“Turn Your Heel Into Your Strength” – Here’s Plucky’s Founder on Navigating the Trickiest Challenges

Hard and uncomfortable conversations are a perennial challenge for managers. And a feeling of aversion to saying it like it is, is a feeling we’re all too familiar with. Who wants to tell someone they can’t have a raise, or that their dream job isn’t in the company’s plans?

Nobody does—or, almost nobody. Jennifer Dary, founder of Plucky, discovered that the conversations that send everyone else into fight-or-flight were precisely the conversations she was good at having.

So she started Plucky nearly five years ago to make a more human counterpart to Human Resources. “I call that employee development, or Adult Development,” she says. “We learn so much as kids that there’s this idea of childhood development. And then suddenly you become eighteen years old — ding! The timer goes off, and you’re supposed to be perfect.”

Dary sees the need for a different concept of learning as adults because everything that happens to your employees and coworkers every single day—at work or not—is influencing how they show up. These situations lead to many of those uncomfortable conversations you don’t like having. And like it or not, having those conversations is your role as a manager, so you better learn how to approach them more confidently and more curiously.

“When people move into management,” Dary says, “the currency of code and pixels evaporates. The new currency is humans, and humans are wily and hard to wrangle. It’s hard to know what metric of success is: Was it a good day if nobody quit? But, great news, humans are going to provide you a career path for the rest of your life. They’re not going anywhere. That currency is solid. So if you become curious about human-wrangling, you’re good.”

a way for engineering managers to improve their 1:1s

Unsolicited plug: Dary developed Plucky’s first product, Plucky Cards, to give managers a way to be curious by elevating rich and unexpected conversations at work. They’re a fun way to mix things up. We bought a pack and use them here at GitPrime and were sufficiently impressed that it prompted us to reach out to see what else Dary had to say about interactions with colleagues.

Your org is an ecosystem

One of Dary’s keys to becoming more comfortable with uncomfortable conversations is to recognize—at every moment, not just the bad ones—that you’re part of an ecosystem. There’s no such thing as an isolated incident.

“What you see are symptoms,” she says. “Someone is coming to you because they need to vent, or maybe they’re lost.”

Sometimes, it’s a manager’s job to solve immediate issues. But in general, Dary suggests that you try to see yourself as a problem solver, a coach, in a more general sense.

“Life is like a giant science experiment. You should just keep coming back to ‘what did I learn from this one? Okay, next time I’m going to try this instead,’ and then you keep trying things.”

That means you’re empowering the people in front of you to grow as individuals by working to resolve their problems. Jumping into a gossip fest—even if you think you’re just commiserating—or passing the buck to get this off your plate will only degrade the entire ecosystem.

“Instead, ask yourself what kind of energy you can help this human go back to their desk with,” she says. “And try things. Really, I think life is like a giant science experiment. You should just keep coming back to ‘what did I learn from this one? Okay, next time I’m going to try this instead,’ and then you keep trying things.”

That doesn’t mean every problem is yours to solve. At times, all you can do is point someone in the right direction to the person who can help them solve their issue. And at other times, you can look at the picture beyond the problem itself. Go have coffee with the apparent problem coworkers just to see how they’re doing. But in every conversation, Dary says, be loyal to the human in front of you.

Now, there are a couple exceptions where direct action is necessary—particularly when it comes to legal things like harassment or sexual misconduct. As a manager of the ecosystem, it’s your job to keep an eye out for those things and immediately elevate those situations to the appropriate person. But by and large, think of your workplace as a community that you’re part of.

Bearing the bad news

It’s often easier to handle the tough conversations when they come to you, than when you have to initiate them. It’s a whole new ballgame when you’re the bearer of difficult news, and these are the conversations we most frequently deflect or avoid.

“Crushing the dream is the thing that people don’t want to do,” Dary says. “And that’s because humans are really actually pretty nice. Why aren’t you delivering the hard feedback? Well, probably because it feels really mean. Probably because you’re somebody who doesn’t want to disappoint someone. And that’s often as simple as it is.”

If you’re reading this hoping to find a solution for breaking bad news later today, you’re out of luck. Dary’s belief is that it’s much easier to break bad news when you are standing on trust with your bad-news-breakee. And that’s something you develop with consistent, genuine contact over an extended time.

“One-on-ones. Cookie breaks. Whatever,” she laughs. “Trust-building happens in the space of a good one-on-one relationship, to the point where, one day, one of you will have something bad to say to the other person… and that person won’t see this as the evilness in you showing up to take them out.”

“You’re creating momentum and space for that trust to happen so that when there really is something to talk about, they know for sure that you won’t bail on them.”

If you’ve established strong rapport throughout your interactions, then you’ll recognize how each of you has seen the other through Major Life Events—and that neither of you is an inherently wicked person. Ergo, there must be business reasons behind the bad news. It’s not personal.

Even if your employees are rote and mechanical in their 1:1s, that’s fine. “You’re creating momentum and space for that trust to happen so that when there really is something to talk about, they know for sure that you won’t bail on them,” Dary says.

Of course, in a moment of crisis or discomfort, this strategy doesn’t help you a whole lot. You can’t go back in time to build trust. But in that moment, even if no foundation has been laid beforehand, she recommends grounding the conversation in directness and empathy. You’re doing no one any favors by skirting the issue or softening the blow.

“As a good manager, you can start the conversation by saying, ‘Listen, I have to tell you, this is hard for me to say,’” Dary points out. That’s not going to make the conversation any happier, but it’s going to make it easier and clearer for both of you.

Rethinking skip-level 1:1s

Part of the reason the words “manager” and “management” inspire cringing is because those are the folks responsible for bearing you all manner of news, including the ugly. Getting called in to see your boss has a certain “oh crap” reputation. So getting called in to talk to your boss’s boss must be a really bad sign, right?

It doesn’t have to be, Dary says. Even a monthly or bimonthly skip-level 1:1 can be really helpful for both the employee and the higher-level manager, if it’s conducted genuinely and consistently—again, to build trust.

“Sometimes, for the employee, skip-level one-on-ones help clarify the larger system,” Dary says. “They realize, oh, my manager isn’t actually an asshat. It’s that they’re getting pressure from all these other places.”

So hold skip-levels on whatever schedule works for your team, and not just when there’s pressing issues to discuss. Invite the person across from you to share how things are going at work, and be open to hearing what’s going on at home. And respond to what they share with empathy—both for your 1:1 directly, and for anyone they’re having problems with, too.

“I’m not a psychic but I’ll tell you what, if somebody’s suddenly showing up with a different energy, something’s going on.”

“I often ask people, if they’re having problems with a coworker, ‘Oh man, what’s going on with them?’” Dary says. “‘What’s happening outside of work? What’s going on there?’ Because I’m not a psychic but I’ll tell you what, if somebody’s suddenly showing up with a different energy, something’s going on. And sometimes they share those things, which helps to clarify what’s happening and allows people to have more patience and empathy. But even if they don’t, getting them to think about the other perspective is helpful.”

Skip-levels aren’t just beneficial for your employees, though; they also give you a luxury perspective on how your direct reports are managing their teams. You practically get a mini-consultant to share with you how life is on a given manager’s crew.

“You’re not on a fact-finding mission to fire people,” Dary stresses. “It’s more about getting cues as to what kind of curriculum your report needs.”

You might have to read between the lines, but you’ll see quite clearly if, say, a manager is having trouble delegating effectively. You can take that knowledge not to punish or reprimand, but to use your next 1:1 with that manager to encourage them to delegate, model it for them, and generally go for that adult development that’s so important in Dary’s view.

“Skip-levels give you a blueprint to what that manager who reports to you actually needs to learn,” she says.

Turn your heel into your strength

Some companies try to do away with the stigmas (and the discomfort) attached to “managers” and “Human Resources” and by doing away with those roles altogether. For example, many people are wary of words like “power,” or “hierarchy,” so it only makes sense that we see companies move towards flat organizational structures

But Dary’s not having any of it.

“I think the itch they’re trying to scratch is ‘no, we’re all cool, we’re not like that,’” Dary says. “But you can’t just be the anti-. You have to stand for something. And often, whatever your biggest weakness is, whatever your Achilles heel is, is also your superpower.”

This approach offers you the biggest learning moments of all. Rather than trying to avoid or smooth out the scenarios that cause you the greatest discomfort or challenge, step into them. Welcome them. And allow that radioactive spider bite to turn you into a stand-out human being.

“Whatever your biggest weakness is, whatever your Achilles heel is, is also your superpower.”

For many managers, the big fear is the hierarchy. Even with all Dary’s advice above, they’re still uncomfortable with the concept of ‘bosses’ and ‘managers’.

“If you find yourself running an organization and you are compelled to say you’re flat, take the fear out of organizing a hierarchy and say, ‘We’re going to do it a new way. The right way,’” Dary says. “Go little by little as it feels right and go slowly into it. Find your own way.”

She is inspired by a story about a man who keeps a slip of paper in his wallet. The paper reads, “That which hinders the task, is the task.”

“So if you’re like, ‘I don’t know what the org chart should be, we’re just trying to make software here’… sounds to me like the work for you is organizing the company,” she says. “That could end up being something you write years of blog posts about, podcast, giving talks about how you structured your company authentically. That becomes your superpower.”

And it doesn’t have to be anything as large as your company org chart. You can revolutionize the way you have coffee with your peers. But whatever makes you uncomfortable isn’t to be avoided. It’s to be embraced as your chance to learn how to do it more authentically—and to revolutionize how you, the team, and maybe even how the industry, work.


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