The 3 Scary Conversations Every Manager Needs to Have With Their Direct Reports

The types of conversations managers tend to avoid

Manager and employee


Profile Picture
Kelly Poulson51
Coach. Career Navigator. Ass Kicker. Dog mom.
June 24, 2024 at 4:24PM UTC

Being a manager isn’t an easy gig. Often, people land in management roles simply because they had skills in their day job and it was assumed that they’d do well leading a team. It’s rare that these folks receive much support from their organization on how to evolve into a solid leader and they are usually left to fend for themselves. 

The skills that got you to your goals as an individual contributor aren’t likely the same skills you need to be a successful manager. Most leaders either try to wing it and figure it out for themselves, or treat their teams as they’d like to be treated. That can leaves direct reports frustrated or confused. If you feel like you’re avoiding one of the conversations below, it’s time to face the music. Your team will appreciate it.

1. “You are falling short.” 

Giving someone constructive feedback is challenging. Even when you’ve got the best of intentions, there are so many factors at play. No one particularly enjoys hearing about what they are doing wrong or how they aren’t meeting expectations. However, that doesn’t mean it’s ok to avoid the conversation. You may see it as mean to speak with someone about their challenges. But if you truly care about them and their growth, it’s the kindest thing you could possibly do for them. Have an open dialogue about what expectations are and where they might be lacking, then brainstorm along with them ways to enhance this skillset going forward. Make it known to your team that you are here to support them and are invested in their future. Being willing to have this conversation openly will go a very long way in enhancing your professional relationship with a direct report, if done well. 

2. “You are crushing it.” 

You’d think most people would jump at the chance to shower praise on their rock star employees, but most don’t. Lack of time or worries about it being uncomfortable prevent leaders from providing recognition regularly. What a bummer! In order for people to continue to evolve, they need feedback. If they are doing an excellent job, they need to hear from their manager not only that it’s occurring but what makes this skillset so important or how it impacts the overall picture of the business. This type of conversation motivates your team to keep going for the gold. Saying “great job” every now and again when you pass a team member in the hallway isn’t going to cut it. Positive feedback needs to be consistent and tailored to the person’s needs. For instance, shout outs at a huge company meeting won’t go over well for your incredibly shy person. But for the person who loves being the center of attention, that might be exactly what she wants. In order to do this well, you need to know your team well enough to provide the type of recognition they’d desire. Make it a priority for your team and beyond. It will work wonders. 

3. Any conversation that shows vulnerability and opportunity for growth.

At some point in our world, people got the idea that admitting you don’t know the answer or expressing your feelings about a situation is the wrong way to go. Now, sometimes that might be the case. But often, it is in those moments that trust is built amongst you and your team. Being willing to say you don’t have the answer to every challenge they face or that you’re also frustrated with how a certain process has been occurring is something that shows your human side to your team. They want to know they aren’t working for a robot. Don’t get me wrong: there’s a difference between full disclosure and intentional sharing. Be mindful of that line. In the same respect, even if you don’t know the answer, they want to know that you’ll work with them to figure it out. Shrugging and calling it a day isn’t the kind of support anyone needs. Go the extra mile. 

No matter where you are on your leadership journey, it is not ok to avoid conversations simply because they might be difficult. Difficult conversations are those that tend to have the most impact on individuals, teams, businesses and ourselves. If you’re feeling nervous about having these types of conversations, seek out guidance from HR, your manager, a coach or the plethora of books and online learning options out there. The most important thing is that you’re brave enough to go for it, because you know open conversations will lead to growth and evolution. And we all want that. 

Don’t miss out on articles like these. Sign up!

Kelly is a human resources pro and coach who helps people find and achieve what they want career-wise and beyond. Coaching, training, recruiting – if you name it in the world of HR, she's done it in a variety of industries. Her advice has been featured on The Muse, Career Contessa, Levo, Workology, among others. Learn more by scoping her out at

Why women love us:

  • Daily articles on career topics
  • Jobs at companies dedicated to hiring more women
  • Advice and support from an authentic community
  • Events that help you level up in your career
  • Free membership, always