How to Have Difficult Conversations With Employees (and Why It Matters)

An inevitable part of leadership is addressing concerns with employees as they arise. Learning how to have difficult conversations with employees is a valuable skill that benefits everyone in the organization. So, what makes some conversations at work so challenging? 

“Difficult conversations tend to be any interaction where the individual we’re speaking to may have a strong emotional reaction,” says Tori Rochlen, Director of Learning Success & Enablement at SkillCycle. 

As tough as it is to conduct these conversations, “leaders cannot fix problems that we can’t even talk about,” says Gartner. Yet many managers aren’t sure how to give employee feedback in a way that feels meaningful or will inspire change. 

Some have never learned how to provide negative feedback to employees without souring the working relationship with that individual, making these interactions especially fraught. 

In this article on how to have difficult conversations with employees, we’ll explore:

• Why employers often avoid tough conversations
• How to have difficult conversations with employees
• A 3-step difficult conversation framework you can follow
• The consequences of avoiding difficult conversations
• How to nurture a culture of open communication and feedback

 

Why Employers Often Avoid Tough Conversations

Difficult conversation examples include unsatisfactory performance, upcoming changes in job function, or interpersonal issues. 

They can take almost any form, which is part of what makes them so challenging. There’s no way to rehearse precisely how each type of conversation might go in advance because every employee and situation is different.

“These conversations could be about performance, forthcoming changes, or other challenging topics,” says Rochlen. “The lack of practice in navigating a heightened emotional response can make a manager fearful about having these discussions.”

Yet, as much as employers may feel tempted to sidestep uncomfortable exchanges, learning to provide feedback appears necessary for success. 

Well-developed skills in coaching and giving feedback are common in companies that are getting performance management right. Over 70% of participants who felt their companies deliver effective performance management systems also indicated that their management team was trained in coaching and giving feedback, according to McKinsey. 

The ability to effectively deliver feedback and communicate with employees is vital, while coaching supports employees in building skills and performing to their highest capacity. 

The Consequences of Avoiding Difficult Conversations

Dragging your heels on tough conversations can eat away at relationships between team members, driving down their ability to work together. 

“We cannot assume issues will disappear if left unaddressed,” says Rochlen. “Problems escalate, which impacts employee engagement and performance.”

Ignoring problems can create disastrous consequences that can affect how effectively a company can operate. For example, if one employee engages in behavior that negatively impacts the company and nobody mentions it, other employees may assume that behavior is condoned and adopt it themselves. 

In these situations, avoiding one conversation might create multiple friction points or poor performance in your company. Left unchecked, you may find these issues shifting the culture of your organization.

When to Have a Difficult Conversation With an Employee

Timing is everything. You can master every framework on how to have difficult conversations with employees, yet if you pick the wrong moment, the message won’t land. Use the checkpoints below to decide when a talk is due, and when a quick pulse check might suffice.

Six signals it’s time to speak up

1. Performance dips without explanation
   If an employee’s work quality drops, deadlines get missed, or customers start complaining, it’s time to have a tough talk before those bad habits stick.
2. Repeat behavior after prior feedback
   You coached once, maybe twice, but the issue keeps resurfacing. This is the classic setup for a tough conversation with employees that escalates from reminder to plan of action.
3. Team morale takes a hit
   Tension, gossip, or visible frustration on Slack often points to an unresolved issue. Addressing the root cause quickly shows you know how to start a difficult conversation with an employee and safeguard team culture.
4. Values misalignment becomes public
   Look, when someone’s actions clash with company values, like honesty or inclusion, waiting to step in sends the wrong message. Having a tough talk right away protects the brand and shows everyone what we stand for.
5. Safety or compliance is at stake
   Any breach in procedure, from data privacy to on-site hazards, calls for an immediate, clear conversation. This is one of those hard conversations with employees that cannot wait for next week’s one-on-one.
6. Career development stalls
   If someone’s growth has plateaued, a candid check-in keeps ambition alive and prevents disengagement down the line, proof that having difficult conversations with employees can be a gift, not a punishment.

Balance Urgency With Readiness

• Prepare, then approach: Gather facts, examples, and potential solutions so the dialogue feels constructive.
• Choose a private, neutral space: Even a well-meant talk feels punitive if it’s public.
• Check emotional temperature: If either party is upset, schedule the meeting soon, but not in the heat of the moment.

When you nail the timing, the rest of the process, whether you use SBI, GROW, or another model, flows more naturally. Getting comfortable with having tough conversations with employees early keeps small sparks from becoming five-alarm fires and positions you as a coach, not a critic.

Common Signs That a Conversation Is Overdue

You can’t fix what you don’t address. Watch for these red flags that signal it’s time to start having difficult conversations with employees:

Signal	What You’ll Notice	Why It Matters
Persistent performance slips	Missed deadlines, lower quality, or rising error rates	Delays having tough conversations with employees may turn small gaps into chronic underperformance.
Repeat behavior after prior coaching	The same issue resurfaces within weeks	Shows your earlier feedback didn’t stick; it’s time for a deeper hard conversation with an employee.
Team tension or complaints	Colleagues vent to you or HR about one person’s conduct	Morale (and retention) crater when leaders sidestep conflict.
Misalignment with company values	Behavior contradicts stated culture pillars	The longer you wait, the weaker your cultural credibility.
Visible disengagement	Quiet-quitting signals: camera off, minimal input, tardiness	Addressing it early proves you know how to have a difficult conversation with an employee before they walk.

Balancing Timely Feedback With Emotional Readiness

Knowing when to have a difficult conversation with an employee means checking two clocks:

1. Issue clock — act quickly so details are fresh and stakes stay small.
2. Emotion clock — give both parties a beat to cool off, ensuring the talk is constructive, not combustible.

A good rule: schedule the meeting within 24–48 hours of the trigger event, but never in the heat of the moment. That timing keeps facts accurate while honoring psychological safety.

Why Early Conversations Prevent Bigger Problems

• Stops rumor mills: Fast, clear communication cuts off speculation.
• Reduces turnover costs: Employees who feel heard are 62 % less likely to search for new roles (LinkedIn Learning Report).
• Protects productivity: Addressing friction promptly keeps projects on pace.

In short, the sooner you lean into difficult conversations with employees, the less likely you’ll need crisis management later.

How to Have Difficult Conversations with Employees

Some managers are unsure how to give effective employee feedback, and especially worry about how to give negative feedback to an employee. 

However, putting off these kinds of conversations can have adverse effects on the entire company. A better approach encourages viewing these interactions as opening a dialogue rather than a one-way feedback channel. 

You can increase the effectiveness of a discussion by being aware of your emotions and choosing a time to talk that aligns with the seriousness of the conversation. Paying attention to these details can help you navigate the conversation confidently.

“Identifying your own emotions as you approach these conversations is important,” says Rochlen. “Being in a heightened state of emotion yourself is unlikely to help you illustrate impact in a way that is helpful to the employee.” 

Remember that modeling calm and consistent discussions can help influence communication throughout your company. With time, these conversations will become the norm instead of heightened or frustrating exchanges.

Try the 3-Step SBI Difficult Conversation Framework

One popular framework that can be helpful as managers learn how to have difficult conversations with employees is the SBI framework. It includes situation, behavior, and impact. 

“Giving feedback is a change management process, and people must desire change in order to shift behavior,” says Rochlen. “You can only inspire that by highlighting the impact of someone’s behavior.”

Let’s look at one difficult conversation example: Imagine you need to speak with an employee about using their mobile phone during a meeting. You could remind or scold the employee after the meeting, but they may not be motivated enough to change their future behavior. 

Instead, using the SBI framework, you’d describe your concerns using the following three steps:

1. Situation

Mention the specific time and situation where you noticed the behavior. “I’d like to speak with you about something I noticed during this morning’s meeting with our new client.”

2. Behavior

Outline the behavior you observed: “I saw you using your phone during the meeting and appearing distracted as we outlined the project timeline.”

3. Impact

Describe the impact the employee’s behavior has as objectively as possible. “I’m concerned you may not have all the information you need for this project we’re working on. Without it, you may not be able to be effective in your job, and that could affect the outcome.”

Expressing your concerns in statements that follow this framework helps keep the conversation clear and objective. It also allows you to outline what was observed and why you are bringing it to an employee’s attention. Then you can ask the employee to share their thoughts on the situation. 

“The impact is the most important piece of this framework,” says Rochlen. “It helps illustrate why the feedback is important for the employee to hear.”

 

What to Do After a Difficult Conversation

A tough talk isn’t finished when you leave the room. Closing the loop is what turns hard conversations with employees into real change. Here’s a simple after-care plan:

1. Summarize commitments in writing

Send a brief recap; what was discussed, the agreed-upon actions, and the follow-up date. This removes ambiguity and shows you know how to have a difficult conversation with an employee and translate it into next steps.

2. Provide resources

Whether it’s coaching sessions, an online course, or a mentor, make support concrete. Linking the conversation to visible help reinforces that you’re invested in their success.

3. Schedule a quick check-in

Within one to two weeks, hold a pulse meeting to review progress. Regular touchpoints keep momentum high and prove that having tough conversations with employees is part of an ongoing growth cycle.

4. Watch for ripple effects

Monitor team dynamics, project timelines, and customer feedback. Early detection of new challenges lets you intervene before small issues balloon.

5. Tie improvements to recognition

When you see positive change, highlight it publicly or privately, depending on the employee’s preference. Recognition closes the feedback loop and shows performance conversations feed directly into motivation, an idea we explore further in Managing Performance.

Below are five examples of difficult conversations with employees you might face, plus a quick script starter for each. Adapt the language to fit your culture and the individual:

Scenario	Why It’s Tough	Script Starter
Chronic lateness	Affects team scheduling and fairness	“I’ve noticed you were late three times this week. Can you walk me through what’s happening and how we can fix it together?”
Performance slump	Missed targets hurt results and morale	“Let’s review last month’s goals. Where do you feel blocked, and what resources would help you get back on track?”
Disrespectful behavior	Undermines psychological safety	“Yesterday’s meeting got heated. Your comment to Alex sounded dismissive. Can we talk about what led to that moment and how we can ensure respectful dialogue going forward?”
Request for promotion without readiness	High emotions around career growth	“I appreciate your ambition. Let’s map out the skills and results needed for the next level and set milestones over the next quarter.”
Policy violation (e.g., data security lapse)	Legal and reputational risk	“Our records show sensitive data was shared outside protocol. Let’s clarify the policy and outline steps to prevent this in the future.”

How to start a difficult conversation with an employee in each case follows the same pattern: describe the observable behavior, explain the impact, invite their perspective, and co-create a plan. Mastering that structure turns even the most tough conversations with employees into opportunities for better performance and stronger trust.

How to Nurture a Culture of Open Communication and Feedback

Regular check-ins and conversations can help reduce the trepidation both managers and employees feel when a more serious discussion needs to happen. They also can ensure that staff feel comfortable offering their own feedback in return and discussing solutions. 

“It starts with enriching relationships and building trust,” says Rochlen. “Getting to know people as individuals and connecting with them when nothing negative is happening goes a long way.”

There is clear value in nurturing a culture of open and frequent communication and feedback with employees. With an understanding of how important it is to address issues as they arise and a framework to help keep conversations calm and productive, you’ll nurture stronger connections and higher engagement among your staff.

There are ways for your whole team to feel more comfortable handling difficult conversations at work. Book a call to learn more.

FAQs

What if an employee becomes defensive or upset?

When an employee becomes defensive or upset, stay curious and grounded in specifics: restate observable behavior, acknowledge feelings, then pivot to problem-solving, e.g., “I hear this is frustrating. Let’s figure out how we can fix it together.” This keeps the tough conversation with an employee on track and preserves trust.

Do I need HR to be present during a serious conversation?

You don’t usually need HR for performance-focused feedback; a manager-employee meeting often suffices. Bring HR in when policy violations, legal risk, or potential termination are possible; HR protects both parties and ensures the employee review process follows company guidelines.

Can difficult conversations be done remotely?

Yes. Difficult conversations can be done remotely by treating them like in-person talks: choose a private video call, turn cameras on, minimize distractions, and share a written recap afterward. Remote or not, the principles of how to have a hard conversation with an employee remain the same, clarity, empathy, and concrete next steps.

How do I handle repeat issues after a tough conversation?

Handle repeat issues by escalating from feedback to a documented improvement plan with timelines and resources; if behavior still doesn’t change, move to formal HR procedures. Consistency shows you’re serious about having tough conversations with employees and upholding performance standards.