Leadership, Like a Letter, Takes Time: Why Upskilling Must Be Part of a Human-Centered Strategy – The Aspen Institute
In a world that moves at the speed of a notification, where conversations are cut short by distractions and relationships are reduced to transactions, something important is slipping away: the depth of human connection. We are in desperate need of leaders and organizations that will not let it slip away from us.
Look at these mailboxes. I walked by them and considered what they represented. People would take the time to write a letter — to consider their words, to connect with someone who mattered, to share something meaningful. And for those receiving, they’d peek through the glass to see if something was there — perhaps just once a day. And once received, they would take the time to read, reflect, and absorb. It was deliberate. It required thoughtfulness and patience. It built relationships.
This is not about nostalgia. I am not advocating that we return to an era before technology, nor am I suggesting that efficiency doesn’t matter. It does, but efficiency-driven leadership — starting with assembly lines, management theories rooted in control, and decades of MBA programs focused on optimization — has contributed to how we got here.
Efficiency without humanity has left us with a leadership deficit. And now, we stand at a defining moment — where we have the opportunity to move forward by integrating human-centered leadership into the future of work. Not as a retreat to the past, but as a deliberate evolution to unlock what makes people truly capable in an era of transformation.
The best leaders are not task managers; they are developers of people. They understand that leadership is not about delivering quick results at any cost, but about creating environments where people grow, thrive, and contribute at their highest levels.
Empathetic and collaborative leadership requires the same qualities that letter writing once did:
The best organizations know this. They don’t just develop individual leaders — they develop leaders who develop others. These leaders create environments where potential can be cultivated and opportunities are unlocked. That’s the difference between good leadership and transformative leadership. And yet, many companies fail to make this connection.
Here’s the problem: Organizations often separate leadership development from upskilling efforts. They invest in specific (and sometimes siloed) initiatives — technical training, digital transformation, even durable skills, and AI-driven efficiencies — but forget the need to invest in leaders, for they are the ones who make learning stick.
It’s a critical oversight. Without strong leaders who foster learning cultures, upskilling becomes temporary, rather than a sustainable advantage. Leaders who are skilled in coaching, mentoring, and creating psychological safety will drive workforce transformation far more effectively than any standalone program. However, leaders can’t develop these qualities without being invested in and supported to grow these skills — without the time, opportunity, and commitment to getting better at them.
The opportunity ahead of us is not just about technology or efficiency — it’s about what humans are capable of when leadership fuels growth. This is a call to action for leaders to stop managing and start developing, to stop optimizing and start elevating.
We don’t need to go back. We do need to move forward — by recentering leadership on the power of human connection, development, and the ability to cultivate talent for a rapidly changing world. The best leaders will not be those who simply drive performance; they will be those who help people rise.
The way forward is clear:
Are you just texting? Moving at speed to share quick thoughts? Or are you writing letters — taking the time to craft them, deliver them with care, and ensure they leave a lasting impact?
For executives and the C-suite: Are you taking the time to build leaders who craft letters? Ones who can be thoughtful and drive performance and transformation? Or are you texting to fill leadership roles?
Because leadership, like a letter, is an opportunity to connect, to build, and to develop. But only if we slow down long enough to do it right. (This isn’t about literally writing letters — though that’s cool. It’s about applying the principles letters represent: thoughtfulness, depth, and meaningful connection in leadership.)
It’s time to lead differently.
Chris Trout is a consultant to UpSkill America and Executive in Residence with the Education and Career Mobility Fellowship.
UpSkill America, an initiative of the Aspen Institute Economic Opportunities Program, supports employers and workforce organizations to expand and improve high-quality educational and career advancement opportunities for America’s front-line workers. We seek to create a movement of employers, civic organizations, workforce intermediaries, and policymakers working collaboratively to implement education, training, and development strategies that result in better jobs and opportunities for front-line workers, more competitive businesses, and stronger communities. Follow us on LinkedIn and learn more at upskillamerica.org.
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