The best way to fix a borked work relationship is to just avoid ever talking about it, right? Right?
This week, we hear from letter-writers who are feeling trapped by their workplace relationships. One has a colleague who constantly escalates problems to management without talking to them first. Another quit their job a month ago, but is still being asked for free labor from their old workplace. Join Jen and Sara as they help these letter-writers prepare to have some difficult conversations, reset their barometers of what’s “normal” in the workplace, and decide what behavior they’re willing to accept from their coworkers moving forward.
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Jen Dionisio 0:00 I'll be honest, for a good chunk of my professional life, I would have rather stuck a fork in my eye than have a "let's talk" conversation with a colleague. But I learned over time that by like not going straight to the source and speaking candidly, very rarely did anything change.
Sara Wachter-Boettcher 0:35 Oh, my God, Jen, I'm so happy you're taking the wheel today. I am completely vacation brained.
Jen Dionisio 0:40 Oh, it's so soon. What, you have two days till you go to Austria?
Sara Wachter-Boettcher 0:43 Two days and then, y'all, I'm gonna be going hut-to-hut hiking in the Austrian Alps. And either you heard that and you're like, "Oh, my God, that sounds amazing," or you heard that and you said, "Yeah, absolutely not." Either way, I'm excited for it.
Jen Dionisio 0:58 Oh, it's gonna be incredible. Well, I will let you take it as easy as possible today so you can get ready to get out of here after this.
Sara Wachter-Boettcher 1:07 Well, on that note, welcome to Per My Last Email—the show about what to do when work gets weird. I'm Sara Wachter-Boettcher.
Jen Dionisio 1:13 And I'm Jen Dionisio. So Sara, what kind of weird are we covering today?
Sara Wachter-Boettcher 1:18 So today's show is all about standing up for yourself and, like, how do you reset expectations in a work relationship?
Jen Dionisio 1:25 This has been coming up on a lot of my coaching calls over the past couple weeks. I'm talking to a lot of people who really started their jobs in like, hustle mode, you know? So all of those people-pleasing behaviors are out, and they've been saying yes to everything, and they've been so helpful, but then once they get burned out, they worry that starting to set boundaries now, after they've presented very differently, makes it too late.
Sara Wachter-Boettcher 1:52 Oh, I so feel for that. And I have definitely heard that a lot as well, and it's one of the things, you know, I keep coming back to that when you train people to expect you to always be there and always be helpful and always jump in, that's what they learn. And it oftentimes ends up kind of backfiring on people. Like, it makes them feel valued at first, but it then makes them feel valued in these really small ways, and not actually for the real expertise that they bring, the perspective that they bring, but just for the fact that they can be kind of a workhorse, and like, I just want everybody out there to be valued for something deeper than that.
Jen Dionisio 2:28 Yes, oh, when you look at my grave at the end of my life, I really hope it doesn't say something like "Really put in a lot of overtime."
Sara Wachter-Boettcher 2:37 "Did three people's jobs without complaint."
Jen Dionisio 2:41 "Said yes to every weekend request."
Sara Wachter-Boettcher 2:44 No, absolutely not. Okay, Jen, let's dig into these questions, though, because I think we got some people to help today. Are you ready?
Jen Dionisio 2:52 I am.
Sara Wachter-Boettcher 2:57 Okay. Our first dilemma today comes to us from a content designer who's working in big tech.
PR 3:03 I recently joined a company where escalation is common practice - to the point that if I say I'll deliver something on a certain day and that day rolls around and I haven't yet handed it off, the PM goes to my manager before checking in with me (i.e. not when it's late, but when it might be). When I joined, I took over work for someone whom they didn't consider very reliable. Then, there were unexpected approvals that the PM knew about but weren't shared with me until well into the project/just before handoff. The PM knew this, and my manager, thankfully, has my back. But, I feel like I'm starting out from a very defensive position, and am working very hard not to play the blame game, while trying to figure out how to level out our standing.
I'm working on building trust, and maybe it's just going to take time, but I was hoping that being new would give me a bit of a jumpstart. How do I (and is it possible to) push the reset button on this relationship?
Jen Dionisio 3:57 Oh, my god.
Sara Wachter-Boettcher 3:59 Yeah. Okay. So Jen, I want to call this person PR, for "Push Reset." So I'm curious what you think; can she push reset here? And, like, how can she push reset here?
Jen Dionisio 4:10 I actually absolutely think that PR can push reset. I think my gut in hearing this, even with that groan, is that there is actually, like, a lot of room to improve this situation. It sounds like PR and her PM haven't gotten the fresh start that both of them need. And it sounds like fear and anxiety are kind of driving this dynamic, even though, like, there's a whole new cast of characters in the mix from who was there before.
Sara Wachter-Boettcher 4:38 Yeah. And it sounds like this is just such an easy place for PR to start to, like, fret and spiral and try to prove herself. And, you know, I just don't think that that's gonna make PR feel better. And so, Jen, I'm wondering where you'd start.
Jen Dionisio 4:50 Yeah, I think PR, we're gonna have to go inside before we go outside. I wanna start with you, not because you are at all to blame for what's going on, but because I do want you to be as clear and confident as possible before you talk to your PM about what things have been like for you since you started. You've described yourself as being in a defensive position. And I know for me, when I feel like I'm under a bunch of scrutiny, I tend to really overdo things. I get really perfectionistic about my work, which tends to slow me down. I really hyper-fixate on like things, like language choices and like how I'm expressing every thought in my head. I start obsessively documenting things to cover my ass.
And I definitely take that scrutiny really personally, and I think of it as this, like reflection of my skill or competence, which all of that ends up being completely exhausting. And so PR, like, that's what being on defense looks like for me, but I'm curious what that looks like for you. What is the impact of that on how you're feeling about work, how you're doing your work, and how you're engaging with your teammates around your work? Is it triggering you to overdo it, or is it more sapping your motivation? It could be that it's like making you feel insecure about your work, or more irritated that you're not being recognized for being the responsible colleague that you are. Or it might be making you act kind of meek and agreeable, or, on the flip side, maybe it's making you really argumentative and short with people.
Once you've gotten really clear on what being on defense looks like for you, what I'd like you to do is actually try to picture the opposite of being on defense. Maybe you can base that on how you've acted and felt at previous jobs or in really successful collaborations or projects that you've been on in the past. You know, it could be painting a picture of how you'd like to be showing up instead. Whatever approach you take, basically, it's just really important to have a reminder that you have other options for how you're being, and I think that can also help you really recognize this moment as abnormal and give yourself a vision of what a better normal could and should look like for you. So often people find themselves in situations like this and go into that people-pleasing mode, and you sort of think, like, "If I can just prove I'm trustworthy and reliable and capable, then this situation will resolve itself. So let me do and show and say more."
Sara Wachter-Boettcher 7:31 Yeah, I have seen that one a lot: "Oh, you're afraid I can't deliver on time? Well, I'll show you. I'll over-deliver. I'll do everything. I won't stop delivering." And it's like, okay, hold up. We don't need to do all that.
Jen Dionisio 7:43 Yeah, because it's not sustainable, right? Like,
Sara Wachter-Boettcher 7:45 No.
Jen Dionisio 7:46 You will exhaust yourself trying to prove yourself in that way. And it actually doesn't guarantee that the other person will get past their own, like fears or worries or biases to even see all of these things you're doing behind the scenes to try to put them at ease.
Sara Wachter-Boettcher 8:01 Totally. I see this so often where people are working so hard, and they feel like their efforts are invisible because they aren't talking about it. They're just like, "Well, I just have to prove it, but I can't have a conversation about it." And then the other party, if they already have a story in their head about what's happening, or have a story in their head about what you're like, their brains really love to hang on to those stories and like, look for confirmation that what they already think is true. Simultaneously, our brains like to discount anything that negates the story we've already told ourselves.
So if you try to just overwork and overwork and overwork and think that that's going to change someone's perception, it might not because their perception is so clouded by bias. I mean, that's a human thing, and something has to actually disrupt that. And oftentimes it's not enough to just try to prove yourself. That's a way to just get really tired. Anyway, Jen, let's say that PR isn't going to go down that path of just like proving themselves over and over again, so after they've looked internally, what do you think they should do next? Like, how do they start making those inroads with their product manager?
Jen Dionisio 9:08 You know, it sounds like, from what PR shared, that they're pretty emotionally intelligent and have a good sense of the context that's underlying all of this. PR said that she's trying to avoid the blame game, and that she's like working on building trust. And when I hear that a big goal here is to kind of level out the playing field between the two of them, I mean, to me, that feels totally attainable. It doesn't sound like PR is trying to, like, "win," which is usually a really unproductive goal for trying to find common ground.
Sara Wachter-Boettcher 9:42 Yeah.
Jen Dionisio 9:42 But it sounds like PR is genuinely trying to create a better outcome for both herself and the product manager. And does the PM share that goal? I don't know. The question I'd pose to PR is to start to understand, if not, what is motivating that PM to behave the way they are? Sara, I think this is where your 3P's framework might help PR get much clearer on what this looks like from the PM's perspective.
Sara Wachter-Boettcher 10:11 Yes.
Jen Dionisio 10:12 As a reminder for everyone, I know we've mentioned this before, but the 3P's are Perspective, Pain Points, and Priorities. So the perspective piece is asking yourself questions like, "What do I know about what things look like in this person's world? What is their day-to-day experience like?" For pain points, the second P, it's questions like, "What do I know about the pressures and challenges that this person faces in their own work?" And then the third P, priorities, is around questions like, "What do I know about how they define success and what really matters to them? Sara, I think we can fill in some blanks here based on what PR shared.
A definite priority for this PM seems to be getting work in on time, if not early. But the question is: why? Beyond the obvious, what's driving that? PR mentioned that the person who previously had their role wasn't very reliable, and maybe that caused friction on the team. Maybe that caused friction with leadership or other key stakeholders. You know, maybe a pain point is that, because of all of these earlier setbacks or stumbles, the PM is like really under fire from people to be delivering everything perfectly and punctually and without any ripples, and their own fear of the team missing the mark is really making them do these frustrating things, like talking to PR's manager before talking to PR. Or it might be impacting the quality of their own work, which might explain the like last-minute info about approvals that really threw PR off. I, like you, Sara, come from consulting, so escalations have been a regular part of my work life.
Sometimes they're really helpful and really needed, but other times it feels like, "Did this really need to go up the chain? Or could you have solved this with a very quick conversation or email?" I'm thinking of one particularly frustrating example from a past job where a PM escalated my team member's work to me, and it was really early in the project, so I was confused by how things had gotten like this dire and intense so quickly. I had been reviewing their work and presentations and had seen nothing alarming. I felt even more confused because I could not find anything to flag as faulty.
And ultimately, I found out that the PM came to me before speaking to either of those people. And that really pissed me off, because it turned what could have been a normal feedback conversation with those folks into like, a big fucking deal that also my boss got pulled into. But like in hindsight, I found out that there were things happening to that PM that I just wasn't really aware of at the time. You know, a lot of that pressure coming from her was actually truly coming from the project sponsor, who was like, "Why is content strategy on this project?" Like, they were already primed to try to find faults. And it wasn't even just the content strategists, like that sponsor was pretty suspicious of everyone. So the wider team, not just my two people, were also getting secondhand heat from this PM, who herself was getting micromanaged.
And we learned that that anxiety was really at the root of what caused her to start micromanaging everybody else. Her anxiety was super high because she had been removed from a previous project and was worried she'd get fired if this one didn't go well. And so, like, I didn't have that info when the PM started chatting with me about my team members. And, PR, I'm guessing you don't have that complete story either. Now, you can make some educated guesses, and since it sounds like you have a pretty solid relationship with your new manager, they might actually have some insight into what the PM's life and history is like that might fill in some blanks for you, too. But also, I want to remind you that, like even our most educated assumptions should be held kind of lightly. We can't actually know what's in someone else's head. So the best way to get the information you need and to really answer the questions that are in those 3P's is to go to the source: your PM.
Sara Wachter-Boettcher 14:38 Yes, okay, I'm so glad we're here. I think this absolutely warrants a direct conversation with the PM.
Jen Dionisio 14:43 I mean, it's where all roads will ultimately lead, unless PR just decides to quit.
Sara Wachter-Boettcher 14:49 Yeah.
Jen Dionisio 14:50 And it doesn't seem like that is an option to entertain this early in the process. PR, if you are following these suggestions, then you should start to really like, get a sense of what you would imagine a healthier relationship looking like between you and your PM, and then you'll have some context for what's getting in the way or making that harder than what it needs to be. But it's gonna take two of you to hit that reset button, which means, yeah, talking it out. Unfortunately, it does sound like you're gonna be the one who has to initiate it. So you might want to think about some ways that you can introduce this issue.
Maybe you keep it general, like, "I'd like to talk about how we can best support each other on this project." Or you could get more specific about one of the situations that has really caused you a lot of stress, like, "I noticed that my manager was messaged instead of me when you were worried about this deadline. It caused me a lot of stress. Can we talk about how we might handle moments like this in the future?"
Sara Wachter-Boettcher 15:54 You know, I could even see PR potentially going further than like, "How might we handle moments like this?" and actually starting to make a request, like, "Hey, I can see why you'd be worried about hitting deadlines, you know, given what's happened in the past. If you're feeling worried like that, I just ask that you please come to me first to check in before asking my manager. I want to be a great teammate, and I want us to trust each other. And for me, having that open line of communication is going to really help."
Jen Dionisio 16:19 Ooh, yeah, that amount of directness and candor also gives that PM a sense of your 3P's, which are also really important in this dynamic. But PR, however you introduce it, like, the goal should be less about rehashing what's happened before, and more about how you want things to work and how you want to work together moving forward. What does a relationship look like that gets both of your needs met? What does it require of you, what does it require of them, and what are the obstacles that you might need to prepare for or really stay aware of as you're working through this new dynamic?
I'll be honest, for a good chunk of my professional life, I would have rather stuck a fork in my eye than have a "let's talk" conversation with a colleague. But I learned over time that by like, not going straight to the source and speaking candidly, very rarely did anything change. I keep trying to anticipate their needs and meet them, get upset when their behavior didn't change, and then, like, repeat the cycle over and over, which left me just like, anxious and frustrated until something external resolved the issue for us, like a project ending or somebody leaving the company entirely. And PR, I know you don't want to continue that cycle, so my hope here is that your PM actually doesn't either, and I think by opening up the conversation, you're giving both of you a chance at having a successful and collegial relationship and maybe someday even a friendship. It's not going to happen overnight.
As you mentioned, PR, like you've been working to gain their trust, and I suspect now they need to do a little work to gain yours. But once you've had this initial conversation, you can refer back to it when things get wobbly again. Like, "Hey, managers told me you were asking when I'd have this deliverable ready. Last month, we talked about you checking in with me first. What made it hard to do that this time?"
Sara Wachter-Boettcher 18:18 I love that question. I love it because it doesn't chastise the other person, like, it's not, "How dare you go over my head again," which I suspect would not result in a very productive conversation. But it's more like, "Hey, can we have a moment where we might trigger some reflection from that, PM?" It's like a moment of pause to be like, "Oh, maybe we slipped up here."
Jen Dionisio 18:38 It lets you kind of intercept some of these really, like, reflex actions and behaviors right when they start so you can, like, work together towards maintaining the relationship that you'd both rather have. Nobody's gonna get it 100% perfect or right. You know, if your PM is used to getting really anxious about not knowing where deliverable stands and feels like they need to talk to somebody, they might slip out sometimes, but then you can kind of come back to those agreements and try again and be more aware of what things you might be doing to trigger each other.
I can't guarantee that your PM is going to be an active participant in this process. They may want to hold on to their defensive posture much more tightly than you are holding on to yours. But the good thing is that maybe your worst case scenario is that you can have confidence that you've done the mature, responsible thing, and hopefully feel a lot less pressure to try to prove yourself to the PM.
Sara Wachter-Boettcher 19:38 Yeah, I'll underline that, because I think it's so important to remember, PR, that you don't control how your PM reacts. But we do tend to feed off of each other's emotional states and meet people where they are. You know, if you've ever been talking to somebody who was really agitated and getting more upset, and then you found yourself getting more upset, it's really common. And so it sounds like, right now, your PM is stuck in that state of worry, and some escalation is coming out, and you've recognized you don't want to meet them there.
You've recognized you don't want to live that way. You don't want to be on defense. And so the work that we're talking about here is really about grounding yourself so that you don't meet them where they're at and instead show up more intentionally and calmly. And what that does is, in addition to keeping you calm, it actually gives your PM a chance to meet you where you are, instead of you meeting them where they are. And I hope they take that chance. I think their worry is valid. It's okay to be worried about something not going to plan. It's okay to be worried about somebody missing a deadline, especially if you have some baggage around that, but I hope this gives them a chance to really think about their behavior and to think about whether their behavior when they're worried is actually how they want to be showing up.
Jen Dionisio 20:47 PR, I'm really sorry that this is how you're starting your new job. I'm sure it's really frustrating and a little bit worrying too, but I truly do have high hopes that this is a bump in the road that you're going to get past and that your PM is going to join you on, so good luck.
Emily Duncan 21:04 Hi. It’s Emily—PMLE’s producer. Over the past few months, reading your submissions, Sara, Jen, and I have noticed a pattern: a lot of you out there are questioning all the things you’ve been conditioned to do and be—and getting curious about what it would be like to try something else. That’s why we’re so excited to tell you about our next big community event. It’s called Flip the Script, and it’s a virtual mini-retreat on August 2. We’ll kick off with Jen talking about how to start again when you’re feeling totally lost, and close with Sara helping you rewrite the stories you’ve outgrown. In between, we’re welcoming Active Voice community members to discuss how they’ve learned to let go of who they’re supposed to be—and guide you through practices that celebrate who you are right now. The event is pay-what-you-wish and will be recorded if you can’t attend live. So go to https://www.activevoicehq.com/events to get your ticket. We can’t wait to see you there!
Sara Wachter-Boettcher 22:03 Okay, Jen, are you ready for our next question?
Jen Dionisio 22:05 Yeah, bring it.
Sara Wachter-Boettcher 22:07 Okay, so this one comes to us from a nonprofit leader. Let's hear it.
PD 22:10 I left my Executive Director job last month, and started a new job. I was at my previous role for 3.5 years and gave 3.5 weeks notice. Since I left, the board chair of my former organization has texted me several times with questions. I am now a month into my new job yet I have tried to be helpful. This past weekend he texted me several times on Saturday afternoon. He asked me to meet with him this week to give my advice and knowledge about a situation currently happening at the org. He didn't apologize or indicate that this request was unusual, just told me to keep in mind that he wasn't available on Thursdays. I have never been in a situation where a former employer has texted me and asked me to do uncompensated work for them. It felt disrespectful and inappropriate. I told him I was unavailable to text or schedule a meeting because it was the weekend and I was at an event. Then I haven't followed up.
I left this job because of the board's general lack of care for my well being. I'm now in a place where I am seeing what it looks like to be treated differently. Perhaps for this reason this exchange really upset me. I felt like even leaving this job wasn't saving me from the pattern of mistreatment I had experienced and it brought back a feeling of despair I thought I left behind. I don't think he thought he was being inappropriate but I don't think it's my job to tell him how to treat people. At least it isn't anymore. I also know that I need to be better at saying no. For what it's worth, I am happy to answer questions from staff and the interim who was my deputy because they are lovely people who love and respect me. And they also would never text me on a weekend and demand my time in that way.
How do I disrupt this pattern and let them know that I am not available, but do so without having to do emotional labor or having a difficult conversation. I thought leaving was a clear signal that I didn't want to work with them anymore. BTW he has said he was interested in having an exit interview to hear about why I was leaving and it never happened.
Sara Wachter-Boettcher 24:11 Jen, this board member has some audacity. Not even asking, but just assuming she's available at his whim.
Jen Dionisio 24:18 There are so many board members that just think the world revolves around them like, no thank you, sir. Keep your freaking money.
Sara Wachter-Boettcher 24:26 And she's not even getting any money. Like, she doesn't work there.
Jen Dionisio 24:30 Yeah.
Sara Wachter-Boettcher 24:30 "I don't work here, sir." Okay, but I do understand why this would be hard. I would have a hard time with this as well.
Jen Dionisio 24:35 Totally.
Sara Wachter-Boettcher 24:36 Let's call this question asker PD, for "Pattern Disruption." So my first question to you is, what might PD do about this board member, knowing that she's not interested in like, repairing the relationship. She's really only interested in him respecting her boundaries?
Jen Dionisio 24:51 I mean, PD, this is one of the rare occasions when I will give you permission to just straight up ghost this person if you want. Ignore their calls and texts. You can consider this sort of your like zero emotional labor option, because, to your point, like, none of this is your job anymore.
Sara Wachter-Boettcher 25:07 Yes, this is an option. And you know, PD, since you don't want to repair the relationship and you don't work there anymore, I think it's really healthy to remember you don't owe this to him or to anybody else. However, I will also say I know that the nonprofit world can be pretty interconnected, and I know that sometimes there can be some reputation risk if you just, like, ghost a board member that could potentially have ramifications down the line. And, like, I don't know how much PD cares about that right now, but maybe she does.
Jen Dionisio 25:33 Yeah, I think hearing that PD is wanting to get better at setting boundaries and, like, learning how to say no, it makes me think this might actually be a nice, low stakes way to get some practice doing that with somebody who doesn't have the same amount of power over you right now that they would if you were directly working together. I don't mean to say like low stakes to diminish how stressful the transition's been, but really it is just that reminder that you don't need to negotiate with this guy. You actually only need to tell him where you stand.
Sara Wachter-Boettcher 26:04 Right. Like, what's he gonna do? Fire you?
Jen Dionisio 26:05 Yeah.
Sara Wachter-Boettcher 26:06 Again, you don't work there.
Jen Dionisio 26:07 Yeah. "Fire me. Great. I already left." So I'm like, kind of picturing that PD could send one of two different types of emails.
Sara Wachter-Boettcher 26:20 Email, email. Okay, let's pause here. I love that you mentioned email, because PD talked a whole bunch about being texted and called and like, maybe that kind of communication is normal in their org, but it feels particularly intrusive and personal when you, again, do not work there anymore. So I really support this idea of shifting to email, because I think it can kind of like formalize the communication: "Dear sir, I am writing you today to provide you with this important bulletin about how things will be." I think it sort of sends a message also that you're just not going to engage via text. That like, that's not what you're doing. It's like, "Stop lighting up my phone. I don't answer that." And if every time somebody tries to text you, you refer back to email, that can send a message. Anyway, Jen, tell me about these two emails.
Jen Dionisio 27:04 Okay, so I would imagine the first would outline the conditions of your engagement with him and other board members. So something like, "I am available to answer questions via email only on Mondays and Thursdays. Any messages received outside of these days will be addressed on the next Monday or Thursday." So sort of like training him out of this expectation of, like, immediate reaction and response. But there is actually a big, huge problem with this option, and that is, you are still offering to participate and engage, so you know you're also opening yourself up to him ignoring your instructions and continuing to upset you.
And you're continuing to do unpaid work for this person who, as you said, actually caused you to leave the org, which is not great. So I'd say the other type of email you could send says something more to the effect of, "As a professional courtesy, I have continued to answer questions and address issues in the org through my transition. However, I don't actually have the capacity to continue responding to these requests. So moving forward, I ask for you to address any questions or ideas to the Interim Executive Director and not me. I am wishing you all the best in this new chapter, peace out forever." Maybe not that part.
Sara Wachter-Boettcher 28:30 But like, "Wishing you all the best in this new chapter," is such a subtle middle finger, and I love that.
Jen Dionisio 28:36 Again, to the point of why email is probably the best medium for this, you have now this request and this boundary clearly defined and very clearly documented. And if the board chair protests, then you can ignore it. If the board chair continues to reach out, you can ignore it too. And I know you said your interim is a really lovely person, and I'm sure you may feel some guilt sending this guy their way, but the truth is, they are getting paid to deal with him, and you're not. And if you want to donate any free labor, you can use it to support them instead of the board chair. So problem solved.
Sara Wachter-Boettcher 29:18 Well, one problem at least.
Jen Dionisio 29:20 Yeah.
Sara Wachter-Boettcher 29:20 I was also really struck by PD's mention that the situation brought back a feeling of despair, which, despair is always a flag word for me. And she also says that she needs to be better at saying no. And so Jen, I'm wondering two things, like, one, how might she work through her feelings about her old job so she can kind of put it to rest emotionally? And then two, what would it look like for PD to work on setting and communicating healthier boundaries in this new chapter of her life?
Jen Dionisio 29:46 I think it's so common to find your escape from like a really toxic workplace and feel like, "That's it. I'm moving on, and now everything is just fine." Problem is those three and a half years you spent at this nonprofit, PD, you're not going to just jettison all those feelings and memories because you aren't on the staff list anymore. I don't know all the details about your time there, but that sudden swell of despair definitely suggests that it was a really tough time, and it still weighs on you pretty heavily. So I'm wondering what closure might look like for you. Maybe it's processing your experience with a therapist or a coach or friend.
Maybe it's giving direct feedback to former colleagues and the board members about how they treated you. Maybe it's like something more personal and unique to you, like rituals around writing letters. Like maybe one to your past self or a kiss-off letter to your org that you never send but lets you really get all of that anger out. However you do it, I think the important thing is just to process your feelings, understand potential triggers for the future, and reclaim the parts of you, like, these really wonderful parts of you that may have been kind of diminished or wounded while you were there, so you can live this new chapter of your life without being haunted by the past, and can really enjoy the good that is here and will be coming in the future.
Sara Wachter-Boettcher 31:19 Oh, I love all these ideas, like writing this letter to yourself, or, you know, just doing some of that reflection. But I'm wondering, when you say, like, "process your feelings and understand potential triggers," I'm curious if you can give any questions that PD might ask themselves to help them, like, figure out what those even are?
Jen Dionisio 31:35 Yeah, you know, I'd ask myself questions really rooted in the experiences I've had. So they might be things like, "When was I most stressed at this job? What made my relationship with the board most challenging? What regrets do I have about things I said yes to or no to?" And I'd also couple that with questions that look at the good from that time too, so that you know, you also get a sense of what you want to protect in this new job. Like, "What am I proudest of from my time there? When did I feel the most like I really belonged? What activities gave me the most satisfaction day to day?" So I think from there, you can start to reverse engineer what some of those negative triggers are, and, like, what some of those positive ones are too.
Sara Wachter-Boettcher 32:23 So if PD does some work to, like, reflect and get a little bit more closure from that past job, how might you address the other comment, which is, like, "I need to be better at saying no," what can they do to kind of bring what they're learning into that new job?
Jen Dionisio 32:39 You know, I'm hearing such a strong story in this I think a lot of us tell ourselves this that like, "I'm bad at saying no. I'm bad at saying no in X kinds of situations." PD, I really hope that you're not beating yourself up for that. You were a different person when you were the ED of this nonprofit, and you've learned a lot from that experience. And so like, while you're coming to terms with what's happened again, I think it's really important to have a vision for how you want to show up now, and it sounds like you'd like to show up as someone who sets and honors their boundaries and says no when they need to. That's your story now. You know we tell people that you have boundaries, whether you share them with people or not, and you can tell what they are when they're being violated.
You know, those feelings of upset, whether that manifests as like irritation or confusion or panic and anxiety, like, they can tell you a lot about what behaviors you can and can't tolerate. And once you start to spot those signals, you can decide what boundaries you need to set that will protect you from experiencing those emotions again and again. And it sounds like right now, you're in a pretty supportive space at the new company, and I think that sounds like a much safer spot to start practicing these boundaries than where you were before. Say, you start getting weekend texts from one of your teammates, like, what's the boundary you might set knowing that's not something that works for you? Maybe it's something like, "Hey, I'm off the clock this weekend, but I'll give this a look on Monday when I'm back in the office." Is that going to be a little scary to do the first time? Absolutely.
It might be scary to do forever. You might start to tell yourself more stories about how you're being too rigid or not helpful, or, you know, whatever criticism runs through your head, and yeah, that's gonna feel a little bad and icky, but so does taking time out of your weekend to deal with work. And sure, there's absolutely a chance that the other person will push and press and try to get you to do what they want, but there's actually as likely a chance that the person will just be like, "Cool, roger that. Talk Monday," with no drama at all.
Sara Wachter-Boettcher 35:05 And you know, if the person does push and press and try to force you into it, I feel like that tells you a lot about them and about how you might need to protect yourself from them, as opposed to actually being a reflection of you.
Jen Dionisio 35:18 Yes, and so like practicing these hard conversations actually lets you get a lot of intel about what these other people are all about and who you can trust and who you can't. Sara, whenever we talk about this, like, I love how you always say, "Practice saying the words with your mouth."
Sara Wachter-Boettcher 35:39 I do say this a lot. I said it on a call yesterday. I think about this often, because it's so easy to be like, "Oh yeah, I learned the skills for hard conversations. Got it." But then you never actually say it out loud, and it stays hard. I think the first time I realized this was like, 10 years ago or so, a friend needed to negotiate a salary, and it was way more than they'd ever been paid in the past, and they were really terrified to say the number out loud, it felt like foreign and uncomfortable. And so I think that can be true for any hard conversation, and definitely about boundaries. It's like, "How do I even use those words?"
Jen Dionisio 36:16 Yeah, like when "No. Period," is not in your vocabulary, it's gonna feel really uncomfortable to speak for a while.
Sara Wachter-Boettcher 36:23 Yeah, like so for this friend, what we did is we just went back and forth on the phone together, saying the salary number out loud over and over again. She would say it, and then I would repeat it a little louder, and then she would repeat it a little louder, and then at some point it was just a number. Like, you know when you say a word so many times that the word stops seeming to have meaning to you? That's what we did. And then at some point it was just like, she could say that word all day.
Jen Dionisio 36:46 I love that you mentioned that because I did something similar in this theater class I took. It was around kind of breaking people-pleasing behaviors. You'd practice with a partner, and they would say, like, "Please," in these, like, increasingly dramatic and emotional kind of tones, and then I would have to respond by saying no with the exact same energy. You know, so like, "Please?" "No." And it was so silly, but it was also so powerful, like, because, like, you're saying, the repetition took all of the sting out of the word.
Sara Wachter-Boettcher 37:25 Yeah, it's just a word.
Jen Dionisio 37:26 It's just a word. And I always recommend starting with some low stakes no's to build up that muscle if maybe you don't have a friend or a colleague that you could practice with. So like, let's say that you're invited to, like some event or meeting. That's a pretty common situation where we just kind of reflexively say yes, even if we don't need to be there, or we don't want to be there. We're super busy. It's inconvenient. So what would it be like to try a "No thanks," instead of coming up with some like, long winded apology or excuse about why you can't join? And you may find that at first, it's a little easier to do that over email or like a chat than in real time. If you type something out, you type your no out, you can get more comfortable saying no while also buying yourself time to think.
Practice following any request of you, whether you're interested in it or not, with something like, "That sounds great, but I need to think about it and get back to you." As somebody who really likes to say yes to things because I get excited about them, like I have also had to practice saying no to things I want to say yes to because I know I don't have capacity or energy or time for it. So I want to really reiterate that it's okay to practice and prepare and not be good at this off the bat. It's all strides towards getting more and more comfortable and more and more desensitized to the use of that word no. You know, and it's also really beneficial right now, as your new colleagues are getting to know you and your preferences to kind of see some of these initial no's, however big or small they are, so that they set these expectations that you're not a default yes to everything that comes your way.
And so, like, right now I'd recommend thinking of one boundary that you'd like to start practicing, and give yourself permission to be as awkward or uncomfortable through that practice as you need. There's also nothing wrong with naming that. I could imagine you saying something like, "I took a lot of weekend calls at my last job, and it really started to make me burn out. I hate saying no to you, but I also know if I say yes, I'll end up paying for it." Kind, normal, healthy people will not fault you for that. They may even actually admire you for it. You might inspire them to do it too. And frankly, anyone who does fault you for that probably needs to check in with their own baggage and their own boundaries, because that is not about you.
Sara Wachter-Boettcher 40:10 Amen. If only more bosses and board members would do that work, our inbox would be a very different place.
Jen Dionisio 40:16 Sure would. So take care of yourself, PD, and remember, you actually are on the other side already. So don't let those old ghosts drag you back into the past. Say no to that.
Sara Wachter-Boettcher 40:30 Again, you don't even work there.
Sara Wachter-Boettcher 40:41 And that is it for this week's episode. Per My Last Email is a production of Active Voice. Check us out https://www.activevoicehq.com/ and get all the past episodes, show notes, and full transcripts https://pmleshow.com/. This episode was produced by Emily Duncan, and our theme music is "(I'm A) Modern Woman" by Maria T. Go buy her album at https://thisismariat.bandcamp.com/. Thank you to Push Reset and Pattern Disruption for submitting their stories for today's show. And thank you so much for listening. If you have a work dilemma that's eating away at you, send it to us. If you go to https://pmleshow.com/ you can submit your story right there. See you next time.