This week on The Lift, Ben is joined by Justin Kerr, also known as “the efficiency monster,” a former senior executive at brands like Levi’s, Uniqlo, Old Navy, and Gap. Justin is the author of the “survival guide” How-To series (How to Cry at Work, How to Quit Your Job, How to Write an Email, and How to Be a Boss).
Key takeaways:
- Over-communication at work reduces anxiety and “status check” micromanagement
- Clear expectations and deadlines are a core leadership skill, not just a nice-to-have, especially when managing up and across teams
- Time management and early-morning routines create more freedom outside of work
- Structured one-on-ones and pre-read agendas make meetings more efficient, build trust with executives, and speed up decision-making
- Small process improvements (like better emails and links) compound into big efficiency gains, so you don’t have to “change the whole system” to make work easier
- Remote work has real limits for learning, feedback, and leadership development, and in-person connection still plays a crucial role in how teams grow
In this episode of The Lift, Justin Kerr introduces us to his niche superpower: known as the “Efficiency Monster,” Justin is obsessed with making work simpler, faster, and less stressful through clear communication, sharp time management, and ruthless expectation-setting.
Justin’s philosophy can be summed up in three words: send more emails.
Not longer emails. Not more confusing emails. But more proactive, specific, expectation-setting messages that keep your boss, peers, and stakeholders fully informed so they never have to chase you for status. That one extra “FYI” or deadline reminder may take another 30 seconds in the moment, but it can save you hours of scrambling, anxiety, and follow-up meetings down the line.
Justin explains why over-communication is not a weakness or a sign of insecurity. It’s actually a high-level leadership skill. If your boss is asking you for status, Justin says you’ve already failed. The anxiety in the system shows up as “just checking in” emails, Slack pings, and surprise questions in meetings. Sending more thoughtful updates up front fills the space before it floods with concerns.
A big part of Kerr’s framework is his obsession with time. He’s a committed morning person and spent two decades in corporate roles without ever working past 5:00 p.m. – not because he was coasting, but because he built his days differently. He’d start extremely early, completing his deep work in those quiet morning hours before the offices started bustling. During that time, he’d send the emails, updates, and pre-reads that made the rest of the day run more smoothly.
For Justin, time equals freedom. Working in corporate America wasn’t selling out; it was a way to fund his creative life, which included bands, record labels, zines, and later, books. All of that was only possible as long as he kept his workday tight and efficient. That meant a radical commitment to priorities. He argues that if you don’t know your top three priorities in life, it’s almost impossible to design your schedule in a way that makes sense.
This conversation also dives into one of Justin’s favorite tools: the structured one-on-one meeting. In his view, you cannot be truly good at your job without a recurring 30-minute one-on-one with your manager. But it’s not enough to just “show up and chat.” He recommends:
- Sending a written agenda by 5:00 p.m. the day before, so your boss can pre-read and prepare
- Printing or bringing that agenda into the meeting, in priority order, to build momentum: quick wins first, harder asks later
- Treating that time as your responsibility to manage, not just something the boss drives
This approach works at every level, even for the C-suite. Executives, Justin notes, are often lonelier and more uncertain than people realize. They want clarity, confidence, and structure from their leaders, not more ambiguity.
Justin breaks work down into two simple domains: people and process.
- People: relationships, trust, triggers, and individual differences. We all bring our family histories and emotional wiring to work; a manager’s tone or look might trigger old childhood patterns. Without self-awareness, it’s easy for simple feedback to spiral out of control.
- Process: the repeatable workflows – emails, forms, slides, approvals – that either make work easier or wildly inefficient.
According to Justin, most people are waiting for some “grand organizational redesign” to fix broken processes. But real progress comes from small, local improvements: adding the right link to an email, creating a simple agenda template, or sending a pre-read to a difficult stakeholder so they can’t derail a meeting with “I’m hearing this for the first time.”
Finally, Justin shares his hot take on the future of work: Remote work doesn’t fully work – at least not for everything. While digital tools can streamline process and documentation, he believes leadership, learning, and relationship-building still require in-person time. In his view, AI and automation should handle more of the process work. But the human side, including feedback, trust, creativity, and culture, happens best when people are actually together.
If you’ve ever felt buried in Slack messages, frustrated by vague expectations, or stuck in a cycle of last-minute requests, this episode will give you practical and immediately usable tools to change the dynamic.
And yes, you may walk away sharing Justin’s belief that the secret to an easier work life might just be three deceptively simple words: send more emails.
Links:
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
