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A
Hi, it's Helen from the Squiggly Careers Podcast. And before you listen to today's episode, I just wanted to let you know about some news that Sarah and I are very excited about, and that is that our new book, Learn Like a Lobster, is ready to pre order now. We really care about everybody learning and growing at work, but we know it is not easy to do, and so we're borrowing some brilliance from lobsters to help you to do it. The book takes three inspiring and surprising abilities of lobsters in terms of how they grow and applies it to how we can learn at work. So if you want some inspiration and you need some practical insights to support your learning, growth and development, this is the book for you. And if you pre order now and send your Pre order to helloearnlikealobster.com you can join the Lobster Library, where we have a community of lobster learners ready for you to learn with some live sessions. And this will all happen before the book arrives. So pre order the book now, send it to hello@learnlikealobster.com and get started with your learning straight away. Now let's get onto today's episode. Hi, I'm Helen.
B
And I'm Sarah.
A
And this is the Squiggly Careers podcast, where each week we borrow some brilliance from different people and places and turn that curiosity into useful actions for your career.
B
And this week, we're experimenting with a slightly different format. I feel like experimenting has been our word of the year this year. And what we've done is we have picked a theme, hard Conversations. So hopefully something that we all need a bit of support on. I don't think it's a skill that AI anyone ever says to me, yeah, that's I'm amazing. I'm amazing at hard conversations. And what we're going to do is we're going to hear three different experts share their borrowed brilliance from slightly different angles on this area.
A
And the hard conversations that we're going to be tackling are, number one, conflict in a team, Number two, what to do when you feel defensive in a conversation, and number three, speaking out when something doesn't feel right. Which one of those, which one of those do you think you need to borrow some brilliance about?
B
Well, all of them for a start. As somebody who doesn't love conflict find, I do find hard conversations hard. But of those three, I think particularly conflict in a team, I probably practiced when you feel defensive, what to do. I think I have some, like, coping mechanisms in those moments and probably because it's we're in like quite a high trust team. We know each other so well. I feel like I can speak out when something doesn't feel right. And it's way easier in the job that I do today versus maybe jobs I've done in the past. But I think in our team we probably don't have conflict in a way that is useful at the moment. So I feel like it's a gap we've got. So that one, I, when I was thinking about these different conversations and re listening to our experts, that was the one. I think I've, I've kind of gone a bit further than just listening. I've like reread some things. I think it's that one for me. How about you?
A
I think the second one about feeling defensive in a conversation where there's conflict and I was trying to work out why. And I think, I think sometimes it's, I just, I care so much about what we do and we put so much of ourselves into what we do that when, when conflict arises in the course of our work, I'm, I think I just want to defend because I'm like, well, but I'm just, I'm just trying. I've got good intent and sometimes I think it's almost like the care gets in the way of me. Like, I don't know, managing the conflict constructively even like I might get an email from somebody. And so it's not always conflict in a conversation. It might be conflict in different form of communication and it's, you know, whatever. It's someone who doesn't agree with something. And my first thought is to kind of defend why we did it rather than perhaps like manage that conflict in a different way or look for the learning or all the things that we're going to hear from our experts about what we should do differently. But yeah, that's probably my. I have to work a bit harder at that. I don't need to defend all the time, I think.
B
So first we're going to hear Helen talking to Amy Gallo about conflict in a team. I think what's really interesting about this is conflict is part of every job and every place that we work. But as somebody who's conflict avoidant, I think I sometimes forget that intentional conflict and useful conflict is part of being a high performing team. And actually it's something that Amy Edmondson often says is that if you're not hearing bad news, if there aren't hard conversations happening, like that's not good for you, that's not a good sign. So I think that I find that kind of particularly interesting because I'm like, well, how can we get better at that? Because lots of organizations actually we talk to, you know, they have got positive cultures where people want to work, but everyone also recognizes you need that high care, that high challenge. But practically, how do we do that? So that's really interesting. And there is a really useful HBR article which it has prompted me to go back and reread, which is about preempting conflict in a team. And the reason, if you're listening, it's worth spending some time on that is it outlines five different conversations that you can have in a team and it gives you the questions to ask. And actually Helen and I were talking about this beforehand. If you go through some of that, and I think if you try out some of those questions, what we think it might particularly help you with is conflict that actually you don't need to have. So basically, you know when you wind people up.
A
Pointless conflict.
B
Yeah, pointless conflict. Or people like you and I have it sometimes, right. You get a bit antsy with lecture. Yeah. And it's niggly, but for sort of no good reason. So if you're going to have conflict and like useful disagreement, you. You want it to be to like build something better or to like say the hard thing. You want it to be helpful, not like actually just annoying. And you talk about in this clip, which really made me laugh when I was listening, the difference between being irritated by other people and trying to do a bit of a reframe from irritated to intrigued. And I think knowing you so well, I was like, really? I was sort of smiling away to myself thinking, oh yeah, I can sort of spot sometimes when Helen's like making that move.
A
I know that Sarah will know like some specific meetings that I have in when I'm like, I'm trying to do that so hard. But I really value Amy's advice. Like, we've followed Amy for ages and I really, I remember this conversation. So I was so pleased to just get Amy in a room, having followed her work for a while. And you know, after you listen and maybe you read the article that, that Amy recommends and also like highly recommend following Amy, also reading her book. She's brilliant on the topic of conflict.
C
Well, it is a career defining skill in many ways because think about it, there's no such thing as a conflict free office. You've worked many places. I can't imagine any of those places. Did not have difficult conversations, did not have conflicts.
A
Right.
C
They are going to happen. And the people who can bring different perspectives together can navigate those conversations, can advocate for themselves, for their teams, can facilitate. Facilitate constructive discussions. Those are the people who often go far in organizations. Very rarely, although it does happen, does someone get to the top of an organization by being afraid of conflict. So for personally, it's really a career defining skill.
A
It makes me think about. We talk quite a lot about psychological safety, Amy Edmondson's work. One of those seven dimensions is the ability to have tough conversations. And I think to have tough conversations, being able to understand people's preferences and the impact on that as a team of conflict or kind of debate type conversations would really help people to understand and empathize. Because what might be tough for you might be very different than what's tough for Sarah. And there's some understanding that needs to be reached in order to do that in a supportive way in the team. Yeah.
C
There's a great HBR article called how to Preempt Team Conflict. I don't love the preempt because I don't like the idea that you're trying to get rid of it. But I don't think that's really the author's intention. It's actually a series, I think it's five conversations that a new team can have about the their work styles. It's a great article because there's a list of questions as well for each of the conversations and they can be facilitated or a leader can run the conversation. But it's a way for people to get to know one another's styles. A lot of it is about a clash of working styles. And that can be as simple as I show up to meetings on time and you always show up five minutes late. So we start every meeting with me resenting you. Right. And so then everything goes sour the minute we start talking. And those are very simple things. If we just discussed ahead of time, are we going to be on time? If you're running late, can I not take it as a sign of disrespect? Right. Is it the fact that you just have a busy schedule or your assistant over schedules you.
B
Right.
C
What is it that we can agree on is going to be our working norms and helps me develop a little bit compassion for when you show up and I'm not really into what you've decided to do or your style.
B
Right.
A
Something that helps me in case it helps anyone else is I sometimes think that. And I've had to work on this really, really hard. But I try to be intrigued over being irritated I like that. Yes. Yeah. And I still get irritated, but rather than go, oh, so annoying, or this, why are we doing this? I try to go, okay, that's your trigger. You're a bit irritated by this person in the situation. Like, flip really quickly to being intrigued and maybe ask some questions. What's happening at the moment? Is there something that, you know, you need to talk about before we get onto this topic? Yeah, and just I've generally found that that's brought the person back to me in some way, like on some kind of level that we can move forward product. So, yeah, I would recommend that as a mindset and approach to kind of being intrigued over being irritated.
C
Well, and just being curious. I mean, I think if you can start any difficult conversation, you sit down, if you can start with a question, a genuine question. Right. Something you don't know that you want to know about the situation or the other person. It just sets the tone that I'm not going to just, you know, monologue here. I'm not going to bulldoze my opinion through. I'm going to actually engage in a conversation and it engages the other person so they have to show up to the table. So if you're dealing with an extreme avoider, asking a question helps them hook into the conversation in a way.
A
Are there any other top tips that you have for how conflict can be really productive in the workplace?
C
Yeah, I think one of the things we often forget, and I say this as a seeker who spent most of my adult life entering these conversations trying to prove I was right, which is an incredibly rewarding thing when it happens, but not a great way to have productive conversations. So I think one of my top tips is to think about what is your goal? What is it you're actually trying to achieve in this conversation? Is it that you need a strong working relationship with your boss who you're having the conflict with? Is it that you need this project to just get done or get done on time or get done within budget? Or is it that you just want to get out of this conversation so you can calm down and come back later and have a better conversation? If you think about what is my goal, and if your goal is a shared goal with the other person, you. You get bonus points because that's a great place, a foundation from which to have a conversation. So that's one of the things I often ask myself as someone who sort of leaps into these conversations, eager, sometimes guns a blazing, right. I try to think, what am I actually trying to achieve here? What is it that I need and usually it means that I have to put down the need to be Right.
A
Now we're going to move on to what to do when you feel defensive in a conversation. And our expert here is Celeste Headley who spoke to Sarah about. It's quite an interesting point that we've put pulled out of the conversation here because it's not something that I would really, I wouldn't expect Sarah to be talking about affirmations, which is, which is the direction that the conversation goes in. And Celeste does acknowledge that, you know, even the word affirmations can sometimes turn people off, but actually it can help you when you are in a conversation and maybe feeling a little bit of conflict. So I found it a useful listen and also I really enjoyed the whole, the whole episode. I think Celeste is very practical, but this little clip will help you particularly maybe if you have that, that thing that I do where you feel a bit defensive in a conflict conversation.
B
And if you do want to hear more from Celeste, her TED talk is short, funny and practical and it's a good recommendation and it's all about how to, it's actually 10 ways, I think to have better conversations. So it goes broader than what to do when you feel defensive. But I, I have re watched that a few times and I think what she manages to do is make kind of very typical conversation situations and scenarios, give you really kind of practical advice like what you might do in that moment. So here we've kind of zoomed into if you're feeling defensive, like what can help you. But if you do want to dive deeper generally into just improving the quality of your conversations, her work is really worth spending some time with.
D
Let me give you some very practical tips on how to get through these conversations. Number one, if you allow someone to feel proud, a sense of pride at the beginning of conversation, it makes it more likely that they will be open, open minded and open to being wrong, open to new information. So sometimes I'm completely blatant about this and I will say listen, here's what the research says. So let's start there. Tell me about the best thing that's happened to you in the past month. Tell me about, brag for me for a second and tell me about, you know, something you're really proud of and that works very reliably. You can get through these difficult conversations in a number of ways. But again, I want to give people actionable tips that they can actually. So for example, in order to get through a difficult conversation, this might surprise you, but you can use affirmations. I realize that a lot of people have a wonky view of affirmations. It seems like the kind of thing you do for self help or whatever that may be. But in fact, it's pretty surprising how effective self affirmations are at actually carving new neural pathways in our brains. So, in other words, you can use affirmations to retrain, train your brain so that when you get negative feedback, you don't have a defensive response, but you have a productive response. You can use them as a way to shift your brain from retaliation when you are criticized to questioning and curiosity. So whatever it is that is most difficult for you over the course of a difficult conversation, and this is the first step, obviously becoming aware of what you're like in these conversations, what is it you struggle with? Do you become defensive? Do you not like getting negative feedback? Are you a tone police person? In other words, are you worried about the way someone phrases something rather than the meat of their message? Whatever it is that you struggle with, write yourself an affirmation to defuse that bomb and repeat it in your head. As the conversation begins to become difficult, you can take a breath, you can tell the person you know, give me just a moment to think this through and repeat your affirmation to yourself. I'm here to hear. Listen to this other person. I don't need them to like me, but they may have an insight that will be of use to me. So I'm going to listen without judging. I'm going to do all this. Whatever your affirmation is that works for you, use it. And when you finish the conversation, use it again.
B
So we hope you found listening to Celeste helpful, and maybe it's even changed your mind on affirmations. I don't know if it's changed my mind on the word affirmation, but I do believe in the principle. Well, if anything, I think for me, it's sometimes about just having those shortcuts. Maybe I like that word better. Shortcuts to remind your brain how to behave. I think that's how I see them. Or sometimes I think it can be reframes. You know your point earlier about irritated versus intrigued. I'm like, that's basically a reminder for your brain about how you want to show up and how you want to behave. So, you know, call them. Call them what you will. The last person we're going to hear from is Dr. Sunita SA. Both Helen and I were reflecting on just how good this conversation was. She is brilliant. And if you said to Me, do you want to read a book about defiance and being defiant? I would say no.
A
Like that. That.
B
That feels so far away from my personality, I sort of can't almost connect the dots with how that might be useful. And then you spend some time with Dr. Sunita and you realise a. Her definition of defiance is a really useful one. So it's about acting kind of in alignment with and being consistent with your values. And then really what she is helping us to do is to speak out when something doesn't feel right. And we know from another brilliant female leader, Margaret Heffernan, that 85% of people have concerns about work that they don't share. So she calls that like organizational silence. So lots of us are not saying something when we spot that there's an issue or a challenge. And this doesn't have to be. We were saying before, there are those moments in your career where there are big things that you might want to speak out about. A toxic culture, somebody else's behavior that you think feels inappropriate. There are also loads of small examples of when we speak, we should kind of speak out because we spot a process isn't quite working or something's taking longer than we'd imagined. And I think often we all just live with it because we're so busy getting stuff done. We were talking about today, you know, the sort of the sticking plaster mentality of going, oh, but we just need to sort this now. And then you move on to the next thing and you move on to the next thing and you don't ever quite press pause and just do that kind of fast flag of, oh, this is kind of feeling difficult, or this is. This isn't feeling like it's working the way that we'd hoped.
A
So just to connect the dots with innovation, because you might be thinking, oh, what's the motivation for me to. Because it defines. Is difficult because you're probably going to do something you're not doing at the moment. And so you might need to connect to a motivation. So one could be, well, it will help me build a better relationship, it will help me feel less frustrated about something. Fine. But actually slightly different. DOT is around innovation. I was with one of the companies that we work with yesterday, Langerock, and I was listening to their Director of Technology and Innovation, Chatham, and he was talking about, you know, part of innovation is consciously spotting when things aren't working well. You know, like a broken process, wasted an organization and being that person who says, we don't need to do it like this, like that there is A better. And I think actually maybe like part of defiance is being the person who spots what's going wrong and then is happy to speak up about it. It's not always like, you know, conflict in a conversation. I think it could be, you know, you're kind of being defiant about the way things have been done, might not be the way that we always need to do them. And so I think there's potential benefit here for solving problems, being the person who creates new ways of doing things as well.
B
Yeah, it links really nicely to critical thinking because actually, when you describe it in that way, I'm like, oh, I'm quite good at that bit of it. Also. Definitely a connection here. And I think this is true with all of the three experts that we've heard from today in all of these different conversations is I think you all, you have to put these conversations within your context. So if you are in a high trust environment, then I think it just naturally makes all of these three things easier. Does it make them easy? But I think it makes them easier. I think if your, you know, organization, your team is feeling difficult, then I think you have to work out, like, how to do this in the right way for, like, where you are and also give yourself a break. Because I have definitely been in places where I've been beating myself up that maybe I haven't been speaking out as much as I felt like I wanted to or should, but it felt, you know, there wasn't very much support around or, you know, if I was going to be doing that, I would of. I was going to be doing that by myself. And it was very risky. So I think also sort of acknowledging and just recognizing, like, what feels right for you, what feels relevant for you, if you're in a good, you know, a good team, supportive manager, then I think, like, really challenge and push yourself, which I think is where we are. We're like trying to really push ourselves. Whereas, you know, maybe you, you can do this in much smaller ways as well.
E
Just to first of all, take a step back and really understand what I mean by defiance. Because as you said, there is this negative connotation about defiance when we're children. Right. Like a defiant child is seen as a negative thing. And I grew up believing that because we start equating our socialization, that compliance equals good and defiance equals bad. But when you delve into it, there's serious problems with compliance, you know, even if we think about in the workplace. One survey found that nine out of 10 healthcare workers on average, which is a huge amount. Nine out of 10, most of them, nurses, don't feel comfortable speaking up when they see a colleague or a physician making a mistake. So we really do want to think about what we're doing when we sacrifice our values or find it so difficult to speak up at certain times. And there is a myth that defiance has to be loud, aggressive, violent. But my definition of defiance is that it's simply acting in alignment with your values when there is pressure to do otherwise. It's a skill set that's necessary and available for all of us. So the five stages of defiance. The first stage is tension, and that's when we feel that tension between what's expected of us and what we think is the right thing to do. That tension can manifest in many different ways. So some people can feel an ease in their stomach. They can feel a dry mouth, mouth, their throat constricting, a headache. So there's many different ways that we feel that tension. But we can really try to understand what we feel in our own bodies, because that tension is actually a very useful warning sign for us that something is wrong, and perhaps we do need to defy in this situation. So what we often do when we feel that tension is that we disregard it. We think it's not worth our doubt, or the other person probably knows better, especially if they're in authority. And so we try to sweep it away. And we shouldn't do that. We should move to the stage two of defiance, which is really acknowledging that tension to ourselves. So rather than disregarding it, we feel it, and we acknowledge there's something I'm uncomfortable with. So that's just to yourself. Now we move to stage three, and this is a really critical stage, and this is about vocalizing that tension to somebody else or asking questions. Why I say this is a critical stage is because. Because the research shows that if you can get to this stage where you externally vocalize your uncomfortable feeling or you're asking questions, then you're more likely to get to the last stage of defiance. Stage five, because you can't go back in time now and say, oh, you were fine with it all along, because you've told someone now. And so that cognitive dissonance would be too much. So at this stage, you're still in a subservient position. All you're saying is, I'm not comfortable with this, or you're asking people, what do you mean by that? Can you clarify this? Or have you considered this instead? So you're asking questions. This is not about confrontation. This is about curiosity in a way, curiosity and clarification. But why it's so important is that that clarification really raises the volume on the situation. And so you're not disregarding your tension, you're acknowledging it to yourself. And now you've vocalized some questions to someone else else or some statements that I'm not sure I'm comfortable with this. I'm not quite sure about this. Stage four, it could be seen as a threat of non compliance, but you're simply saying, I don't think I can do this. You know, I'm not comfortable with going ahead with this, I can't do this. And this is the stage where you have to continue to say that. You can't just say it once and then if you're pressured go back down again. But if you stick to saying that, then you will get to the final stage of defiance, which is your act of defiance. Now the wonderful thing about that is right at the beginning when I spoke about the tension at stage one, if we just try to disregard it, what I found in situations where, okay, I'm just going to go along with this is that tension usually grows and you remember and you regret afterwards and you feel awful. But if you can get to stage five of defiance, that tension just melts away. It feels really good to act in alignment with your values.
A
So we hope you have enjoyed listening to that conversation with Dr. Sunita and actually all the conversations today. As we said at the start, it's a. This is a new format for us. We've got so many episodes with experts and we're trying to work out how to bring their brilliance back and this is one way that we thought might be useful. So please let us know. We'd really love some feedback on this format because we can go back to the other episodes. We can put them together in ways that we think might be useful for you at work. You can always email us with your feedback. It's just helenand, sarahquigglycraft careers. Com and we'll put all the links to things that we mentioned in the show notes as well. So if you want any of those articles, for example, or you want to listen to the full length episodes, that's where you'll be able to find them.
B
That's everything for this week. Thank you so much for listening and back with you again soon. Bye for now.
E
Bye everyone.
Episode: 3 Hard Work Conversations & How To Handle Each One with Confidence
Hosts: Helen Tupper & Sarah Ellis
Date: December 2, 2025
Featured Experts: Amy Gallo, Celeste Headlee, Dr. Sunita Sah
Episode Theme:
How to handle three of the most challenging types of workplace conversations—conflict in a team, defensiveness in dialogue, and speaking out when something doesn’t feel right—using insights from top experts to help listeners approach each with greater confidence and practical strategies.
Helen and Sarah experiment with a new episode structure, curating and discussing the practical wisdom of three experts on different “hard conversations.” Their aim is to break down real-world challenges most professionals face, providing actionable advice to make these difficult dialogues less daunting and more productive.
[06:40–11:30]
Why Conflict Matters:
Normalizing Conflict:
Preempting Pointless Conflict:
Tip: Reframe Irritation into Curiosity:
Tip: Clarify Your True Goal:
Memorable Quotes:
[12:56–15:30]
Opening Up Conversations:
Start by inviting people to share a recent success, which helps lower defensiveness and creates openness.
Celeste Headlee: “If you allow someone to feel a sense of pride at the beginning… it makes it more likely that they will be open, open minded and open to being wrong, open to new information.” [12:56]
Using Affirmations as Mental Shortcuts:
Practical Steps:
Memorable Quotes:
[20:14–24:40]
Redefining Defiance:
The Five Stages of Defiance:
Innovation Tie-In:
Context Matters:
Memorable Quotes:
For feedback on this format or additional questions, listeners are invited to email: helenandsarah@squigglycareers.com
This summary captures the heart of the episode—actionable wisdom for tough work conversations, straight from experts, with relatable host perspectives and practical advice.