54. Tough Conversations: Tips and Tools for Leaders to Discuss Time Management and Productivity with your Team Member

Tips and Tools for Leaders to Discuss Time Management and Productivity with your Team Member

As a business leader or team member, sometimes difficult conversations need to happen to work effectively together. However, these conversations don’t need to be as stressful as you may think! It is possible to have tough conversations while maintaining professionalism and solution focused.

I had the opportunity to discuss how to have a tough conversation with a business owner named Carolin Serena. She shared a situation in which she had to navigate a challenging conversation with an employee. I guided Carolin through this conversation, helping her clarify her desired outcome. We practiced communicating in the form of asking and requests. We end with an important reminder that our measurement of success cannot be another person’s response or feelings.


Main Episode Takeaways

  • How to have tough conversations without playing the blame game. 
  • The importance of deciding the intention and desired outcome of a hard conversation.
  • How effective communication is a crucial part of team leadership.
  • Boundaries is a learned skill.

Want to learn more about boundaries?

– Boundaries quiz HERE
Take my Boundaries 101 Course
– Do you want to overcome your hurdles of people pleasing? Book a free call with Mary!

54. Tough Conversations: Tips and Tools for Leaders to Discuss Time Management and Productivity with your Team Member

Mary: Let’s talk boundaries. I’m here with Carolin Serena and we are discussing boundaries today. Hey, Carolin, 

Carolin: Hi I’m so happy to be here. 

Mary: Can you tell us a little bit about you and how we can help you today? 

Carolin: Yes. So I’m a business owner and I have a virtual assistant agency where I support business owners to get the support that they need in their business. And so I’m excited to talk about boundaries with you. 

Mary: Awesome. Awesome. When it comes to boundaries in your business, what’s the hardest part for you lately?

Carolin: Yeah. So there’s several things that come up. I think one of the biggest is how to have hard conversations either with clients or with the virtual assistants. One thing that I’ve noticed that has come up several times, both with myself and with clients is boundaries when it comes to time for the assistants that we are working with. So when we have assistants that are paid hourly and we have an expectation that a certain task will take a certain number of hours and it exceeds that significantly, like how to approach that and how to set boundaries in that situation and how to have conversations about that.

Mary: I agree. This is a topic that I bet listeners can relate to. So anyone who is managing a team of contractors and there’s billing on an hourly rate, This is a conversation that is important one to be able to have. So I’m glad that you’re here and and sharing this with us. Can you give us like an example of something that might be going on now or recently did so that we can dive in to the scenario.

Carolin: Yeah. So there was a task that I assigned to a VA and it’s something that takes me like about an hour or so to do and it was a newer task for them. So I had the expectation it would take them maybe two to three hours and in reality it took like over eight hours. And so when I got back that report with, with how long it took them, I was shocked and kind of confused of like, But what were you doing for those eight hours? Like, how, how could it possibly take you eight hours to do this? I know it’s going to take you longer than me. And there’s a learning curve. But like, I don’t, I was like, really just confused. And so I think bringing up the situation is a little tricky when you have a virtual worker like I do. Because There’s this, I want to make the best assumptions that they actually took eight hours to do this, this task, but I don’t want them to feel like me bringing it up is accusing them of Logging hours that they didn’t actually work, right? Like, I want them to feel like we can have an open conversation about the situation and I’m not attacking them, I’m not accusing them, and I don’t want them to get defensive, even if they don’t think that I’m accusing them of, you know, falsifying time clocks, there’s still this concern of like, I don’t want them to feel like I’m devaluing the effort that they put into that, right? So it’s a tricky conversation, in my opinion, to bring up because there’s, there’s so many ways the conversation could go, and I really Want to avoid them getting defensive because then that’ll negate any progress in communication 

Mary: Okay, so I think this is relatable. What are some generous assumptions that we are gonna make about the VA in this situation? 

Carolin: Yeah, that they are dedicated to their job. They’re doing the best that they can and that they actually took eight hours to accomplish the task. 

Mary: Mm hmm. And are you wanting some help with the conversation with your team member? Are you wanting some help with the conversation with your client? Tell me a little more about that. 

Carolin: Let’s yeah, so let’s make this more towards my, like, direct assistant. This is kind of what, what happened with the direct assistant. 

Mary: All right, so what would you hope to get out of the conversation? 

Carolin: I would like, I think, to clear the confusion, right? So I’m feeling confused, so I want some clarity so that I can kind of clear that confusion. And I also would like something moving forward, like if this situation were to happen again, what that’s going to look like, and maybe even how to prevent that from happening again. 

Mary: Okay. So your measurement of success sounds like would be clarity around what happened and a plan for how to mitigate this in the future. 

Carolin: Yes. 

Mary: Okay. Sounds good. So how do you usually communicate with your team members? 

Carolin: Yeah, so if it’s something simple, we have a messaging app that we use, but if it’s something more like this, we have regular zoom meetings to talk about things that require a little bit more of a conversation. So I could bring it up during one of our scheduled meetings.

Mary: Okay. When you bring it up to her or him how could you do that in a way that has a clear intention and a measurement of success? How could you start that conversation with intention and desired outcome? 

Carolin: I’m not certain off the top of my head what the answer would that be. So I’m thinking just, I have that worry that they’re going to take things the wrong way. So I want to make sure that I set the tone for the conversation that it’s not accusational. I’m not sure exactly what to say to do that effectively. 

Mary: Okay. So what if you just said something like, Hey, I’d like to talk to you about fill in the blank. I’d like to talk to you about …

Carolin: this task that you just completed.

Mary: Because… what’s the reason you want to talk to her?

Carolin: Because I was expecting it to be two to three hours to complete the task when it took you eight hours. 

Mary: Right. How could you say that in a way is maybe just the facts, like I noticed 

Carolin: the number of hours that it took was different than what I expected.

Mary: Yep. So we want to neutralize, right? Just own this is my thoughts. 

Carolin: The language is not blaming. It took you this long seems a little blaming. 

Mary: Right. So I noticed on the invoice, the number of hours was this and I was expecting it to be something more like this, right? And what do you want to get out of this conversation again?

Carolin: I want to understand what happened and I want to have a clear plan for preventing it in the future. 

Mary: Okay. Sounds good. And do you want to give her any generous assumptions? Do you want to kind of offer your generous assumptions of them at this point in the conversation? 

Carolin: So sharing those generous assumptions that I have, is that going to be helpful to kind of keep the conversation more open, communication wise? 

Mary: It’s up to you if you want to kind of give those generous assumptions, but when you explained to me a couple of minutes ago that you are really concerned that you, you know, feel a little bit nervous about how this conversation will go, that sometimes we might choose to share our generous assumptions to kind of soften that so that the person isn’t therefore defending something that you’ve already generously assumed of them. 

Carolin: Okay, so in this situation, I would like to share just kind of soften that sounds like a great idea. So it would just be sharing like, I’m sure it took you eight hours and you worked really hard on it. I’m grateful for your hard work. I’m just trying to understand what went into doing that work so that in the future, I can support you, right, to be more efficient. 

Mary: Awesome. And do you have a request or an ask of her or him?

Carolin: Not in this particular scenario, but I, there is at least I, as a business owner and working with others who have virtual assistants, I see this as a pattern. And so I’m aware that this needs to be something that we prevent moving forward, right? So there needs to be something to prevent this from being an ongoing situation. 

Mary: Sure. So the problem to be solved here, to me, sounds like it’s time estimation. Yeah. So when you’re having these hard conversation, an easy tool is to talk about time estimation as the problem to be solved. And so that takes the focus off of the individual that you’re in the conversation with, their performance. And it makes it a problem that you guys can both work towards solving together. 

Carolin: Okay. Awesome. So what would that conversation look like? When it comes to type of estimation. 

Mary: You get to decide. Yeah. I mean, one option is that you can say I’d like to focus the rest of this conversation on time estimation because I understand that time estimation is a learned skill and the amount of time that I estimate, the amount of time that the client is expecting, the amount of time that you estimate, we want those to be as close to each other as possible. And so let’s come up with a plan and some strategies to kind of make sure that this time estimation isn’t becoming an issue in the future. 

Carolin: Yeah, and so maybe it would be setting some sort of like, I would like for us to, when I delegate something that I have a time expectation for, I’m going to share what that expectation is and if it takes you longer than that expectation, so maybe my expectation is two to three hours, and if you get to that three hour mark, and it looks like you need more time, I would like for you to communicate with me before moving forward and letting me know like where you are in progress. Because sometimes what I’ve noticed, at least as a business owner is sometimes what they’re doing to complete the task I can guide them halfway through to help them complete it in a more efficient way. But if they’re just trying to trudge through on their own. Then it’s going to take that full eight hours. Right? So there might be something that I can do to support them mid project if I get that, that kind of immediate feedback.

Mary: Yes. I love that shared accountability and shared responsibility. And it does feel better to me that we have conversations with our contractors as negotiating agreements with them. So I have several contractors that work for me in my business and I don’t take the approach that these are rules that they need to follow. I do take the approach that we have an agreement and We are going to get really clear about what our agreement is. We’re going to negotiate our agreement. We’re going to check in about our agreement. And those conversations tend to be less stressful and more effective. 

Carolin: Yes, of course. And I do think it’s important to delegate responsibility, but I’m still We’re partners in this. Like, you can come to me at any point and I’m gonna make sure that you have what you need to be successful and I’m not just pushing rules onto you, right? 

Mary: Okay. So, let’s practice. You be yourself and I will be your team member. How’s that? 

Carolin: Oh, you’re putting me on the spot, man. 

Mary: I know. It’ll be so fun. Let’s go. 

Carolin: Okay. So I say, Hey, I wanted to talk to you about this task that you did and when I got your time sheet I was surprised because the number of hours that were clocked on your time sheet for that task was different than what I expected. It took, I think, eight hours and I was expecting like maybe two to three. So I’m, I’m sure it took you that eight hours and I’m so grateful for your hard work and really accomplishing that. And you did a great job. I’m just trying to understand like what the reason why it took that amount of time so that we can kind of understand for the future how I can support you to be more efficient in completing that in the future.

Mary: I don’t know why it took me so long. I was doing my best to figure it out and I had to look up some things. I had to do some Google searches and things like that for things I didn’t know, but I was trying so hard to get it done and I worked hard on that. 

Carolin: I’m grateful for your hard work. Do you have an estimate for how much time it would take you to do it the next time?

Mary: I don’t know. I hope it would be less time the next time. I hope I can do it in two or three hours, as you expect. 

Carolin: Okay, so if you try to do it next time within that time frame, I’d like you to communicate with me because there might be some ways that I can support you in kind of learning how to do it more efficiently. So if you get to the place where it’s taking two and a half to three hours and you still have quite a bit more to do. I want you to check in with me and pause and kind of give me a report, like a status report of like where you’re at with that task. And we can assess together like where are you at? What support do you need? And like maybe I can help you complete it in a more efficient time frame. Does that sound good to you?

Mary: Yes. 

Carolin: Awesome. And I think moving forward, just to clear any confusion for future tasks, if I have an expectation for how much time I think something should or would be able to like accomplish something, I will communicate that when I share that task with you. So that way, I can be clear of like, hey, I want you to do this. I think it should take two to three hours, and then it will have that kind of communication for any future tasks. If there is a time estimation attached to it, and you are reaching that limit of time that I’m estimating, just let me know. Let me know that you’ve reached kind of that limit, and Like where you’re at, and then we can kind of see, like, where we want to go from there.

Mary: Okay, and then I’ll try to watch how much time it’s taking me. 

Carolin: Yeah, yeah, and I think it takes a little bit of practice, especially with new things. So I understand it takes a while when you’re trying something new, you’re trying to figure it out, and there’s a lot of Google searching, which can take a while. But being mindful of how you’re estimating and gauging time would be really appreciated. 

Mary: Okay. Thank you. 

Carolin: Thank you. How’d I do? 

Mary: How do you think you did?

Carolin: I think I did okay. 

Mary: I think you did great. What, what did you learn? 

Carolin: Oh, that’s a great question. Yeah, I, I was unprepared for the initial response of like, I don’t know how much time, which is probably the most appropriate response. But cause I wanted an answer and you didn’t give me one. So which is normal, right? But I think I had to realize like, I don’t, I don’t actually need an answer. I just wanted one because I was annoyed and surprised, right? So it was really more about like troubleshooting and getting to the core of like, what do I really want out of this conversation, which is to prevent future instances.

Mary: Sure. So, your measurement of success in difficult conversations, remember, it’s not the other person’s response or feelings. It is, were you clear? Were you kind? And did you say what you needed to say? 

Carolin: Yeah, I think the conversation did accomplish those three objectives. 

Mary: Awesome. So, by that measurement of success, I think you did an amazing job.

Carolin: Yeah, thank you. 

Mary: Yeah. All right. Well, let’s wrap up here. What are some of your takeaways from our conversation? 

Carolin: I think it was really helpful to me to see that I needed to create a plan for the future with what, how I want to, and it came down to time estimation and that that was the thing that needed to solve for, for the future. And having that felt really good. And then that’s a small shift in delegation, right? That I’m communicating time estimation when I have an expectation for time. So, obviously not everything is going to include a time estimation, but if I already have an expectation, I need to clearly communicate that. Because if the time goes over what I’m estimating, and I haven’t communicated it, it’s on me. 

Mary: Yes. So we have boundaries around who’s responsible for what and who’s not responsible for what, what we’re willing to do, what we’re not willing to do which is amazing. And I love all of this. And I promise you that these conversations will get easier as you continue to practice them because boundaries is a learned skill.

Carolin: Thank you so much. It’s been super helpful. 

Mary: I’m glad. Right. Have a great one.