Leaders have conversations with their employees every single day. But whether it’s a casual check in, a regularly scheduled team meeting, or a crucial conversation, they look much different now.  

With people working remotely or in a hybrid environment, they aren’t in the office as often as they used to be. Those natural conversations we used to have in the hallway or at a colleague’s cubicle just aren’t happening. We may converse over the phone or video conferencing, but when you do not see someone in person, you cannot really get a feel for how they are doing. You cannot see how they are dressed or how their body language may be off. If we only see a headshot, we will miss those contextual clues.  

Times of Reflection 

The pandemic and “The Great Resignation” caused reflection. Workers are reconsidering their priorities in life and how work plays into that vision. And because it is on employees’ minds, it needs to be addressed by leaders.  

Leaders should reflect on how their employees can thrive in today’s workplace. How can they inspire them to do their best work and quiet thrive rather than just quiet quit? Managers need to better understand their employees’ experiences and their perspectives to form a partnership to improve the workplace for everyone.  

To get there, it is going to take a great conversation.  

But First, There’s Pre-work 

It is the leader’s responsibility to set a culture of collaboration and create that open conversation, but it must be done in a way that is natural. And if this has not been a priority or top of mind for the leader in the past, it can feel very strange. For example, if you just announce unexpectedly that you are going to start having one-on-one meetings with employees and asking very probing questions, that could feel very confronting to some people.  

That is where pre-work comes in. The pre-work will vary based on the company culture and the type of relationship you already have with your employees. Here are five examples of pre-work that may need to be done before you attempt the great conversation: 

  1. You may need to have an overt conversation and explain that you are shifting your priorities. Tell your employees that you want to prioritize your working relationship and one of the ways you want to do that is by having more regular conversations with each of them. Discuss your vision and what you would like to see happen in the long term so you can provide context for your employees.  
  2. You may need to illustrate to your employees how difficult it is to connect in today’s office, depending on the work environment you have created. Give them examples of how communication has decreased, how it is affecting the organization, and how you want to change that.  
  3. You may need to personally share yourself. How are you feeling? How are you managing work-life balance right now? What is your ideal workplace? People are more likely to be more open if you are vulnerable yourself. 
  4. You must be transparent with your direct reports as to your intention behind having these conversations. There is likely to be suspicion, especially if you try to start this initiative suddenly without explanation.  
  5. You must be authentic. Whether you send out a company communication about the new initiative or speak one-on-one with employees about your goals, do not make it seem like you are checking off something on your ‘to do’ list. It should not sound formal, nor contrived.  
Avoid Sending Warning Signals 

I work with so many coaching clients who do not trust their bosses, who have lost respect for their bosses, and are just overly suspicious of anyone trying something new. One recent client comes to mind who puts up walls with her supervisor. Angela (not her real name) does not think her boss has the highest emotional intelligence, so she shuts him out. She is a good employee and does her job well, but she does not put in any effort into building a good rapport with him.  

So, if Angela’s boss suddenly said he wanted to improve the culture by having regular conversations with her, her guard would immediately go up and she would shut down. She tends to always look on the bright side so she would paint a glossy portrait of how she is doing with short answers like “Everything is great!” She would go through the motions required of her, but she would not be open to the boss digging deeper. 

But, if the boss is willing to show Angela that he is working on himself and trying to improve as a leader, I think she would be open to it. That could be as simple as reading a leadership book and sharing some of the points from it, or attending a virtual leadership workshop and putting some of what was learned into practice, or even better, engaging in executive coaching.   

Angela would feel as if the boss were trying to work on himself, so she would be willing to meet him halfway.  

Customize your Conversations 

When you are determining your structure for these conversations, consider what works for your employees and acknowledge that they will all have unique needs. A monthly meeting may be okay for some but not for others. Some employees will want a formal meeting on a specified date and time, while others may want a more casual gathering like a short weekly check-in or a longer monthly lunch date.  

Set up with each individual employee what is supportive for them based on their feedback and give them different options that you would be willing to commit to. Make it clear that this is not an obligatory check-in, but rather time spent together to foster a deeper relationship with better company culture and communication as the end goal.  

Once that groundwork has been built, the employee will be more willing to have conversations. Go into these meetings with an open mind and legitimate curiosity to learn the story of your employees.  

Need ideas to get started? You should use a mix of work-related and personal open-ended questions. Here are some questions to ask your employees: 

  • How are things going? 
  • How have you been able to weave in your talents and skills in to the work you do here in this organization? 
  • What do you enjoy most about your job? 
  • What do you like least about your job?  
  • What are your priorities in life? What are some of the ways that I (or the organization) could help you achieve / maintain those priorities? 
  • What hobbies do you enjoy?  
  • How can I support you? 
  • Is there anything I have not asked that would help me understand you and your work experience? 

Of course, it goes without saying that when you are listening, be an active listener. Ask your employees to elaborate and “tell you more.” Employees will be more engaged in the process if they feel as if they are being heard. 

Follow Through or Don’t Do 

Now that you have put in the effort to get to know your employees and what motivates them, put what you have learned into practice. There needs to be a level of implementation to show everyone you are acting on these conversations. People want to see how their work contributes to the well-being of the business.  

Take a hard look in the accountability mirror before you make promises to employees in these conversations. Be open and honest, and do not give empty guarantees that you cannot fulfill. If an employee is asking for something and you know the constraints of the budget or other factors in the company that could be obstacles, be as transparent as possible with the employee as to what may or may not actually happen in the future. This could present an opportunity to explain why certain decisions have been made up to this point, but you can also share the organization’s priorities that are relevant to that person.  

These should not be one off conversations, but rather an ongoing partnership. Provide action items and a timeline for next steps. Then follow up as to the progress so that your employees see that what happens in these conversations equates to action in the organization.  

Getting to know your team members as individuals takes time, but these great conversations will reap benefits for years to come.  

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