# Workplace Surgery: Managing Someone Who Keeps Pushing It

- **Episode:** [206](https://agents.truthliesandwork.com/episodes/206.md) (2025-06-17)
- **Type:** workplace-surgery
- **Tags:** managing-difficult-employees, boundaries, leadership
- **Time:** 47:41–53:34 (start 2861s)
- **Listen:** [https://truthliesandwork.com/206?t=2861](https://truthliesandwork.com/206?t=2861)

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[47:41] Al Elliott: Okay, Lee, question number 3. How do you manage someone who keeps pushing it? I've read this before
[47:47] Leanne Elliott: Push it real good
[47:49] Al Elliott: That's got a different— that's a different pushing, I think. Moving on to this. I manage around 20 people, and honestly, I find it hard to get the balance right. I'm either too soft or too harsh. One team member's constantly late or leaving early, always with a personal reason. It's been going on for weeks. I finally listed out all the times that she's left early, and she just replied, you approved them all. I did not. Then yesterday I asked her to do a report and she told me I should do it myself
[48:18] Leanne Elliott: Wow
[48:18] Al Elliott: My own manager's avoiding the issue. I'm stuck. How do I handle this without making things worse? Hey, I want to hear this answer
[48:25] Leanne Elliott: 20 people is a lot, actually, so I'm not surprised that you're not getting the balance right with everybody. Um, yeah, go a bit easy on yourself. That's a, that's a tough one. Um, I'm sure you're engaging in your own training and professional development to help you with this, so I won't Even dip my little toe into that side of it. Um, this is— it goes back to that incivility in the workplace, doesn't it? This isn't digital, it's, it's, it's face to face. Um, but it is these types of, of little behaviors. I mean, I'm not gonna lie, if I had a manager who came, who let this behavior continue for 2 weeks and then came with me to a long list of things that irritated me about them, about me, do you know what I mean?
[49:03] Al Elliott: Mm-hmm
[49:03] Leanne Elliott: Then I'd, I'd probably be a bit like, oh, well, you said I could as well. I think that would probably— yeah. kick in my little, um, yeah, defense response. I don't think you handled that in the brilliant way. If you notice the behavior— and this is all what it comes down to, is having difficult conversations, which is one of the worst and hardest things about being a line manager— the most important thing about having a difficult conversation is to have it really early so it's not that difficult. The longer it goes on, the more difficult it gets, and the more you dread that conversation. I think it was Was it, um, Kat who was on the show probably 50 episodes ago said the more uncomfortable it is, the more needed that conversation is. So I think the fact that you left it 2 weeks hasn't helped. I think by the sounds of it, there is some misunderstanding around the flexibility this person has in their workplace that might just need to be reiterated to them in terms of why they You know, if they do have to leave early, how that process is managed, whatever your internal process is. And if you don't have one, then kind of what do you expect if you're not, you've not got those boundaries? Sorry, our dogs are, as we did say at the beginning of the show, are around and starting to get a bit vocal. We've ignored them for about 45 minutes now, so that might be why. So, yes, I think reiterating what is your policy around flexibility, what is your preference as a manager in terms of how that is requested, make sure you're flexible as well, because the more rigid you are, it isn't going to help to rebuild what is now Tipping into a difficult relationship. I think finally, giving this person again the benefit of the doubt. If you've asked them to do a report and they've said no, why have they said no? Have they said no because they don't want to do it, they can't be bothered, and they think you should do it because that's your job? Or is it because they don't feel capable or confident enough to do it? Is it a stretch activity that you've given them? Yeah. And we know from lots of research around this in terms of this type of delegation is if you delegate in a way that's like, I understand that this might sound like a big ask, I understand that this is new to you, that it's going to really push you out of your comfort zone. I think because of how you handled this task previously and the levels of communication you showed, the level of insight, the level of, um, analytical thinking you showed, I think this is going to be a really great task that's going to push you, but in a way it's going to be really great for your development. I'll work on it with you, or we'll check in, um, as and when. And kind of framing it like that— again, we know from the research that building up somebody's confidence when we delegate a task massively increases the likelihood that they're gonna, gonna accept that, accept that challenge. So I think there's some things that you could be doing here in terms of your management, assuming this person isn't just really awful. It might be that they are. It might be that they're going through something. Why are they having to leave? early every day? What is going on there? It sounds like this— a little reset conversation is needed in, in terms of this person, in terms of the policy around leaving work early, in terms of why they didn't feel able to take on that extra report, and just a little bit of a welfare check in terms of why they're needing that flexibility. Is everything okay? Is there something going on that you could be supporting them with?
[52:13] Al Elliott: Yeah, excellent answer. And I think I'll just add one, one last bit to that, is saying, is it— is this Out of your 20, is it just a problem with one person or are you having this problem with most of your people? Because if it's most of your people, it probably is your management style. If it's just the one person, everyone else is cool as a cucumber, then maybe, I mean, has that, was that one person potentially up for your job as manager at one point? Um, I like the answers. Maybe there's something terrible going on in their life. Yeah. If you go back to, uh, Christina Hockett from last week, she was talking about divorce, um, and how that's got a huge impact on, on work, you know? And so, Perhaps this person's going through a divorce. I don't know. Maybe they're at a bereavement. You don't know. Like Leanne said, in fact, first thing you need to do is email Leanne and have like 20 minutes with Leanne. She will tell you how to fix this. Um, secondly, it may be you, but thirdly, it may only just be that one person and maybe you're just unlucky that that one person is making your life a little bit hell. Just like a lot of people have got one bad manager in their life making, making their life hell. And if you got rid of that one bad manager, everything'd be cool
[53:13] Leanne Elliott: Yeah, yeah, there's some, there's some investigation here, isn't there, in terms of whether it is you or whether it is this person, or more than likely a small combination of both. Um, but yeah, to, as Al said, I offer a link to book a call with me direct, and I offer it free, half an hour advice to anyone who, who needs it. I'm not trying to sell you anything, just trying to help. So, um, yeah, get in touch