Leadership Squared

I coach leaders into Culture Architects. With over 20 years of Executive Leadership experience, I share my strategies with leaders on how to develop culture, inspire connection, and drive performance.

Leadership Coach | Keynote Speaker

Vistage Worldwide, Inc.

As a Vistage member, I am committed to elevating my company and my community. Vistage is the world’s largest CEO peer advisory and executive coaching organization and has been helping business leaders make better decisions that get better results since 1957.

Member

Q Works Group 

Managing Partner of The Q Works Group, Inc., which has provided Talent Management since 2002.  We have expanded our service offerings to include Consulting and Corporate Services that fits nicely with our Recruiting and Staffing Services.  I currently work with Organizations to assist them in leadership, behaviors and engagement by working through a series of exercises to identify change.  I thoroughly enjoy Speaking to Teams and Organizations.  
Q Works Group models behaviors through our Core Values: Integrity, Commitment, Kaizen and Fun.  Additionally, our Mission to build and support people in our local communities.

Managing Partner

Eliassen Group

Managing P&L and overseeing all Strategic and Tactical Operations.  My role is to Coach and Develop the Talent in my Organization and create long term opportunities for my teammates.  I focus on two areas - Associate Compensation and Associate Career Development.  When I meet the needs of my teammates, our retention increases.  We were able to build and grow the Region to over $20M in Revenue the first two years.

Vice President - Southeast Region

Eliassen Group has been driving the success of our clients, consultants, and employees within Technology Staffing and Consulting Services since 1989. For nearly 30 years, we have been at the forefront of innovation by uniting talented people and quality solutions within successful companies to help them attain their business objectives. Our solution oriented approach to understanding your needs ensures that we identify and represent the best possible talent available in the market, personally selected and matched to your requirements by our highly-tenured, extraordinarily capable recruiting team. Our consulting divisions include expertise focused on Agile, Big Data, Biometrics & Data Solutions, Creative Services, Government Services, Life Sciences and Workforce Management. Eliassen Group is privately held and headquartered in Wakefield, MA.

We have experienced significant growth (Over 150%) in our first year.  We thrive on "making the future you happy with the today you".  It is important to drive a fun but winning culture and following the "Hope is NOT a Strategy" philosophy.  It is important to plan your efforts as specifically as possible.  Additionally, to distinguish ourselves from our competitors with our Consultant population.  They are the heartbeat of our professional existence.  That all starts with building a strong internal Team that cares about people.  

I focus on two main areas with our internal Team: 
1. Associate Compensation 
2. Associate Career Development
If I can assist by providing individual performers with the tools necessary to achieve their goals, we all win.  If you want to be a part of a "Growth Vision" where people are not a number, please reach out to me!

Regional Director - Southeast Region

Kforce Inc

Responsible for growth in Charlotte, Raleigh, Louisville and Cincinnati Markets.  Combined, these Markets grew consistently Year over Year.  Overall, we grew these Markets to over $50M in Total Revenue.  We increased headcount and EBITDA.

Market Vice President - The Blue Ridge Area

We continue to see accelerated revenue growth year over year.  2011 achieved 43% growth which followed 67% growth in 2010.  Our local team continues to grow in tenure and experience level.

Managing Director

Senior Account Manager

Pfizer Pharmaceuticals

I sold in the Cardiovascular, Urology, Neurology & Pain divisions.

Sales Representative

TEKsystems

I primarily sold to Oil and Gas/Energy sector.  I also held functions in the Banking vertical as well.

Account Manager

Welcome to the future of leadership. My name is Clegg, and I specialize in activating the full potential of individuals and teams to drive innovation, collaboration, and cultural transformation—Turning Your People To the Next Level. You can’t expect the best leaders if they’re not the best version of themselves.

In today’s rapidly evolving landscape, traditional top-down leadership models no longer deliver the results organizations need. I focus on Next-Level Leadership Training that amplifies human creativity, connection, and purpose—ensuring your people are engaged and fully "on." This leadership aligns business goals with personal fulfillment, setting the foundation for enduring success.


What You Can Expect:

🔑Leadership Evolution: Learn how to transform outdated management approaches into dynamic, people-centered strategies that work
🔑Retention Through Reputation: Build a team that stays because they feel seen, heard, and valued
🔑Innovation-Driven Results: Unlock your team’s creative potential and ensure your organization stays ahead in a world driven by AI & constant change

Do you need to

👉🏼Turn your team into high performers who are motivated and aligned with your vision
👉🏼Create a leadership pipeline that embraces creativity, connection, & co-creation
👉🏼Equip your leaders with tools that foster trust, psychological safety, & collaboration

If so, you're in the right place.


Why My Approach Works

I created The Future You Program, a revolutionary leadership training solution for organizations ready to break free from traditional, task-oriented models. This program delivers tangible results by focusing on human-centered leadership and empowering leaders to lead authentically.

Through a mix of executive leadership coaching, group training, and a proven framework, I help organizations create workplaces where talent thrives, innovation flourishes, and results follow. Whether it's transforming emerging leaders or strengthening executive teams, the impact is immediate and measurable.

Outcomes You Can Expect

✅ Leaders who ignite creativity and collaboration across their teams
✅ Reduced turnover and a magnetic culture that attracts top talent
✅ Teams that are inspired to innovate and push boundaries
✅ Learn to measure your culture objectively

Engagement Options

🤝Tailored Leadership Coaching for Executives & Teams
🤝Cohort-Based Training with The Future You Program
🤝Keynote Speaking on Humanized Leadership & Innovation

A turned-on team means a turned-on organization

Let’s start your leadership evolution: www.calendly.com/cleggculture

“My son was born with a police escort.”

Not a metaphor. A literal one.

It was 5 a.m. and the roads were empty. 

We’re headed to the hospital for my wife’s scheduled C-section. 

I take a left turn, maybe a little fast, maybe a little too “optimistic” on a red light… and suddenly, blue lights in the rearview.

My wife is glaring at me. 

The officer taps on my window.

Me: “I’m sorry if I was going a little too fast.”

Officer: “Actually, you ran a red light.”

Me: “I’m sorry. My wife and I are headed to the hospital because she’s having a baby.”

Officer: “OMG. Are you going to Tomball Hospital?”

Me: nods

Officer: “Follow me.”

As we pull out behind him, my wife says, “OMG, Clegg. You just lied to a police officer.”

I look at her and say, “You are having a baby.”

Her: “It’s a scheduled C-section.”

Me: “He didn’t give me time to explain.”

So that morning, we rolled into the hospital with full lights-and-siren escort. Not because I was a great driver… but because a kind officer decided to believe a nervous dad.

That baby we were rushing toward that morning is the one we’re celebrating today.

Grateful for the kid who showed up in this world with a police escort and has made our lives louder, fuller, and better ever since.

Happy birthday, buddy. ❤️

Michael B. Clegg

We install your leadership operating system → Your best people stay, your leaders align, and your culture scales with trust. Driven by LeaderLens™ insights & the L² Framework.

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“Your exec team isn’t broken, the OS is”

 Most executive teams aren’t broken.
 They’re just running on an outdated leadership operating system.

Here’s how that usually shows up:
 • Your best people quietly wonder how long they’ll stay
 • Decisions drag or get revisited 3–4 times
 • “Culture” feels like a poster on the wall, not how work really gets done
 • Everyone is busy… but the most important work keeps slipping

It’s not a “more talent” problem.

It’s an operating system problem.

Install a better leadership OS, leaders start to:
 • Tell the truth faster
 • Trust each other more
 • Make cleaner, faster decisions
 • Create a culture that scales with trust and clarity

That’s the work I do with senior teams.

If you’re thinking, “We’re good… but not yet the team we need to be for where we’re going,” comment “OS” and I’ll send you the simple model I use to map a leadership operating system.

#leadershipsquared #leaderlens #teamlens

We get to spend time with those we care about.  Having both boys back under the same roof with their sister is such a blessing.  

I work hard so these kids have more than I have - which doesn't take much. 🤣 

I wish my entire network a Happy Thanksgiving.  

For those that lost loved ones since the previous Thanksgiving, I'm praying for you all.

𝐈'𝐦 𝟓𝟐. (𝐲𝐢𝐤𝐞𝐬 😱 )𝐇𝐞𝐫𝐞'𝐬 𝐦𝐲 𝐚𝐜𝐜𝐨𝐦𝐩𝐥𝐢𝐬𝐡𝐦𝐞𝐧𝐭𝐬:

Helped develop great leaders over the past 20+ years by helping them become self-aware and build executive presence.

Generated $500K in revenue in less than 2 years with Leadership Squared.

Working with Fortune 20 clients and presenting to rooms of dozens of C–Suites from different companies.

I've coached football for two decades and have over 100+ wins.  The coaching environment is less important.  

Knowing how to connect with humans is.

Next up: Helping multiple Founders, Executives, Entrepreneurs and C-Suites turn their leadership teams into high performers.

Click here to apply: https://lnkd.in/eucp-JjP

#leadershipdevelopment #leaderlens #leadershipsquared

Most leaders think they’re self-aware.
The research says otherwise.

Organizational psychologist Dr. Tasha Eurich found that while 95% of people believe they’re self-aware, only 10–15% actually are.

That gap is why I’ve started talking less about “external self-awareness” and more about executive presence.

Because at its core, executive presence is simply this:

The impact your leadership has on the people around you—especially under pressure.

It’s not polish.
It’s not performance.
It’s not a perfectly rehearsed “executive” persona.

One leader in our program was known as “the nice boss.”

His team liked him. They also didn’t fully respect him.

He avoided hard conversations.
He softened every piece of feedback.
He thought he was protecting relationships.

In reality, his team was constantly guessing what he really thought.

And when people have to guess, they usually fill the silence with something negative.

Once he got honest feedback through coaching, he made one crucial shift:

He started having the difficult conversations he’d been avoiding.

Clear expectations.
Real-time feedback.
Straight talk, delivered with respect.

The result?

Trust went up, not down.
The team finally knew where they stood.

His presence in the room changed—calmer, clearer, more grounded.

Executive presence is earned, not performed.

You don’t get it from a title or a TED-style presentation.

You earn it by telling the truth, kindly and consistently, when it really counts.


In January, I’m running a small executive leadership cohort focused on building this kind of presence under pressure.

If you’re a CEO, founder, or senior leader and want the details, comment “presence” or send me a DM and I’ll share more.

#selfawareness #leadership

𝐅𝐫𝐨𝐦 𝐫𝐮𝐧𝐧𝐢𝐧𝐠 𝐨𝐭𝐡𝐞𝐫𝐬' 𝐞𝐦𝐩𝐢𝐫𝐞𝐬 𝐭𝐨 𝐛𝐮𝐢𝐥𝐝𝐢𝐧𝐠 𝐦𝐲 𝐨𝐰𝐧

I used to be a corporate executive who climbed the ladder, came into crappy markets, developed people, built the market, hired leaders, and moved on to the next.

It sucked because I hit my ceiling at $300-$400K and stopped dreaming. I thought I wasn't deserving for more.

Then I bought a business that turned into a disaster post-pandemic with over $1m in debt and a partnership that wasn't aligned.

But then in March 2023, a man jumped off a bridge in front of my truck. I ran over him, and he didn't survive. 
That sent me spiraling for months until one conversation with Dr. Benjamin Hardy helped me find my future self.

Which led me to starting Leadership Squared in January 2024, generating $500K in less than 2 years, buying out my partner, completing my TEDx, starting my book, and now helping Founders and Executives develop leadership teams that actually perform.

Want to know more? Comment YES and I'll send you the details.
#leadershipsquared #tedx #leaderlens

Top-down leadership used to work.

In today’s VUCA landscape, it’s a liability.
𝐕𝐨𝐥𝐚𝐭𝐢𝐥𝐢𝐭𝐲. 𝐔𝐧𝐜𝐞𝐫𝐭𝐚𝐢𝐧𝐭𝐲. 𝐂𝐨𝐦𝐩𝐥𝐞𝐱𝐢𝐭𝐲. 𝐀𝐦𝐛𝐢𝐠𝐮𝐢𝐭𝐲.

You know the acronym. 

You’re living it.  In that world, leaders can’t just direct.

They have to activate human creativity, connection, and purpose.

Next-Level Leadership looks like:
 • 𝑳𝒆𝒂𝒅𝒆𝒓𝒔 𝒘𝒉𝒐 𝒂𝒓𝒆 𝒕𝒉𝒆 𝒃𝒆𝒔𝒕 𝒗𝒆𝒓𝒔𝒊𝒐𝒏 𝒐𝒇 𝒕𝒉𝒆𝒎𝒔𝒆𝒍𝒗𝒆𝒔, 𝒏𝒐𝒕 𝒄𝒐𝒑𝒊𝒆𝒔 𝒐𝒇 𝒕𝒉𝒆𝒊𝒓 𝒃𝒐𝒔𝒔
 • 𝑻𝒆𝒂𝒎𝒔 𝒕𝒉𝒂𝒕 𝒄𝒉𝒂𝒍𝒍𝒆𝒏𝒈𝒆 𝒆𝒂𝒄𝒉 𝒐𝒕𝒉𝒆𝒓 𝒘𝒊𝒕𝒉𝒐𝒖𝒕 𝒇𝒆𝒂𝒓 𝒐𝒇 𝒑𝒖𝒏𝒊𝒔𝒉𝒎𝒆𝒏𝒕
 • 𝑷𝒆𝒐𝒑𝒍𝒆 𝒘𝒉𝒐 𝒂𝒓𝒆 𝒇𝒖𝒍𝒍𝒚 “𝒐𝒏,” 𝒃𝒆𝒄𝒂𝒖𝒔𝒆 𝒕𝒉𝒆 𝒘𝒐𝒓𝒌 𝒄𝒐𝒏𝒏𝒆𝒄𝒕𝒔 𝒕𝒐 𝒔𝒐𝒎𝒆𝒕𝒉𝒊𝒏𝒈 𝒕𝒉𝒂𝒕 𝒎𝒂𝒕𝒕𝒆𝒓𝒔

This kind of leadership aligns business goals with personal fulfillment.
That’s not fluff. It’s the foundation for enduring performance.

That’s the work I do with executives and their teams:
turning “good leaders under pressure” into next-level leaders who can actually handle the future.  

Teaching 𝐫𝐞𝐚𝐜𝐭𝐢𝐨𝐧 𝐯𝐬 𝐑𝐄𝐒𝐏𝐎𝐍𝐒𝐄
If you have an emotional leader, helping them understand the difference between the two makes a world of difference.

If your 2026 strategy is to have “better leadership.” .…but your leadership doesn’t have a real operating system, you’ve already got a gap.

𝐌𝐨𝐬𝐭 𝐨𝐫𝐠𝐬 𝐚𝐫𝐞 𝐛𝐞𝐭𝐭𝐢𝐧𝐠 𝐛𝐢𝐠 𝐨𝐧:
 • Ambitious growth targets
 • Complex change
 • New markets, new products, new expectations

And then hoping their leaders will “rise to the occasion.”

Hope is not an operating system.

In January, I’m launching a small Leadership Operating System Cohort for 10–12 leaders who want to:

 • Keep their best people
 • Align their senior team
 • Build a high-trust culture that can actually scale

𝐖𝐞’𝐥𝐥 𝐮𝐬𝐞:
 • LeaderLens™ Diagnostic process that will provide you with a lifetime of information from less than 30 minutes of effort. 
 • PDP® to understand behavior wiring, pressure responses, working style and capacity and how you make decisions. 
 • The L² Framework to install shared language, tools, and habits you can take back to your org.

We turn data in to a humanizing leader strategy. 

This is for CEOs, Founders, and People leaders who either:

Want to join personally, or want to sponsor one or more key leaders for the next level

If you want details before I talk about it publicly, DM me or comment “COHORT” and I’ll send you the 1-page overview.

Retaining top talent is (usually) a trust problem.

Most organizations don’t have a “top talent” problem.

They have a trust problem.

Your best people rarely leave because of the company.  They leave because of what it feels like to be led.

𝐋𝐨𝐰-𝐭𝐫𝐮𝐬𝐭 𝐞𝐧𝐯𝐢𝐫𝐨𝐧𝐦𝐞𝐧𝐭𝐬 𝐬𝐨𝐮𝐧𝐝 𝐥𝐢𝐤𝐞:

“I don’t know where I stand.”
“We say one thing in the room and do another outside it.”
“Decisions change depending on who’s in the meeting.”

𝐇𝐢𝐠𝐡-𝐭𝐫𝐮𝐬𝐭 𝐞𝐧𝐯𝐢𝐫𝐨𝐧𝐦𝐞𝐧𝐭𝐬 𝐬𝐨𝐮𝐧𝐝 𝐥𝐢𝐤𝐞:

“I know the real priorities.”
“My leaders tell me the truth, even when it’s hard.”
“We can disagree without it turning political.”

You don’t retain top talent with snacks, perks, or off-sites.
 
You retain them with aligned, high-trust leadership.

That’s why my work focuses on installing a leadership operating system that scales trust, not just performance.

When I speak to my Vistage Worldwide, Inc. counterparts, these are the priorities that I help them focus on.

If you’re quietly worried about losing one or two key people in the next 12 months, message me with the word “TALENT,” and I’ll share 3 trust questions I always ask executive teams.

#leadershipsquared #leaderlens #stayinterviews

𝐃𝐎𝐍'𝐓 𝐠𝐢𝐯𝐞 𝐲𝐨𝐮𝐫 𝐥𝐞𝐚𝐝𝐞𝐫𝐬 𝐠𝐞𝐧𝐞𝐫𝐢𝐜 𝐥𝐞𝐚𝐝𝐞𝐫𝐬𝐡𝐢𝐩 𝐭𝐫𝐚𝐢𝐧𝐢𝐧𝐠

Most Founders and Executives are sending their teams to generic leadership training programs.

The problem with this is they focus on KPIs and technical skills but ignore the foundation: self-awareness and executive presence.

This leads to leaders who know the theory but can't build trust, retain talent, or actually perform at the level your business needs.

After helping develop great leaders over the past 20 years and generating $500K in revenue in less than 2 years, here's what I'd do instead.

𝐏𝐃𝐏 + 𝐋𝐞𝐚𝐝𝐞𝐫𝐋𝐞𝐧𝐬 𝟐.𝟎

This is because 95% of people think they're self-aware, but only 10-15% actually are. Your leaders can't perform at 8-9/10 professionally if they're at 5-6/10 personally.

Which leads to teams that build real trust, retain top talent, and scale your business without you becoming their firefighter.

Now, Founders and Executives, you can think about it like this…

Are you trying to train leaders who know theory but can't execute? Or are you trying to develop leaders who actually perform and grow your business?
#leaderlens #leadershipsquared

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