How To Have Difficult Conversations As A Leader

Having difficult conversations as a leader with individuals or teams happens fairly often. Sometimes these conversations take place numerous times a day. Difficult conversations may include employees not meeting expectations, mistakes that are being made, personality conflicts, and a number of other items that take place in team situations on a regular basis. Not only are these conversations difficult, but they can also be stressful and awkward. Here are some tips to help make having difficult conversations easier.


Before diving into specific tips, the overarching message is that laying groundwork before having these types of conversations is key. Doing a number of small things to help prepare yourself for these types of conversations is the key to making them easier.

Be Clear With Expectations

Spend time clarifying roles, assignment details, and responsibilities for all team members. This information should be specific and can include job descriptions, task assignments, due dates, and so on. Make it a point to document this information so you have something to reference in the event that a follow-up conversation should take place. Having something to point to helps when it comes to having a difficult conversation.

Seek & Listen To Input

Building in feedback loops is a great way to receive input from the team. Although it may seem like leadership messages and direction is clear, there may be a misunderstanding somewhere. Listen to your team to understand their workload, other priorities, or gaps in communication. Sometimes listening to the reason why a team member may not be meeting expectations is a way to fix any misunderstandings.

Negotiate and Agree To Terms

This advice seems official and contract-like because it is. Every time a leader provides documented expectations or directions, they are entering into an agreement with their team. Leaders are saying, “this is what a team member is responsible for, this is what I expect them to do, and this is the end result that we’re looking for”. By expressing this information and listening to input, leaders are essentially entering into an agreement with their team. If terms aren’t being met, reviewing those details makes having difficult conversations less stressful. Leaders can also use goals as a way to document and agree to what those responsibilities may be.

Explain The Big Picture

When specific direction is provided by a leader and the recipient doesn’t understand the meaning behind a task, the team member doesn’t understand what it means in the big picture. The team member may not see the importance and because they’re not sure what the task means, it’s less important to them. Take a few moments to explain the big picture to get everyone on the same page and motivated to move forward.

Ask ‘Why’

If a team member isn’t meeting expectations and it’s time to have a difficult conversation, ask them why. Maybe they have other items on their plate that they feel are a higher priority or there’s a misunderstanding somewhere. If expectations are documented, it’s easy to say something like, “This task was scheduled to be completed by you last week and you had agreed to complete within the timeline specified. Why was the deadline missed?” Understanding the reason why will give the team member an opportunity to explain themselves which helps with associated stress levels.

No Surprises

No one likes surprises, especially when it comes to having difficult conversations. Have frequent conversations with your team and provide feedback on a continual basis. This could take place in weekly 1-to-1’s or included in review cycles. Avoid delivering feedback rarely or only once a year. The team or individuals in a team should know where they stand at all times.

Be Open & Honest

When it comes time to having a difficult conversation, be open and honest. This is not an opportunity to be mean or abrasive, but rather an opportunity to be direct. If a culture is built upon being open and honest, it’ll help make these types of conversations much easier.

Having difficult conversations as a leader is stressful. However, taking time to lay the appropriate groundwork will help make having difficult conversations that much easier.

What do you do as a leader to provide leadership training to your team and alleviate the stress of having difficult conversations?