25 January 2023 |

The OFFICIAL People Pleaser’s Guide to Hard Conversations


Okay, people pleasers, this edition of Leader’s Lens is for you.

It’s time to have that conversation you’ve been putting off. The conversation with the person you really care about. You have feedback you need to give them, but you’ve been avoiding it because of how much you care about this person.

I get it. You don’t want to hurt their feelings or make future conversations awkward.

The idea of having this conversation makes you feel uncomfortable or anxious. Give yourself some grace. It’s natural to feel this way. Conflict can be challenging for even the most experienced leader.

This is the OFFICIAL People Pleaser’s Guide to Having Hard Conversations. LFG

Before I break down the steps you need to take to have a conversation that makes an impact, let’s look at what happens when you continue to avoid these conversations:

  • Employees become disengaged
  • Lack of trust among team members
  • Leaders get accused of picking favorites
  • A lack of accountability among team members
  • People don’t have the opportunity to get better
  • Problems and issues are not addressed and resolved
  • People become anxious and wonder why their boss is avoiding them

You don’t want any of these things on your team. You are either building the habit of immediately having critical conversations or avoiding them.

Write this down somewhere: 

Don’t wait 10 days to have a conversation that will take 10 minutes.

The secret is learning to have this conversation with grace.

Here are the 5 steps you need to follow:

1) Separate the person from the action

The conversation is not about the person you are talking to. 

The conversation is about something they did.

  • They called out sick
  • They missed a deadline
  • They said “um” 100 times giving a presentation

Here is an example, “You are awesome. I know you care about your teammates, and you show it with how consistent you are in stepping up and supporting people. But when you consistently show up late to meetings, it can make people feel like you don’t value their time.”

When we focus on the action needing change, it allows people an opportunity to grow.

2) Focus on the specific details

Bringing specific details to the conversation will help you be confident in the message you are delivering. It will also help your teammate understand the severity of their actions.

If someone has the habit of constantly interrupting, they might not be aware of how often it happens or the impact of their actions.

As a leader, the goal of giving feedback is to help a person grow and develop, not to make sure they know who the boss is.

When you face resistance to feedback, be sure you have specific examples you can reference that helps paint the picture. To reinforce the importance of the change, be sure they clearly understand what changes need to be made and how this change will help them reach their personal goals.

3) Focus on the future

The best feedback is not focused on who the person is now. It is focused on helping them reach their potential.

If I’m at a networking event with broccoli in my teeth, tell me. By not telling me you are preventing me from reaching my potential. I don’t want to be walking around a room of founders, talking about my podcast with broccoli in my teeth.

Even though it might be slightly awkward to bring it up in the moment, you would be holding me back from reaching my potential by avoiding the conversation.

Don’t avoid the conversation. 

Talk about the elephant in the room.

4) Be transparent

Start the conversation by explaining what you want to accomplish and how you are feeling. Being willing to be vulnerable will help put your teammate at ease and help them feel comfortable doing the same.

Words that work, “Before we get started, I just want you to know that you aren’t in trouble. I just am hoping to understand a few things better, so I know how to support you best.”

Having hard conversations early means you can get in front of problems before they become bad habits that negatively impact your team.

When you avoid conversations, they grow and infect other people. And suddenly, one person’s problem becomes a much more time-consuming team culture problem.

It’s a big deal!

5) Be curious instead of critical

Come into every conversation with an open mind, assume best intentions, and focus on what you need to do to help.

The truth is not everyone will be a fit for your organization, and there will be times you need to fire an employee. But if you come into conversations assuming a misstep was caused by a misunderstanding, you’ll build a team of people who know you have their back and are ready to help crush your competition.