--- title: Box CEO Aaron Levie on the AI Fluency Skills Leaders Need Right Now description: Breaking news and analysis from time.com. Politics, world news, photos, video, tech reviews, health, science, and entertainment news. canonical: https://time.com/partner-content/charter/box-ceo-aaron-levie-on-the-ai-fluency-skills-leaders-need-right-now/ author: Jacob Clemente article:opinion: false article:content_tier: free article:published_time: 2026-05-31T10:30:00.000Z article:modified_time: 2026-05-29T21:54:43.558Z article:section: Charter og:title: Box CEO Aaron Levie on the AI Fluency Skills Leaders Need Right Now og:description: Breaking news and analysis from time.com. 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Time charter * [leadership](/partner-content/charter/tag/leadership/) ## leadership # Box CEO Aaron Levie on the AI Fluency Skills Leaders Need Right Now  by [Jacob Clemente](https://time.com/author/jacob-clemente/) Senior Reporter, AI & Work May 31, 2026 10:30 AM UTC  Art: Charter  by [Jacob Clemente](https://time.com/author/jacob-clemente/) Senior Reporter, AI & Work May 31, 2026 10:30 AM UTC This week, Charter released a new research playbook titled “Getting Ahead of the Leadership Gap” about the leadership pipeline problem that companies find themselves in amid the aftermath of the pandemic, the arrival of generative AI, and the push to flatten organizations. The playbook includes research and reporting, expert interviews, and case studies on how to tackle the issue head-on. You can **download it** [**here**](https://www.charterworks.com/download-getting-ahead-of-the-leadership-gap/)**.** One of the chapters focuses on how business leaders need to role model AI use—and improve their AI “fluency” by not only understanding the technology but reimagining how their business uses it. [Aaron Levie](https://www.linkedin.com/in/boxaaron/), CEO of cloud-storage company Box, is a clear example of such an executive. He [uses AI extensively](https://www.linkedin.com/posts/boxaaron%5Fat-box-were-100-focused-on-being-an-ai-first-share-7320471552649498624-R%5FDe/?utm%5Fsource=share&utm%5Fmedium=member%5Fdesktop&rcm=ACoAACCYHKUBljStDrAgr3%5FsZFJ1n4OEuCMI6BA), and he’s one of the more outspoken business leaders about the technology’s impact on [work](https://x.com/levie/status/2052566788236509254) and [jobs](https://x.com/levie/status/2044621545348481285). You can read our extended interview with Levie in the playbook. Here are highlights, edited for length and clarity: Sign up for Charter's newsletter to get the handbook for the future of work delivered to your inbox. Email Address You can unsubscribe at any time. By signing up you are agreeing to our [Terms of Service](https://www.charterworks.com/terms-of-service/) and [Privacy Policy](https://www.charterworks.com/privacy-policy/). **You've** [**talked about**](https://x.com/levie/status/2048537503972684252) **some of the late nights you've spent using AI. What are you typically working on?** Sometimes it's vibe coding, and I'll do that for prototyping a new feature, seeing how something might need to manifest within the product. It's all in the category of prototyping, nothing that we would actually release or anything meaningful from a production standpoint. Then on the other side, I'll use AI similarly for just a lot of my own work automation tasks, where I'm trying to do research on a market or I need to get account intelligence about customers. **How has AI most helped you in your role as CEO?** On a personal productivity level, there \[isn’t just one\] single use case I could point to…I'm traveling to a city and I want to figure out what customers I should go meet with. That might normally be a 10-hour project for an analyst or for a chief of staff to go do. Now it's a 10-minute activity for AI. I have agents running multiple times a day for that kind of category of task. If you're a really big business, they have this thing often called the ‘Office of the CEO,’ and it usually has two, three, or four people in it who are all doing a bunch of work on behalf of the CEO—what to do about the events that they're going to, which customers to meet with, which relationships to maintain. But 99% of companies don't have an office of the CEO. \[AI\] gives you the ability to have that same kind of leverage. **In a** [**recent interview**](https://www.wsj.com/video/series/wsj-leadership-institute-leaders/box-ceo-aaron-levie-on-the-future-of-ai-automation/81DE6A5E-1F7D-4907-9E25-88E9F46DA1BB) **with The Wall Street Journal, you said AI could give frontline managers the ability to produce more outputs as individual contributors, not just through the employees they manage. You described it as a ‘player-coach’ dynamic. How is this playing out at Box?** Usually, you take your best individual contributors and you turn them into managers. Over time, those managers become much more about managing the people and the system and orchestrating the work, rather than being a contributor themselves. That can go extremely well, but sometimes you can atrophy your skills \[for\] particular domain-specific work. Our best people managers are also active contributors \[to\] real work products. They're the design manager who also produces designs. They're the engineering manager who really dives into the code. What AI lets you do—because it lets you be in two places at once—is you could be doing the team management side, but you can also have agents going and building something or executing something. **Is this an expectation for top leaders at Box as well?** I mean, I'm doing it, so I don't see why everybody else isn't. **You’ve staked out clear positions about how you expect AI to affect work—you talk about** [**Jevons paradox**](https://en.wikipedia.org/wiki/Jevons%5Fparadox) **and the fact you want to use AI to allow Box to do more, rather than the same with fewer resources. How do you balance the need to have a clear vision on what AI means for your company with the need to be adaptive?** I'm willing to adapt my view on things. I will admit that I'm a hammer, seeing everything as a nail on this topic \[of what automation means for work and jobs\]—simply because my brain is so wired to this. It's been a view I've had for at least 15 years. We didn't really think about automation when we started Box, but I started to think about automation more as we were scaling. I developed this sense that there's so much work that has to get done, but it prevents the company from growing. If you could automate that work, you'd actually grow faster, which would cause you to hire more people and do more as an organization. AI, to me, is just another supercharger of that same dynamic. I haven't seen a lot of evidence that would veer me off from that thinking. Now, there are some areas where more nuance is useful. There are some frontline customer-support roles, for example, that will be under pressure as AI can handle more of that work. But even in those kinds of roles, what we actually see happening is as soon as you relieve that frontline work, you have even more customer interactions, or you have the ability now to have even more strategic customer interactions, which often lets you just repurpose that talent to a different part of where that work happens. **How do you build trust internally around AI and what it means for them?** Our strategic message is very clear: We are going to use AI to get more done, and we want everybody ‘on the bus’ at Box to be a part of that journey. The only way that you won't go along with us is if you choose not to. We are hiring in almost every function at Box right now. We've tilted the percentages differently because of the needs of the business and because of what AI can do. But we are going to keep growing as an organization, and AI will be used for us to be able to have more output and be able to better serve our customers. --- ## Read more from Charter [READ MORE](https://time.com/partner-content/charter/) [Open article: Dr. Becky on What Good Parenting and Good Leadership Have in Common](https://time.com/partner-content/charter/dr-becky-on-what-good-parenting-and-good-leadership-have-in-common/)  ### Dr. Becky on What Good Parenting and Good Leadership Have in Common [READ MORE](https://time.com/partner-content/charter/dr-becky-on-what-good-parenting-and-good-leadership-have-in-common/) [Open article: The Three Ingredients for Building Trust](https://time.com/partner-content/charter/the-three-ingredients-for-building-trust/)  ### The Three Ingredients for Building Trust [READ MORE](https://time.com/partner-content/charter/the-three-ingredients-for-building-trust/) [Open article: 10 Lessons on AI Transformation—and Leadership—from Top HR Leaders](https://time.com/partner-content/charter/7383559/10-lessons-on-ai-transformation-and-leadership-from-top-hr-leaders/)  ### 10 Lessons on AI Transformation—and Leadership—from Top HR Leaders [READ MORE](https://time.com/partner-content/charter/7383559/10-lessons-on-ai-transformation-and-leadership-from-top-hr-leaders/) --- ```json [{"@context":"https://schema.org","@type":"NewsArticle","@id":"https://time.com/partner-content/charter/box-ceo-aaron-levie-on-the-ai-fluency-skills-leaders-need-right-now/","mainEntityOfPage":{"@type":"WebPage","@id":"https://time.com/partner-content/charter/box-ceo-aaron-levie-on-the-ai-fluency-skills-leaders-need-right-now/"},"headline":"Box CEO Aaron Levie on the AI Fluency Skills Leaders Need Right Now","datePublished":"2026-05-31T10:30:00.000Z","dateModified":"2026-05-29T21:54:43.558Z","description":"","url":"https://time.com/partner-content/charter/box-ceo-aaron-levie-on-the-ai-fluency-skills-leaders-need-right-now/","keywords":[],"thumbnailUrl":"https://static.time.com/v3/assets/bltea6093859af6183b/blt65545ac877dfda24/6a1a0ad06c0c2c2bfa79115c/Aaron_Levie.jpg?branch=production&width=1200&quality=75&auto=webp&crop=1200:675&height=675","author":[{"@type":"Person","name":"Jacob Clemente","jobTitle":"Senior Reporter, AI & Work","url":"https://time.com/author/jacob-clemente/"}],"articleSection":"Charter","image":[{"@type":"ImageObject","url":"https://static.time.com/v3/assets/bltea6093859af6183b/blt65545ac877dfda24/6a1a0ad06c0c2c2bfa79115c/Aaron_Levie.jpg?branch=production&width=1200&quality=75&auto=webp&crop=1200:675&height=675","width":1200,"height":675,"headline":"Aaron Levie.jpg","caption":"","creditText":"Art: Charter","representativeOfPage":true}],"publisher":{"@type":"Organization","name":"Time","url":"https://time.com/","logo":{"@type":"ImageObject","url":"https://time.com/images/logo.png","width":528,"height":156},"foundingDate":"March 3, 1923","sameAs":["https://www.facebook.com/time","https://www.instagram.com/time/?hl=en","https://twitter.com/time","https://www.pinterest.com/timemagazine"]}},{"@context":"https://schema.org","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"https://time.com/partner-content/charter/box-ceo-aaron-levie-on-the-ai-fluency-skills-leaders-need-right-now/","name":"Box CEO Aaron Levie on the AI Fluency Skills Leaders Need Right Now"}}]}] ```