5 Tough Conversations Managers Need to Have

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You don’t get promoted for your communication skills—but the moment you step into leadership, they become your most important asset. Whether you’re an engineer growing into influence or a manager leading a team, knowing how to navigate the human side of work is essential.

In this session, we’ll cover five of the toughest conversations you’ll face at work: underperformance, giving feedback, saying “no,” career growth, and setting boundaries.

You’ll walk away with practical, repeatable frameworks to approach each conversation with clarity and confidence—building trust, strengthening collaboration, and showing up as the kind of leader people want to work with.

This talk has been presented at React Summit US 2025, check out the latest edition of this React Conference.

FAQ

Kellie is a senior engineering manager at Zapier with over a decade of experience in engineering leadership. She has been with Zapier for seven months.

Kellie has a background in social work, public health, and psychology. She is a trained therapist and incorporates this into her management style.

Tough conversations are important because avoiding them can lead to bigger problems, resentment, and hinder team growth. Addressing issues directly helps everyone involved.

The CARE framework involves Clarifying issues with specific data, Asking for support needed, Redefining expectations together, and Establishing regular check-ins.

Managers should use the STAR framework: be Specific, ensure feedback is Timely, focus on Actions, and use Relevant examples.

Acknowledge the importance of the request, explain trade-offs, and offer alternatives. This approach is strategic and helps in managing up.

Use the GROW model: discuss Goals, assess the current Reality, explore Options, and determine the Willingness to pursue the path.

State boundaries clearly, explain the business reason, offer alternatives, and stay firm while acknowledging others' feelings.

Encourage blameless feedback, provide positive feedback opportunities, and promote feedback between peers, managers, and direct reports.

Document shared notes for agreements and private notes for personal observations. Use tools like Notion or AI note-taking apps like Granola.

Kelly Vaughn
Kelly Vaughn
37 min
18 Nov, 2025

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Video Summary and Transcription
Kellie emphasizes the importance of having tough conversations in management, addressing underperformance using the care framework and support strategies. The STAR framework is highlighted for handling difficult feedback effectively. Effective communication with superiors involves acknowledging trade-offs and framing discussions around revenue impact. Setting clear communication boundaries is crucial for work-life balance and team efficiency. Encouraging a feedback culture, addressing promotion discussions transparently, and handling micromanagement concerns with empathy are key points discussed.

1. Managing Tough Conversations in Management

Short description:

Kellie, a senior engineering manager at Zapier, discusses the importance of having tough conversations in management. She highlights how avoidance of difficult discussions can lead to escalating problems and emphasizes the need to address issues promptly. Kellie encourages a shift from fixing individuals to understanding and supporting them. She introduces the topic of underperformance with a relatable scenario involving a senior developer named Sarah.

I'm super excited to talk to you today about having tough conversations. I know this is a little bit of a divergence from a lot of the technical talks you've likely been hearing today. I'm also proud to announce that I do not mention AI in this talk at all. So that should be pretty cool. So a quick intro. I am Kellie. As mentioned, I am a senior engineering manager at Zapier. I've been here for seven months now, so still definitely on the newer side. I've been in engineering leadership for over a decade, and I call myself a recovering entrepreneur as well. If you founded a company, it's a little exhausting. Trying to run two companies at the same time is not my best move ever, and I no longer run either of them. But the more interesting part of this and why I'm talking about this today is I am a trained therapist. I went to school for nothing related to engineering. I have a master's in social work and public health and psychology. I collect degrees for a living. So this definitely comes through with my management style and the kind of conversations I have.

Before we dive in, curious, how many of you are managers today or are interested in becoming a manager at some point? Cool. Yeah. And if you're not, a lot of this is still absolutely going to be relevant to you because you're going to learn how to have these conversations with your manager as well. I know for a fact that managing up is pretty hard for most of us. And so you're going to have a good opportunity to learn how to do that. So why do these conversations matter in the first place? I want you to think for a moment. Have you ever had like lost sleep over a conversation you've been needing to have, but have been putting it off? Maybe it's feedback you need to give somebody. Maybe you need to set a boundary, or maybe you're just trying to address some sort of underperformance. And if you're nodding along, you're really not alone here. As managers, we tend to get extensive on-the-job training for budgets, strategy, project management, technical skills, but rarely do we actually learn how to manage teams, how to have tough conversations with people.

And because of that, one thing that I've learned over time is avoidance is not neutral. So every day when you're not having that conversation, the problem just continues to get bigger. It continues to fester. Resentment starts to grow. And once it gets to a point where you've been holding off for so long, that's when the conversation really doesn't go well. So just remember, while you're losing sleep over having that conversation that you know you need to have, chances are the person on the receiving end knows that that conversation needs to happen as well, and they're also losing sleep over it. So the best thing you can do is just push through it because avoidance hurts everybody. So I want you to kind of take this part away as we're talking through these five types of conversations. In my therapy training, I learned something that changed completely how I manage folks, and that's avoidance is actually a trauma response. How we avoid difficult conversations is usually some form of protection. Something happened, and therefore, we're just trying to protect ourselves. Nobody wants to be uncomfortable. Nobody wants to be in a position where they feel discomfort. And so we usually avoid them, but by avoiding that, we're also depriving our teams from growth opportunities with these conversations that you really need to be having. So as you're thinking through this, the main thing I want you to be thinking about is moving away from a mindset of how do I fix this person to how can I understand what's going on with them, and how can I best support them through this process? And with that, let's dive into the first conversation. So we're gonna talk about underperformance first. Let me paint a picture that feels familiar. And side note, I will have these slides available to you afterwards. So you'll catch on the last the very last slide if you want to copy anything in there as I walk through frameworks. So reading this here. Sarah, a senior developer on your team, has been missing deadlines for the past six weeks. Her code quality has dropped, and other team members are starting to pick up their slack. You've hinted at issues in standup, but nothing has changed. The team is getting frustrated, and you're worried about losing good people.

2. The Care Framework for Addressing Underperformance

Short description:

Discussing the care framework for addressing underperformance in management. Emphasizing the importance of specific data and support in difficult conversations. Encouraging collaboration and regular check-ins to ensure ongoing support and improvement.

Does this sound familiar? You ever have somebody on your team who's kind of falling behind for some reason or not doing their best work, and you feel like you need to stand up and say something or do something, and it's really hard conversation to have. As we walk through this, I'm going to be walking through frameworks for each of these five top conversations. The first one I want to talk about is the care framework. It's called care because that's literally what you're doing. You're caring about the situation, you're caring about the individual, and you're showing that you care about their success. You want to clarify it with very specific data, not your performance has been slipping, but more focusing on three of your last four deliverables were two to three days late.

You want to emphasize facts over feelings. Next, you want to ask the support they need. This is the magic question because you don't actually know what's going on. Maybe something's going on in their personal life that you have no idea because they haven't talked to you about it. Maybe they're overwhelmed, maybe they're bored, maybe they just need additional training. You want to co-create this path forward. You want to make sure that they're invested in this situation or this solution as well. And lastly, establish regular check-ins. This is one of these things that a lot of folks forget to do.

You have a conversation, you're like, okay, I have the conversation, I can move on now. You want to be establishing this regular check-in schedule to make sure that you're actually following up with them and they're following through and they continue to feel supported. That is not just this one time thing. What does this look like? This potential response to the situation would be, Sarah, I've noticed that three of your last four deliverables have been completed two to three days after the agreed deadline, including yesterday's QA review, which flags several issues that are unusual for your work. Help me understand what's happening from your perspective. What support do you need to get back on track?

QnA

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