In short
A Squiggly Careers episode on “hard conversations,” covering three scenarios: conflict in a team, what to do when you feel defensive, and speaking up when something doesn’t feel right. It uses advice from three experts plus examples like pointless “niggle” conflict (e.g., irritation vs curiosity) and workplace “organizational silence.”
Guests (experts) and backgrounds
Amy Gallo (conflict expert; referenced via HBR and Amy Edmondson’s psychological safety work). Celeste Headley (communication expert; TED Talk on improving conversations). Dr. Sunita Sar (defiance/speaking-up expert; defines defiance as value-aligned action under pressure).
Key claims
Useful conflict is necessary for high-performing teams; preempt team conflict via structured conversations about working styles. When defensive, use self-affirmations and start with pride/positive framing; shift from retaliation to curiosity. “Defiance” is acting in alignment with values; tension is a warning sign—progress through stages to vocalize discomfort and, if pressured, refuse.
Notable examples
Discussing meeting norms (e.g., punctuality resentment); reframing “irritated” to “intrigued” and asking questions; healthcare workers (9/10) not speaking up about mistakes; innovation by flagging broken processes.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOExploring Hard Conversations
0:54 to 1:14
Helen and Sarah discuss the importance of addressing hard conversations in the workplace.
“That's the energy State Farm brings to insurance.”
Exploring Hard Conversations
1:29 to 2:51
Helen and Sarah discuss the importance of addressing hard conversations in the workplace.
“And this week, we're experimenting with a slightly different format.”
Understanding Team Conflict
2:52 to 4:50
The hosts delve into conflict within teams, discussing its necessity and management.
“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.”
Preempting Pointless Conflict
4:51 to 7:00
The hosts talk about strategies to manage and preempt unnecessary conflict in teams.
“So basically, you know, when you wind people up.”
Cultivating Curiosity over Irritation
7:01 to 8:13
Learn how to shift from irritation to curiosity to handle conflicts better.
“You've worked many places, I can't imagine any of those places did not have difficult conversations, did not have conflicts, right?”
Setting Goals in Difficult Conversations
8:14 to 11:17
Discuss the importance of having clear goals in conversations that involve conflict.
“I think it's five conversations that a new team can have about their work styles.”
Handling Defensive Responses
11:18 to 14:01
Explore strategies to manage feelings of defensiveness during conversations.
“person, you get bonus points because that's a great place, a foundation from which to have a conversation.”
The Power of Affirmations in Difficult Conversations
14:01 to 15:44
Learn how affirmations can help shift your mindset during tough discussions.
“I realize that a lot of people have a wonky view of affirmations.”
Exploring Defiance and Its Importance
15:44 to 16:45
Discover the concept of defiance and its role in expressing values at work.
“And maybe it's even changed your mind on affirmations.”
Defiance as a Tool for Innovation
16:45 to 19:16
Understand how speaking up can lead to innovation and improved processes.
“So she calls that like organizational silence.”
Show all 11 chapters
Understanding the Stages of Defiance
19:16 to 24:54
Learn about the five stages of defiance and their significance in personal values.
“We're like trying to really push ourselves.”
Transcript
Automatic transcript. May contain errors.0:01This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required, compatibility and availability varies 18+. good sleep is everything that's why ollie's science back support is made with a blend of melatonin and l-theanine for both kiddos and grown-ups so when your mind won't switch off you've got something that can help erasing thoughts and restless nights won't stand a chance find ollie's sleep solutions for the whole family at ollie.com that's o-l-l-y.com This episode is brought to you by State Farm.
0:53You know those friends who support your preference for podcasts over music on road trips? That's the energy State Farm brings to insurance. With over 19 ,000 local agents, they help you find the coverage that fits your needs. So you can spend less time worrying about insurance and more time enjoying the ride. Download the State Farm app or go online at statefarm.com. Like a good neighbor, State Farm is there. Hi, I'm Helen. And I'm Sarah. 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.
1:29And 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 anyone ever says to me, yeah, 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. And the hard conversations that we're going to be tackling are, number one, conflict in a team.
2:03Number 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 do you think you need to borrow some brilliance about? well all of them for a start as somebody who um 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 um 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.
2:51But 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? I think the second one about feeling defensive in a conversation where there's conflict and I try 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 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.
3:42And so it's not always conflict in a conversation. It might be conflict in a 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. So first, we're going to hear Helen talking to Amy Gallo about conflict in a team.
4:13And 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. um and actually it's something that amy edmondson often says is that if um you're not hearing bad news if there aren't hard conversations happening like that's not good for you that's that's not a good sign um so i think that i find that kind of particularly interesting because i'm like well how could 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 has prompted me to go back and reread which is about pre-empting 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 And if you go through some of that, 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.
5:36So basically, you know, when you wind people up. Pointless conflict. Yeah, pointless conflict. Or people like you and I have it sometimes, right? You get a bit antsy with lecture. Niggles. Yeah, and it's niggly, but for sort of no good reason. so if you if you're going to have conflict and like useful disagreement 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 uh in this clip which really made me laugh when i was listening the difference between um 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.
6:23I know that Sarah will know like some specific meetings that I am in when I'm like I'm trying to do that so hard but I really value Amy's advice that 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 Amy recommends and also like highly recommend following Amy and also reading her book. She's brilliant on the topic of conflict. Well, it is a career defining skill in many ways, because think about it, there's no such thing as a conflict free office.
7:01You've worked many places, I can't imagine any of those places did not have difficult conversations, did not have conflicts, right? 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 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. It makes me think about, we talk quite a lot about psychological safety, Amy Edmondson's work.
7:37One 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, 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.
8:12But 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 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. Yeah. 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.
8:48And 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? Right. What is it that we can agree on is going to be our working norms? and it 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 right something that helps me in case it helps anyone else is I sometimes think that and I've had to work on this 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 it's so annoying or this why are you doing this I try to go okay that's your trigger you're a bit irritated by this person in the situation.
9:35Like flip really quickly to being intrigued and maybe ask some questions. What's happening at the moment? Is there something that you need to talk about before we get onto this topic? 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 productively. So yeah, I would recommend that as a mindset and approach to kind of being intrigued over being irritated. 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?
10:05Something 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. Are there any other top tips that you have for how conflict can be really productive in the workplace? 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.
10:52So 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 a conflict with? Is it that you need to 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 get bonus points because that's a great place, a foundation from which to have a conversation.
11:28So 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. 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 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 the direction that the conversation goes in.
12:03And 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 you're maybe feeling a little bit of conflict. So I found it a useful listen. and also I really enjoyed the whole episode. I think Celeste is very practical but this little clip will help you particularly maybe if you have that thing that I do where you feel a bit defensive in a conflict conversation. And if you do want to hear more from Celeste her TED talk is short, funny and practical. It's a good recommendation. And it's all about how to it's actually 10 ways I think to have better conversation so it goes broader than what to do when you feel defensive but 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 make 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 and her work is really worth spending some time with.
13:09Let 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-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.
13:46You can get through these difficult conversations in a number of ways. But again, I want to give people actionable tips that they can actually use. 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 your brain so that when you get negative feedback, you don't have a defensive response, but you have a productive response.
14:33You 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 diffuse that bomb and repeat it in your head.
15:15As 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 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. 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 um so you know call them call them what you will the last um person we're going to hear from is dr sunita sar 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 like that that 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 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.
17:13So 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 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 frustration about something fine but actually slightly different dot is around innovation i was with one of the companies that we work with yesterday langer rock 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 waste in 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 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 will 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 doesn't 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 have I was going to be doing that by myself and it was very risky um 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.
20:22We're like trying to really push ourselves. Whereas, you know, maybe you can do this in much smaller ways as well. 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, especially 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.
21:10So 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.
21:56So some people can feel an amuse in their stomach, they can feel a dry 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.
22:34We 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 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.
23:22And 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 attention. You're not. You're acknowledging it to yourself. And now you've vocalized some questions to someone else or some statements that I'm not sure I'm comfortable with this.
24:00I'm not quite sure about this. Stage four, Or it could be seen as a threat of noncompliance, 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 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.
24:44But 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. 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, 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.
25:20You can always email us with your feedback. It's just HelenAndSarahAtSquigglyCareers.com. And we'll put all the links to things that we mentioned in the show notes as well. So if you want to know those articles, for example, or you want to listen to the full-length episodes, that's where you'll be able to find them. That's everything for this week. Thank you so much for listening. I'm back with you again soon. Bye for now. Bye, everyone.
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From the publisher
🦞 Join our Learn Like a Lobster Sprint: https://bit.ly/4oZzJ3F
This week, Helen and Sarah revisit insights from three podcast guests—Amy Gallo, Celeste Headlee, and Dr. Sunita Sah—to tackle a topic many of us shy away from: difficult conversations.
From team conflicts and moments of defensiveness to speaking up when something feels off, these everyday challenges can shape how we collaborate, grow, and thrive.
In this episode, you’ll learn practical strategies to handle tension with ease: turning irritation into curiosity, using affirmations to stay grounded, and recognising the early “tension signals” that signal it’s time to speak up. You’ll learn how to navigate disagreements without defensiveness, communicate with confidence, and act in alignment with your values—even when it’s uncomfortable.
Episode 516
🦞 Pre-order Learn Like A Lobster:
🇺🇸 PRH US – https://bit.ly/3KxTeBn
🇬🇧 Amazon UK – https://amzn.to/3KcRZaR
📚 Resources Mentioned
Getting Along by Amy Gallo - https://bit.ly/43XtfdJ
Celeste Headlee’s TEDx talk: 10 Ways to Have a Better Conversation - https://youtu.be/R1vskiVDwl4?si=3PFsc2v2v1xK9fy_
Dr. Sunita Sah’s Defy: The Power of No In A World That Demands Yes - https://bit.ly/3KfPuF7
How to Preempt Team Conflict — Harvard Business Review - https://hbr.org/2016/06/how-to-preempt-team-conflict
Previous Squiggly Careers interviews with:
Amy Gallo - https://youtu.be/iO7Q1g7u0SY?si=Pm5srmx-7AgkjIaP
Celeste Headlee - https://www.youtube.com/watch?v=IC9kT476GL4
Dr. Sunita Sah - https://open.spotify.com/episode/6ELoznhCWtk5vlONAlY3wC?si=z6i8C1JOT_21aQ0HeNiZzQ
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