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Say what? The transformative power of radical candor at work.

Most leaders learn through experience—by seeing what works and oftentimes learning the hard way. This might mean watching an employee walk out the door and never to return, or inspiring a bad review on Glassdoor. We’re each bootstrapped by our successes and failures, by our mediocre management training, and the concept of Radical Candor™—saying exactly what you think—was likely not part of our leadership playbooks.

Radical Candor can be uncomfortable. It’s something different than “being political” or playing it safe. It can also be transformative. Candor, Inc.’s framework for delivering radical candor is a powerful tool for providing better impromptu feedback, whether you’re giving criticism or praising a job well done.

It’s a framework that seems to resonate. As I interviewed leaders at various points in their management careers, there was often a nod of recognition, and even a few aha moments, as if to affirm, “Yes,

Whether giving radical candor or taking it, many leaders can identify pivotal moments in their careers when the one-two punch of “challenging directly” and “caring personally” changed their own course or impacted the careers and lives of their teams for the better.

Breakfast with a side of candor

Years ago, Anne Raimondi, SVP of Marketing at Zendesk, was tasked with letting an exceptionally talented, smart product manager know that his team, which included his direct manager, found him difficult to work with. This product manager, whom we’ll call James, was working on some of the company’s most strategic projects, but people were avoiding him because he was quick to complain and to point out others’ failures whenever he was frustrated.

It wasn’t a conversation that Raimondi was looking forward to having. In fact, she felt stressed going into it. She booked an offsite breakfast meeting, hoping to set the tone and signal that this conversation was not going to resemble an ordinary one-on-one.

She began the conversation with: “I really care about you and I want you to be successful. You’re one of the brightest people on the team and right now you’re failing.”

Naturally, James was surprised and defensive—this wasn’t the breakfast he’d anticipated. His reaction was to offer excuses for why projects weren’t succeeding. And although Raimondi acknowledged his point of view as valid, she then got specific about how many times people had complained to her about working with him, and challenged him to start coming up with solutions instead of letting his frustration take root.

The next week, his direct manager asked her: “What did he eat at breakfast? He’s shown up as a different person.” At the time, Raimondi didn’t know that she’d delivered her feedback with radical candor—but she had.

“What did he eat at breakfast? He’s shown up as a different person.” At the time, Raimondi didn’t know that she’d delivered her feedback with radical candor—but she had.

“My motivation wasn’t to tell him he was wrong,” Raimondi explained. “It was to tell him that he wasn’t being successful, and that I wanted to help him be successful.” She knew how much he wanted to succeed, and she felt they had enough trust between them to be that candid. She also knew that the stakes were high. If she didn’t take a direct approach, they were soon going to be having a conversation about parting ways instead.

Results may not be immediate

Radical Candor isn’t a perfect recipe for a happy ending, especially when the interaction comes as a formal review or at the point of a performance improvement plan. Radical Candor is, almost always,

Delivering praise that is specific and sincere, and—especially, criticism that is kind and clear—involves some cocktail of discomfort and bravery. And it’s not enough to give the feedback and walk away. After delivering feedback, it’s just as important to witness how your feedback is received.

And it’s not enough to give the feedback and walk away. After delivering feedback, it’s just as important to witness how your feedback is received.

This includes watching for what’s going on nonverbally, with an employee’s body language. The same feedback might incite one employee to roll their eyes and another to nod earnestly, depending on the kind of day they’re having.

“The goal is to strive for Radical Candor in every interaction,” says Candor, Inc.’s COO Russ Laraway. “Strive for good feedback, but then gauge it so that you understand whether it’s effective.”

In Raimondi’s case, the longer she and James talked over breakfast, the more she could see that he’d heard what she had to say. After that, witnessing the changes James made at work gave her the confidence to continue down the path of challenging directly. Even so, she admitted, “There have definitely been times when I gave feedback and could see that I was not coming across—when I felt like, ‘Ah, I’m not succeeding through this.’”

Be helpful: Easier said than done

According to Candor, Inc.’s framework, when you’re clear about what’s wrong, and why, and can offer criticism in a spirit of helpfulness, as Raimondi did, you help your employee to fix the problem. You may not have all the answers, or even the ability to actually help, but as Candor’s site says, “What you care about is helping others do the best work of their careers,

In another story, a talented individual contributor (we’ll call her Kate) moved into a team manager role. All started well, but after awhile, her team seemed unhappy and her projects were falling apart. Kate couldn’t quite put her finger on why, especially because it seemed like she was working hard to do all the right things. Fortunately, her manager, after doing a little discovery around the issue, was able to tell it to her straight: “You’re spending too much time trying to be a good people manager, but it seems like you don’t actually like managing people. You’re drained by one-on-ones and you really miss doing the work yourself.”

Ouch, right? But it was true. After moving back into an individual contributor role, Kate was back on track. It wasn’t her manager’s intent to fire her; instead, she wanted to help steer Kate back towards a role she’d thrive in.

Situations like this aren’t uncommon—people in the wrong role or desiring a role that isn’t available. As Tom Keiser, Zendesk CIO and SVP of Technical Operations, shared, “Feedback is about being completely honest. You’re providing performance feedback about the person’s role, but you have to do it in the context of what their aspirations are. Sometimes people’s aspirations are greater or different than the opportunities they will have inside of the company.”

These kind of career conversations can be hard, but are key to helping employees develop their skills toward their longer-term goals. Keiser tries to approach conversations like this by thinking about how he wants to be managed and communicated with.

“I deserve a promotion.”

Moments of radical candor are often prompted by having to respond to outsized expectations. Years ago, a woman reporting into Yoon Chung, Head of Global Program Management at Symphony, was particularly ambitious. Her colleagues found her unapproachable and distant, but she had the confidence and drive of an entrepreneur. Chung met with her monthly for semi-formal performance reviews, which gave him the chance to regularly offer praise and criticism.

In response to her drive, he often had to pepper his responses with probing questions, to challenge her and to see whether she’d thought things through. One day, she told him that she was ready for the next level—but it wasn’t just that she wanted to advance to the next stage of her career. She wanted to advance by several levels.

“Let me be honest with you,” he replied. “You will not meet that goal based on what you’re doing now, and how you’re acting. You’re all about processes and tools, but not about people. You come off as only caring about yourself.”

Teary and defensive, she replied, “You’re wrong. I’m not that person.”

Based on situations in which Chung found himself similarly challenged by a boss, he recognized that she was having an emotional reaction and needed time to self-reflect. But what happened later was inspiring. She started to approach her job with more humility and, in turn, began to rapidly move up through the ranks. By following Chung’s advice, she’d discovered her passion—people—and began to naturally become the leader she’d always wanted to be. Today, they’re still in touch. At her wedding, Chung was even approached by the groom who said, “Thanks for being hard on her when no one else wanted to be hard on her.”

For Chung, it was simple: “I did it because I cared.”

The T words: Trust and team-building

Another manager relayed a similar story of a rising star. The employee was extremely smart and valuable to the organization, but she spent all her time managing up, which meant that her peers didn’t view her as a leader. Without channeling some energy into her peer group and working to build those relationships, she wasn’t primed to succeed in a leadership role.

This feedback came as news to the employee, who countered, After taking the time to talk through the feedback, the manager better understood where the employee was coming from. As a mother to young children, she often felt like her time was limited and approached the workplace with a rigid sense of schedule. Peer lunches seemed like an extravagance. The manager—also a mother—was then able to offer more specific, empathic advice and helped her to understand that time spent getting to personally know peers was a valid and important investment in her career. As the employee began to branch out, her manager felt confident promoting her.

Sometimes rapport building happens organically, once you create the space for it, and a culture of open, direct conversation. Other times, manager-employee relationships need to be helped along. Keiser, who leads a team of IT professionals, tries to build in offsites and moments for the team to get to know each other better. “Once you work through and overcome things together,” he said, “there’s a degree of trust that allows you to have a very efficient kind of candor.”

Sometimes rapport building happens organically, once you create the space for it, and a culture of open, direct conversation. Other times, manager-employee relationships need to be helped along.

Similarly, Matthew Kantelis, Director of Strategic Alliances at Avalara, shared, “We do a lot of things to fast-track our ability to get to know people and build personal relationships with them.”

Kantelis is a self-described Millennial, and a big believer in bringing your whole self to work. Through observation, he’s gotten the sense that past business cultures asked people to leave their personal lives at the door. “But that’s changed,” he said, “and I think it’s a change for the good.” At Avalara, he believes his role as a leader is to help employees maximize their potential both inside and outside of their current role. “One of our Guiding Principles in our Manifesto (a 5-year strategy) is about the ‘Power of Orange’, and how we’re expected to challenge each other, but also to respect and support each other, with what we call ‘radical transparency’”.

Some might say that’s a tall order, but he cited an example of an employee who excelled at work but also had a lot of personal goals. “If she’s happy at home, I know she’ll do better at work,” he said. “It depends on each individual. But you have to be invested in your employees and you have to know who they are, what’s going on in their lives, and what’s impacting them.”

Kantelis’ own moment of “radical transparency” came before he moved into a leadership role. Some changes were being rolled out at the company and during the course of a meeting about the changes, he got a bit animated. Immediately afterward, his boss pulled him aside and said, “I appreciate your enthusiasm, but when you get that animated in public, people follow you. You ended up making everyone in the room overly worried about something that should have been easily resolved. You need to be aware of the effect you have on others, because otherwise you won’t understand your surroundings and how people respond to you in public.”

By pulling Kantelis aside, immediately after the fact, the criticism made sense in context and challenged him to begin to refine the way he interacted with people around him. This ultimately helped propel him into a leadership role, but it also opened the door to a better way forward, for everyone. That’s radical candor.

Learn about the pitfalls of mean bosses and "Manipulative Insincerity", and why being too nice will always backfire.

Suzanne Barnecut is a content marketer for Zendesk and a frequent contributor to Relate. Fascinated by technology, but a diehard reader of paper-made books and sender of snail mail. Find her on Twitter: @elisesuz.

Illustration by Andrea Mongia.

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