6 Secrets to Taming the Toughest Work Conversations Revealed by Top Tech Execs

As an IT leader, having those tough conversations with team members who might be slacking or failing to meet expectations can be extremely challenging. Whether it's about underperformance, lack of commitment, or behavior issues that affect the entire team, addressing these problems head-on is crucial for the success and well-being of your team.

Fortunately, some of the top tech executives have shared their expertise and insights on how to make these difficult conversations less painful and more productive. According to Orla Daly, CIO at Skillsoft, it all comes down to whether the individual is meeting performance expectations and contributing positively to the team and the broader culture. Daly highlights that to have a successful conversation, it's essential to approach the discussion with an open mind, be equipped with facts, and have examples of behavior or missed expectations to provide context.

Approaching the conversation with empathy and emotional intelligence is equally vital. These power skills can't be developed overnight, and practicing them frequently can make a significant difference in the success of the conversation. To help leaders develop these skills, Skillsoft recently developed a generative AI-powered coach called CAISY, which provides a safe environment for leaders to practice and receive personalized feedback after each simulation.

When preparing for a conversation with an underperforming team member, Ola Chowning, a partner at ISG, recommends gathering as much objective information as possible, including metrics, KPIs, and personal observations. Chowning suggests that behavior issues are often best approached in a servant leadership manner, focusing on external factors that might be impacting the direct report's focus, attention, or mental health. This approach helps to identify the root cause of the problem and address it effectively.

David Pumphrey, CEO at Riveraxe, emphasizes the importance of considering the subject's perspective and understanding their goals and aspirations. By providing constructive guidance and support, leaders can help team members overcome challenges and improve their performance. Pumphrey suggests that active listening and open-ended questions are essential for a productive conversation and that additional support, such as coaching or training, might be necessary to help the team member get back on track.

Setting clear objectives is also crucial when preparing for a conversation with a direct report. Jean Magny, President and CIO at Genius Solutions, recommends meeting with the leader informally to set the meeting's specific objectives before scheduling a formal discussion. This approach helps to ensure that the conversation stays focused and productive, and that the team leader understands what is expected of them.

Matthew Franzyshen, Business Development Manager at Ascendant Technologies, stresses the importance of being mentally prepared for the conversation. This involves being in the right headspace, being objective, and maintaining a professional demeanor throughout the conversation. Franzyshen suggests that having a plan in place for how to approach the conversation is crucial, including knowing what you want to achieve from the discussion.

Lastly, Dieter Hsiao, CEO at DIVISA, recommends listening without judgment to fully grasp the direct report's perspective. By asking probing questions, leaders can determine the root causes of underperformance and provide specific, constructive feedback and recommendations. Hsiao emphasizes that the goal of the conversation should be to address issues as transparently and supportively as possible and to get performance and dynamics back on track.

While having difficult conversations with team members can be challenging, it's essential to approach these conversations with an open mind, empathy, and a clear understanding of what you want to achieve. By following these tips and insights from top tech executives, you can make these conversations less painful and more productive, ultimately leading to a more successful and harmonious team.