Sympathetic or Just Plain Mean? Insider Tips for Difficult Conversations

Picture of John Doe

John Doe

Patrice Barber, CEO of Career CNX and National Speaker

As a manager, there are times when you need to provide feedback to your staff. Oftentimes, managers tell the employee that the feedback is not personal – it’s all in service of supporting the business.

But all feedback is personal – whether it’s positive or negative.

How do you provide advice to your employees and ensure that they actually hear it and can take action? 

By utilizing these tips for difficult conversations.

Understanding Your Employee

Providing feedback today is part of an ongoing process that started on the employee’s first day. Success is more likely if you prepare your employee for the process of getting feedback on their performance at work and learn more about that employee’s goals.

Begin with the end in mind.

Getting to know your employee is a crucial ingredient in understanding their motivations and ultimate performance. Your staff members have private lives outside of the workplace – their manager needs to be aware of those activities. Try to understand how their outside lives affect their daily work life.

For example, there’s a critical deadline and John got most of his work done – but not all of it. As the manager, when you are left with no other choice but to ask for overtime. 

There are effective and ineffective ways of getting the work done.

Given John did not get his work done by Friday morning, and the Monday deadline cannot be slipped, how can we empower John to solve the problem?

One manager’s approach is to tell John he needs to work Saturday. 

If John  is active in animal rescue causes and is part of the committee planning a Saturday fundraiser for the local shelter, asking John to work that Saturday will likely be met with unspoken opposition.

Another approach is to explain to John the impacts to the team of not getting the work done, and ask John what he sees as options to meet the hard deadline. Explaining that John will need to work the weekend to meet the Monday deadline, gives clarity to the situation. 

Understanding that John has a commitment and allowing him to select the timeframe of his work shows that his manager honors that obligation. Leadership’s empathy and sympathy help John commit even more to his job and to his team.

A great guide to learning about your employees is the Chemistry of Connecting.

Chemistry of Connecting – 4 C’s and 3 I’s

Within the Career CNX learning modules is a section on connecting with others. This training contains an explanation of the 4 C’s:

  • Career
  • College
  • Children
  • Community/Charity/Church

And the 3 I’s:

  • Information about
  • Invitation to
  • Introductions to

These seven items are a starting place for managers to continue to get to know and understand their employees – and for employees to understand their managers. 

As managers, keeping track of the data you learn about your employee can be challenging. One solution is the Career CNX app, which stores this information and allows for easy recall. Notebooks or spreadsheets could also be used.

By delving into these areas, whether you are networking outside the company or chatting with your peers, these are the topics that are most likely to spur additional conversation and deeper understanding.

Interested in more information on leadership? Check out this article: How to Master Adaptable Leadership.

The noblest pleasure is the joy of understanding.

Listening and learning about people is the first step in providing assistance and feedback. If Emily is a brilliant developer but finds it difficult to talk with customers about issues, perhaps customer support is not the right place for her. 

Peer to-Peer Group Support

Encouraging employees to form peer-to-peer support groups is one way managers can help to empower their employees. Ultimately, each employee is responsible for their own career path. Managers and mentors offer advice and guidance – and peer groups can do the same. 

Employees are often more open in a group made up of people at the same level or perhaps one level above. These groups can be internal to the organization, or external and comprised of people in similar positions in different companies. 

Peer-to-peer groups provide support to individuals by giving them a forum in which to articulate their wins and their challenges. A diverse group may be able to give advice on how to overcome challenges to help the individual meet their goals. 

As you navigate through your career and leadership style, use active listening to hear alternative ideas. Other people and other people’s ideas often inspire a broader vision that leads to a more concise idea and action.

Promoting Action

To help employees articulate their challenges, ask them to formulate the challenge in the form of a question.

For example, if the challenge is

I can’t get my manager’s attention to sign off on these invoices,

that challenge in the form of a question is

How do I get my manager’s attention for signing off on these invoices? 

This frames the situation as an action that can be taken.

In order to help employees proceed toward their goals, managers need to inspire a culture of collaboration with their employees. Get to know them as people and as workers. Once there is a deeper understanding of the individual, conversations around improvement and development become much easier.

For more information on how managers and employees can foster a deeper understanding, contact us at

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