S1E3: Jennifer Dary on Becoming a Manager and Firing People with Grace

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Firing people is hard, especially when you have a small, close-knit team. But it’s an absolutely essential part of running a successful business. Learning to let people go with grace and kindness is a skill that Jen Dary teaches people to do well.

In this episode, Jen talks to Andi about the struggles of becoming a manager, leading with values, and how to fire people with kindness.


Jen Dary:                      I love talking about firing people. That should probably be the tweet when you release this to the world, even though it’s hashtag within reason.

Andi Graham:               Starting and running a business is hard. Starting and running a values based business is even harder. Hey there, I’m Andi Graham, and this is Walk the Walk, a podcast for entrepreneurs who make tough choices in the name of integrity every day, even when it’s hard. Today we are talking to Jen Dary, she’s the CEO of Be Plucky. Be Plucky prepares and enables the next generation of leaders to lead with empathy, vulnerability, and confidence. She does that through leadership coaching, new manager trainings and generally she just helps people work with people, through one-on-one coaching, she does a workshop called So Now You’re a Manager, which is a two day leadership training for new managers, she does employee experience audits, onsite and annual retreat workshops, and she even created this cool pack of cards that are questions to guide your one-on-ones as a manager with your employees. You can find Jen at beplucky.com.

Andi Graham:               I started working with Jen about five years ago or so. She did some one-on-one leadership coaching for me in a really difficult time where I was having a really tough time figuring out how to fire people. I know that sounds crazy, but even when it was the right decision for my business and the right decision for the person I was letting go, I didn’t understand how I could do it with compassion and empathy. So Jen has some really interesting things to say about that. As you’ve heard, she really likes to talk about firing people, but she made me feel better about making those decisions, about how to do it, why to do it, and when to do it, and hopefully she’ll do the same for you. So here’s Jen.

Andi Graham:               One of the things I wanted to talk to you about that I’m really interested in is you run this workshop called So Now You’re a Manager, which I think is infinitely interesting because, especially in the tech industry, we often promote people into managerial roles that don’t know how to do so. But what I’m interested in is the people who you work with in those workshops and what their alignment with core values looks like. What is your experience with how they bring that to the table and their managerial outlook?

Jen Dary:                      Well that’s a good question, and I will frame it as So Now You’re a Manager, it’s a two day workshop and it’s for people specifically who are I say zero to five years into management. So they are new-ish managers. And I also do a version of that in-house, sometimes at companies, but the reason that I feel so strongly about this external version is that the in-house ones, your boss is in the room. And I think that there’s a ceiling on which some level of vulnerability can happen when there’s power dynamics. And we can just say it’s not good or bad, it’s just present, and it affects the way people interact a little bit. And so, in this way, people are able to get out of the bubble of their company and interact with other people, across industries even, who are having the same work on their plate. This work of managing humans, of somehow getting the best work out of a person in front of you, and what questions you should ask them, and how to run one-on-ones, and that kind of stuff.

Jen Dary:                      And it is really beautiful to see people say, “Oh my gosh, I thought it was my company,” or, “Oh my gosh, I thought it was me.” And actually no, it’s just the work of managing. It’s hard. It’s like parenting, right. There are just some [inaudible 00:03:31] that are hard, and managing is one of them. And so I say that because we cap at 22 attendees for this event, so it’s not huge. And each person is going through, I don’t know, a journey, let’s say, across those two days of saying what is my personal leadership style? Given who I am and what I studied and what my experience was, and what shot I got to take at becoming a manager. And then how does that match or not match with the company that I work at?

Jen Dary:                      And the question of values may not come up as explicitly as that, but that’s what’s the invisible stuff going on during the whole time, right. How do I become a champion for this place that gives me a paycheck? How do I push back on things I agree with or don’t agree with? The whole topic of managing up is rife with this, which is a term that I use to say how you sort of support and ironically manage the person who you report to, right. Hierarchy there. And ultimately I think this, in combination with the coaching work I do, it’s always about the person in front of me, and let’s just start with who that person is and what their values are. Then we can extrapolate to larger groups or organizations from there.

Andi Graham:               That’s a good point. And I love that, becoming a champion of the place where you work, because that’s definitely what we expect our managers to be is, if we’re doing this right, they should be exhibiting all these things, just we would assume preternaturally, but of course it’s not, right. It’s something we have to ingrain, and something we have to teach, and something we have to show with our own behavior. So I think that’s really interesting. So do you ever find that the managers you’re coaching or that you’re teaching are struggling with that alignment? They’re like, “I want to lead in this way and it doesn’t match with what they’re expecting of me.”

Jen Dary:                      Yeah. And I’m lucky that I don’t work with any evil people, so it’s not usually that far off. But something as simple as, let’s say you have someone who’s a bit more of a junior manager, and they are going to take a little risk because it’s their first time trying something, right. They have an instinct for a performance review or whatever it is, a piece of feedback, and their manager is uncomfortable with that risk. And so now all of a sudden you have this misalignment. You have one person who’s experimenting because it’s new for them, and it’s a new job and they have instincts on that. And then you have the higher-ups, so to speak, who really need to measure how long a leash that person can have. And so where I see those values getting bruised is when the rubber meets the road. Everyone enjoys promoting people. “Ah, we’ve promoted you, congratulations. Now you’re a manager.” But will you let that person try things? Will you let them stumble a little bit? Will you let them fail a little bit?

Jen Dary:                      All within an appropriate amount of containment, you don’t want anything inappropriate to happen, but what’s the combination of training for a new manager and the combination of letting them learn? And do they have a manager who will give them space to learn? That is the hardest part about managing up. I hear this all the time. “They tell me I have the power to make decisions, but then if I don’t make the decision they want, they take it back.” And that is so infuriating. We’ve all been teenagers, right. We have all been teenagers and it’s like, “My mom and dad said I can do what I want, but then I didn’t do the thing they chose, and now I’m in the doghouse,” whatever it is. And that’s really hard. It’s really hard for the person being managed. It’s really hard for the person doing the managing in those cases.

Jen Dary:                      And as a coach and as a teacher, the simplest truth is this is hard for everybody. So everybody in the picture, this is hard for. You’re a parent, you know this. It’s hard for the kids. It’s hard for the parents. So again, I just think that continued clarity of, I don’t know if it’s values, really I just think the best leaders are the people who know themselves, who know their limits, and they know their strengths, and they know when to ask for help, and they’re generally confident. Those are the best leaders because they’re going to be able to say, “I’m nervous to give you the leash, but okay. I won’t check in with you for another week. I trust that you will find your way,” right. Or whatever it is. But the best leaders are the ones who can not hold back because of fear, and not hold other people back because of fear. Does that make sense?

Andi Graham:               Yes, that makes sense. I love that. I love it very much. So well, it’s interesting to me because I needed to hear all of those things. So we just promoted a mid level directors up to VP level here at the agency as we grow, and I’m realizing that I’m still holding a very tight leash, and so I probably needed to hear that and let them have a little bit more leeway.

Jen Dary:                      Yeah. And I hold that so lovingly because I know how hard it can be to delegate, especially if you’re talking in a smaller agency where there’s partners who own the business, and then a whole bunch of other people who don’t own the business. The level of risk is very different depending on the role you have, but in order to make people who are fulfilled in a management practice or fulfilled in a power position, they have to actually some power. They have to not just have it on paper or on their business card.

Jen Dary:                      They have to actually be allowed to make decisions and say, “My gut tells me, and my spidey sense tells me we should turn this client down because of how rude they were to seven people.” They need that to be honored by people above them. Or if not, then just demote them and don’t give them a position of authority, or have a hard conversation about it and say, “I’m sorry. I know how this is looking, but I’m feeling nervous.” Those kinds of vulnerable conversations are so helpful, even when they don’t go the way everybody wants, because everybody at least knows they’re trying.

Andi Graham:               I totally agree. And that’s actually one place where we bring our values into that conversation. And so there’s not just an anecdotal, “I feel like this person’s being rude,” it’s a, “Here’s the things they’re violating that we truly believe in.” And so our team, at least, bring that to the table when they come to us and say, “We want to fire this client, these are the things they’ve violated.” So it helps us have sort of guardrails around that conversation, which is nice.

Jen Dary:                      Oh man, this will probably not be a surprise to you, Andi, but I went to see Oprah two weeks ago in San Francisco. She’s on a tour, and she had this moment that I’ve been thinking about, and what you’re saying is reminding me of it. She talked about this concept of intention, and again, we’ve all heard what intention means, what’s your intention, blah, blah, blah. But she talked about it as a manager, and she said that when she used to run her show, I don’t remember the book, but she had read a book and she realized that she didn’t want her producers to come and pitch her project ideas, they also had to include intention with that. What is the intention for this show you’re pitching? Why should we do it? Some of the producers reacted really poorly to that. They were saying, “What’s my intention? I don’t know. Put Brad Pitt in a chair, put you in a chair. That’s the intention. It’s entertaining, right.”

Jen Dary:                      But she pushed back on them and she said, “No, you bring an intention, and if it’s aligned with what my intention is, and I’m the boss, then we’ll do the show.” And Andi, I’m not kidding you, I saw her, I think it was three weekends ago, and there have probably been three to five decent decisions for Plucky that I have made using that question. What is my intention for this moving forward? And grounding myself in okay, this is a cool wacky idea I have for a product, but what is the intention here? And it allowed me to see I don’t know if we’ll make enough money to cover the investment, right. Or what is the intention for this workshop I’m doing in the middle of a damn virus out there? All those kinds of questions.

Jen Dary:                      And I think what you’re talking about in your staff bringing those violation conversations is, “Hey, our intention was this, and this client’s intention was different. Red flag. Alert. Let’s talk about it.” And that’s great. I think any time that those flags get tripped is an opportunity to converse about it. And I agree with you much stronger that those values are not just painted on the wall, those values should be almost as an agenda item on every hard conversation meeting, and decisions in particular, hard decisions.

Andi Graham:               I love that. So talking about hard decisions, one of the most insightful things that you brought to our relationship when we first started getting to know each other, and when I was working with you as a coach many moons ago, I’ve matured so much since then, you’d be so proud. And I’ve had those conversations a million times. But I was really struggling with a particular employee who I knew I needed to let go, and I don’t think I’d ever fired someone, or let someone go in a way that this person needed to be let go, which was just general misalignment of his best interests and mine, of the agency’s best interests and where he needed to be performing, but also just behavioral stuff.

Andi Graham:               Other times I’d done, it was very clear infractions, right. It was like you’ve been late every day, or you’ve screwed this whole thing up, or whatever those things are. And so you really taught me how to let people go with grace. And I would love to talk a little bit about that, and how I can still stay true to being a kindhearted human, and being a people’s first organization, but making those difficult decisions and what that looks like.

Jen Dary:                      I love talking about firing people. That should probably be the tweet when you release this to the world, even though it’s hashtag within reason. I love talking about it because it is such a great opportunity that could either go tragically, and end in many years of shame and therapy, or could go gracefully, to use your word, and everybody’s going to feel a little bruised after it, but everybody’s able to take a high road. So I kind of had this theory, and it’s a very weird metaphor, but hang with me, it’s like those plastic Easter eggs at Easter that you fill with jelly beans and stuff, right. There’s two sides, and my theory is that on one side you have an employee, or a potential employee who you might hire, who has a skillset, and a timeline, and a budget for the work that they want to do. Then on the other side, you have an employer, and they also have a timeline, and a budget, and skills that they need a person to do.

Jen Dary:                      And when all of that lines up, it’s that really satisfying click, like that Easter egg has. And then you should hire that person or retain that person, right. But because humans change, and because business has changed, sometimes there’s an unclick. Sometimes the person says, “Well, I was hired as a junior front end, but actually I’m kind of interested in being more full stack. Is there an opportunity for me still at this company?” And they will unclick and ask that company, “Hey, you got any backend work for me?” And the company then can say, “You know what? We do. Come grow in this way with us.” And then there’s that click again. Or the company could say, “Geez, I know you’re interested in that, but we’re really focusing more on front end and design, so we’re probably not the right fit for you.” And at that moment, that person then gets to go find a different company that can fulfill that need.

Jen Dary:                      This metaphor is so simple because it is about the very simple question of is this still a match? Is what you came in with and what your expectations were for this relationship together, is it still the same as what it was before? And if it isn’t the same, are we still okay with how it could evolve into a new version of that? And when we’re talking about firing someone, or letting someone quit, both are departures, right. On both sides it’s just a moment where one side might say, “What you need from me is not what I can give you anymore.” So whether that’s an employer saying that to an employee, “What you’re hungry for, what you’re interested in is not what I can give you anymore. We’re going to let go here.” Or the employee saying, “What you need me to be doing is not interesting to me either and I’m going to peace out of here.” There’s power on both sides.

Jen Dary:                      And so when I talk people through letting someone go, the thing is, it’s actually a great problem to have because people that are having a hard time firing somebody, it’s because they’re really nice, and they really want to care for someone. And then they make up all kinds of things in their heads. How many mortgages I’m paying through these people, their health benefits, all that stuff is really loaded in this country at this point. But in truth, everybody already knows, intuitively, when they are on your shit list. And so by not naming that, you are betraying that intuition every day for them. So if they come in and they’re the one that’s late 50 times a week, and they know people are talking about that, they know that must be coming up in meetings, they’ve seen your passive aggressive performance reviews about it, they know it’s a thing.

Jen Dary:                      So the longer that you don’t take action on it, the more trepidatious they move through the world, the more fake it is to them because they know sort of on some level they’re getting away with something, and nobody’s taking them to task, and they’re just waiting for that shoe to drop. And if you have ever been in that situation, waiting to know if this job is going to end, or just all kinds of things, diagnoses news, or pregnancy news, any of those moments, right, you know that the worst is the waiting. As soon as you just have the news, you can process and move forward.

Jen Dary:                      So I am very encouraging of people to name what’s not working and then to have a real conversation, and to say, “Listen, I don’t think we’re on the same page with this stuff, and I’m here today to tell you that today’s going to be your last day. And we appreciate your contributions so far.” Again, follow all your HR guidelines that you don’t get sued. But I think there’s a lot of ability to have that conversation, and there’s going to be some relief, honestly, on the other side. Like, “Oh, okay, at least this is over now. At least they have told me the news, that I’m moving on.” It’s that waiting, that purgatory, that just super sucks. So unless you can be really direct with the person, it’s actually worse to keep them. [crosstalk 00:17:56] disappointing.

Andi Graham:               So what if you’ve had that conversation with people and they’ve been very clear, like, “Oh, I can fix this. I can do this, I can do this, I can do this. I didn’t know those were the expectations. Now let me wow you,” and then it drags on, and then it drags on, and then it drags on. And now you’ve gotten so far into it that it’s a-

Jen Dary:                      Yes. Well that is the moment where I the … I live in California now, but I’m from New York and I always say a lot of what I teach feels more emotional based, or soft skills, whatever everybody wants to call it, but I am still a New Yorker at heart. And that is the time when I say to you, “This is a business, not a college. You have to make money.” So if this person has not gotten their stuff together, the best of intentions, that is fantastic, appreciate the intention, but if it doesn’t come across fast enough, and it doesn’t improve fast enough, this business is not just surviving on invisible dollars. We need to be productive. We need to make that happen.

Jen Dary:                      And for reasons that are above my pay grade, and you should probably have a therapist on to talk about, but some people never quit a job. They will never quit a job because they were taught not to quit. And they were taught that the way work ethic works is you just keep going, no matter how dysfunctional or busted it is. So for those people, especially if you can tell, “Dang, this isn’t a click anymore, this isn’t a match anymore, we’ve got to move you on here. And I know that you are not strong enough to quit this job,” then that is actually another version of it too.