"A person's success can usually be measured by the number of uncomfortable conversations he or she is willing to have." Timothy Ferriss

In every organization and in every office, there is someone avoiding a difficult conversation with a team member. Maybe someone is habitually tardy. Maybe your new hire isn’t following the dress code. Maybe a personal conflict between two associates has gotten out of control. Whatever the issue, most managers dislike confronting employees and wait far too long to have the necessary conversation. Don’t avoid difficult conversations. The performance of your team, the productivity of your organization and your happiness depends on it!

The Scott HR Road Map for Difficult Conversations

Initiating a simple, but difficult conversation at work can be a real roadblock, but avoiding these conversations can stall workplace productivity and detour successful teams. Follow the Scott HR road map to turn a difficult conversation into a compelling performance coaching session.

Step 1: Do Your Homework

The more you prepare for this conversation, the better the meeting should go. Document the problem and write a script using factual language. If multiple people have complained about the issue, document their feedback.

One reason we might avoid having a difficult conversation with a team member is that we don’t want to hurt their feelings or make them feel like they are doing a bad job. If you care about this person’s growth and development, then you should care enough to have hard conservations that will help them grow.

Step 2: Be Direct, But Caring

The best feedback is straightforward and simple. “I am talking with you because this is an issue that you need to address for success in this organization.” Explain the issue and why it is a problem.

Telling someone that they need to make a change (to improve or keep their job) can be hard. Care enough to have difficult conversations!

Step 3: Ask for Input

Ask if the employee understands and what support they need. “I have some thoughts about what we can do, but do you have any ideas about what needs to change?”

Asking for input isn’t the same as saying ‘Any questions?’ Asking for input is how leaders gauge understanding, willingness to engage and underlying attitudes. Listening to feedback is how leaders communicate respect, care, and concern for those around them. This is a key step in a difficult conversation! Asking for input and truly listening is a leadership skill you can use to benefit many situations. It’s easy to skip this step, but crucial that you ask, listen and respond. You might be surprised at what you hear!

Step 4: Commit to a Plan

Reach an agreement about what the individual will do to resolve the issue. Set a due date – tomorrow, if appropriate. Make another appointment after the due date to review progress and prevent backsliding.

When leaders care enough about their team to have difficult conversations and proactively address problematic situations, they will commit to a plan for success. It is the employee’s responsibility to fulfill the plan, to resolve the issue as discussed, but at least two follow-up appointments must be scheduled by the manager! Follow up creates accountability, which allows for long-term improvement. Is there a request or an issue that YOU need to follow up with? Take five minutes and do so!

Step 5: Be Positive

Always end the meeting on a positive note. Your employee should leave thinking they can do better. You want them to feel accountable to the plan and committed to meeting their goals.

Have you ever scripted the END of a difficult conversation you will have with a team member? Ending the conversation well is just as important as the beginning. What you say and do in the last two minutes of the conversation will determine how they feel about the interaction once they leave your office. Consider how you can use honesty, personal caring, and encouragement to help them feel responsible and positive about the outcome. How will you approach your next difficult conversation to ensure success?


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“Kristin has been a valuable resource in providing coaching and counseling for some unique situations. Kristin’s enthusiasm and ability to quickly gain the confidence of the employee while delivering very candid feedback has definitely provided positive results to our team.”

Division Manager, Government Agency


“We look forward to improving communication across the board, moving forward. In addition, I’ve personally seen how hard Scott HR and our office staff have worked over the past six months to make this company better than it has ever been. Their constant drive, like yours as a team leader, has inspired me to step my game up. I’m more focused than ever to build onto the legacy of our organization. Without committed team members and valued customers, there is no business.”

Area Supervisor, Retail Store

Growing People Grows Your Business

Scott Human Resources offers management coaching and leadership training to teach you how to radically improve your approach to employee management.

Leaders who use Radical Engagement find that they:

  • Have happier, more productive employees
  • Form solid and intentional relationships with team members
  • Hire the right candidates
  • Reduce turnover with effective onboarding
  • Improve communication and help the team exceed their goals

Want to learn more? Call 785-272-5410 to talk to an HR professional today, or complete the contact form to get in touch with Scott Human Resources.

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