CMO, Paramount Wellness Retreat
Set Clear Expectations For Over-Reliance Issue
I had a team member who frequently relied on others to complete their share of the workload, which was causing strain within the group and leading to frustration among their peers. I knew this would be a difficult conversation, but I approached it with the mindset that constructive feedback paired with clear expectations could lead to growth. I began the conversation by acknowledging their contributions, making sure they felt valued for what they were doing well. This helped set a positive, non-confrontational tone and ensured they understood my feedback came from a place of support rather than criticism.
Next, I transitioned into discussing the issue directly, highlighting specific instances where their over-reliance on teammates had disrupted workflow and added pressure on others. Rather than placing blame, I focused on the impact their behavior had on team dynamics and overall productivity, ensuring they could see the larger picture. I asked for their perspective, giving them space to share any challenges they were facing that might be contributing to the behavior. This opened the door for an honest dialogue, and they admitted feeling uncertain about certain tasks, which led them to delegate more than was appropriate.
From there, we identified specific tasks where they could take full ownership, breaking them into manageable steps to help build their confidence. To ensure accountability, we set clear boundaries for collaboration and agreed on regular check-ins to track progress and address any challenges. Over time, they rose to the challenge, improving their skills, becoming more independent, and contributing more effectively to team projects. This experience reinforced how clarity, accountability, and goal-setting are crucial when addressing underperformance, and it strengthened my belief that difficult conversations, when handled with empathy and directness, lead to meaningful growth.
Maddy Nahigyan
Chief Operating Officer, Ocean Recovery
Delegated Tasks To Improve Project Management
As an executive recruiter, one of the most memorable coaching conversations I had was with a senior project manager who consistently missed client deadlines. What made this situation particularly challenging was that she was highly skilled technically and well-liked by her team.
I scheduled a private meeting and started by sharing specific examples—three major projects that had fallen behind schedule in the past quarter. Instead of immediately offering solutions, I asked her to walk me through her project management process. This approach helped us identify that she was taking on too many tasks herself instead of delegating to her team members.
The conversation wasn’t easy. There were moments of silence and some defensive responses, but we kept the discussion focused on specific behaviors and their impact on team results. Together, we created a simple action plan: she would delegate at least 30% of her current tasks, hold weekly check-ins with team leads, and use project management software to track deadlines more effectively.
Three months later, her team completed two major projects ahead of schedule. The key lesson we learned was that performance issues often stem from fixable problems rather than lack of skill or effort. By approaching the conversation with curiosity instead of judgment, we turned a potential conflict into an opportunity for growth.
Julia Yurchak
Talent Sourcing, Acquisition & Management Specialist| Senior Recruitment Consultant, Keller Executive Search
Implemented Task-Prioritization System For Efficiency
An account executive struggled with managing multiple clients, leading to missed deadlines. I framed the discussion around efficiency, not personal failure, to keep morale high. We implemented a new task-prioritization system that simplified their workflow. Within a month, they became one of our most organized team members.
I used positive reinforcement alongside constructive criticism. Acknowledging what they did well before addressing weaknesses kept them engaged. They took feedback seriously without feeling demotivated. Now, they consistently deliver results with precision and confidence.
Jason Hennessey
CEO, Hennessey Digital
Focused On Coaching To Improve Deal Closures
I once had a direct but supportive conversation with a loan officer who was struggling to close deals and meet production goals. Their confidence was slipping, and it was starting to affect both their motivation and the team’s overall goals.
Instead of making it purely about performance metrics, I took a coaching approach and focused on understanding what was holding them back. Through our conversations, it became clear that ineffective lead follow-up was the biggest challenge. The loan officer was not using our CRM tools to their full potential, which meant opportunities were slipping through the cracks.
Together, we developed an action plan that included weekly check-ins and additional training. I also connected them with one of our more experienced loan officers who helped mentor and teach them. This allowed the loan officer to learn and watch in real-time what other loan officers were doing and what was making them successful.
Over time, the loan officer who was struggling became much more productive and gained lots of confidence in handling leads efficiently. This experience reinforced how important it is to coach, not just critique. When struggling employees get the right support, they are far more likely to turn things around!
Jay Sobo
President / CEO, Liberty Financing LLC
Supportive Conversation To Address Subpar Work
I’ve had some tough discussions around performance with a few of my team members, and from this, I know that how it is approached makes a difference. I previously had a team member whose work was subpar. Instead of heading toward feedback, I thought deeply about what my ideal outcome was. What had changed? What barriers were in their path, and how could I assist? When we finally met, I made sure to keep the tone supportive and calm.
I began the conversation by mentioning the strengths in their work and how well they were doing. As was stated earlier, this is crucial so that the meeting is not one-sided. I then proceeded to the deficit side where I pinpointed their challenges, providing several examples to mitigate the chances of misinterpretation. I was careful to make it feel like constructive criticism, rather than aggression. The major change was in how I attended to their version of the truth. I had some ideas to discuss with them, but one of the more prevalent issues was external to their performance. We also set specific goals to ensure that there was high clarity on expectations going forward.
Ultimately, the dialogue was not limited to articulating criticism but also attempting to comprehend one another and collaboratively restore some order. During the ensuing months, there was tangible effort put forth, and I think that it is safe to say that we both felt as if we were part of the same group. Although difficult talks like this one can often feel uncomfortable, empathy and a sincere will to assist in any way can result in impressive outcomes.
Nathan Barz
Financial Advisor, Management Expert, Founder and CEO, DocVA
Balanced Accountability And Empathy For Improvement
Difficult conversations define leadership. A senior team member, known for strong performance, started slipping on deadlines. Instead of leading with criticism, the approach was simple: “I’ve noticed a change—what’s going on?” That opened space for honesty. Personal struggles were affecting focus, and rather than just pushing for improvement, the conversation turned to solutions—adjusting workloads and offering support. Within weeks, performance bounced back. More importantly, it reinforced a key leadership lesson: accountability and empathy aren’t opposites. The best outcomes come from balancing direct feedback with genuine understanding.
Anupa Rongala
CEO, Invensis Technologies
Used Open Communication And Empathy
When I had to address a team member’s underperformance, I focused on open communication and empathy. I started by scheduling a private meeting to discuss their performance, ensuring they felt heard and understood. I used a solution-oriented approach by identifying specific areas for improvement and offering support through mentorship and additional resources. This method helped build trust and clarity, resulting in noticeable performance improvements and stronger team collaboration. Clear communication and empathy are key to navigating tough conversations effectively.
Sahil Sachdeva
CEO & Founder, Level Up PR
Curiosity Led To Solutions For Missed Deadlines
A senior team member, once a top performer, started missing deadlines and delivering inconsistent work. Instead of assuming the worst, the conversation began with curiosity: “I’ve noticed some shifts in performance—what’s on your plate right now?”
This opened up an honest dialogue. It turned out they were struggling with prioritization amid shifting project demands. Rather than prescribing a fix, the discussion focused on shared accountability—refining workflows, setting clearer milestones, and introducing periodic check-ins.
The result? Performance rebounded, but more importantly, it reinforced a culture where challenges are addressed through collaboration, not confrontation. The real lesson? Tough conversations are not about correction but about alignment and growth.
Arvind Rongala
CEO, Edstellar
Encouraged Feedback As Collaboration
One of the toughest conversations I’ve ever had was with a very talented team member who consistently missed deadlines and got into fights with other team members. The work was great, but the delays and drama were presenting real problems for the team.
I appeared curious, instead of appearing as a critic. I wanted to understand what was going on, what was challenging, and how we could improve it together. As it turned out, they were feeling overwhelmed—not by the work itself, but because they were too perfectionistic and struggling with team drama.
We tackled it two ways: prioritize decisively, shift the focus from “perfect” to “done,” and open the lines of communication to solve team tension before it was an issue. I encouraged them to see feedback as collaboration, not confrontation, and regular check-ins kept things on track.
The result? Not only did they better meet deadlines, but they also became a bridge between teams rather than a point of contention. Hard conversations don’t have to be about calling someone out—they should be about calling them up. When people feel heard, they’re much more open to changing—and that’s how you build a better team.
Vasilii Kiselev
CEO & Co-Founder, Legacy Online School
Balanced Honesty And Support For Inconsistent Work
A team member’s work had been inconsistent, which directly impacted client satisfaction and began to strain our professional reputation. Recognizing the urgency of the situation, I approached the conversation with a balance of honesty, clarity, and support, aiming to address the issue constructively without discouraging them. I began the discussion by acknowledging their strengths and past contributions, reinforcing my belief in their potential. From there, I provided clear, specific feedback, using concrete examples of where their work had fallen short and detailing the impact it had on the client relationship. I was careful to focus on behaviors and outcomes rather than personal attributes, ensuring the conversation felt solution-oriented rather than critical.
After presenting the feedback, I encouraged them to share their perspective, giving them space to express any challenges or obstacles they were facing. Through this dialogue, I discovered that they were struggling with time management and lacked certain technical skills required for the project. Instead of dwelling on the issues, I shifted the focus to solutions, offering resources for improvement, such as additional training materials and access to a mentor. Together, we developed a Performance Improvement Plan (PIP) that included specific, measurable goals, clear deadlines, and regular check-ins to monitor their progress.
Over the next several weeks, I maintained an active support role, providing consistent feedback during follow-up meetings and celebrating small improvements to maintain their motivation. Gradually, their work quality improved, and they successfully rebuilt the client’s trust through more consistent and accurate deliverables. The situation reinforced the importance of clarity, constructive feedback, and ongoing support in performance coaching. It also reminded me that effective leadership means balancing accountability with empathy, and that addressing performance issues directly, while equipping team members with the tools they need to improve, leads to both individual and organizational growth.
Darryl Stevens
CEO, Digitech Web Design
Opened Honest Dialogue About Workload
We once had a senior developer struggling with deadlines and making repeated mistakes in code reviews. Instead of jumping straight into performance issues, we started with a simple question: “How do you feel about your workload?” That opened the door for an honest conversation.
He admitted feeling overwhelmed by too many complex tasks, unclear priorities, and mounting pressure. Instead of just pointing out mistakes, we worked with him to break projects into smaller, more manageable pieces. We also set up quick daily check-ins to catch problems early.
The result? His performance improved, and he felt more in control of his work. More importantly, he appreciated that the conversation wasn’t about blaming him but about finding solutions together. Difficult conversations don’t have to be confrontational. When we listen first and focus on fixing the problem, not just pointing it out, it builds trust and drives real improvement.
Vikrant Bhalodia
Head of Marketing & People Ops, WeblineIndia
Empathy And Clarity Improved Missed Deadlines
I had a difficult conversation with a team member a few months ago regarding their performance. They had been consistently missing deadlines, which was affecting the overall project timeline. I knew I needed to address it, but I wanted to approach it with empathy and clarity rather than making them feel attacked.
I scheduled a one-on-one meeting in a private setting, where I first acknowledged their strengths and the positive contributions they had made. Then, I addressed the specific performance issues by focusing on the impact it had on the team and the project. I made sure to listen to their side and tried to understand if there were any underlying issues contributing to their struggles.
The conversation ended up being productive—my team member shared that they were overwhelmed with personal matters and struggling with time management. We worked together to set clearer expectations and develop a plan to help them get back on track, including offering support through time management tools.
As a result, their performance improved significantly, and they appreciated the opportunity to discuss the challenges they were facing openly. This experience reinforced the importance of having honest, constructive conversations with a focus on finding solutions rather than just pointing out problems.
Nikita Sherbina
Co-Founder & CEO, AIScreen
Encouraged Data-Driven Insights Over Intuition
A senior strategist resisted using data-driven insights, relying too much on intuition. I showed them campaign reports where data-backed decisions outperformed guesswork. Instead of demanding change, I encouraged experimentation to let results speak for themselves. This shift in mindset helped them embrace data for strategic decisions. I made the conversation future-focused instead of dwelling on past mistakes. Shifting the focus to opportunities for growth made them receptive. They committed to a new learning path that strengthened their skill set. Today, they proactively bring fresh insights to the team.
Marc Bishop
Director, Wytlabs
Curiosity And Restructuring Addressed Burnout
When a team member isn’t meeting expectations, addressing it with clarity, respect, and a solutions-driven mindset is critical. One instance that stands out was when a senior team member, who had been with us for years, started missing deadlines and delivering subpar work. This wasn’t just affecting internal workflows—it was impacting client projects, which we can’t afford in PR.
Rather than immediately taking a corrective stance, I first approached the conversation with curiosity. I scheduled a private one-on-one and opened by acknowledging their previous strengths: “You’ve always been a reliable and creative force on our team, so I want to check in because I’ve noticed a shift.” From there, I asked open-ended questions to understand if something external was affecting their performance.
They were struggling with burnout and unclear expectations on shifting priorities. Together, we restructured their role to match their strengths while ensuring accountability. The result? They regained confidence, improved their performance, and re-engaged with our team culture. Instead of creating conflict, the conversation strengthened both trust and productivity.
Kristin Marquet
Founder & Creative Director, Marquet Media
