Invisible PM Skills (And How To Hone Them)

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Galen Low: Well, that mission critical call with your toughest stakeholder is finally finished. You breathe a sigh of relief. 

It went... fine... But you can't help but feel that you may have botched your justification of the new timeline, and there's a chance you were a bit too defensive when you pushed back on their additional feature requests.

You ask your team on Slack how they felt it went, but all you get are a few thumbs up. 

Why didn't they teach you how to navigate tough conversations like these when you were getting certified? Shouldn't there be a way to build this experience without the stakes being so high? 

If you've been looking for ways to learn and practice people skills in a way that doesn't entail a career-limiting faceplant, keep listening. We're gonna be digging into some key mindset shifts and a few specific tactics that will turn tough conversations from being one of your greatest fears to becoming one of your new favorite past times.

Hey folks, thanks for tuning in. My name is Galen Low with the Digital Project Manager. We are a community of digital professionals on a mission to help each other get skilled, get confident, and get connected so that we can amplify the value of project management in a digital world. If you want to hear more about that, head on over to thedigitalprojectmanager.com.

Okay. Today we are talking about those crucial, but otherwise adjacent and kind of invisible skills that separate the great project managers from the rest of the pack. We're gonna be diving into what those skills are, the impact that they can have, and also how to hone them because most of them don't have a class or a textbook.

With me today is Jen Dary, a leadership coach, a speaker, and founder of Plucky—a coaching and consulting firms that moves humans forward in their careers. 

Welcome, Jen!

Jen Dary: Thank you, Galen. It is very much an honor to be here. You are well-known, I would say, in many circles. 

Galen Low: And you as well. I'm gonna get to it later on. I'm going to flatter Jen because a lot of the folks in my community have user services of Plucky, know you personally, have benefited from what you do and have moved themselves forward in their careers as creative humans. So we're gonna dig in there, we're gonna dig in there, but I'm giving away some of the punchlines. 

So you speak a bit about just Plucky, like why did you start doing what you do and how exactly does Plucky help humans move forward in their careers? 

Jen Dary: The endless question that I wake every morning wondering, Galen. So Plucky, my background is I was the director of employee development at a digital agency in New York about 10 years ago, and I love that job.

You know, as many of your listeners know, a small business can be, or a small agency, I should say, can be really exhilarating in the way that you many hats. And then at some point you wonder if you just need new hats. And around this time I had my first son and I took some maternity leave. And the long story short is it led me to wonder like, who am I now, right?

Am I gonna stay home full-time? Am I gonna go back full-time? I'm gonna do halftime. And I often talk about how parenthood is this lovely invitation, I guess, in life that you never realize that it's this moment where it says, who are you now? And there are other moments like that in life, but that one was very convenient to me where I said, okay, hang on.

Let me just take a beat from the momentum of my life and say, what should I be doing next? Now Galen, we are just meeting each other. But I would never have predicted that I would start my own business. I'm a very like, good student, oldest child. What shall I do for you? I love having a boss. You know, I love jumping above the bar. But again, the long story shorter is that somehow I thought, I wanna do what I'm doing in-house, but for many places.

And so I started in a consulting capacity. Very quickly it evolved into coaching because I really what I was doing. And at this point I am about nine and a half years, and lucky is just this little bright spot in my life, a large, bright spot even I can say. And I would say about half my time is spent one-on-one coaching, so that tends to be with leaders or emerging leaders.

Then I do a random bunch of stuff outside of that, like I teach a manager training, and I have little products that I've invented. Sometimes I do podcasts like with people like you. And yeah, that's kind of the backstory there. 

Galen Low: That was actually something that struck when I was creeping you on the internet. I was like, this is such a humble page about Plucky, about Jen. And then I've been talking in my circles, you know, about mentorship, about coaching, and you keep coming up and you're everywhere in the press. You have your course which I love. Cohort-driven course called "So Now You're a Manager", which very much resonates with me. Even just title alone, you're everywhere.

Jen Dary: Yeah. It's a mouthful if I can say for a CEO purposes. It's like I sometimes feel like I'm very subversively, don't assume things about me. Google add things, you know, which is really probably counter to what I should be doing, but I felt like, so now you're a manager was like one of those moments someone would talk to you about when you actually got that role. 

And I believe very strongly that becoming a manager is an identity moment where you need to sort of again, sort of say, wait, who am I now? Because now I could maybe fire someone. Now I could give promotion or not give feedback on someone who is a friend of mine two weeks ago and I am now their manager.

So all of those really tricky things happen and I think it's really important to, atleast just have some intention around what that identity might be for you moving forward. 

Galen Low: I really like that existential moment and these identity moments. Actually, a lot of the folks who have mentioned Plucky in my conversations are project managers who have found themselves in more of a leadership style role, and I feel like their path, you know, they're paving it as they go. Sometimes they're the first of their kind. 

I'm just wondering, I mean, you've worked with some project managers. Do you feel like it's a pretty good fit for what you do?

Jen Dary: Oh my God. I mean, how are they not a fit, right? Because you've got people who are driven and I took like so many notes here. I'm just gonna look at this cuz it's about two pages worth of reasons why PM should definitely hang with me.

Number one, you have people who must have people skills to get their job done, because they are this middle space between client services for the most part and team. And so you need to be productive and people skills are of a must-have. I'm sure we'll talk more about that. But you've also got the idea that they're holding stress, pressure, tension, and often there is not really a safe space for vented out.

I always teach people you vent sideways and up. You do not vent down, which means that's sort of the traditional hierarchy in an org chart, right? But like you do not vent to your team because you are bringing a burden to them with that power.

And then they're gonna struggle to like, uh-oh, my boss is unhappy. I mean, every once in a while you're having whatever, you're having lunch, you're having drinks, and you say things, and that's okay for the most part. But in general, you need to have safe spaces for you to sort of let go of some of that stress that inevitably comes with PMs.

You know, I'm not doing therapy here. It's not only venting, it's trying to be productive with that feeling too. But I feel like PMs are very often in those spaces. And then to be very honest, I think that there is a lot of questions that PMs sometimes get stuck in, which is, what am I after? I'm a PM. 

Okay, I'm a senior PM. Maybe I'm a vice president of PM, but then what? And so there's question mark about career path there. Where are they going? And I'm a good space for processing that kind of question too. 

Galen Low: I love that word holding and letting go of this like stress. And it resonates a lot with some of the conversations I have where, you know, I think a lot of ways project manager role, especially in the agency world, it's not always seen as a leadership role, if you know what I mean. 

And yet, you kind of need to develop these leadership skills cuz you are leading a team, you know, atleast to deliver a projects. And then it's yeah, there aren't a lot of parameters on the whole venting thing, so I love that. Sideways. 

Jen Dary: No, I mean, your word about invisible is extremely true. Because I would say that a PM at their best are invisible, actually. And if they are not invisible, there's probably something going on. Yeah. 

Galen Low: Things should be moving well, and that makes it seamless. If things are not moving well, and then it becomes painfully visible, 

Jen Dary: totally and it's not all on them, right? There could be many other things that are problematic, not the individual themselves, but yeah. In the best days ever, things go smoothly, and in your average day, there are bumps. And a strong PM who is balanced and I would say confident even in who they are and who they're not, is going to be able to take those bumps in the road and not only manage their own fulfillment and motivation and stress, but also convey that to the team. Because that sort of balance has ripple effects on the people around you.

So even the client comes and they're freaking out for you to say like, okay, we've got a lot going on. Let's just take a beat. I wanna make sure that I have every note that you need to give me right now, right? Like the way my voice sounded kind of welcoming to the mess, the very big mess that the client is giving to you, for you to receive that with a welcoming voice.

Even if in the back of your head you're like, oh, you're killing me. You know, that is part of client services, right? And then to turn around to the team and to say, everyone, everyone, this was a great job and there's room for improvement. So here's what we're gonna do next, right? Again, you don't have to swallow it. I want to be clear that you need ventilation there. But you know, it's a big part of presentation, I would say, for PMs.

Galen Low: That was such a good mini lesson. Just there. There is a little snack right there. 

Jen Dary: To talk alert. Yeah. 

Galen Low: Little value Mom, right here on the DPM podcast. I think that is a really good segue. Overall, we've been talking about sort of this invisibility of a project manager's role. And one thing I wanted to just kind of dig into is just this notion that, yeah, we are navigating all the time and there's good days and bad days. 

And I think sometimes the way that project management is trained is it's like keep things perfect when it finally goes off the rails, cuz it will, then it's like, you know, you have to go to DEFCON 1 and get it back on the rails. But in actuality, it's like giving ourselves and our team disgrace to like make mistakes and have tough days in between.

But then the net result is that if you look at it from far enough away or if you look back at it in from the future, it's like, yeah, that went really, really well. Even though we all know that projects just don't go perfectly, and yet there's this sort of level of training where we're like, here's how you make it perfect versus the other stuff, right? The mess. 

Jen Dary: Totally. 

Galen Low: So just to kind of tee it up, I mean, I've always been adamant about the fact that the skills that I use the most as a project manager or as a people leader or as a specialist, are the skills that I didn't learn from a textbook, I didn't learn in the classroom. They're things that I've honed on the job and usually quite tediously. And almost always quite painfully. 

So you probably see a lot of this. We're on the same wavelength here, but when it comes to just people leaders and roles that rely heavily on people's skills, what is your like top skill that is the most sort of untrained, but the most necessary skill that helps folks do their best job?

Jen Dary: Well, like 10 come to mind, but I will try to condense it into, I actually think the number one skill, this is not just for PM, but for anybody. If you need to hire somebody, I would say the number one skill to hire for is self-awareness. If you are hiring someone who knows the limits of what they can do before they need to ask for help, and then also that they're comfortable asking for help past that point, like hire them right now and probably give them bonuses all the time.

Because that is such a shortcut to a strong employee. I wonder what's going on over there? Or are they passive, aggressively mad at me? Or did they get pissed that they didn't get that promotion? Or someone who can express themselves is just a huge gift to the team. I would also say that within this same ballpark, you need someone who is able to handle conflict.

Because that's really a lot of what we're talking about here with the tension and the pressure and the stress. It's conflict. It's the fact that someone's expectations did not meet someone else's. And I mean, Galen, if there is like the enemy of the universe, it's conflict. Nobody wants that. In the States, we just had Thanksgiving. I can guarantee you that I probably should have like 50 new clients by tomorrow because if I was focusing on family systems, I sure would after that, you know, holiday runs through the system. But yeah, no, in truth, the ability to almost, not just only handle conflict, but in a weird way, almost welcome conflict.

If you can be a person, again, I'm gonna say confidence, which I said a few minutes ago too, but if you can be a person that knows who you are and you have self-awareness of that, and you can be a person that says, uh-oh, what's going on over there? Let's talk about that. The whole world will love you and they'll probably never leave you alone.

You'll probably just always be now in conflict. But man, I would take a guess that your listeners, or at least many of them have come from a backstory of handling conflict well. So if you're a good PM, it's possible that in your family of origin, you were the person that handled conflict. Or in your group projects in school, you were the person that kind of rallied things around, right?

There's a type, almost like a template probably of the kind of human that thinks, you know, it's a great idea, budgets and deadlines, woo, sign me up, right? That's like a certain personality trait. And so I would say that probably if you are a PM right now, you have some atleast kernel of ability to welcome conflict or you're interested in that.

Galen Low: And first of all, just to rewind a bit there, because the bomb that you dropped, I think was that self-awareness piece. If you're gonna hire for something, hire for self-awareness. And yet, I don't think I've seen a single job posting out there that's like, we're looking for someone who's just self-aware, and knows their limits and can raise their hand and ask for help. Like I've never seen it there, but it is such an interesting thing to look for. 

And where would you suggest finding that first filter for that? Maybe it's not the job posting. Maybe it is, maybe it's the interview?

Jen Dary: It's a good question. I'm gonna talk about this from my side of the house. If you're an engineer, it's very possible that people just wanna see your LinkedIn, or you know, they're gonna shortcut that. But if you do have the opportunity to have some sort of cover letter, even if it's as simple as an email, I think there's a way to be very honest. And maybe even a little bit yourself, and that is like a first little flame of that. And then definitely when you get to the interview, I mean, we do not put in our job descriptions, right?

But we do instinctively as we kind of build some of these questions into it, like, tell me about a time when, tell me about a failure that you navigated. So the 'tell me about' is story and what we're listening for under your story is, are you the bad guy in the story? Are you the perfect angel, good guy in the story? 

Which point people are like, hold the phone, something's wrong here, right? So they're sniffing it out, actually. And I think we are listening for that, but we, my usage of the word there maybe is the way to name it and help us talk more about it. Yeah.

Galen Low: No, I love that. I have had those moments, interviews. I'm interviewing someone and I get the story of, here's me throwing my team under the bus and I did a great job. If it wasn't for the team, I think it would've been a perfect project. I'm like, yeah, this interview's over. No. 

Jen Dary: And isn't it funny that we meet there? But an example of that is like literally the opposite of what they want to happen. What they want to convey is, I am so perfect. Please trust me with it. But you're like, I don't trust you. Because that whole story was way too one-sided. So ironic. 

Galen Low: And even something you said earlier, which I think is ironic and true, right? It's like maybe just try and sprinkle some of yourself into your cover letter. Which by definition is like, it's a letter about you, and yet we do have to say it out loud, right? Because there's a game to be played, to look excellent, to look amazing and put your best foot forward and maybe some of those things that you consider to be yourself are actually weaknesses that you don't wanna put in a cover letter, that you don't want to infuse into a story about when things went wrong on your project.

It's not necessarily, you know, I know I joked earlier on about, you know, cutting interviews short because thought they might be too egotistical, but sometimes it is because we think the game is to look as great as possible in all of these things instead of being ourself. 

Jen Dary: Yeah. I was coaching someone recently and she was preparing to go into an interview and we kind of got to the point of conversation in that if you wear a version of a mask for the interview, and you get offered the job, then you're going to need to keep wearing that mask. So make sure you don't do that . Right. And I'm not saying pretend you had experience that you didn't or lie about stuff, but if you walk in as your earnest self, if you get that job, , you're gonna be way more set up for success both intrinsically in you by your motivation and the people who are receiving you.

I'm gonna put in my blazer or my cool red shirt because this gives me my power and I'm gonna be presenting myself differently versus I'm putting on this fancy outfit because I think they will like it more. 

And so if you can air on the side towards what empowers me in this interview, I think that's the right one to 

be on.

Galen Low: That's super interesting. I love that. I wanna just circle back around to conflict because I think it's a massive. one And we were talking about this notion that, yeah, sometimes it is baked into individual personalities to sort of run towards a problem. I've learned everything I know about conflict, which is not much, and I mean conflict and not necessarily conflict resolution.

more just like engaging in conflict. I Learned it the hard way. Don't think I ever got good at it. Didn't really have an opportunity to practice it until, you know, it was something that I was doing in the job. . So I would imagine that it's something that people bring to you as well. 

They're like, listen. I'm not comfortable with conflict. I do it, but you know, I'm really need a better way to navigate that. I'm just wondering like is there a specific challenge that you find people come to you about when it comes to conflict and also any stories? 

Jen Dary: Yeah. Well, I would say that often people aren't gonna vocalize it with that word directly. I'm gonna listen underneath and hear, ah, there's conflict here. But for example, they might say, you know, I feel like I have a ceiling on my growth of this company and I'm not sure how to ask for what I want, or if that means they're gonna like, assume I'm leaving, right? Like this moment of, is it a threat for me to ask what I want?

And if I want something that's higher or more ambitious, are they going to assume you've now basically raised a flag that you're leaving? And now we're definitely not gonna give you away. And especially with, I would say smaller companies and smaller agencies for sure, there's this kind of like loyalty, family, betrayal stuff that can be happening, right?

If you decide to leave and that's ugly. And if you're running a small business like that, I would say don't do that. Call me, I'll talk you off that, you know, vibe right now because you are really shooting yourself in the foot. If you are the person that can say, go spread your wings. I'm sorry we couldn't give you the spot you wanted here, but we are just not built for that.

You'd be really shocked to see how many people actually fly back at some point. And, or look for partnerships or acquire you or, I mean, a million different things, right? So don't burn bridges. That's like a big one. Another way that people kind of call me with, you know, there's somebody that emailed me a few weeks ago.

And he was like, of the 15 people in leadership team, that sounds really big, but I think it's a couple tiers. Of the 15 people, 13 of them don't trust me. What consultant should I call? And I was like, well I hope this isn't too rude to say in an email, but are you sure this is the right job for you?

Like 13 of 15 is big odds there. And the fact that he could voice that was a level of self-awareness, I will say. Uh-oh, 13 of 15 people don't trust me to lead this company. I don't know what consultant is bringing that back, you know, without a hell of a lot of money, time, years of sort of coaching and redirecting.

You can go buy EOS books. Cool. Now we're on traction. Now we're on these other things. Great. It's distracting from the fact that something is off and maybe the right move there is to gracefully say, this isn't working. Now how could I handle this conflict? Maybe I need to step away. Is there somebody else, a budding leader that I could hand things over to? And you know, again, people have boards or people have advisors or whatnot, but nobody ever thinks about that. But sometimes it's time to leave. 

Galen Low: You know what, it's really interesting because when I play the word conflict in my head, the picture I have is winning a fight. And that's not necessarily what we mean. What you just described there are like conflicting needs and priorities, maybe conflicting cultures. And it doesn't mean you have to square peg, round hole until it fits, and then you win the fight. It's actually might just be the best solution to the problem. And I think probably a lot of PMs can relate to that as well.

It's not fight with your tech lead, it's not fight with your UX designer and win because you're the project manager. It's what is the best, how do we figure out the best path forward that is going to work for folks? And even just swinging back to what you said at the beginning, right? That your little masterclass on tone and delivery and what that sounds like is actually more the spirit of what conflict should be in the workplace. 

Not loud voices and winning a fight, but recognizing and being self-aware of conflicting needs and priorities and finding the best outcome and maybe running towards that. And that's actually quite a noble thing. Not running to go, you know, verbally punch somebody in the face. Cuz you love it. But actually because running towards a solution actually coming from a constructive standpoint. 

Jen Dary: I think in 2022, I can count on the fingers of one hand how many times I've heard of or been, you know, sort of invited into, we need help with this conflict cuz people are yelling. It's actually the opposite. It's passive aggressive. It's thumbs up on Slack messages. It's like, you know, the dot, dot delete, dot, dot, dot delete. It's like this level of conflict, which is even like worse. It's poison, right? 

And it's hard, especially now everybody's remote. It's hard to feel like there's a way to walk into that conflict. Even if you send a Zoom, like, Hey, can we talk? I mean, I literally have a whole product line called "We Can Talk" because I always teach the three scariest words in the English language are "can we talk?" If somebody says that to you, Hey, can we talk? You're like, Oh God.

Galen Low: My back's up right now. 

Jen Dary: Yeah. Yeah, right? Like I know, exactly. You just got bar feet. It's like if somebody says, can we talk to you? You're immediately prepared in that fight or flight mode. So be the kind of person who can receive that question well. Say, yeah, of course we can talk. What's going on? Even if you're nervous inside. I'm not gonna say that I'm not nervous when I handle that, but it goes a hell of a lot better when I start the conversation with that.

Yeah, of course we can talk. What's going on? And then the listening becomes very important there. Listen to everything they're saying. Don't have the next response on the tip of your tongue, and you just wait for their mouth to start moving and then you say your thing. You have to wait and pause and hear what they actually said. Cuz very often what they actually say is so much less bad than what we thought it was gonna be. 

Galen Low: That's actually really interesting. Is managed moment where you're like, okay, don't do that thing that, you know, if you were to hit with a hammer, you would kick, but don't do that thing. Pause and like say, you know, be in this mindset.

Say these words, be open to what this person's going to say after "can we talk?" And then go from there. Rather than, you know, arm for a battle that actually isn't a battle, because in our head we're like, oh, this is gonna be a conflict. This is a fight I need to win. Whereas actually it's a conversation and you know, someone needs to play their hand before you know what to do with the next so run towards that. 

Jen Dary: Yeah. You know, another thing I'll throw out here is that I teach this class called "So Now You're a Manager", right? And so it's for folks who are within their first couple years of management. And I always say that there's what I call "creator grief" that I often see somebody who's been promoted to management. Which means they used to be the person that makes the thing, they coded the thing, they designed the thing, they worked in the weeds on PM and now you're promoted to lead those people. 

And so you're doing a lot of like paperwork and reviews and all this kind of stuff, which doesn't sound very fun, compared to the creators, right? And so I actually think management is a creative practice or it can be. And you can just change your currency from, oh, okay, I used to have code. Now my currency is humans. 

And what that means is I'm gonna create differently and I'm gonna think about different personalities on the team. People who are better at sales calls, people who are not as good, you know, who need more help with public speaking or whatever.

Galen Low: Let me do a quick, think about...

Jen Dary: Talking about managers and creative practice and...

Galen Low: Currency, and Becca's gonna help us. 

Jen Dary: Yeah. So my take on this is that PMs can have creative practices in their work. The currency is different, especially if you're managing here. You have the humans on your team. You have the skills available to you there. You have people who are more junior and more senior, and so you get to sort of make that picture or use that toolkit or paint kit, I guess, with who we wanna say for creativity to set something up for success. You wanna say, oh, this is a client who's very forward and really, you know, driven in this way.

Who are my best teammates to put on that client? And this is the art of resourcing, right? It's figuring out who would best be matched, not only to work together internally, but also to work on this client. Sometimes you have the luxury of talking about it like that, and sometimes you don't. But either way, the mindset of it, "what shall we make today?" is very different than like, "what did we miss today?" Or like, "how are we already behind or laid on something?" And it changes the way you show up to work.

Galen Low: I really like the currency aspect because I'm willing to bet that some project managers, if asked what the currency is, they might say deliverables and status reports. But the shift is actually, your currency is humans and probably some conflict, but it's a creative endeavor. Try and make this work, right? It's creative problem solving. It is, you know, to your point, resourcing. But resourcing the right people for the right situations. Not necessarily just a spreadsheet of how many hours people are available, but actually how to be strategic about it. And then that last thing, which is actually you're probably being strategic. 

Your currency is humans and you're probably being more strategic than you think, and that's why you get sent on this path towards different types of leadership roles or different types of roles that involve managing people. And there might not be a lot of trail blazers ahead of you from where you stand, but it is, you're arming yourself with those skills to be a better leader.

Jen Dary: I mean, honestly, we're talking about the invisible stuff today, right? And I would say that emotional labor is a big byproduct of this, which means that you're tired and sometimes for you to handle and control all of that energy in the room, or energy in the conflict or the exchanges, it's very fatiguing.

So I would say another element of why I end up coaching someone sometimes is that there's like, I don't wanna say like a self-care element. It's not like go get a massage, but it's a sense of like, how do you restore yourself once you are depleted? At the end of a long day where you've handled people all freaking day, you need a way to get rid of that.

And so I'm saying this very meta, right? That's my job too. I hold stuff for people all day. So take a nice long walk around your neighborhood or cook dinner with jazz on, or you know, whatever sort of your MO is. But be sure not to skip that because it will build and then your whole weekend you wanna be with anybody.

You know, like there are ways that I'm a massive extrovert, but there are ways that now at this point in my career, I need to not be with people in the same way, because I'm very aware now of this one's not having fun at this PTA meeting. And you know what I mean? It's like nobody's paying me. This is unbillable work, but I can't really turn it off. So sometimes I just need to make sure I'm not in the room too often if it's not restorative in that way. 

Galen Low: Isn't it interesting that some of the things that are invisible are the things that we end up holding? Because I think, you know, maybe it is just embedded in the way you know, we as adults developed, right?

That we are rewarded for these things that are quite tangible and visible, right? Hey, you got that thing done on time. Yay. You don't take that home with you necessarily. You're like, I did the thing. It's done. But the invisible stuff is the things that you hold cuz no one really said, hey, good job understanding this stakeholder's needs, and then resourcing the right person.

And then, I mean, it does happen, but not often, right? And you kind of have this weight. And then to your point, some of these things are things that are always on skills, right? It's not like you create a status report and then you stop. It's like you are being perceptive about humans, you're being empathetic, you're trying to create psychological safety, and sometimes that doesn't switch off as easily. So I like that self-care aspect.

Jen Dary: Yeah. Absolutely. I mean, I would guess that if you're a PM listening to this, you are also in charge of some freaking committee out there. Like you've definitely got promoted, so to speak, to head of volunteers for, again, your kid's school or the local church or synagogue or the whatever your neighborhood watch. Like you are definitely in charge of something else.

Or if your friends go out to dinner, you are the one that picks where you're going. Like, these skills don't turn off at 5:30. They persist with you so, while that is actually charming and a bit endearing, it's also a potential threat to your balance. So to make sure, number one, that you're not the only person like yourself that you hang out with, I think community is really important. Even this conversation is a level of cathartic. 

Maybe people listening also feel that, and I hope they do, that you are tired and you're not the only one. There are others like you and maybe your PM friends can talk about it, but may if even if they don't like me and Galen get you. 

Galen Low: We see.

Jen Dary: Sometimes just to feel like someone is talking about this stuff, that's the subversive thing. 

Galen Low: Absolutely. I love that. I wanted to circle back on two things. The first one is personality types. Cause we're talking a bit about this. We're like, okay, yeah, you might be this type. If anyone's listening, and they're like, actually I'm not that type. I don't run towards conflict, you know, I'm not the head of a committee. Does that mean I can't do this Jen? 

Jen Dary: Yeah, that's a great question. I don't think I would ever want to tell someone you shouldn't do something. But I do think that you wanna do some gut checks on your self-awareness and truly the question of fulfillment. So if what's laid out in front of you, if it doesn't check all your Myers-Briggs boxes or whatever, but you feel fulfilled at the end of the day, God speed, go do it. 

But there are lots of, again, invisible forces on us that try to convince us that X, Y, Z is the way. So, for example, expectations from our parents growing up, or you went and you got this degree from this college or university, which says that it should spit you out into this role with this pay grade.

I was a junior PM with other junior PMs and now they're doing this thing and that means I should do it, right? There's all kinds of pressures societally and professionally. So if you are a little round peg square hole and whatever, you can be an introvert in PM like all these things are possible, but it is worth taking a beat and saying, is this my idea of fulfillment or other people expecting that to be fulfilling for me? And that's another thing, right, that I coach a lot of people who have maybe made it 10, 15 years into their career and it's like this very scary moment where they say, uh-oh, why am I doing this again? And it's cuz somebody else wanted that to happen.

All of us have had some version of that. And so to have a safe person myself is kind of what I'm saying, or any coach really, but like, you know, to have a safe person to open that up with and say, I might be lost. I mean, that's a big deal. And I will say, especially for someone who is a CEO or a founder. Uh-oh, what if I'm not in the right job? Well, that's a lot of pressure. I'm the only person in many cases that they can say that too, cuz you don't wanna shake the boat before or rock the boat before that is necessary internally at an all hands.

Galen Low: Right. Yeah. This boat full of people. Hey, I'm not so sure about this everyone.

Jen Dary: Totally. Second thoughts everybody, but see you on Monday. Have a good weekend. Yeah.

Galen Low: No, I think that's really interesting about that safe person. And I think, you know, I was thinking about this all the way through, you know, these invisible skills, you don't get trained on that much. And when they do get trained, especially personality types, you know, they can be crushing because you learn them on the job and you probably didn't do it great the first time.

And that faceplant hurts and it may have limited your career. And, but talking about that safe person, like what are some ways, if we were to talk about conflict, for example, like what are some ways to like practice that and like get better at it? Maybe not, you know, when it's that big client, that big meeting where your career depends on it, and you're like, well, now's the time for me to try and be good at conflict and here we go. Is, are there lower stakes ways to learn and practice these skills? 

Jen Dary: I mean, absolutely. The first thing that comes to mind is sending back your food at a restaurant.

So if you asked for, I don't know, no olives and it came with olives. It is like, I would say, a very high percentage of people that are gonna pick 'em off and be pissed about their dinner. But you asked for something so you can say, I'm very sorry to do this, but I really don't like olives. And I'd like to ask if they could make me one without olives. And then just, what are you gonna do? I mean, it's, you know, you are the eating there. You are allowed to ask for what you want. So that's the tiniest bit of conflict.

Now, I say this very lovingly because my husband would never do this. He's from the Midwest. He is very...

Galen Low: You gotta pick off these olives.

Jen Dary: He's amazing, but like, oh yeah, a hundred percent. He would be like, bring more olives. Sorry to bother you, you know, but I air more on that side because the other thing is that my feeling about, I'm from New York, so like I have a different vibe there. But if I don't say that I didn't want olives and I don't get it changed, I'm sitting there with passive aggression.

I'm eating this pizza I don't even like, and then I'm smiling fakely at the end saying, oh, it's great. 

Galen Low: Thumbs up in Slack, right? Yeah, thanks.

Jen Dary: And now I'm giving, yeah, right. Exactly. And I'm giving this like tip because waiters, they make no money, and so I feel like I have to give a 20% tip and whatever. But I'm pissed about it. And now that's the energy that leaves that dinner. Versus, that was a scary moment but I'm glad I said something and now I really thought that pizza was great, you know, or whatever it is. So that is like a good way to start building muscle there. You could also say 'no' to something. That's a great other way to start just warming up to conflict.

If people are saying, Hey, we appreciated how you planned the whole holiday party last year, would you just do it again in your free time? And you could say, you know what? I really can't this year, but I'm happy to give my notes to whoever else you find. The good way, friends who are listening, to do this is to pretend you've had some sort of epiphany or magical dream.

You wake up and say, you know what? I actually had a dream last night that I have been saying 'yes' to too many things. So I'm gonna ride that dream into this conversation and say, I really think I shouldn't plan the holiday party this year. I, it's just an instinct in me. It's my gut. You have to make up a dream.

You could just say, you know, I realized this morning on the train ride in that I'm saying 'yes' to too many things. It's sadly a imperfectly timed question you're asking me, so I'm happy to turn over my notes, but I have to say 'no' this year. That's scary, right? Scary to say no, especially to a potential, you know, maybe your boss or your manager, but that is another way to just flex a little bit of that muscle towards conflict.

Galen Low: I love that. And there's so many tactics in there as well, that you just mentioned. 

Jen Dary: Yeah. I know. That's because people need to believe that there was a disruption to allow your change. So I had a dream. I went on a vacation. I woke up this morning, I looked out the train, like I you just, it's like an indie movie. You know, like, and then the transformation happened and I was able to say 'no' to your tiny meeting request, you know, whatever.

But sometimes you need to feel that vibe in that way because your identity does need to shift towards something maybe more balanced or healthy. So a disruption, regardless of how silly it seems, is the way for you to eek forward in that identity tweak that you're hoping to make.

Galen Low: I love that sort of practice in every day and the fact that these aren't just work skills. They're just human skills. They'll probably benefit you, yeah. If you keep getting asked to plan the holiday party and, and, right? 

Jen Dary: Yes. Yes.

Galen Low: Oh, I love that. Listen, I wanted to round out with last question. That might be a big question for our last question. But you know, we've been talking about these things that are invisible and untrained. 

You just told me that it's pretty easy to practice, why do you think these aren't things that get trained? Like if I take a project management course, how come there isn't like a, Hey, we're gonna practice saying 'no' for a week. Why isn't it baked into the way we learn or teach?

Jen Dary: I mean, that's a million dollar question, right? Or probably 10, no, $44 billion question at this point, cause things are inflation. I think it's cuz it's really hard to measure. And I mean, we are swimming in a spreadsheet community here, right? So that even is more exacerbated, but I believe that these invisible questions, it's hard to say, I got it, or you got an A on it, or whatever.

It's really hard. It's not mathi in that way. So that's why it doesn't show up in textbooks. You also can't do it at scale. Like if you grading papers, you could sort of, you know, it'll take you a while, but you get through it. But at scale, could you handle conflict in the classroom? How is everybody doing? No. You'd need one-on-one time. 

So another way to track that is time and experience. So it's not a textbook, but it's time you've lived, it's experience you've lived in your life. Some people at like 20 have so much more experience with conflict, another person at, you know, 50. Depending on where you've grown up and your life and what jobs you've had.

So the last thing kind of, I feel about that it is not a very tangible thing that people will approve your prof dev budget for. 

Galen Low: Right. Yes. 

Jen Dary: It's like, oh, go talk about your feelings. I mean, people are so annoying like that. Or people who have the purse strings because it's like, man, what do you think is going on under all this? Yes, it's the feelings. If you want people to sell more, let them get experts at feelings and then watch every single contract that comes in the door after that.

So it's an investment for sure with, for someone to pay for a coach or a class or anything on this social, emotional realm I would say, man, it is a great ROI for anybody on your team to take that kind of resource.

Galen Low: I love it. There you have it. I also, in my head, I pictured the saying 'no' class at scale. It's one multiple choice question. The options are yes or no. And then you get a certificate that says, yeah, you're great at saying no. A hundred percent you, you say no the right way. The end. I'll take my $44 billion now.

Jen Dary: Oh my god. Well earned. That is a great idea. In fact, have you ever seen that website? I don't know if it's still up, but it was like isitchristmas.com or something? And it would just, you were refreshed, no, no, no. Until one day it's yes. So this is your question should totally be a simple website, which is, do you want to do that?

Galen Low: There you go. 

Jen Dary: No, no, no yeah. That's the return. 

Galen Low: I love that. Awesome. Jen, thank you so much for your insights today. You dropped some value bombs, I learned some tactics as well. I'm gonna say no to planning that holiday party. I'll cite my epiphany on the train and and I'm on my merry way to practice saying no, and be ready for a bit of conflict.

Just before our listeners go and you, I guess, how can folks learn more about you, hear more from you, learn more about Plucky?

Jen Dary: Yeah, so the simplest way is to sign up for the newsletter, which we will probably put that in show notes. I send it once a month. I tell stories about work and life in the world, and I give you, you know, like heads up on tickets that are coming up for sale.

We sell out pretty quickly first "So Now You're a Manager". So if you're interested, the best thing to do would be to get on the wait list of the current one that's sold out, or to subscribe to that newsletter, and then you'll hear about that. And I am no longer on Twitter. Spoiler. I know. Yeah, I left because of some recent management changes.

And so what that means is that for a small business I need to look in other areas. So I'm definitely on LinkedIn with Plucky. We have a good amount of followers there. And then I'm also on Instagram. Again, I'll share all that with Galen. So, so you have it in the show notes. But those are the best ways and honestly, you could just email me hello@beplucky.com. You could just send me an email and tell me what you thought about this.

Galen Low: Find me on email. 

Jen Dary: Yeah. Yeah. I always write back to those, it's like my favorite thing when people write and tell me what they're thinking and, you know, I can just shoot you something back. I'm a very, in case you haven't noticed, very people oriented person. So I always love connecting with people. 

Galen Low: Definitely add all of those links there and Jen's email in the show note. 

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Until next time, thanks for listening.