6 ways to prepare for a difficult conversation with a direct report

IT leaders face many challenging tasks, but few are more daunting than engaging with a direct report who has, in one way or another, become unreliable or neglectful.

There are various reasons why a manager or executive may need to have a frank conversation with a direct report, says Orla Daly, CIO at training services provider Skillsoft. “Fundamentally, it boils down to whether the individual is meeting performance expectations and contributing positively to the team and broader culture,” she explains.

The success of such a conversation largely depends on the leader’s ability to understand different perspectives, ability to communicate clearly, and observe for cues for how the message is landing.

Are you prepared to handle a conversation with a failing report? Here are six ways to make a challenging discussion less painful and more effective.

1. Keep an open mind

It’s important to approach the discussion equipped with facts and an open mind, Daly says. Before going into the conversation, create a rounded-out view of the situation from multiple perspectives, she advises. “Having examples of behavior or missed expectations can also help bring context to the individual, so it’s important to think about these things before going into the discussion.”

A conversation’s success depends on the leader’s ability to understand different perspectives, communicate clearly, and observe the subject for cues on how the message is landing. Power skills, such as empathy and emotional intelligence, are essential for any modern leader and can be the difference between a successful and unsuccessful interaction, Daly says. These skills can’t be developed overnight; instead they need to be studied and practiced frequently.

Daly notes that Skillsoft recently developed a generative AI–powered coach — CAISY — to help leaders develop interpersonal skills and practice in a safe environment that offers personalized feedback after each simulation. One scenario requires employees to deliver constructive feedback to an underperforming team member.

“During the simulation, the learner is presented with different strategies to effectively manage a challenging situation with empathy, patience, and a proactive, solution-oriented approach,” Daly says.

2. Approach with a servant leadership mindset

Prepare for your discussion by having clear examples of the behaviors or performance that needs to be addressed, advises Ola Chowning, a partner at technology research and advisory firm ISG. Obtain as much objective information as possible in the form of metrics, KPIs, and personal observations.

“It may also be beneficial to chat informally with members of the leader’s team, or their peers, under the guise of a quick general catch-up,” prior to your meeting, she adds.

Behavior issues are often best approached in a servant leadership manner, Chowning says. “Ask if there are external factors that may be impacting the direct report’s focus, attention, or mental health.” Performance issues are typically more factual, but a servant leadership approach may also be appropriate if the questions are related to internal factors or constraints that are hindering performance. “From there, the conversation can flow to results, examples, expected changes and consequences.”

3. Consider the subject’s perspective

Prepare for the conversation by reviewing the discussion’s objectives and understanding the individual’s perspective, says David Pumphrey, CEO at healthcare software and IT advisory firm Riveraxe. He suggests both active listening and asking open-ended questions.

Provide constructive guidance when required. “When one leader struggled with streamlining processes, I suggested starting small by automating appointment scheduling, then build from there,” Pumphrey says. “My advice and experience helped get the leader back on track.”

When additional support appears necessary, Pumphrey recommends turning to further steps, such as coaching or training. “I once brought in a consultant to help a leader strengthen communication skills,” he recalls.

If all else fails, consider reassigning the individual to another position, one that more closely matches their talents and abilities. But this should be employed as a last resort, Pumphrey warns. “With support, many leaders improve, but sometimes a change becomes necessary for team and business success,” he explains. “I aim for leaders to get back on track before a leadership change.”

Still, the team and objectives must always come first. The conversation’s goal should be to provide the direct report with opportunities and resources for improvement, but also to make difficult decisions when required. “Strong leadership and communication are the key.”

4. Set clear objectives

Before scheduling a formal discussion, meet with the leader informally to set the meeting’s specific objectives, suggests Jean Magny, president and CIO at Genius Solutions, a manufacturing operations ERP provider.

As the meeting opens, focus on listening to gain full context and understand the direct report’s perspective, Magny advises. “Ask open-ended questions to make sure you have a complete picture before providing guidance,” he says. “If you identify issues that need to be addressed, be direct yet constructive with specific examples and suggestions for improvement.”

If further action is needed after the initial discussion, determine the appropriate next steps, which could include coaching, training, or changes in responsibilities. As a last resort, bring in HR or reassign the team leader if you lose confidence in their ability, Magny says.

“With open communication and support, many issues can be resolved to get the team functioning well again,” he says. “But in some cases, a leadership change becomes necessary for the good of the team and the success of the project or business objectives.”

5. Prepare yourself mentally

It’s important to ensure that you’re mentally prepared for the conversation, says Matthew Franzyshen, business development manager at IT services company Ascendant Technologies. “You want to be in a headspace where you can approach the conversation with objectivity so you can focus on facts and maintain a professional demeanor,” he says.

“Before calling the individual into your office, make sure you have a plan in place for how you would approach the conversation in a way that remains civil, professional, and collaborative,” Franzyshen advises. Focus on the conversation’s goal. “Do you want to change their behavior, are you looking for an explanation for the issues faced, or a combination of both?” It’s important to know your goal before beginning the conversation.

6. Don’t rush to judgment

Listen without judging to fully grasp the direct report’s perspective, recommends Dieter Hsiao, CEO at digital consulting agency DIVISA. “Ask probing questions to determine the root causes of underperformance and provide specific, constructive feedback and recommendations.”

If challenges persist despite engagement and support, the individual’s role may need to be reevaluated. “Changing leadership can be hugely disruptive, so I make every effort to provide opportunities and resources for improvement before taking that step,” Hsiao says. “Open communication and a collaborative approach are key to resolving most issues, but the success of the team and business objectives must come first.”

Involving other parties should only become necessary if the direct report could benefit from additional coaching, training, or independent mediation. “The goal is to address issues as transparently and supportively as possible to get performance and dynamics back on track,” Hsiao says.