How to Have Difficult Conversations at Work | Tara McAlister

Fernanda: Hi everyone, welcome back to this YouTube channel for leadership development. Today I'm excited because it's my very first video on this channel with a guest, and my guest today is Tara McAlister.

I'm going to bounce it over to Tara so that she can introduce herself and tell us a little bit about what she's doing. Then we are going to dive into a discussion about having difficult conversations. Tara, welcome as our first guest, and I appreciate you being here. Would you mind telling us a bit about yourself?

Tara McAlister: Well, if I'm the first, that means I'm the best, right? No, just kidding. Or the worst—I don't know! Thank you so much for having me on here. I love talking about people, and I've actually been in HR for almost 30 years.

I love helping solve people problems for businesses through my company, The People Strategy. I enjoy working with business owners to help them find ways for their teams to work better together, whether that means helping them understand expectations or communicate more effectively.

Around 70% of issues really stem from miscommunication. That is especially true on teams when we miscommunicate or avoid communicating altogether because a conversation is difficult. That can lead to lost revenue and people losing positions or jobs. Developing the skill set to have difficult conversations helps business owners and managers do their jobs better, which helps the entire company.

Fernanda: Absolutely, I completely agree with you. I think I've been on both sides: the manager trying to figure out how to have the difficult conversation, and the person on the receiving end.

It's never easy because there is a human side to leadership and operations. A lot of times people in companies like to pretend psychology doesn't exist, but it's very much there. Since you have a ton of experience, could you share some examples of situations where someone might struggle to find the courage to have a difficult conversation with a colleague or employee?

Tara McAlister: One example that comes to mind involved an employee who was excellent at her job—so excellent that we promoted her. However, it was probably not the right time, and she wasn't ready for the promotion.

As she settled into the position, she began underperforming. We realized it was time to have a conversation with her about it. Here was a high performer who had always done well, and now we had to sit down and say, "You're not doing well, and this isn't like you."

Her direct supervisor came to me and said, "I can't tell her; how do I do this?" I told him it was the right thing to do. When I sat down with her, I said, "Let's talk about where you are right now."

Once we met on that level and she felt understood, she was actually relieved that we weren't avoiding the issue. She was able to say, "I am failing, and I need help."

What I learned that day is that people respect you more as a leader when you're willing to step in and have those conversations directly. As an HR professional, I've handled termination discussions and performance meetings. While they are difficult and uncomfortable, they have to happen.

As a leader, you must handle them constructively and respectfully. You can't just vaguely say, "You're doing a bad job." You have to specify what you're seeing and ask what resources are needed to help them improve.

Sometimes it isn't performance-related; it might be personal hygiene or body odor. That is especially delicate because it's deeply personal. Sometimes it turns out to be a reaction to a new medication they aren't aware of, or a strong perfume.

When presented constructively, specifically, and professionally—focusing on the impact rather than attacking the person—it can actually strengthen the relationship. However, when people avoid these conversations or handle them poorly, it can cause significant damage.

Fernanda: I've definitely seen both sides—people who handle it well, and people who avoid it entirely. In your experience, why do people avoid these conversations? What advice would you give to a newer manager who feels intimidated by the process?

Tara McAlister: I once worked with a newer manager who managed an older employee she viewed almost as a mother figure. The employee began underperforming, and the manager was hesitant to address it because of that dynamic and her respect for the employee's tenure.

I told her, "You have to explain the impact on the team and hold her accountable. If you hold everyone else accountable except her, what message does that send to the rest of the team?"

As a manager, you have to be direct: "Here is the performance we're seeing, and here are the resources to help. Let's work on this together."

Another example was a quiet, introverted manager dealing with an employee with a very dominant personality who took over every meeting. Nobody wanted to confront her because she was so boisterous. The manager worried that addressing it would cause friction.

I asked her, "What is the long-term effect if you don't address this? People will see your meetings get derailed, and your credibility as a manager will suffer."

We sat down and mapped out what this employee brought to the team—her drive and ability to hit deadlines—as well as the drawbacks of her behavior. We role-played the conversation with me acting as the employee.

The manager was able to frame it constructively: "You drive projects forward and keep deadlines on track, but during meetings, others hesitate to speak up because your presence fills the room. I know that's not your intention, but it prevents others from contributing."

The employee hadn't realized her impact. Because the feedback was planned and delivered constructively, it led to a positive outcome.

Difficult conversations can be constructive if you plan them ahead of time. Know what you're going to say, define your ultimate goal, and be prepared to pause the conversation if it stops being productive. You can always say, "This might not be the best time to continue. Let's reconvene tomorrow when we can both approach this constructively."

Fernanda: That is such an important tip. It reminds me of the Situation-Behavior-Impact model mentors shared with me when I was leading teams.

I used to write down the situation, the observed behavior, and the impact on a notepad—almost like a script—especially when I had to address issues with my own superiors. Planning ahead and mentally preparing makes a huge difference. Being ready to pause the discussion if it gets emotional is equally valuable.

Tara McAlister: You also have to anticipate pushback, whether it's deflection like "Everybody else does that" or someone giving you the silent treatment.

If someone deflects by mentioning others, you can redirect: "Today, my focus is entirely on you because your growth matters to me. I'm not criticizing you; I'm investing effort into your development because I value your contribution."

If they shut down, you can say, "You may not be ready to discuss this right now, but we will address it. Silence doesn't mean we bypass the issue." Anticipating those reactions during the planning stage is essential.

Fernanda: Being a leader is far more complex than people realize. It isn't just delegating tasks; you have to navigate the human side of accountability and feedback. When having these difficult conversations, do you recommend documenting them immediately, or keeping things verbal initially?

Tara McAlister: In HR, documentation is our love language! I recommend having the verbal conversation first, followed by a recap email.

You might write: "Thank you for your time today. I know these discussions can be tough, and I appreciate your cooperation. As discussed, while your drive is valuable, taking over meetings can prevent others from participating. I appreciate your commitment to working on this, and my door is open if you have questions."

This creates a clear, dated record showing mutual alignment, while also acknowledging the effort it took to have the conversation.

Fernanda: It recognizes that both people involved are human. There's often anxiety and vulnerability on both sides, which makes that empathy so important.

Tara McAlister: Everyone wants to feel that they are doing a good job and earning that metaphorical "gold star." That's why acknowledging their effort during the conversation matters.

Equally important is recognizing improvement afterward. With the employee who dominated meetings, I noticed her actively making space for others, and I praised her for it later: "I noticed you held back today, and did you see how Nick spoke up more than usual? You enabled that."

Highlighting that progress turns the feedback into an ongoing win. It reinforces growth and builds stronger leadership habits.

Fernanda: It requires preparation and genuine intentionality. It shouldn't be handled impulsively or when a leader is stressed or emotionally activated. Having a bad day is definitely the wrong time to initiate a difficult conversation.

Tara McAlister: Absolutely. The employee needs to understand your intent clearly: "My goal isn't to upset you; it's to help this team communicate better and work cohesively." Clarifying your motives upfront prevents them from feeling singled out or attacked.

I often open by saying, "We have a tough conversation ahead, and it's just as difficult for me to bring up as it might be for you to hear, because I genuinely care." When people sense that care, they are far more receptive to the feedback. Communicating that intent clearly is an essential part of the planning process.

Fernanda: So true. Tara, thank you so much for joining and sharing these insights. Before we wrap up, where can the audience connect with you?

Tara McAlister: You can find me on LinkedIn, Facebook, and Instagram under Tara McAlister or The People Strategy. I love working with business owners to clarify expectations, improve team dynamics, and recruit and retain top talent. I also enjoy connecting and networking with leaders looking to grow their businesses.

Fernanda: Having nearly 30 years of HR experience means you have a wealth of knowledge to share. Maybe a podcast should be next on your list!

Tara McAlister: I really do love talking about it!

Fernanda: Thank you again for being here. To everyone watching, if you found Tara's advice helpful, please like, subscribe, and share this video. We'll see you in the next one!

Fernanda Brasileiro

People Development Consultant & Strategist

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