Transcript

Chris LoSacco: Yeah, I’m gonna turn the radio off.

Gina Trapani: (Laughs) Yeah, that station is not helpful.

(Both laugh)

Chris: That’s right.

Gina: I’ve had to learn.

[POSTLIGHT INTRO MUSIC]

Chris: Hello and welcome to the Postlight podcast. I am Chris LoSacco, the president of Postlight, and I’m joined as always by my co-host and partner in this business, Gina Trapani, CEO. How are you, Gina?

Gina: I’m doing great.

Chris: Great.

Gina: What’s up? What’s up? How’s it going?

Chris: It’s going good.

Gina: Good morning.

Chris: It’s going good. There’s lots of things. There’s always lots of things.

Gina: There’s always lots of things. 

Chris: And I think what we should talk about today is how to handle…

Gina: All the things?

Chris: All the things!

Gina: Yes! We should… let’s talk about this. Because on a daily basis, actually, we talk about… on some level, we talk about how to handle all the things.

Chris: Yeah. Well, how long did we look at our calendars yesterday?

Gina: Oh my gosh.

Chris: Just to try and figure out what our week looked like.

Gina: Where to fit everything.

Chris: Yeah.

Gina: It was a long time. And I looked at you…

Chris: Literally hours, I think.

Gina: It was. I looked at you and I was like, “I… this… why have we spent so much time moving boxes around on a grid?” 

Chris: Rectangles in a week, is like… (Laughs)

Gina: Yes. Oof. (Laughs) You know, in my sort of trajectory in my career from, like, individual contributor to leader…

Chris: Mhm.

Gina: That trajectory, there was a point where I was becoming more of a leader, and I would come home, and it was always around Thursday night. And I’d be having dinner with my family, and I would say to my wife something like this: “This week, man.”

Chris: (Laughs)

Gina: “It was a lot. It was a lot.”

Chris: It was a lot.

Gina: “And you know what, I’m almost there. And as soon as this…” Insert whatever big thing was happening…

Chris: “Then…”

Gina: “…is behind me, then I’m gonna be golden.”

Chris: Oh my God.

Gina: Then I’m just… it’s gonna be so normal after that. Like, it’s gonna be cool and chill and I’m gonna feel like I have everything under control. I don’t have everything under control right now. But that’s just this week.”

Chris: Right.

Gina: “Next week is gonna be better.”

Chris: (Laughs) I’m laughing because I have had that exact conversation probably 400 times.

Gina: A million times. Right! So then it got to the point where I didn’t realize it, but every week I was saying some version of this to my wife.

Chris: Right.

Gina: So there was a point where I made the face, I guess? That I’m about to say… and she looked at me and said “This week, man.” With a big smile on her face, like…

Chris: (Laughs) Really?

Gina: Just outwardly mocking me. And she was like, “You say this every week. You should just know…”

Chris: Wow. Wow.

Gina: “I just want you to know, you say this every week. I feel like you’re telling yourself a story about how it’s gonna get easier or less hectic, and it’s not. And you should know.”

Chris: Oh my God. (Laughs)

Gina: It was… it was a rough moment.

Chris: It was… that was a rough moment, but also it’s like, you know, you need the mirror held up to you every once in a while.

Gina: Oof.

Chris: Or it’s like…

Gina: Oh, it’s brutal. When it’s your spouse who knows you the best?

Chris: Yeah…

Gina: It’s kinda brutal. It was a brutal moment of reckoning and self-awareness.

Chris: Brutal but necessary.

Gina: Brutal but necessary. Right. So I had to get to this place where I was like, “Oh. This is normal.”

Chris: This is normal.

Gina: When you are a leader, by definition there are always going to be more things that need your time and attention and decisionmaking.

Chris: Exactly.

Gina: And people who need you. There are going to be more needs than you have capacity.

Chris: Always. 

Gina: Always. Every day.

Chris: Right.

Gina: And that is a normal state. Nothing’s broken.

Chris: Right.

Gina: That is part of being a leader.

Chris: Yes. And it is a losing proposition to think, “I just need to get on top of everything…”

Gina: Get on top of it. Yes.

Chris: “…so that it all fits.”

Gina: Yes.

Chris: Because you need to step back and realize, it’s never going to fit. You are… you always have to prioritize. You always have to decide, “Where am I going to spend my energy, because I will never get to the bottom of the list.”

Gina: That’s right. I mean, ‘cause the only other option – and I tried this in different ways, is like “I’m gonna wake up at 5 and do two hours of heads-down work before the day starts,” or…

Chris: I’ve done that too.

Gina: “…after I get my kid to bed, I’m gonna handle my email at night.” And this is the thing: this works for some folks, like people have different work schedules and all the thing. And you should manage your time the way that works for you. But the “just do more hours…” “I’m just gonna work this weekend,” is another one that we’ve seen, a pattern that we’ve seen.

Chris: Mhm.

Gina: It worries me, because it feels like an unhealthy pattern, because then on Monday when folks come in exhausted ‘cause they’ve worked all weekend, I’m like “This isn’t… (Laughs) This isn’t sustainable.”

Chris: No, it’s not good. Right.

Gina: Right? So there’s the brute-force method of “I’m just gonna put in more hours,” but that doesn’t work. It’s not sustainable.

Chris: Right. Well, so… can I add two things to this?

Gina: Yeah.

Chris: Are you making your best decisions at 9:30 or 10 o’clock at night? When you’re tired and you’ve just been through a whole…

Gina: No. No.

Chris: No! You’re not. You’re not clearheaded, you’re not being thoughtful.

Gina: That’s right.

Chris: You might, you know, you might have had an espresso after dinner and you’re, like, trying to push through. And yeah, you can respond to a lot of email or write a lot of Slack messages, but are you making good calls? Which is paramount, as a leader. That is what you need to be thinking about, is “How am I making good decisions? Especially for the people around me.” Right?

Gina: Yes.

Chris: I’m setting direction, I am… I’m charting a course forward.

Gina: Yes.

Chris: And if you’re not bringing your best thought and your clearest mind to those kinds of things?

Gina: You’re putting the group and the business or the org or the thing that you’re leading at risk.

Chris: Exactly. Right. You’re completely missing the point of what you have to do.

Gina: Yeah.

Chris: So that’s number one. Number two, people look to leaders to set the tone.

Gina: Yes.

Chris: And if you are the one who is working all hours, you’re putting in time on the weekends, you are constantly playing this game of catchup where you just have to burn the candle at both ends, that’s the example that you are setting for the rest of your company, the rest of your group, the rest of your team.

Gina: Right. You’re showing up at meetings frazzled and overwhelmed, and “Ugh, I’ve got so much going on.” People see, people read those signals.

Chris: Right. And they start to think “Oh, if I’m… success for me is that I have to be…”

Gina: Like that.

Chris: Frazzled, and putting in…

Gina: Overwhelmed, and…

Chris: And then what happens? The work suffers, teams start to break down. It’s not good, it’s not healthy. And I mean healthy in a sustainable way.

Gina: Yeah.

Chris: So it’s absolutely the wrong… it can be this enticing idea, that like, “Oh, well I just need to… if I just sneak in a little bit more here or a little bit more there…”

Gina: “I’ll be on top of it and then I’ll feel relief.”

Chris: “I’ll be on top of it.”

Gina: “Yeah, and I’ll get the trophy.” (Laughs)

Chris: Yeah. (Laughs) And it might work in targeted ways, you know, targeted moments…

Gina: Sure.

Chris: But it’s not a good long-term always solution.

Gina: Yeah, and I mean, look. When I’m responding to something late at night or I’m frazzled or just low on gas, I’m gonna show up more impatient, a little bit shorter, harsher.

Chris: Yeah!

Gina: Little less empathetic, a little less care… you know? Not only making bad decisions, but just not communicating the way I want to show up as… not being able to show up the way that I want to show up as a leader, right?

Chris: That’s exactly it.

Gina: Yeah. So, if the fact that you’re always going to have demands on your time and attention and decisionmaking ability, are always going to be bigger than what you have, there’s I think a really important – critical, actually – leadership skill, which is… and this is going to sound a little woo-woo, and I can’t believe I’m saying this, but I’m gonna say it.

Chris: (Laughs) We’re in.

Gina: Setting and holding boundaries.

Chris: Yes.

Gina: Is so important. 

Chris: Mhm.

Gina: You know, there’s prioritizing, but there’s also boundaries. There’s also saying, like, “I can’t make this meeting, but you know who can? This person.” Or “Please let me know if there’s something you need me for later.” There’s just being, just, a ruthless prioritizer. And saying “You know, this recurring meeting? It’s run its course, we don’t need this anymore. We can end this, and if you need, you know, let us know.”

Chris: Yes.

Gina: Or, “This particular pursuit? I have all these other tasks that are more important, and more important to the business.” Right? And so, I’m just gonna decide not to do this thing.

Chris: Right.

Gina: Being okay with…

Both: Not doing something.

Gina: The lower-priority stuff, yeah. Another thing that I think is really important as leaders, and I think we talked about this a little bit… it’s really easy to just constantly react to fires and to incoming requests. So, like, you’re reacting, you’re always reacting. 

Chris: “What’s next?” 

Gina: “I’m fixing, I gotta run here, what’s the…” Yeah. But it’s so important to… and I think this is part of setting boundaries, which is sitting down and looking at your… and I do this kind of in the morning. And sometimes… you know, we just talked about working on the weekends… sometimes on Sunday evening as I’m looking at the week, “What are my priorities?”

Chris: Yeah.

Gina: What are the things that are most important this week?

Chris: Right.

Gina: And once that’s clear, and other stuff comes at you, it’s very easy to say “You know what? This, actually, this isn’t important right now. I’m gonna delegate this, I’m gonna defer this, or I’m gonna say ‘This doesn’t have to be done, actually.’”

Chris: Right. Yep.

Gina: You don’t have to deal with this right now.

Chris: Yep.

Gina: This takes a level of sort of executive functioning. (Laughs)

Chris: Well…

Gina: Just this level of inward-facing, “Let me look at my calendar, let me look at my task list, let me look at the things that are in front of us and what’s most important for…” in our case, the business, but maybe this is a team that you’re coaching or a nonprofit that you volunteer for, or, I don’t know, a knitting group. Whatever. Anything, any situation where you’re a leader…

Chris: Right.

Gina: You have to think about what’s most important to this group, and where do I focus my limited time and attention and energy and decisionmaking?

Chris: Exactly.

Gina: You’ve only got so many decisions that you can make well in a given day.

Chris: In a given day. Yeah. 

Gina: Which ones are you gonna do?

Chris: Yeah. So, you said two verbs in your sentence, right? Setting boundaries, and…

Both: Holding boundaries.

Chris: And we should talk about holding. But you’re making exactly the point that I wanted to make with setting, which is, it should derive from… what is critical to your business? What are the things that are going to move the needle for you, right? And your company or your group or your division, whatever the organization is. And then make sure that the way that you are setting your boundaries is aligned with that. So, for example, we’re a client services business. That means we need to be talking to clients. So one of our boundaries is, we don’t decline client meetings because of internal meetings.

Gina: That’s right.

Chris: Our clients take priority.

Gina: Over everything.

Chris: And if we need to have a conversation with a project that is not going well, or a new prospect that’s really exciting, we are always going to prioritize that, and we’re always going to make the time for that. And that can be disconcerting, you know, at first, for people to be like “Well, wait a second, we had our one-on-one scheduled,” or “What about this really important marketing session that we were supposed to have?” And it’s like, I get it. But the client’s gotta come first, we are a client services business. Everyone needs to do that calculus for themselves.

Gina: That’s right.

Chris: What are the things that are going to impact the core function of this group, and how do I make sure that those things are defining the boundaries?

Gina: Yes.

Chris: Or, those are… those are how the boundaries are drawn.

Gina: Yeah. I mean, this is… you know. “I have a client call, I can’t make it ‘cause I have a client call,” everyone in our, in Postlight and in NTT data as well…

Chris: Right.

Gina: No one ques… like, “Yes. You should speak to your client.”

Chris: Right. Right.

Gina: “That takes precedent.” And that’s so true for our business too. And I think for a lot of businesses, right? There’s like, new business coming in, or orders, or demand for your services, and then there’s delivery of your services or goods, you know.

Chris: Sure.

Gina: And at any given moment in time, I had to really… (Laughs) I thought that you had to have this very complex model of a business in your head to run it, you know, go down all the details. It’s actually not true.

Chris: (Laughs) Yeah. Yeah, yeah, yeah.

Gina: If you zoom out. Zoom out, there’s like… supply and demand. It’s just two things, right? It’s supply and demand!

Chris: Supply and demand.

Gina: And we play the supply and demand game just… it’s every day.

Chris: Every day. Yes.

Gina: And so, you know, at any given moment in time we’ve had delivery issues, meaning we don’t have enough people to staff, we have a couple client engagements that are not going the way that they were going… we would turn our attention to, how do we optimize great delivery and make sure that we are serving our clients on time? And then there are times when new business is soft…

Chris: Right. Right.

Gina: And it’s not coming in at the rate… right? And so we want to turn our attention… So there have been times when we’ve been… We know, we can see, looking at the business and the supply and demand levers and where they are, we’ve been focused on one, and, you know, we’ve had one of our leaders come to us and say “On the other side, things aren’t going well.” And we’d be like “But… (Laughs) Look at the big picture here.”

Chris: Exactly.

Gina: Right? This is actually the problem.

Chris: Right.

Gina: It’s demand that’s the issue, or it’s supply that’s the issue. So, having just that clarity of the big north star, and also aligning your leaders to it.

Chris: Right.

Gina: Saying “Actually, we have a sales issue right now, we need to be focusing all of our thought there and not fine-tuning our delivery when we’ve got availability.”

Chris: Right. That’s right.

Gina: That’s not the priority.

Chris: This is where good financials come into play.

Gina: Yeah.

Chris: Because, you know, it took us a long time, I think, to realize the impact of… why look at the numbers, you know?

Gina: Right.

Chris: That’s overly reductive, but you can look at numbers in a spreadsheet and think “Okay, I understand why, you know, certain expenses are where they are, and the revenue is where it is, and that’s it.” Or you can say, “This is a decisionmaking lever, and how do I let this financial reporting inform what decisions we’re making?”

Gina: Yes.

Chris: And that’s exactly the point you’re making, right? Because when you look at, you know, your month close numbers, it shouldn’t just be “Okay, I’m keeping a finger on the pulse.” I mean, that’s helpful, but it should also be “What do we need to change going forward?”

Gina: Yes.

Chris: And as we look at our projections for the next month or three months, which is about as far as you can look in this kind of business, how are we letting that inform what decisions we’re making, and where we’re spending our energy on that supply versus demand equation?

Gina: Mhm. Yes.

Chris: And you’re exactly right that it’s very easy to think, well, this is right in front of my face and so I’m just going to react to it, versus stepping back and saying “Where’s the real challenge?”

Gina: What’s our biggest challenge in front of us? Yep.

Chris: Right. And sometimes, maybe more often than not, it’s not actually the thing that’s right in front of your face that seems like the most important, but actually the most important thing is one step away or two steps away.

Gina: Yep. That’s right.

Chris: So let’s go back to… it’s one thing to set the boundaries, it’s another thing to hold the boundaries.

Gina: Mm.

Chris: So, a couple things come to my mind. Like how do you say no? 

Gina: Mhm.

Chris: How do you redirect?

Gina: Yes.

Chris: Especially if you’re getting something that falls into that, like, “it feels urgent” category?

Gina: Mhm.

Chris: You talked before about just sort of letting something fall off the list.

Gina: Slide. Right.

Chris: Or saying, “We’re not going to spend energy on this.” That’s difficult to do. Like, how does that play out in practice?

Gina: This is a big challenge for me. You know, I’m a people pleaser, I want to do all the things. We’re leaders here, I want to take care of all the things. Right? You hold these boundaries, you hold boundaries by saying… first you have to know what boundaries are.

Chris: What they are. Yep.

Gina: Yeah, what they are. And then you have to just kind of calmly communicate them, right? (Laughs) So, like…

Chris: That’s it!

Gina: Yeah. Just… and it’s not, like… not gonna over-apologize, not gonna explain. Just say “I need to leave the office right now. I have other plans. I’m actually, I’m not able to make this meeting, but this person – it would be really good. I don’t think we should focus our energy on… I heard what you said, and I understand that this is a thing that’s going on right now. I think that in the broader picture this other thing is more important, so let’s put a pin in this for now and revisit in a bit.” Or, “I think that this is gonna get resolved by this other thing. Let’s focus there.”

Chris: Mhm.

Gina: There’s like, reframing.

Chris: Reframing.

Gina: Reframing the priority. This is hard, though. Especially when it feels like, “Someone needs me and I’m not immediately at their service.” (Laughs) Right?

Chris: Right!

Gina: And I’m talking about, particularly like, internally.

Chris: Right.

Gina: And look, you have to hold boundaries with a client as well, right?

Chris: Of course!

Gina: Like, this wasn’t our agreement.

Chris: Yep.

Gina: This wasn’t our understanding that this is what we’re delivering. Or, like, we expected that you would deliver this bit of collateral to us that we need in order to get our jobs done and that didn’t happen.

Chris: So therefore…

Gina: Therefore… right, exactly. So, and it’s… and it doesn’t have to be a fire or a blowup or an emotional “I’m so sorry,” and it doesn’t… you don’t have to have a whole thing. (Laughs) 

Chris: No!

Gina: …about, “You did this…” You don’t have to relitigate. It’s just a statement.

Chris: It’s just a statement.

Gina: This is…

Chris: That’s the thing. I actually think it works against you if you make it a whole big thing.

Gina: Yes. Make it a whole big thing.

Chris: You want to de-escalate and make it as normal as possible. And… (Laughs) I laughed when you said “You just need to calmly communicate the boundary.”

Gina: Right.

Chris: That’s the whole story.

Gina: That’s it.

Chris: And it sounds so easy, and it’s not easy.

Gina: Yes.

Chris: It is actually very difficult to do that. And, you know, there are some… like, I love the strategies that you just described, which is like, you can hear what someone is saying and you can acknowledge that it feels urgent and pressing and like it needs to be solved right now, and then also reframe it and redirect it, and say “We’re gonna wait…”

Gina: Right.

Chris: “…to hear the result of this other thing before we do this.” Or, “I know this feels very urgent right now, we don’t need to meet about it, let’s see if it’s still an issue on Monday.”

Gina: Yes.

Chris: And once you calmly communicate it, and especially make people feel like they were…

Both: Heard.

Chris: A lot of the time, they’ll get on board.

Gina: Yeah.

Chris: They’re like, “Okay.”

Gina: “Okay! Sounds like a plan. I want to just… wanted to raise this.”

Chris: Right. “I see that boundary and I’m gonna…” I mean, they’re not gonna say this out loud. But they see the boundary and they’re gonna respect it. It happens with clients, too. I mean, the whole… the name of the game with client services, setting expectations and then meeting…

Gina: Meeting them.

Chris: Meeting them or exceeding them. And if you set the expectation up front that, “Here are the rules of the road,” then when you act in those ways, it’s not a fight, or it’s not a problem, or it’s not a concern, right?

Gina: Yeah.

Chris: You don’t… if you set your working hours, you know, “We are available from this time to that time,” then when people message you out of that time and they don’t get a response, there’s no issue, because it’s like…

Gina: Right. You were clear up front.

Chris: We were clear up front. Here’s the boundary.

Gina: Yeah.

Chris: So… (Laughs) Calmly communicating, setting the boundary. Figuring out how to set them, and how they align with your priorities…

Gina: Right. What they are, what they should be, yep, mhm.

Chris: …and then calmly communicating about them, those are the steps.

Gina: Yes.

Chris: And we’re reducing it to that level.

Gina: Right.

Chris: And we acknowledge that, you know, it’s hard to do that.

Gina: Right, right.

Chris: But that’s the name of the game.

Gina: Simple but not easy. 

Chris: Simple but not easy. 

Gina: Yeah. Because there’s the space of figuring out what the boundary should be. And that’s interesting, right? Like, that’s an interesting thought exercise about your goals and priorities and all those things. But then there’s that practice of set… and here’s the thing. If you set them, if you say up front, “I’m not available from, you know, 6 to 8, because I’m eating dinner with my family,” if you say that up front, then when you’re not available, just like you said, it’s not a surprise. And everyone just accepts. But if you say that and then you are responsive, then it’s like, people are like, “Wait. But you said… you didn’t follow th… you said one thing and then you did a different thing.”

Chris: You didn’t follow through. Right.

Gina: So that becomes, like, a trust issue, and then suddenly that boundary, it’s actually more confusing than not setting the boundary to begin with.

Chris: That’s right. Because then it feels like, “Well, was that really a boundary?”

Gina: Right. There’s a… I don’t know where I heard this. Sort of executive coaching, business maxim, which is like “Show me your calendar and I’ll tell you your priorities.” 

Chris: (Laughs) Wait, what do you mean?

Gina: Like, meaning the way that you spend your time…

Chris: Yeah.

Gina: The meetings that you sit in, and the people that you meet with during the course of a business week…

Chris: Oooh.

Gina: …reflect what your priorities are. Right?

Chris: Got it. Got it.

Gina: And it haunts me.

Chris: (Laughs)

Gina: And you and I are in a lot of meetings together, and we do a Monday morning sync where…

Chris: Yes.

Gina: And this is actually really helpful. This is like, as an engineer I’d call this rubber ducking. You’re more than a rubber duck, Chris. I’ll… (Laughs)

Chris: Can you just define rubber ducking real quick for those who…

Gina: Rubber ducking is when you’re facing a bug or an engineering problem and you can’t, you’re having a hard time figuring out how to fix it. There’s something going wrong and it’s not working the way you expect, and you’re trying to debug it. Rubber ducking is, literally, if you have a rubber duck sitting on your desk, you explain to the duck what is happening.

Chris: Mhm.

Gina: Right? And by the exercise of explaining it, it will bring something to light.

Chris: Yes.

Gina: You’ll think of something you didn’t think of. Oh, did you try this, did you try that. So you and I spend time on Monday mornings looking at our calendar together, saying “Okay, what are the meetings we’re in together? What are the meetings we’re in separately?” And then there’s this part where it’s like “Do we need to be in this?”

Chris: Right.

Gina: Can someone else be in this? Should we decline it? And you and I sort of also… (Laughs) Look at our calendar in desperation, because we’ve got whatever.

Chris: There’s a lot of things.

Gina: There’s a lot of things. And it’s like, then we also have work to do in between the meetings. (Laughs)

Chris: Right. Right.

Gina: And hands-on work. And so it helps a lot, because you and I have this active conversation. I don’t think that I would be as good at managing my calendar if we weren’t having that session where we were, like, talking back and forth. There are very helpful times you’ll say to me, “You know, your meeting day seems not sustainable. You’re gonna be miserable, by 2 o’clock you’re going to be miserable. Why don’t you move this or that?” It’s super helpful. I mean, also… I mean, after 90 minutes of straight video calls, whether it’s 30s or an hour and a 30, you start to just lose your mind.

Chris: Right. Again. It’s like, what are you bringing to that third or fourth hour of meetings? You’re not where you need to be. 

Gina: Right. You just… yeah, you’re wallpaper at that point, you’re a box in the video call.

Chris: Right.

Gina: Yeah, it’s hard to parse new information.

Chris: Rubber ducking the calendar, though, and doing this test where you look at the calendar and say “Does this reflect what my priorities are? And if not…”

Gina: How do I make it reflect?

Chris: Bingo.

Gina: That’s right.

Chris: You’ve also said to me, “We don’t have a client meeting on the calendar in the next 3 or 4 days.”

Gina: Right. Why aren’t we talking to a prospect or a client in the next 3 days, that’s right. There’s something wrong.

Chris: There’s something wrong.

Gina: We should be client-facing.

Chris: Exactly.

Gina: We’re all internal-facing. Why is that? Right? Like, we have to ask that question.

Chris: And when we do that, to your point about reactivity versus proactivity, then we say “Okay, we’ve gotta be more proactive and fix this. How do we get in front of a prospect this week? How do we talk with our digital strategy team and say, we need to, you know, set up a session with X or review this proposal?” Or whatever it is.

Gina: Yes.

Chris: And it drives positive behavior. But you need that moment where you’re saying “Let me analyze this. Let me peel back a couple layers of the onion here to say, are we spending our time in the right places?”

Gina: Yeah. That’s right. There’s also, there’s an energy component too, right? Like, something I said to you recently is, I’m fresher and more energetic in the morning. I know this about myself.

Chris: Oh, yeah.

Gina: After living in my head and my body for many, many years.

Chris: (Laughs)

Gina: And so, you know, with the podcast, there was a point where we’d scheduled a podcast recording late in the day and late in the week.

Chris: I remember this.

Gina: It was 4 o’clock on a Thursday or Friday.

Chris: Yeah.

Gina: And it was just after a long day of meetings, and I was, my energy levels were low. I was feeling just, I was fatigued, and I said to you “I just… this isn’t gonna be a good show.”

Chris: This isn’t gonna work.

Gina: No. I’m not gonna show up excited and happy to talk to you in this moment.

Chris: Right.

Gina: I’m gonna be looking at the clock and being like “Ugh.” You know? So now we record in the morning. That’s something, that’s a… I said that to you, and you were like “You’re right. I feel the same way.”

Chris: And it makes a big difference.

Gina: And it’s 10:30 in the morning, and I’m fresh and energetic. (Laughs)

Chris: (Laughs) You’re ready to go!

Gina: Exactly. Exactly. Yes.

Chris: I want to ask you one more thing. Do you think there’s a gender aspect to setting and holding boundaries?

Gina: Absolutely I do. I do. I think that… (Sighs) I’m gonna make very broad generalizations about gender. But I think that women are socialized to, you know, say yes. To do all the things.

Chris: I think that’s right.

Gina: We see study after study about, you know, women at home, domestic… you know, in parenting relationships or a household in a straight couple where there’s a man and a woman and they both work full-time, women statistically take on more of the duties. It’s funny, something that I have noticed in myself is that if someone at work comes to me with a concern, “I’m concerned about this thing that’s happening…”

Chris: Yeah.

Gina: My immediate reaction is to be like, “I have to resolve this concern.”

Chris: Mm.

Gina: I have to convince this person that it’s not something… we have to come up with an action plan. Like, I take it as a task or a to-do, like “Oh, this person is asking me to solve this for them,” when they aren’t!

Chris: They were just saying something.

Gina: They were just saying something, yeah. (Laughs) And I think that’s just… I don’t know if that’s, you know, I think there’s a gender aspect, I think there’s like, a just… I’m a helper, we’re all helpers, we’re in client services so we’re helpers, right?

Chris: Yes.

Gina: But we’re problem solvers, when we see a problem we’re like, we want to solve this.

Chris: Right.

Gina: But I do think there’s a little bit, there’s a gender aspect. And I think women tend to apologize more.

Chris: Yes.

Gina: This is something I also work on. I find myself starting emails by being, “Apologies for the delay,” and then I backspace, backspace.

Chris: Delete!

Gina: I’m not gonna apologize for the delay.

Chris: There’s no need.

Gina: I’m not gonna apologize for the delay.

Chris: Right.

Gina: I’m responding when I was able to respond, and here’s my response. I’ve been working on that a lot. I’ve been working on, you know, “I think,” or “In my opinion,” okay. Delete. This is how I see it. Like, I’ve definitely worked on being just a little bit more, not having to soften things as much. ‘Cause that is my default bent. And I think part of it has to do with just growing up as a girl, as a woman.

Chris: This is the thing. Yeah. I don’t think this is just your default bent, I think this is… it’s ingrained in society, in the culture.

Gina: Yes. Yes.

Chris: Certainly in America. And I think setting boundaries is one thing, and I think holding them is a whole different thing. And that’s why I come back to, “You just have to clearly communicate what the boundary is.” That is hard. And I think it’s especially hard for women, because there is this expectation or whatever that it’s like, “Well, I have to meet the need.”

Gina: Yeah. I’m here to help. Right. Yeah, yeah.

Chris: We’re, you and I are here, to give you permission that you don’t. You don’t have to do that.

Gina: That’s right.

Chris: You can clearly communicate about the boundary and you’re not doing anything wrong. 

Gina: That’s right.

Chris: It’s perfectly acceptable and normal to say, “I’m not able to do that,” or “That’s not what this team is going to do,” or whatever the case may be. Without apology, and without guilt.

Gina: Explanation or guilt or shame. “I am unavailable” is a statement. (Laughs)

Chris: I am unavailable!

Gina: It’s a statement. It doesn’t have to be like “I’m so sorry, I have this other thing going on, I could maybe move it but I’d kinda rather not.” Like, I go through this whole… (Laughs) But like, I’m unavailable, but here’s someone who might be, or here’s maybe another approach, like I think that’s a good and helpful response.

Chris: Yeah.

Gina: Always, of course, you don’t want to just say “No.” (Laughs)

Chris: Right.

Gina: You want to help your coworkers, you want to help your clients. All those things. But also saying, looking at what you’ve got going on that week, or whatever the request is. If you’re not able to fulfill it, just saying “I’m not able to do this. Here’s maybe another way to approach it.” This is even a generous…

Chris: Right. Or let me redirect you in this way. Yeah.

Gina: Exactly, exactly.

Chris: That’s right. 

Gina: This is something… you are very good at just calm, direct statements of fact, especially in, when things are hot. Like, in a client relationship or with a personnel issue, when things are hot and people are feeling, you are very good at just being like “Here’s how I see it. This is what happened. Here’s what our expectations are, here’s how we think we should move forward.” And I have to say, I’ve really… just observing you handle stressful situations that feel high on the emotional scale, I’ve learned a ton about taking temperature down. Making statements and getting to a place where, like, this is the next step.

Chris: Well, I think I’m also less empathetic than you are.

Gina: (Laughs)

Chris: So there’s like… there’s a balance. (Laughs) There’s a trade-off. Um… but…

Gina: (Laughing) I don’t think…

Chris: But I think… there needs to be… there’s nuance to all of this stuff.

Gina: There is.

Chris: And I am a big believer in trying to just, you know, be very calm and rational and say “Here’s what’s in front of me, here’s what we need to do and let’s go do it,” or “Here’s a different way that you need to approach this and I’m gonna lay it out for you.” And I think that’s an important… like, that’s what you want from your leaders, I think.

Gina: Yes.

Chris: Is to not have, you know, the hot under the collar…

Gina: High emotion, “We need to feel bad about how this went…”

Chris: Right.

Gina: “I have guilt and shame, and I feel bad, I’m sorry…”

Chris: Right. And that’s why people end up working weekends and working late at night, because their boss is, like, freaking out.

Gina: Yeah. Yeah.

Chris: And that’s not the kind of boss you want to be.

Gina: That’s right.

Chris: You know? But you also need to… I think, something that you bring to every relationship and something that I think is important as a leader is understanding where someone is coming from when they approach you.

Gina: Yes.

Chris: Because yes, there are a lot of demands on a leader’s time.

Gina: Yeah.

Chris: But it’s coming from a place of, you know, need or ambiguity or there’s something driving…

Gina: There’s something driving it.

Chris: …why someone is coming to you. And having an understanding and appreciation for that is really important. And it doesn’t mean you have to…

Gina: Solve it, or drop everything.

Chris: Exactly. Exactly.

Gina: And dive, swoop in and fix it. It just means, right, you have to hear it.

Chris: But you should understand it and hear it and appreciate it. And I think you excel at that, and that’s another thing that I think good leaders do, is they listen and they hear.

Gina: Yeah. Right.

Chris: And they say “I get where you’re coming from,” even if that… you don’t need to compromise your boundaries. Right?

Gina: Right.

Chris: You’re just taking it in.

Gina: Yeah. I think there’s both. It’s worth doing that investment of really trying to understand that. I don’t think that you’re not empathetic, I think you’re very empathetic. I think you spend less time worrying about, like… I had to decline something, and I was speaking to you about it earlier. And I said “You know, I feel kinda bad about this.” And you said, “Why?”

Chris: You don’t need to feel bad.

Gina: “You don’t need to feel bad.” And also… you didn’t say this, but implicit in that is “Why waste your time feeling bad about it?”

Chris: Right.

Gina: This is just the reality. You being at this thing is impossible today, and so just say that.

Chris: Right.

Gina: And make it so that’s just not that big a deal.

Chris: I mean, I have to remind myself about this too. It is, you know… it’s very natural to feel, I don’t know what it is. Guilt or whatever. 

Gina: Yes.

Chris: That “Oh, I’m not able to fulfill this thing that’s in front of me.”

Gina: Yes.

Chris: But we should all remind ourselves as leaders that like… again, it comes back to the thing you were saying at the very beginning. There is always going to be more than you can do. You should never think “I’m going to check off every box on the list, I’m going to respond to every single person, I’m gonna be available…” It’s just not possible.

Gina: Yep.

Chris: So give yourself a little leeway and a little forgiveness.

Gina: Yeah.

Chris: Because you’re gonna have to say no, a little bit.

Gina: You’re gonna have to say no.

Chris: And… yeah.

Gina: I have this narrator in my head where it’s like, well, you know, what a CEO, what a leader should be.

Chris: Mm.

Gina: I should do this.

Chris: That’s interesting.

Gina: Yeah, and I’ve had to shut her up.

Chris: (Laughs)

Gina: I’ve really had to shut up the voice about how… what kind of leader I should be.

Chris: Yeah.

Gina: Because honestly, if I get down to it, if I can’t make a thing for whatever reason, it’s like… I’m saying I can’t make a thing because I’m putting my, I’m showing up the way that I need to show up for something else. Right? And that’s a leader… Like, I have to constantly sort of align, this isn’t about being lazy or not caring.

Chris: No. Nope.

Gina: It’s actually just about, I have to direct my time and energy in the right places. Like, that’s the, that’s leader…

Chris: Exactly.

Gina: I don’t want to be, necessarily, the leader who magically appears out of thin air whenever anyone says my name to resolve all your concerns, right? Like, that doesn’t… that’s not sustainable. And it’s not good for the org either. Like, you have to, you know… set a north star for the whole group, right? And drive everybody toward that. But the, like, “You should…” or I… that voice is definitely part of my guilt, and “I feel bad that I had to move this meeting” or whatever. Nope, nope.

Chris: Cut it.

Gina: You gotta turn the radio off.

Chris: You gotta turn the radio off. 

Gina: Yeah. 

Chris: I think this is a perfect place to close it, and I can imagine people listening to this and hearing the same struggles that they are going through.

Gina: Yeah.

Chris: And feeling like, “I have issues, you know, fully realizing what my boundaries need to be, and making sure that they get held.” We can help.

Gina: Yes.

Chris: We would love to talk to you about these things. We know that it’s challenging to be in the leadership seat, and especially when you’ve got demands on putting real things in people’s hands, whether it’s your customers or your team or whatever. And we want to help. So, reach out to us. Hello@postlight.com. We will have this conversation with you, and at the very least commiserate.

Gina: Commiserate. (Laughs)

Chris: (Laughs) About the challenges.

Gina: Yes. About boundaries as a leader. We could do a three-parter on this.

Chris: We maybe should.

Gina: Maybe should. Send us a note, hello@postlight.com. Thanks for listening, everybody.

Chris: Thank you so much, and we will talk to you all soon.

Gina: Bye.

Chris: Bye.

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