Wait, this is hilarious… and on LinkedIn.

Between that funny post and Jason’s’ (I dare say) infamous headline, “Possibly 3 raccoons in a trench coat 🦝🦝🦝🧥,” I knew I had to be “friends” with Jason or at least a follower of this pizza cult. Fast forward six months, and I’m still a huge fan.

In recent weeks, the topics have switched from pizza (all good things must come to an end) to a new topic: black T-shirts.

And more importantly, the thought: could one black shirt change everything?

Here’s my conversation with Jason Donnelly — the creative mind, humorist, and founder behind One Black Shirt — about community, storytelling, and finding meaning (and mischief) in the everyday.

Colleen: Can you start by sharing a bit about who you are and your background?

Jason: I’m Jason Donnelly and I have a writing problem. 🤣

It started in college after reading Fight Club by Chuck Palahniuk. I went on to earn an MAED in Education, and then both an MA and MFA in Creative Writing — the dream was to land a cushy tenure-track teaching position. But after teaching for a bit, I realized it wasn’t for me.

I moved to New York, became a creative recruiter, wrote a bunch of books (fiction, self-help, humor — you name it), and eventually recruited myself into Gary Vaynerchuk’s agency, VaynerMedia, where I learned advertising and social for about five years.

Since then, I’ve bounced around the ad world — iHeartMedia, an agency out of Chicago — and now I’m in Denmark as the Creative and Social Strategist at Moxso, a company doing seriously cool stuff in human risk intelligence for cybersecurity.

I’ve got a 4-year-old son, and while I love Copenhagen, I definitely miss the food in the States.

Colleen: You’ve built a community of over 11,000 followers on LinkedIn — what has that experience been like, and what have you learned from it?

Jason: Honestly? It started from a slightly dark place.

I couldn’t shake this thought about AI — that soon it’s not just going to help marketers, it’s going to replace a lot of us. The ones who’ll survive and thrive are the ones with personal brands, real communities, and people who actually care.

Because on paper, so many of us look the same. But when you’re a brand, you have something extra — a voice, a following, a little power.

That said, by January 2025, I was exhausted by LinkedIn. So many AI posts. So many copycats. So many people posting things they thought they were supposed to say.

So, naturally, I started posting about pizza.

Every. Day.

For nine months.

And somehow, that turned into 5,000 new followers and the title “The Pizza Guy on LinkedIn.” 🍕

It was fun (and ridiculous), but also a marketing experiment. And when it ended, I found myself wondering — what’s next?

That’s where One Black Shirt came in.

Colleen: Tell me about the mission behind One Black Shirt — what inspired it, and what’s your long-term vision for it?

Jason: I was ideating around what to do after pizza (which is definitely not a sentence I thought I’d ever say).

I realized I wear black shirts. That’s… basically it.

And then I thought, I wonder if one black shirt could change anything.

From there, it evolved into something more meaningful — could I use my network for good? Could I tell people’s stories in a way that connects and uplifts?

That became the mission.

So, I started making shirts embroidered with “one black shirt” in simple white lettering. The goal is to sell shirts, yes — but also to tell stories with humor, honesty, and the kind of realness that LinkedIn desperately needs.

Colleen: What advice would you give others about telling their story or sharing their experiences online?

Jason: Be. You.

There are enough fake people on LinkedIn — and in the world, honestly. Say what you want to say, do what you want to do, don’t hurt anyone along the way, and you’re good in my book.

Colleen: In your view, what’s the mark of a great leader?

Jason: A great leader balances reality and dreams — while being fair to the people they lead.

They can be tough or hilarious or anything in between, but if they lead with compassion, I’m in.

Leaders don’t say they’re leaders. You just feel it. You don’t follow because you’re told to — you follow because you want to.

Colleen: When you think about the future of work and leadership, what’s one skill you believe will take people the furthest?

Jason: Drive.

The world changes. Trends change. But drive can’t. It has to be constant — always pushing toward something new.

The funny thing about goals is that they never really end. You cross one off and another appears. Success belongs to the people who keep showing up, evolving, and finding joy in the process.

If you haven’t already, go check out Jason’s work and the movement behind One Black Shirt:

👉 LinkedIn: Jason Donnelly
👉 Shop the shirts + join the story

* contended edited for clarity and readability

It simply doesn’t.

Visibility is knowing what everyone’s working on.
Alignment is knowing why they’re working on it.

You can have visibility across every dashboard, status update, and OKR tracker… and still be completely misaligned.

Visibility gives you the picture.

When you have visibility, you can see the projects, the timelines, and the owners. You know what’s in motion.

Visibility answers:

• What are we doing?

• Who’s doing it?

• When will it be done?

It’s essential — but it’s only the surface.
Because visibility without understanding can create a dangerous illusion of progress. Everyone’s busy, but not necessarily aligned on what matters most.

Alignment creates direction.

Alignment goes deeper. It connects actions to outcomes. It ensures that every team understands how their work fits into the company’s purpose, strategy, and customer promise.

Alignment answers:

• Why does this matter right now?

• How does this move the business forward?

• What trade-offs are we making to focus here?

When teams are aligned, decision-making gets faster, handoffs get cleaner, and resources go where they actually matter. It’s not just movement — it’s momentum with meaning.

Share Leadership &

Example 1: The roadmap trap.

So many teams create a roadmap, share it once, and call it alignment.

But roadmaps don’t create alignment — conversations about them do.

Visibility is posting your Q4 roadmap in Confluence.
Alignment is walking teams through why the roadmap looks the way it does — what got prioritized, what got paused, and what outcomes you expect to see.

Try this:
In your next roadmap review, don’t ask, “Any questions?”
Ask, “What risks do we see to hitting these outcomes?” or “Where might our team’s priorities conflict with another department’s?”
Those questions surface misalignment early, before it turns into friction.

Example 2: Switching from status to story.

Weekly updates are often a visibility exercise — a parade of metrics and blockers that don’t move understanding forward.

Alignment happens when leaders shift those updates from what’s happening to why it matters.

Instead of:
“Marketing is 80% through the new campaign.”

Try:
“Our campaign is built around a message that reinforces the new customer segment we’re testing — so success here informs not just revenue, but product roadmap decisions for next quarter.”

Context transforms updates into alignment moments. It connects the dots across departments and helps teams see how their work contributes to the bigger picture.

Example 3: Planning sessions as alignment rituals.

Annual or quarterly planning isn’t just about deciding what to do — it’s your biggest opportunity to create alignment around why you’re doing it.

Too many teams treat planning sessions as logistical exercises. But the best leaders use them as storytelling moments.

Here’s what that looks like:

• Before setting targets, revisit the company vision in plain language. (“Here’s what we’re building toward and why it matters this year.”)

• Map every key initiative to that vision. (“This product launch isn’t just about revenue; it’s how we strengthen retention in our core customer segment.”)

• Close the session with reflection: “What part of this vision feels unclear or disconnected from your team’s priorities?”

When people understand the why, alignment becomes shared ownership — not just top-down direction.

The illusion of progress.

Visibility is often celebrated because it’s measurable. You can track dashboards, log updates, or show how “in the loop” everyone is.

But alignment is harder to quantify — it shows up in how decisions are made, how trade-offs are discussed, and how teams move when priorities shift.

Without alignment, visibility just makes dysfunction easier to see.

And, the most effective leaders build systems that support both.
They don’t just share information — they build understanding.
They don’t just make roadmaps visible — they make them make sense.

However, this landscape is rapidly changing and founders, solopreneurs, and portfolio careerists are no longer being limited by traditional resource constraints. Why? Because Artificial Intelligence is stepping in as their very first employee.

And we know that AI is no longer just a futuristic concept or a tool reserved for tech giants, it’s now an accessible, practical, and cost-effective team member helping entrepreneurs tackle everything from marketing and customer service to operations and finance — often before they even hire a single human.

AI Adoption Boom for Entrepreneurs

According to the latest 2025 Global Startup Ecosystem Report by Startup Genome, over 65% of new startups integrate AI tools as part of their core operations during their first year. This is a significant leap from just 40% in 2023, signaling a rapid normalization of AI-driven workflows.

Further, a 2025 Deloitte survey of 1,200 small and medium businesses revealed that 72% of solopreneurs and portfolio careerists now rely on at least one AI-powered system for daily business tasks. This includes AI-powered chatbots, automated content creation, and predictive analytics.

This trend is driven by two main factors:

1. Cost Efficiency: AI reduces the need for expensive early hires, allowing lean startups to function effectively without sacrificing productivity.

2. Speed and Scalability: AI tools can operate 24/7, scale with business growth, and perform repetitive tasks faster and with fewer errors than humans.

For entrepreneurs without the capital or bandwidth to hire full-time staff, AI offers a scalable solution. From managing emails and customer inquiries to generating marketing content and analyzing data, AI-powered assistants can perform many functions traditionally handled by entry-level employees.

Who’s Leveraging AI as Their First Employee?

Founders of Early-Stage Startups

For founders in the early stages of business, every dollar and minute counts. Hiring employees is expensive and time-consuming. AI tools provide immediate support in areas like customer service chatbots, bookkeeping automation, and even legal document drafting. This allows founders to validate ideas and iterate faster without overextending themselves.

Founders are using AI for product-market research, automating customer support with AI chatbots, and content marketing. A 2025 CB Insights analysis shows startups leveraging AI saw an average 35% faster time-to-market compared to those relying solely on human resources.

Solopreneurs and Freelancers

Those running one-person businesses or freelance gigs often face the “all hats” dilemma of being their own marketer, accountant, sales rep, and more. AI assistants help them by automating scheduling, managing social media, drafting proposals, and tracking expenses — all without the overhead of an actual employee.

A recent report from the Freelancers Union (2025) found 81% of freelancers use AI-driven apps to automate scheduling, invoicing, and social media posting, freeing up 12+ hours per week to focus on client work and business development.

Portfolio Careerists and Multi-Project Entrepreneurs

Portfolio careerists, who juggle multiple projects or gigs, leverage AI to streamline repetitive tasks and centralize workflow management. AI integrations across different platforms can synchronize calendars, generate reports, and even provide data-driven insights to make smarter decisions quickly. Leveraging AI for cross-project coordination and personalized data dashboards. The Future of Work Institute (2025) indicates that portfolio careerists with AI-enabled workflows increase productivity by 28% and reduce burnout by 19%.

What Does This Mean for the Future of Work?

The idea of AI as a first employee signals a shift in how we think about team building and operational scaling. Instead of waiting to afford human hires, founders can lean on AI to handle foundational tasks and jumpstart growth.

1. Democratizing Entrepreneurship

AI lowers the barrier to entry for entrepreneurship. People who might not have access to large teams or budgets can still build and run businesses effectively by tapping into AI tools.

2. Shifting Roles and Skills

With AI managing routine and administrative work, human roles will evolve to focus more on strategy, creativity, emotional intelligence, and leadership. Founders will spend less time on busywork and more time on vision and innovation.

3. Ethical and Practical Considerations

While AI offers immense benefits, founders must consider data privacy, transparency, and the potential for bias in AI tools. It’s crucial to stay informed and implement AI thoughtfully, ensuring it supports rather than replaces the human touch where it matters most.

Popular AI Tools Powering Founders in 2025

Here’s a quick look at some AI tools transforming the way founders operate:

• ChatGPT Plus & GPT-4 Turbo: For generating content, brainstorming, and customer engagement.

• Jasper AI: For generating content, brainstorming, and customer engagement.

• Notion AI: For AI-assisted note-taking, project management, and collaboration.

• QuickBooks with AI: Automates complex financial reporting and forecasting.

• Zendesk AI: AI-powered customer service automation.

• Otter.ai: AI transcription and meeting summaries.

• Zapier AI Automations: Seamlessly connects apps and automates workflows with AI enhancements.

The common thread is that these AI solutions handle repetitive, time-consuming tasks, letting founders focus on what matters most.

How to Get Started With Your AI Employee

If you’re intrigued by the idea of an AI first hire, here’s a simple roadmap to integrate AI into your startup or solo business:

Step 1: Identify Repetitive Tasks

Look at your daily routine. What tasks eat up your time but don’t require deep creative thinking? Examples might include answering common customer questions, scheduling meetings, or managing invoices.

Step 2: Research and Choose AI Tools

Explore AI tools suited to your needs. Many platforms offer free trials or freemium models, so you can test what fits best. Focus on ease of use, integration with your existing tools, and support.

Step 3: Start Small and Scale

Begin by automating one task at a time. For instance, set up an AI chatbot for your website or automate your social media posts. Monitor the impact on your productivity and customer experience.

Step 4: Train Your AI and Refine

Like any employee, AI requires training and tuning. Provide it with the right data and inputs, customize responses, and continuously optimize workflows for maximum efficiency.

Step 5: Stay Informed and Ethical

Keep up to date on AI developments, and be transparent with your customers and stakeholders about AI usage. Ensure compliance with data regulations and prioritize fairness.

Leveraging AI early can level the playing field, allowing you to move faster, reduce costs, and focus on growing your business without the overhead of traditional hires.

Embracing AI as a first employee doesn’t mean replacing humans — it means augmenting your capabilities and empowering you to build smarter and more sustainably.

So if you’re launching your next venture or managing multiple projects, consider hiring your first AI employee today. Your future self (and your to-do list) will thank you.

Sources:

• Global Startup Ecosystem Report 2025, Startup Genome, 2025

• AI 100: The Most Promising AI Startups of 2025, CB Insights, 2025

• Freelancing and the AI Revolution, Freelancers Union, 2024

• Generative AI Survey 2025, Deloitte, 2025

• Generative AI Is Upending Freelance Work, INFORMS, 2024

• Institute for the Future of Work, Institute for the Future of Work (IFOW),

• Future of Work USA 2025, Future Work Series, 2025

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Very few companies design their systems, cultures, and structures to actively develop leaders. What does it take to build organizations that shape the confident, adaptive, and emotionally intelligent leaders the future demands?

That question sits at the heart of what it means to build not just better leaders, but better organizations.

As we look ahead to 2030 and a new decade of work, leadership, and change, it’s becoming increasingly clear: it’s not enough to develop the leaders of the future—we must also design organizations ready to support them.

That begins with four essential shifts: flexibility, impact, sustainability, and purpose.

Flexibility Beyond Location

Flexibility isn’t just about hybrid vs. remote. That debate is tired.

Future-ready flexibility is about acknowledging that leaders are whole people. They’re committed to their work—but also to their families, personal growth, creative pursuits, and communities. They’ll expect support for all of those dimensions—not just a laptop and Wi-Fi.

Flexibility must mean:

• Autonomy over time, not just location

• Asynchronous collaboration, not micromanagement

• Freedom to contribute meaningfully, not just be present from 9 to 5

The Power of Impact

Impact will define leadership success more than tenure or job titles.

Tomorrow’s leaders won’t be measured by hours logged—but by:

• Results delivered

• Teams supported

• Innovation driven

• Values upheld

They’ll want to work where they can make something better, not just check off tasks.

Embracing Sustainability

Sustainability is no longer a buzzword—it’s a business imperative.

Future-ready organizations will:

• Design systems that are environmentally and socially responsible

• Operate at a sustainable pace, avoiding burnout as a norm

• Align business goals with long-term societal outcomes

Sustainability includes human energy. It’s not just about the planet—it’s about people.

The Driving Force of Purpose

Purpose will be the core differentiator for both leaders and the organizations they join.

More people are asking: “Why does this work matter?”

Organizations that thrive in the future will be able to answer with authenticity—not just a mission statement, but:

• Daily decisions that reflect values

• Work that feels meaningful

• A culture where purpose is practiced, not just posted

Future-Ready Organizational Models

Forward-thinking companies are already experimenting with new frameworks. Here are three models worth watching:

1. Purpose-Driven Organizations

They embed social or environmental missions into core operations—not as a side project, but a strategy. This attracts values-aligned talent and drives long-term performance.

2. Teal Organizations

Popularized by Frederic Laloux, these prioritize:

• Self-management

• Wholeness at work

• Evolutionary purpose

These organizations grow like ecosystems, not machines.

3. Platform Organizations

A modular approach with small, autonomous teams supported by central services. This structure increases agility and allows teams to respond quickly to customer and market needs.

The Role of Future Leaders

To succeed inside these modern systems, tomorrow’s leaders must:

• Embrace lifelong learning and emerging tech

• Lead with empathy, transparency, and adaptability

• Center well-being and belonging in their team design

• Replace control with coaching and shared accountability

• Connect their leadership to real-world impact and meaning

The Future Is Already Here

These shifts aren’t theoretical. They’re happening now.

Organizations that embrace this transformation will not only attract the best talent—but keep it. And those who don’t? Risk losing their brightest minds to systems better suited for the future.

An Interview with Jen Millard: Building Mainelove™ for the Future

When I think back on my conversation with Jen Millard, CEO and Founder of mainelove™, what lingers most is how energized I felt after hearing her story. Jen is one of those rare leaders who brings relentless drive, hard-earned experience, and a deep sense of place to everything she builds. She’s not just starting a company—she’s curating a movement rooted in Maine values, local talent, and a fresh take on what the future of consumer products and leadership can look like.

With over 25 years of experience building consumer, retail, and technology-enabled marketplace businesses, Jen has held executive roles at Mastercard, ZoomSystems, Lifefactory, Saks Fifth Avenue, and various venture firms. Her resume includes helping high-growth startups scale and sell, but what drew her back home was something simpler and more powerful: water.

Bringing the Best of Maine Forward

A 12th-generation Mainer, Jen founded mainelove™ to create a water brand that celebrates and protects the state’s natural resources. After years in big tech and fast-paced VC environments, she wanted to build something that reflected the values she grew up with—sustainability, authenticity, and community. Mainelove™ is more than bottled water. It’s a circular economy initiative that partners with Maine brewers to can local water, keep production in-state, and share the purity of Maine with others.

"Everyone in Maine is proud of their beer," she told me. "And great beer takes great water. So we start there."

And it turns out, the market is thirsty for it. With Gen Z reducing alcohol consumption and demand rising for purpose-driven products, Jen saw a gap—and an opportunity. Mainelove™ water is sourced from one of the purest bodies of water in the U.S., and the entire operation is built to keep jobs, money, and pride within the state.

Entrepreneurship Meets Ecosystem Thinking

As a founder, Jen is all in. “Are you in?” she asks, not rhetorically. It’s a leadership principle she lives by: heart, mind, stomach—everything has to be fully committed.

That same intensity shapes how she builds her team. "I've curated people from my past to join me here," she says. "Everyone on the team has worked with me before. They believe in the product and in the way we work together."

It’s not just about relationships; it’s about agency. Jen gives her people the space to pitch, test, fail, and try again. Salespeople are encouraged to find their own voice and connection to the brand. Whether they resonate with the water, the forest, or the circular economy, authenticity is the only real sales strategy.

Keeping Young Talent in Maine

A core tenet of mainelove’s mission is to stop the brain drain in Maine. With few tech or data jobs, young people often leave. Jen is working to change that. Her team includes a group of paid summer interns from top schools like Villanova and Boston College. They're not fetching coffee—they’re doing real research, leading activations, and learning the art of sales and marketing in the wild.

"I always say, hire students before the world spoils them," she laughed. "They still believe they can change everything."

Leading with Heart and Humility

Jen’s leadership style today is deeply informed by her past. Having led 100-person SaaS companies, wrangled VC boards, and driven revenue under pressure, she’s learned to keep her cool and trust her people.

"I had a big distributor fall through in January. My sales guy thought I’d lose it. But I just said, 'Onward. We’ll get two more.'"

That steady hand comes from experience—and from understanding that early-stage businesses are about learning fast. "You can’t screw up anything that bad this early," she said with a smile.

Flat Teams, Shared Success

Mainelove™ is built as a flat organization. Titles don’t equate to power; everyone shares in the profit. It’s structured as an LLC designed for long-term dividends for both employees and investors. Jen wants everyone to have a stake in the business’s success.

"That’s how people buy into the vision. And that’s how we keep them in Maine."

By the end of our chat, I was seriously considering a move to Maine. Jen’s vision is magnetic, but more than that, it’s grounded. She’s building a brand that doesn’t just sell water—it reflects a way of life. Purpose-driven, sustainable, deeply local.

As she puts it: “As an entrepreneur, ask yourself: are you in? Heart, mind, stomach—all of it.”

With mainelove™, she is. And the results are already rippling far beyond Maine.

Meet Jen Millard
Jen Milliard is an energizing leader with 25 years of experience successfully building consumer, retail, and technology-enabled marketplace businesses. Passionate about helping fintech and commerce startups achieve their full growth potential, Jen brings her intensity for revenue and growth as the CEO of the
emerging brand mainelove™.

A 12th general Mainer, Jen’s current project, mainelove™, culminates in bringing her previous experiences back to Maine. Jen is an active trustee on the board of her alma mater, Colby College, and she has helped shape the entrepreneurship effort at Colby and supported the start-up ecosystem in Maine. After researching several new venture ideas with the intention of bringing the best of Maine forward, she realized one thing everyone in Maine was proud of—their great beer. Great beer takes great water–so
shifting focus from beer to water was a logical place to start.

Jen has a diverse background of experiences that includes executive roles at Manatt, Phelps and Phillips LLP, Sutter Hill Ventures, K2 Ventures, Function Ventures, as well as Mastercard, ZoomSystems, Lifefactory Inc., and Saks Fifth Avenue. With her focus on creating GTM strategies, driving revenue growth, M&A guidance, and fostering innovation, Jen has been instrumental in numerous successful exits
and partnerships, including Dosh, Chowbotics, Nomadic VR, Liquid Death, and Truaxis. With mainelove™, she combines her expertise and passion for the place she calls home.

Some quotes have been edited for clarity and length.

We often talk about how to develop great leaders. But what happens when great leaders are placed in systems that simply weren’t built to support them?

In an era of constant change, emerging leaders—across all generations—are stepping up with bold ideas, adaptable mindsets, and a deep desire to create impact. They’re not waiting for promotions or titles to make a difference. They are navigating ambiguity, pushing for purpose, and redefining leadership itself.

But here’s the challenge: many of today’s organizations are still structured for yesterday’s world.

As Andrea Caldwell, Vice President of Consulting and Coaching at FranklinCovey, explains:

“Organizations are evolving to meet the expectations of future leaders by shifting from rigid hierarchies to more agile, skills-based structures that enable growth and flexibility.”

This evolution isn’t a trend. It’s a necessity. And it starts with a simple but profound question: Are we building organizations that support the leaders we’re working so hard to develop?

From Command and Control to Flex and Flow

For decades, leadership was built on hierarchy, chain of command, and time-in-seat. But the leaders stepping forward today—whether they’re 28 or 48—are fueled by autonomy, real-time learning, and the ability to make meaningful contributions.

The traditional model doesn’t fit anymore.

Future-ready organizations are shifting toward agile, skills-based structures that prioritize:

• Decentralized decision-making, so leaders at all levels can act with confidence and speed

• Cross-functional, project-based work, which encourages collaboration and continuous learning

• A focus on competencies over job titles, recognizing what people can do versus where they sit in a chart

This shift supports not only how people want to work—but how leadership actually happens: adaptively, in real time, and often without permission.

It’s not about flattening org charts. It’s about unlocking leadership wherever it lives.

Culture as Infrastructure, Not Atmosphere

Leadership thrives—or withers—based on the culture surrounding it.

And that culture must be intentionally designed, not left to chance.

Caldwell shares:

“Cultures are being intentionally designed to foster inclusion, purpose, and psychological safety. This is critical to attract and retain next-gen talent.”

But this doesn’t just apply to Gen Z. Mid-career professionals are also demanding workplaces that align with their values. Culture isn’t a backdrop—it’s the infrastructure leaders lean on when making tough calls, taking risks, or navigating change.

What future leaders need from culture:

• Inclusion: Environments where everyone’s perspective is welcomed and heard

• Purpose: A clear connection between the organization’s mission and the individual’s contribution

• Psychological safety: A climate where questions are encouraged, mistakes are learning opportunities, and vulnerability isn’t a weakness

The best leadership development strategy? A culture that allows people to show up fully and lead bravely.

Building Bridges, Not Barriers

L’Taundra Everhart, M.Ed., a national education expert and emotional wellness strategist, offers a powerful reminder: future leadership doesn’t belong to one age group.

“I see a growing gap between those just entering the workforce and those in the later stages of their careers. But when their skills, efforts, and goals are aligned, the collaboration can be remarkable.”

Supporting leaders of the future means designing systems that encourage intergenerational collaboration, instead of pitting experience against innovation.

Everhart also challenges organizations to be honest about expectations:

“Organizations need employees who can produce meaningful results. Employees, in turn, seek purposeful work, fair compensation, and clearly defined benefits. Neither side can thrive without structure.”

That structure isn’t about micromanagement—it’s about clarity: clear roles, transparent expectations, and shared definitions of success.

Great leadership doesn’t emerge from chaos. It grows when people know where they stand—and where they’re going.

From Perks to Wellness Ecosystems

Support for leaders isn’t just professional—it’s personal.

Many are burned out before they even step into formal leadership roles. Everhart calls for a reimagining of how we care for the people we ask to lead:

“Radical shifts in workplace culture and leadership thinking are no longer optional. Wellness ecosystems must be structural, intentional systems built to support the whole person—not just the job title.”

Her shift from offering quick fixes to building long-term, human-centered support systems reflects the future of sustainable leadership.

What this looks like:

• Well-being embedded into team norms and leadership expectations

• Coaching, flexibility, and equity in workload and recognition

• Environments that foster resilience, not just output

If we want courageous, creative leaders, we need workplaces that help them stay well enough to lead.

Learning That Looks Like Leading

Leadership development isn’t confined to the classroom anymore. It’s lived, hands-on, and evolving.

Caldwell explains:

“Career development is becoming more dynamic and personalized, emphasizing experiences that build both leadership capability and reinforce their ability to navigate uncertainty and complexity.”

That means organizations must offer:

• Stretch assignments that build leadership muscle

• Individualized growth journeys, not one-size-fits-all tracks

• Real-time coaching, not just annual feedback

• Skill-building for ambiguity, not just tasks

Leaders don’t need to be taught how to lead from a textbook. They need space to grow into the complexity of leadership in motion.

Invest Early. Show Up Often.

Caldwell closes with a key insight:

“Organizations that are visibly innovative and growing will make themselves more attractive to future leaders. People want to grow with companies that are growing too.”

To send that message clearly:

• Offer targeted, early career development

• Celebrate internal promotions and growth

• Showcase real innovation, not just marketing slogans

• Make the path to impact visible

The message is simple but powerful: “We see you. We believe in you. Let’s grow together.”

A Big Thank You to Our Contributors:
Andrea Caldwell, FranklinCovey
L’Taundra Everhart, M.Ed., BYG! Mixed Greens For The Soul

The Power of One Voice

My first time sitting at a literal board room table was an experience I'll never forget. Picture this: a giant dark wood table, shiny—too shiny—surrounded by at least 20 large, worn black leather chairs that had clearly seen countless important conversations. I was an intern, one of 70 in what was the largest intern group the company had ever had, and we'd been brought in for a roundtable session about three weeks into our internship.

As we went around the table, each intern shared the great things they'd been working on, the projects they were excited about, the learning experiences they were having. When it was my turn, I did the same—I talked about the meaningful work I'd been doing, the mentorship I was receiving, the skills I was developing. But then I did something that, in hindsight, changed everything. I chirped up and said, "but I don't have a work laptop yet."

It seemed like such a small thing. Almost insignificant compared to all the big, important work everyone was discussing. But by 3pm that same day, I was handed a work laptop with the simple explanation: "no one shouldn't have a laptop to work on." That was it.

What I hadn't realized in that moment was that our head of technology was sitting in the room with us. He heard my words, my request, my need, and he immediately set forth an action. It seemed "small" to him most likely, but I think about that moment a lot, especially when I sit in board rooms today.

That experience taught me something profound: your voice matters, regardless of your title or position in the hierarchy. Sometimes the most junior person in the room has the clearest perspective on what's actually happening on the ground level.

The next time I found myself in that same boardroom was four years later, but this time the circumstances were entirely different. I had gotten into work early that morning—not unusual for me, since it's my best time to think—and I was working on a quarterly report to share with stakeholders. My direct boss rushed past me with a quick hello, clearly late for something, then quickly turned around, walked back to me, and asked if I would join him in a meeting.

We exchanged pleasantries as we quickly walked down the hallway, up to the 5th floor, and to my surprise, I walked right into that same boardroom. Seeing many familiar faces, I took a seat in one of those big chairs—now new ones—right in the middle of the table and joined what would become the first of many opportunities to sit at that table and continue to have a seat at all those types of tables after.

The difference between those two experiences wasn't just the passage of time or my growing expertise. It was the recognition that I had earned my place at that table through consistent contribution, strategic thinking, and the courage to speak up when it mattered.

Why Having a Seat at the Table Matters More Than Ever

The concept of "having a seat at the table" has taken on new dimensions and urgency in more recent years. It's no longer just about climbing the corporate ladder or achieving a certain title—it's about ensuring that diverse perspectives, innovative ideas, and authentic voices are represented in the spaces where critical decisions are made.

The traditional gatekeepers of leadership are being challenged, and rightfully so. We're seeing a fundamental shift in how organizations think about leadership, influence, and decision-making authority.

The pandemic accelerated many of these changes, forcing companies to recognize that valuable insights and leadership can come from anywhere in the organization, not just from the C-suite.

But here's what's particularly important to understand: you don't need a title to be a leader, and you don't need a formal invitation to contribute meaningfully to important conversations. Leadership is about influence, impact, and the ability to drive positive change—and these qualities can be demonstrated at any level of an organization.

The most effective leaders I know, regardless of their formal position, share certain characteristics.

They're proactive rather than reactive.
They see opportunities where others see obstacles.
They speak up with solutions, not just problems.
They build bridges between different perspectives.
They find ways to move conversations forward constructively.

Right now, organizations are grappling with rapid technological change, shifting workforce demographics and evolving customer expectations. The companies that thrive in this environment, will be those that tap into the collective intelligence of their entire workforce, not just their senior leadership team.

The Myth of Waiting Your Turn

One of the most damaging myths in professional development is the idea that you need to "wait your turn" or "pay your dues" before your voice matters. This outdated thinking not only stifles innovation and progress but also perpetuates systems that may not serve the organization's best interests.

The reality is that fresh perspectives, diverse experiences, and innovative thinking often come from those who haven't been jaded by the "the way things have

always been done.” motto. When we tell emerging leaders to wait their turn, we're essentially asking them to suppress the very qualities that could help drive meaningful change and improvement.

Consider the most significant innovations and breakthroughs in business history. Many of them came from individuals who challenged conventional wisdom, questioned established processes, and refused to accept that "this is just how we do things here." They didn't wait for permission to think differently or contribute meaningfully to important conversations.

This doesn't mean being disrespectful or dismissive of experience and expertise. Rather, it means recognizing that valuable contributions can come from unexpected sources and that creating space for diverse voices strengthens decision-making processes.

The organizations that understand this principle are the ones that create cultures where psychological safety allows people to speak up, where diverse perspectives are actively sought out, and where good ideas are valued regardless of their source. These are the companies that consistently outperform their competitors and adapt more quickly to changing market conditions.

Five Ways to Secure Your Seat at the Table

Now that we have established the ‘why’ behind having a voice in the important conversation matters, let’s talk about how you can get there and contribute in meaningful ways:

1. Become the Go-To Person for Solutions, Not Just Problems

One of the fastest ways to earn respect and influence is to develop a reputation as someone who brings solutions, not just identifies problems. Anyone can point out what's wrong or what's not working. The people who get invited to important conversations are those who come prepared with thoughtful, actionable recommendations.

This means doing your homework before raising concerns. When you identify an issue, spend time thinking through potential solutions, considering the resources required, anticipating potential obstacles, and understanding the broader implications of different approaches. Present options, not just problems.

For example, instead of saying "Our current onboarding process is confusing and inefficient," try "I've identified some challenges with our onboarding process that are impacting new hire productivity. I've researched best practices from similar organizations and developed three potential approaches we could consider, each with different resource requirements and timelines. Would you like me to present these options to the team?"

This approach demonstrates strategic thinking, initiative, and a commitment to moving the organization forward rather than just highlighting what's wrong. It positions you as someone who can be trusted with bigger challenges and more significant responsibilities.

2. Master the Art of Strategic Communication

Having great ideas isn't enough if you can't communicate them effectively to different audiences. The ability to tailor your message to your audience, choose the right timing, and present information in a compelling way is crucial for gaining influence and earning a seat at important tables.

This means understanding the communication preferences and priorities of key stakeholders in your organization. Some leaders prefer detailed data and analysis. Others respond better to high-level strategic overviews. Some want to see the financial implications first. Others are most interested in the impact on people and culture.

Develop the ability to present the same idea in different ways depending on your audience. Practice distilling complex concepts into clear, concise messages that resonate with different stakeholder groups.

Learn to tell stories that illustrate your points and make abstract concepts more tangible and relatable.

Pay attention to timing as well. The best idea presented at the wrong time may not get the consideration it deserves. Understand the rhythms of your organization, the pressures and priorities that different leaders are facing, and choose your moments strategically.

3. Build Genuine Relationships Across the Organization

Influence in organizations is rarely about formal authority alone. It's about relationships, trust, and the ability to work effectively with people at all levels.

The most influential people I know have invested time in building genuine relationships throughout their organizations, not just with their immediate team or direct supervisors.

This means taking time to understand the challenges and priorities of colleagues in different departments. It means offering help and support when you can, even when there's no immediate benefit to you. It means being genuinely interested in other people's work and finding ways to collaborate and create mutual value.

These relationships become invaluable when you need support for an initiative, when you're trying to understand the broader implications of a decision, or when you need allies to help advance an important idea. People are more likely to listen to and support someone they know, trust, and respect.

But this has to be authentic. Relationship-building for purely transactional purposes is usually transparent and counterproductive. Focus on being genuinely helpful, curious, and collaborative. The influence will follow naturally.

4. Demonstrate Consistent Value Through Small Wins

While it's tempting to focus on landing the big, high-visibility project that will catapult you into leadership conversations, the reality is that influence is usually built through consistent demonstration of value over time.

Small wins, delivered reliably, often carry more weight than sporadic big successes.

Look for opportunities to make meaningful contributions to existing initiatives. Volunteer for projects that others might overlook but that address real organizational needs. Take on challenges that allow you to develop new skills while solving actual problems.

The key is consistency and reliability.

When people know they can count on you to deliver quality work on time, to think through implications carefully, and to follow through on commitments, you become someone they want to involve in bigger and more important conversations.

5. Speak Up with Confidence and Preparation

Perhaps the most important skill for securing your seat at the table is the ability to speak up confidently in group settings, especially when you have something valuable to contribute. This can be particularly challenging for people who are naturally more introverted or who come from backgrounds where they were taught to defer to authority.

The key is preparation. When you know you'll be in a meeting or conversation where you want to contribute, think through your key points in advance. Consider what questions you might ask, what perspectives you can offer, and what value you can add to the discussion.

Practice articulating your thoughts clearly and concisely. Many people have great ideas but struggle to express them in a way that others can easily understand and act upon. Work on your ability to make your point quickly and persuasively.

Don't wait for the perfect moment or the perfect idea. Often, asking a thoughtful question can be just as valuable as providing an answer.

Questions that help clarify objectives, identify potential challenges, or explore alternative approaches can significantly improve the quality of decision-making processes.

How Your Voice Creates Change (The Ripple)

When you successfully secure your seat at the table, the impact extends far beyond your own career advancement. Your presence and voice can create ripple effects that benefit your entire organization and the people around you.

First, you become a bridge between different levels of the organization. You can bring ground-level insights to strategic conversations and help translate high-level decisions into practical implementation strategies. This two-way communication flow is invaluable for organizational effectiveness and employee engagement.

Second, your success creates a pathway for others. When you demonstrate that valuable contributions can come from unexpected sources, you help create a culture where diverse voices are valued and heard. This can inspire others to speak up and contribute, leading to better decision-making and more innovative solutions across the organization.

Third, you help challenge and evolve outdated systems and processes. Fresh perspectives often reveal inefficiencies, blind spots, and opportunities for improvement that may not be visible to those who have been working within existing systems for years.

The Future of Leadership Influence

The ability to earn and maintain a seat at important tables will become even more critical in the future. Organizations are becoming flatter, more collaborative, and more dependent on the collective intelligence of their workforce.

The leaders who thrive in this environment will be those who can build influence through value creation rather than positional authority.

They'll be the ones who can navigate complex, matrixed organizations where formal reporting structures don't always reflect real influence patterns.

This shift creates tremendous opportunities for emerging leaders who are willing to develop these skills and take initiative in contributing to important conversations.

The traditional barriers to influence are breaking down, but this also means that the competition for attention and influence is intensifying.

The key is to start now, wherever you are in your career. Begin building the relationships, developing the skills, and creating the track record that will position you for greater influence and impact.

As you think about your own journey toward securing a seat at the table, consider these reflection questions:

1. What unique perspective or expertise do you bring that could add value to important conversations in your organization? How can you begin demonstrating this value in small but meaningful ways?

2. Who are the key stakeholders and decision-makers you need to build relationships with? What can you do to start creating genuine connections with these individuals?

3. What problems or opportunities in your organization could benefit from your input and involvement? How can you position yourself as someone who can contribute to addressing these challenges?

Remember, getting a seat at the table isn't about politics or manipulation, it's about creating genuine value and building the trust and credibility that naturally lead to greater influence and impact.

It's about becoming the kind of person that others want to include in important conversations because they know you'll make those conversations better.

The table is waiting. The question is, are you ready to claim your seat?

Colleen Millerman is the Founder of The Newleaf Company and Editor of Leadership &, where she advises organizations on strategy, operations, and leadership development. With over a decade of experience leading growth across sectors, she’s passionate about building more human-centered systems and redefining what leadership looks like.

As we cross the halfway mark of the year, the conversation around leadership is shifting toward the skills that matter most, the workforce of tomorrow, and the changing definitions of work itself. From Gen Z’s rising influence to the growing relevance of green-collar jobs, here’s what’s trending this week in leadership.

🔥 Trending Now

1. Soft Skills Are the ‘Needle Movers’
   Jennifer Dulski, CEO of Rising Team, tells Business Insider that soft skills—adaptability, relationship‑building, learning agility—are now the “needle‑movers” in Big Tech career growth. Read more here.
   

2. Gen Z Is Bringing New Skills to the Workforce

   "Gen Z brings fresh perspectives, adaptability, and a hunger to make an impact, but it's on all of us to nurture their potential.” - James Uffindell, CEO of Bright Network

   ---

3. We’ve Heard of Blue Collar and White Collar—What’s Green Collar?

   Tamara Parisio latest article, The Green Collar Future of Work, delves into the evolving landscape where traditional blue-collar and white-collar roles converge. She introduces the concept of the "green-collar" worker—individuals who blend hands-on expertise with intellectual agility, embodying adaptability in our rapidly changing economy. Read it here.

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This article is a part of the monthly June edition of Leadership &. View full version below.

This past weekend, my 18-year-old neighbor Jimmy knocked on my door with a

If we look forward to 2030, one thing becomes abundantly clear: the workforce is undergoing a profound transformation, driven in large part by its newest members.

Gen Z is bringing fresh perspectives, unique skills, and different expectations that are reshaping how we think about work, leadership, and success.

For the first time in history, five generations are working side by side in the workplace. According to the World Economic Forum, by 2034, a full 80% of the workforce in advanced economies will comprise Millennials, Gen Z, and the first Gen Alphas to become adults.

"Gen Z is like a gravitational force pulling all other generations into its orbit," notes a recent World Economic Forum report.

Their values—community, a global mindset, access over ownership, side hustles, and authenticity over polish, are increasingly driving workplace culture across all generations. This multigenerational dynamic creates both challenges and opportunities. The age spread of today's workforce has never been wider, and the experiences characterizing each generation have never been so different.

Think about it: the paper-record environment familiar to anyone entering the workforce before 1990 would be utterly foreign to a Gen Z worker who has grown up with the internet in the palm of their hand.

Yet it's precisely this diversity of experience and perspective that offers tremendous potential for innovation, if organizations can effectively harness it.

Perhaps one of the most striking findings from Deloitte's 2025 Global Gen Z and Millennial Survey is that only 6% of Gen Zers say their primary career goal is to reach a senior leadership position. This doesn't mean they lack ambition. Far from it, rather it signals a fundamental shift in how this generation defines success.

"It's not that Gen Zs lack drive; rather, their definition of success is evolving," explains Elizabeth Faber, Deloitte Global Chief People & Purpose Officer. "Many are prioritizing learning opportunities, mental well-being, and work-life balance over climbing the corporate ladder."

When asked about their strongest reasons for choosing their current employer, learning and development ranks in the top three for Gen Z. This generation is ambitious, but their ambition takes different forms than previous generations.

This shift is already reshaping how organizations approach leadership development. The traditional career ladder is giving way to more flexible, personalized paths that allow for growth without sacrificing well-being or purpose. Organizations that recognize this shift and adapt their leadership development accordingly will have a significant advantage in attracting and retaining top Gen Z talent.

"To foster future leaders, organizations need to remove the perceived trade-offs between leadership and personal fulfillment," stresses Faber. "That means reshaping leadership paths to be more flexible and purpose-driven."

This article is a part of the monthly June edition of Leadership &. View full version below.

This past weekend, my 18-year-old neighbor Jimmy knocked on my door with a tablet, a smile, and a pitch: “I noticed your driveway could use a pressure cleaning. I’ve got time Tuesday or Saturday—what works better for you?”

That’s Jimmy.

Fresh out of high school, average student by his own admission (he’d tell you he only did what it took to get by). But don’t mistake that for a lack of smarts. Jimmy is sharp, resourceful, and incredibly self-aware.

Instead of following the traditional four-year college path that so many of his peers were nudged toward, he made a bold move: he enrolled in a competitive HVAC program at our local state college—one of only 20 students accepted.

He’s already juggling multiple income streams. On weekdays, he works a drive-thru job. On evenings and weekends, he knocks on doors with that same tablet, offers pressure washing services, handles the work, the money, and the responsibility. He’s not “hustling” in the trendy social media sense, he’s building something sustainable.

Something smart.

And here’s the thing: Jimmy is not the exception. He’s the signal.

Gen Z is reshaping the workforce, and they’re just getting started.

Let’s start with who we’re talking about. Gen Z, born roughly between 1997 and 2012, now makes up nearly 18% of the U.S. labor force. By 2025, they’re expected to account for 27% across nations. This generation is stepping into adulthood in a world that looks wildly different than it did even five years ago.

They’re navigating rising education costs, climate anxiety, social and political volatility and doing it with a mix of pragmatism and purpose.

And, when it comes to their careers, they aren’t afraid to walk away from conventional scripts. Many are, like Jimmy, opting out of the “college = success” formula that previous generations were handed.

According to the U.S. Department of Labor and National Center for Education Statistics (NCES) :

• Around 45% of high school grads enrolled in four-year colleges in 2022.

• 17% chose two-year colleges.

• The remaining ~38%? They either went directly into the workforce, enrolled in vocational programs (which are seeing a major resurgence), or pursued entrepreneurial paths—like freelancing, gig work, or launching small businesses.

Career and Technical Education and Trade programs, like the one Jimmy’s in, are booming. Up 16% year-over-year.

The stigma is shifting.

Gen Z isn’t just tolerating blue-collar work, they’re embracing it. Because what they value isn’t prestige—it’s freedom, growth, and balance.

What Gen Z Wants (and Doesn’t Want)

If you’re hiring, managing, or building culture for the future, it’s time to pay attention. Here’s what the research and the real world is telling us about Gen Z:

1. Flexibility is non-negotiable.

Forget strict 9-to-5s and office mandates. Gen Z expects flexibility in when and where they work. In fact, more than 80% say they want flexible schedules. Nearly two-thirds would accept lower pay in exchange for better work-life balance.

2. Pay still matters…a lot.

They’ve watched inflation soar and housing become unaffordable. They carry deep financial anxiety. Studies show Gen Z believes they need to make $170,000+ per year to feel financially stable. Compensation isn’t just about lifestyle—it’s about survival and security.

3. They want to learn and grow.

This generation craves personal development. “Learning and development opportunities” rank just below balance when choosing an employer. They’re asking: Will I grow here? Or will I outgrow this?

4. They seek purpose, not just perks.

86% say a sense of purpose is key to job satisfaction. They research company ethics, values, and social impact before accepting a job offer. If your culture doesn’t align with their beliefs? They’ll leave. Or never apply in the first place.

5. They’re already working.

Even before graduation, many Gen Zers are juggling jobs, side gigs, and entrepreneurial pursuits. Jimmy’s drive-thru shifts and weekend pressure washing gig? That’s not unusual—it’s emblematic. One study found over 70% of Gen Z is freelancing or planning to.

They’re not waiting for permission. They’re building their own ladders.

So what do we do with all of this?

We listen. We evolve. And we stop underestimating them.

Too often, I hear people dismiss Gen Z as flaky or entitled. But if you spend five minutes with someone like Jimmy or look at the data, it’s clear: they’re not lazy, they’re discerning.

They’re not unfocused, they’re re-focused. They’re not rejecting work, they’re rejecting outdated systems.

As leaders, we have a choice: resist or respond. We can cling to old models or we can co-create new ones with Gen Z at the table.

Sources

• Fast Facts: Enrollment, 2023
  https://nces.ed.gov/fastfacts/display.asp?id=98

• Employment and Unemployment Among Youth - Summer 2024, 2024
  https://www.bls.gov/news.release/pdf/youth.pdf

• Deloitte Global Gen Z and Millennial Survey 2025, 2025
  https://www.deloitte.com/global/en/issues/work/genz-millennial-survey.html

• From hire to inspire: Getting—and keeping—Gen Z in manufacturing, 2024
  https://www.mckinsey.com/capabilities/operations/our-insights/from-hire-to-inspire-getting-and-keeping-gen-z-in-manufacturing

• Gen Z Is Abandoning Conventional 9-to-5 Corporate Jobs for More Diverse Work, 2023
  https://investors.upwork.com/news-releases/news-release-details/gen-z-abandoning-conventional-9-5-corporate-jobs-more-diverse

• Freelancing Meets Gen Z Modern Work Needs, 2023
  https://www.upwork.com/research/gen-z-work-requirements

• Labor Force Characteristics (CPS), 2025
  https://www.bls.gov/cps/lfcharacteristics.htm

• Fast Facts: Undergraduate Graduation Rates, 2023
  https://nces.ed.gov/fastfacts/display.asp?id=40

• Fast Facts: Educational Attainment, 2023
  https://nces.ed.gov/fastfacts/display.asp?id=27

• Freelance Forward 2023 | Upwork, 2023
  https://www.upwork.com/research/freelance-forward-2023-research-report

But here's the challenge: there's a disconnect between what hiring managers expect and what Gen Z delivers. It's not that either side is wrong—they're just speaking different languages. And in this gap lies both friction and opportunity.

When Sandra Moran, Chief Customer Experience Officer at WorkForce Software surveyed Gen Z workers about why they leave jobs within their first year, three themes emerged consistently: misaligned expectations, lack of work-life balance, and the discovery of better opportunities elsewhere.

"Gen Z is very different from prior generations in the workplace, specifically because of their on the personal benefit for working, rather than how they may be contributing to the larger organization," Moran explains.

"Prior generations often viewed the relationship between employer and employee indexing toward the employer's power, whereas many Gen Z workers are more interested in understanding what they will get out of the experience."

This shift in perspective isn't entitlement, it's a rational response to a world where traditional career paths have become increasingly uncertain. They've witnessed economic volatility, technological disruption, and a pandemic that upended workplace norms. Is it any wonder they're approaching their careers with a healthy dose of pragmatism?

Research from the National Society of Leadership and Success found that only one in four Gen Zs surveyed believe they know how to network effectively, and the same proportion don't feel prepared to negotiate. These are precisely the "soft skills" that hiring managers often cite as lacking.

But here's where the narrative gets interesting: what if we're focusing on the wrong skills entirely?

The Hidden Strengths of Gen Z

Annie Rosencrans, people and culture director at HCM platform HiBob, challenges the notion that Gen Z lacks soft skills, highlighting instead their natural strengths in empathy, fairness, and respect.

"Rather than a lack of soft skills, Gen Z offers unique strengths that can be nurtured for workplace success," she argues.

The 2025 Deloitte Global Gen Z and Millennial Survey reveals that Gen Zs are more focused on work-life balance than climbing the corporate ladder—

only 6% say their primary career goal is to reach a leadership position. However, this doesn't mean they lack ambition.

When asked about their strongest reasons for choosing their current employer, learning and development ranked in the top three.

What Gen Z brings to the table is a set of adaptive skills that position them perfectly for our rapidly changing work environment:

1. Strong adaptive capabilities and openness to change

2. Quick adoption of new technologies

3. High emotional intelligence

4. Greater likelihood to demonstrate vulnerability, empathy, and tolerance

While Gen Z may excel at digital communication, in-person workplace interactions can be a different story. A survey by learning platform Kahoot of 1,015 Gen Z workers found that 9 in 10 reported experiencing social discomfort at work, with more than half saying they feel it at least half the time.

Sean D'Arcy, Kahoot's Chief Solutions Officer, notes that this discomfort "could present challenges not only for their career advancement but for the team's ability to collaborate and share knowledge. A lack of effective communication and collaboration can also hinder team productivity, disrupt client relations, and lead to inefficient decision making."

But D'Arcy is quick to add an important caveat: "Different generations have their own approaches to work culture, and it is the responsibility of their employers to try and reconcile these differences and get the best out of multigenerational teams."

This is a crucial insight. The solution isn't to force Gen Z to conform to traditional workplace norms, but rather to create environments where different generational strengths can complement each other.

The skills gap between what hiring managers expect and what Gen Z brings isn't a problem to be solved—it's an opportunity to be embraced. By recognizing and valuing the unique strengths of this generation while providing support in areas where they may need development,

organizations can create more dynamic, innovative, and resilient workplaces.

As James Uffindell, founder and CEO of Bright Network, puts it: "Gen Z brings fresh perspectives, adaptability, and a hunger to make an impact, but it's on all of us to nurture their potential. Instead of focusing on what they may lack, we need to create the right environment for their growth."

The future of work isn't about Gen Z conforming to traditional workplace expectations—it's about creating workplaces that can harness the best of what every generation has to offer. And in that collaborative spirit lies the true potential of tomorrow's workforce.

5 Ways Hiring Managers Can Bridge the Gap

1. Reframe "Soft Skills" as "Power Skills"

2. Create Spaces for Open Dialogue and Feedback

3. Implement Development Programs

4. Focus on Cross-Generational Collaboration

5. Prioritize Mentoring Over Managing

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4. Get Ready! Leadership &s June edition will be in your inbox tomorrow.

   

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Let’s get real for a moment,

Today’s leaders are drowning in demands, constant decisions, stretched teams, fractured systems, and the expectation to show up with vision, composure, and confidence through it all.

And while traditional leadership advice still leans on “strategic thinking” and “resilience,” many leaders I work with are quietly asking, “If I’m doing everything right, why do I still feel so off?”

Here’s what most frameworks leave out:

1. You can’t lead from a place you’ve never been in yourself.

2. And if your nervous system is still wired for survival, no mindset shift will create the internal alignment you need to lead sustainably.

Why Strategy Alone Isn’t Enough Anymore

Most leadership development skips a critical step. It teaches you what to think and how to act, but not how to feel safely inside your own body.

That’s a problem.

Because the root of chronic burnout, reactive decision-making, people-pleasing, or even impostor syndrome, isn’t always psychological, it’s physiological.

Research from Dr. Bessel van der Kolk and Antonio Damasio affirms what many of us intuitively know—our bodies store our leadership patterns. Not just our posture or tone, but our stress responses, our belief systems, our leadership triggers. All of it is shaped and held below the surface.

So if you’ve ever found yourself repeating behaviors you know don’t serve you but feel powerless to change, it’s not a lack of willpower. It’s a lack of nervous system integration.

The Real Game-Changer: Internal Alignment

What sets the next era of leadership apart is this—an aligned leader integrates mindset, nervous system, and action. It’s not just about knowing the right thing or saying the right thing, it’s about being resourced enough to embody it.

When your mindset says, “I’ve got this,” and your body believes it, that’s confidence.

When your strategy calls for innovation, and your nervous system stays regulated in uncertainty, that’s leadership.

When your decisions are no longer driven by unconscious fear but by conscious presence, that’s when teams begin to thrive.

Three Embodied Leadership Skills to Practice Now

These aren’t just wellness tools, they’re leadership tools.

Each one raises your self-awareness, recalibrates your presence, and builds capacity to lead from a more integrated place.

1. Tune In to Your Body’s Intelligence

You can’t work with what you don’t know is there.

Self-awareness isn’t just a mindset, it’s a felt sense. The body constantly sends data, but most leaders are trained to ignore it, tight shoulders dismissed as “stress,” or gut instincts brushed off as irrational.

Practice: Pause before your next important conversation. Close your eyes for ten seconds. Ask,

1. What am I feeling in my body right now?

2. Where is there tightness, heat, or stillness?

3. What might this sensation be trying to tell me?

This is leadership intelligence. And the more you listen, the wiser you become.

2. Align Your Mindset With Your Nervous System

Mindset without regulation is a broken feedback loop. You tell yourself, “I’m fine,” but your nervous system is bracing for attack.

Guess what your team feels? The truth.

Instead, let your body lead. Begin with breath, sensation, or grounding, then speak your affirmation. This is where real belief is built.

Try this sequence:

1. Inhale for four counts, exhale for six.

2. Feel your feet. Notice the weight of your body.

3. Then say, “I am safe to lead from truth.”

Over time, this creates embodied confidence, not just performative composure.

3. Design an Environment That Regulates You

Your nervous system responds to everything: your inbox, your Slack feed, even your calendar layout.

If your environment is filled with micro-stressors, you’re asking your leadership to bloom in concrete.

Audit your space:

1. Where does anxiety spike?

2. What drains your energy before 10 a.m.?

3. What boundaries have you postponed setting?

As Brené Brown reminds us, clarity is kindness. And kindness starts with the environment you create for yourself.

From Regulated Leaders to Regenerative Cultures

This work doesn’t just change individuals, it reshapes systems.

When leaders regulate themselves, they model a different kind of power. They no longer lead from urgency, fear, or shame. They create cultures that breathe, where people feel safe to think, speak, and stretch beyond old limits.

As Simon Sinek writes in The Infinite Game, great leadership is not about winning but building something that lasts. And nothing lasting is built on dysregulation.

A Final Truth

You don’t need to do more to lead better.

You need to feel safer in your own body to lead with more clarity, integrity, and trust. Because the most effective leaders today aren’t just strategic. They’re aligned, inside and out.

Wellness and Work in Focus for Mental Health Awareness Month

Welcome to the May edition of Leadership &!

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A Note From Colleen

Welcome to this months edition of Leadership &.

Leadership isn’t about titles or power—it’s about people. It’s about seeing something in someone before they see it in themselves and it’s about stepping up when it’s easier to step back.

But the term leadership is often muddled and that’s why we are working hard to redefine the future of leadership—what it means, who its for and how it will shape the future…

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#1: The Health Cost of Return-to-Office versus Remote and Hybrid Work

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#2: We Asked 100+ Leaders How They Are Focusing on Their Own Wellbeing

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#3: The Power of Play on Productivity and Brain Health

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#4: Why Employee Wellness Programs Are Becoming Business Essentials

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And lastly,

Welcome to this months edition of Leadership &.

Leadership isn’t about titles or power—it’s about people. It’s about seeing something in someone before they see it in themselves and it’s about stepping up when it’s easier to step back.

But the term leadership is often muddled and that’s why we are working hard to redefine the future of leadership—what it means, who its for and how it will shape the future.

And for those of you who don’t know I’m Colleen Millerman—strategist, coach and the human voice behind the &. I created Leadership & as a response to the kind of leadership I wish I saw more: thoughtful, curious, human-centered, and willing to evolve. At Leadershipand.org we explore topics like AI, workplace wellbeing, the future of work, and real stories from leaders redefining what it means to lead today and tomorrow. Our goal is to successfully build a community of over a million professionals, support emerging leaders through scholarships, celebrate incredible leaders with our Excellence Awards, create a home for hundreds of writers exploring all things leadership, and spark a movement that redefines what it means to lead.

This May, in honor of Mental Health Awareness Month, we’re turning our focus to wellness. Not the corporate buzzword kind—but the personal, messy, meaningful kind. The kind that asks: How are you really? How do leaders care for themselves while carrying the weight of others? What does “well” even look like in a world that often rewards burnout?

This edition is full of insights, stories, and practical tools around mental health, boundaries, the science of play, and how leaders across industries are taking care of themselves and their teams.

Thanks for being here; and I hope something in this issue ignites a spark and helps you move forward with a little more clarity, energy, or ease.

— Colleen

The answers we received—from CEOs, authors, coaches, psychologists, and creators were striking not for their grandiosity, but for their intentionality. These leaders are not just surviving high-performance demands, they’re sustaining them by prioritizing their own wellbeing.

And they’re modeling that commitment for the teams they serve.

What We Heard

While each person’s approach was unique, several core patterns emerged:

• Intentional Movement as Restoration
  From “movement snacks” and strength training to gardening and Tai Chi, leaders use physical activity as a daily reset.

• Time in Nature as Therapy
  Walks outdoors, morning sun, grounding in gardens—leaders are turning to the natural world to recharge, reflect, and regulate.

• Mindfulness and Quiet Solitude
  Meditation, breathwork, journaling, and creative roaming surfaced as tools to calm the nervous system and sharpen clarity.

• Boundaries from Tech and Work
  Whether it’s phone-free mornings or evening shutdowns, leaders are consciously creating space between themselves and constant digital noise.

• Simple, Repeatable Rituals Over Complex Hacks
  Consistent morning routines, recovery minutes between meetings, and protected downtime show a move toward sustainability—not perfection.

• Emotional Awareness and Self-Empathy
  Many leaders acknowledged the importance of emotional intelligence, energy management, and giving themselves permission to rest or say “no.”

• Creative and Reflective Practices
  Music, journaling, prayer, and intentional quiet were described not just as hobbies—but as essential parts of staying centered.

• Wellbeing as Leadership
  Perhaps most powerfully, leaders are recognizing that caring for themselves isn't a personal indulgence—it’s a professional responsibility. Many are modeling this mindset visibly for their teams.

Hear From the Leadership Experts

The best teams I have been fortunate to be a part of incorporated play into our workdays. But, somewhere along the way, "play" got a bad rap in the workplace. We started thinking of it as unproductive, childish, or something to squeeze in after all the "real work" was done.

Maybe the ‘work hard, play hard’ mentality actually killed it.

But, what if we think of play as the real work? Or at least a secret ingredient for doing it better.

Research has shown that just 45 minutes of play per week can boost productivity by up to 20%. Triggering a release of endorphins, which help reduce stress, improve brain functionality, and even stimulates creativity.

In short: it's like giving your brain a green smoothie and a double shot of espresso matcha—at the same time.

Play is Healthy

According to the American Journal of Play (yes, that's a real thing and yes, it's delightful), play improves cognitive flexibility, emotional resilience, and problem-solving skills.

Adults who play regularly report lower stress levels, better memory, and stronger social connections.

Translation: Play more. Feel better. Work smarter.

Remote and Hybrid Teams Need Play More Than Ever

Remote and hybrid teams have a lot going for them—flexibility, autonomy, work-life balance but they also face big challenges like isolation and disconnection.

This is where play becomes a power tool. A little bit of structured fun can go a long way in building trust, boosting communication, and sparking real human connection across screens and time zones.

According to a Gallup report, teams with strong social connections (read: people who actually like working together) are twice as likely to be highly engaged and show 21% higher profitability.

Turns out, play isn't just good for your soul — it's rocket fuel for your brain, your team, and yes, your bottom line.

Braid: Bringing Play to Your Slack Workspace

Enter Braid, a company that gets it.

Used by top companies like: Uber, Square, Accenture and Drippi AI.

Braid is building playful Slack games specifically designed to bring remote and hybrid teams closer together. Think quick, fun activities like trivia, icebreakers, challenges, and mini-games—all seamlessly woven into your workday.

Instead of scheduling another awkward Zoom happy hour (you know the one), you can weave tiny moments of connection and laughter right into the flow of work.
Easy, authentic, and actually fun.

PLAY FOR FREE TODAY BY DOWNLOADING THE SLACK APP.

OR UNLOCK ACCESS TO MORE GAMES AND SAVE 15% FOR YOU AND YOUR TEAM FOR THE YEAR WITH THIS LIMITED OFFER 👇

Save 15% on Braid

Why It Matters

The future of work isn’t just about where we work, it’s about how we feel while we do it. And play is part of the answer.

• It boosts productivity

• It strengthens relationships

• It makes work a whole lot more human

Because at the end of the day, people who laugh together, think better together.
And teams that play together? They win.

Sources:

• Boost Productivity 20%: The Surprising Power of Play (Forbes)

• Stress Relief from Laughter? It's No Joke (Mayo Clinic)

• The Benefits of Play for Adults (American Journal of Play)

• Braid: Playful Slack Games to Boost Team Engagement (Braid)

• State of the Global Workplace Report 2023 (Gallup)

*Some of the links in this email are affiliate links, which means I may earn a small commission if you make a purchase through them. There is no extra cost to you, and I only recommend products or services I truly believe in. Your support helps me continue providing valuable content. Thank you!