Aware of biases toward executives, SKY-HI builds a "gentle" company.

Dentsu Inc. Youth Research Department "Wakamon" (hereafter Wakamon), a planning and creative unit exploring emerging values with the vision "Designing the Future from the Perspective of Youth," researches the management mindset essential for future leaders.

From this work emerged the concept of "Flat Management." Its core idea is to create a "comfortable team" not by leaders imposing top-down directives, but by respecting subordinates and team members and engaging with them on an equal, horizontal level.

This series features interviews between Wakamon members and prominent figures practicing such "Flat Management." In the third installment, Wakamon's Rei Nagi speaks with SKY-HI, an artist active across diverse fields including rapper, trackmaker, and producer.

In 2020, SKY-HI launched his new management/label company BMSG, stepping into the role of entrepreneur. What insights into organizational structure has he gained through his various roles, and what are the underlying principles driving his approach?

Why SKY-HI Treats His Own Employees "Gently"

Nagi: In recent years, many managers have voiced concerns about not knowing how to interact with subordinates or younger generations. Amidst this, I saw SKY-HI mention that he "tries to be kind to his own employees, above all else." The choice of the word "kind" felt very contemporary and resonated with me, while also striking me as a uniquely chosen term for how he approaches his own staff. What was the thinking behind this?

SKY-HI: "Kindness" is actually one of my company's core values. For external communications like our website, we state "Essentially Kind," but internally, we simply say "Kind." It's a feeling I personally hold dear.

I believe work, from start to finish, is entirely about communication with people. Within that, differences in career paths and abilities, and failures, are inevitable.

In my current position, the relationship between myself and my employees is almost always "equal." Any employee's failure becomes "my own failure," and anything I do affects all employees. Thinking that way, if I were to scold "myself" every single time "myself (the employee)" made a mistake, I couldn't survive. If I ruled through fear, that would ultimately come back to haunt me too. I feel that if I can't be kind, everything spirals downwards.

Nagi: So you value a mindset where you consider how your actions affect others and how they ultimately come back to you. As a "business owner," what do you specifically watch out for when interacting with employees, affiliated artists, and especially younger generations?

SKY-HI: The artists signed to my company are mostly between 15 and 24 years old. While our staff spans a wide age range, many are also in their 20s, and they have very little social experience. Looking back to when I was 17 or 18, in the opposite position, I often got "teased" by my seniors, and I felt quite averse to it. When it's someone senior or above you, there's this atmosphere like, "If you get hurt, it's your own fault," or "Don't take it so seriously." I really hated that. Even if the person saying it meant it as a joke, I know firsthand how young people, unaccustomed to that atmosphere, can get hurt. So, it's less about being careful and more about not doing it because I know from experience.

It wasn't "ordering" or "asking" – "being easy on subordinates" felt just right.

Nagi: In past eras, many people in higher positions ended up unintentionally doing things to younger people that they themselves disliked when they were younger. Even though they understood they shouldn't do things they disliked being done to them, they often did them anyway. Amidst that, it's wonderful that you've managed to translate that awareness into actual action.

SKY-HI: Regarding the teasing dynamic we discussed, it's good to keep in mind that "communication becomes harder when interests clash." No matter how you feel, the difference in positions inevitably affects things. In my case, being an artist means I have more name recognition and influence than a typical business owner. That's an unchangeable fact, which is precisely why I believe you can never be too considerate toward employees. For example, if I happen upon staff having an after-party following a live show, I get self-conscious. I worry, "Maybe everyone can't relax and enjoy themselves with me around" (laughs).

Nagi: Is that more out of concern as the president, rather than because of conflicting interests?

SKY-HI: Yes. But even in something like a drinking party, when communicating with people of different ages or hierarchical positions, conflicts of interest naturally tend to arise. Subordinates benefit from being favored by their superiors—they get better treatment and find it easier to advance. As you climb the ranks, these situations increase, so I think it's tough unless those in higher positions are self-aware. Conflicts of interest involve both "benefit" and "harm."

That said, it might be unrealistic to expect someone who hasn't been conscious of this before to suddenly change their mindset. Like building muscle, it's probably best to gradually increase the frequency of being mindful and build it up over time. Even then, mistakes will inevitably happen, so I think the only way is to repeatedly reflect on them, thinking "I messed up."

Nagi: You mentioned subordinates gaining more "benefits" when liked by their superiors, but nowadays, some argue the opposite – that leaders should be liked by those below them. The idea is, "We may hold positions of power, but ultimately, we can't succeed without those below us supporting us."

SKY-HI: I totally get that mindset. To put it in similar terms, for me, it's less about "giving orders" and more about "being vulnerable." Lately, I've come to believe that allowing subordinates to see that vulnerability is actually better for both sides. It's kind of my natural style, but the word "vulnerability" really resonates with me.

Nagi: So, intuitively, you feel things just work better that way?

SKY-HI: That's part of it, but also, when communicating, it feels good when someone relies on you. Balance is key, but I feel that balance is shifting in modern times. In that sense, I think "ordering" from boss to subordinate might be too heavy-handed now.

Nagi: Not "command" or "request," but "lean on." Indeed, if you say, "Let's not command, let's just request," leaders lacking balance might end up only making requests, leading to subordinates pulling away. That word feels so apt that I want to use it in a book I'm currently writing for leaders (managers and others in positions leading teams or organizations).

The key is to be aware that biases can't be eliminated

Nagi: I get the impression that many people at startup-type companies share books or manga they enjoyed reading with their subordinates. Do you ever recommend books you're interested in to those around you, SKY-HI?

SKY-HI: Honestly, I'm a bit afraid when people ask me for book recommendations. I worry my suggestions might end up biased. For example, if I recommend a self-help book, the person might get completely brainwashed. On the other hand, if I recommend a novel and they don't like it, I'd be shocked, thinking maybe I have no taste (laughs). Thinking about it, books are tricky.

Nagi: Listening to you, I get the impression you're very conscious about staying as level-headed as possible in your communication with others. When someone asks, "Tell me what books you like," I feel like most people would probably share their favorites without worrying too much about bias, even if it's inevitably present. While some conflict of interest is unavoidable, are you consciously trying to minimize that bias?

SKY-HI: I'd say bias is unavoidable, so I believe it's crucial to at least be mindful of it to make things enjoyable for both parties.

Nagi: The very realization that "bias can't be removed" is itself the first step toward flat communication. I think many people struggle to connect well with younger generations because they don't grasp this point. If there was a specific moment that led you to this way of thinking, could you share it?

SKY-HI: For me, it probably started when I founded BMSG and began hiring people. I started feeling "scared" and thinking about it when people I didn't know personally began joining the company. For modern business leaders, being disliked by employees carries a very high risk. Of course, for talents, being disliked also carries significant risk, but if a leader is disliked by their staff, I feel it won't just mean the work doesn't go well. I've only been running the company for two years, but I've seen people fall from grace in just two years. I've seen many people succeed or fail simply because they added another layer of responsibility.

The worlds of entertainment and the underground. These diverse points of contact with society became opportunities to view the organization from the outside.

Nagi: Similarly, I think some leaders struggle because they can't easily accept the idea mentioned earlier – that "mistakes happen" and "people are different from me." In the past, society had a "correct answer" for career paths, but that's no longer the case. I believe the trend now is that individuals can choose: to work hard, or to do the bare minimum at work and focus on enriching their private lives.

We've previously organized one form of this "correct answer" as the concept of a "Rich Career." A Rich Career prioritizes success in society and professional achievement above all else. However, I believe we're now in the era of "Rich Life." It's not just about corporate career success or social standing; it's about enriching one's own life. Furthermore, since the richness of one's life is something each person defines for themselves, while building a fulfilling career is certainly part of that, it's crucial to recognize that not everyone shares the same perspective. If leaders fail to understand these values, I believe there will be a significant disconnect with the younger generation. SKY-HI, you mentioned somewhere before that you work while maintaining 1-on-1 communication. When did you start thinking about beginning with the recognition that "every individual is different"?

SKY-HI: Regarding specific management practices, it's been within the last year or so. But the idea that "everyone is different"? I think that's been with me for quite a long time. Having many points of contact between myself and society probably influenced that in a positive way.

I spent a long time active in the group "AAA (Triple A)," which gave me many opportunities to observe society through the lens of "entertainment." In the entertainment world, social influence extends far beyond just the entertainment market. While building a career in showbiz brought its share of difficulties and stress, witnessing that world was incredibly valuable.

On the other hand, starting around age 18, I also immersed myself in the underground hip-hop scene, where I've been active even longer than with AAA. There, I encountered many people living in worlds distinct from the so-called "entertainment industry." Among my senior rappers, some worked at major staffing firms while pursuing music, and others had jobs they couldn't openly discuss. Since everyone created songs while maintaining their own connections to society, there were moments when their music revealed multifaceted perspectives on the world.

Back then, Japanese hip-hop was commercially stagnant and far from "buzz," making it impossible to turn into a fashion statement. Precisely because of that, I saw a lot of the essential elements. Being exposed to that while belonging to an organization made me realize the "abnormality" of the world and organization I was in. I think it also made me recognize that if you only know one place, you might not notice the abnormality of that organization.

There are no "tendencies and countermeasures" in communication. First, avoid "crude labeling."

Nagi: For the leaders (managers/executives) of companies reading this article or the book we're currently writing, how do you think they can become more accepting of diversity? Personally, I'm not actually very fond of the term "diversity." I feel that by framing it as "diversity," other important nuances might get lost. However, many people fundamentally struggle to accept or even grasp the concept of diversity itself. Figuring out what steps to take just to get them through that initial threshold feels incredibly difficult and challenging.

SKY-HI: As a starting point, I think it's about recognizing that people are fundamentally different, so "one-size-fits-all solutions" are basically impossible. For example, when interacting with someone, the ways you respond and the options you have branch out and multiply. While experience is needed to become better at communication, you can't use the same approach with everyone and expect it to work. That's why blindly following how-to books can lead to trouble.

Lately, I feel like we're forcing people into boxes by slapping on rough labels or categorizing them too easily. People aren't that simple or crude; each has their own individuality. I think that's been a crucial element these past few years. Even catchy words like "diversity" or "the relaxed generation" carry a certain violence. It's a bit like how catchy dance moves in the chorus become all the rage, and the music itself stops being listened to. So, while I'm not strongly opposed to "diversity" per se, I really understand the feeling you're describing.

Nagi: The tricky part is that the people least likely to think they're treating others carelessly are often the ones actually being careless or responding superficially. I feel like there still aren't many people who are consciously aware of their own distance, their position relative to others, and their communication. That carefulness is probably the most crucial part.

SKY-HI: That's true. But I think that by consistently throwing out these jabs—through articles like this or books being written—you might find that certain sensibilities start to shift intuitively over time. That's probably just the times we live in.

Moving forward, this series will continue exploring "Flat Management" by interviewing leaders across various industries. Stay tuned!