CEO, Highland & Haskill Creek • Founder of Classy (acq. by GoFundMe) • Founder of nonprofit, Save Farmland

Every week I tackle management, operations & startup topics that are helping 250,000+ people. Sign up free: www.scotchisholm.com

I also run a leadership accelerator that helps founders develop into top CEOs. Apply here: https://joinhighland.com/apply/

My backstory: 

🚀 Founder of Classy, SaaS for nonprofits raising billions per year

🎗️ Acquired by GoFundMe in ‘22 to create largest giving platform in the world

🌲 Investor in dozens of startups out of family fund, Tall Timbers Holding Co, (Ripple, FanDuel, Hubble, Casetext, etc.)

🏔️ Founder of Highland, leadership accelerator & community for founders

🏡 Co-founder of Haskill Creek, modernized & healthier version of a Walgreens or CVS 

⚽️ Co-owner of Albion Soccer Club, top youth soccer club in country

🧑🏼‍🌾 Founder of Save Farmland, a nonprofit protecting local farmland & food 

⚙️ Industrial engineer & lean six sigma nerd, UMass Amherst grad 

❤️ Board experience: Nature Conservancy, Abundant Montana, Team Rubicon, Street Soccer USA, Montana Pediatric Cancer Foundation

It's been a wild ride. If you're interested in any of the above, please visit my website and reach out to me there. 

www.scotchisholm.com

Scot Chisholm

Getting pushed out of my own company taught me what a CEO actually does...

In 2017, I got called to my lead investor's office in La Jolla.

I waited 30 minutes in the conference room. Then the head of the firm walked in.

"The partners aren't happy with Classy's performance. We think it's time for some change." Two missed quarters. That's all it took.

I had built the company to tens of millions through brute force. But something had gone wrong. Growth slowed. I had become the limiting factor.

I hated them for it. But they weren't wrong.

I was more builder than scaler. More brick layer than architect. It took 24 months to buy them out and get us back on track. Some of the darkest times of my life, but also the deepest reflections.

That experience lit a fire under me to understand the CEO role better than anyone they could bring in to replace me. Not to become the next Jobs or Bezos. But to answer basic questions no one could give me:

What should I be doing all day? What should I focus on? What does a CEO actually do? So I obsessed over studying the best CEOs in the world. What separates the ones who scale from the ones who plateau?

I found that every great CEO masters 7 core responsibilities. I now call them the CEO-7.

I wrote a complete breakdown in yesterday's newsletter. 

If you wanna check it out, I'll drop it in the comments.

Operator & Investor • Founder of Classy (acq. by GoFundMe) • Building Highland, Just, Haskill Creek

How defining “great” changed our culture (and decision-making):

A new hire asked me a simple question after onboarding:

“What does great look like here?”

I didn’t have a clean answer.

Not because we lacked ambition, but because we’d never clearly defined it.

Mission, vision, and values weren’t enough.

What we were missing was our perspective on excellence.

That gap pushed us to document our company standards. The non-negotiables that guide decisions when things get messy, fast, or ambiguous. Inspired by how Patagonia articulated its philosophies, we created standards that outlived leadership changes and scaled with the company. 

Here's how I defined them 👇 

***
ps. If you want to read my in-depth article I wrote on this exact topic, I'll drop the link in the comments.

How to define what great looks like:

Here's how to create an unstoppable strategy in 3 simple steps:

First, what is a strategy? Most leaders get this wrong. Strategy is not vision. Strategy is not goals. It's the bridge between the two. Strategy is your unique approach to achieve vision. It shapes your annual goals and daily execution. Vision leads to strategy, which leads to goals.

To create an unstoppable strategy, you need three things:

- Unique approach
- Measurable impact
- Target market

I call this "strategic AIM." A stupidly simple, crystal clear description of strategy that anyone can understand.

1. Approach
What's our unique approach to accomplishing the company's 3 to 5 year vision? Why will people choose us? How are we 10x better than the competition? What are 3 to 5 core bets, multi year initiatives, that we will pursue? Your unique approach creates differentiation at all levels.

2. Impact
What does success look like when we achieve our 3 to 5 year vision? How do we measure it and track along the way? Customer impact, financial impact, shareholder impact. Get crystal clear on what success looks like from day 1.

3. Market
Most leaders target anyone that will buy from them. This is the wrong approach. Instead define exactly who your target market is. Think of it like an archery target. Primary is the inner ring, secondary is the 2nd ring, tertiary is the 3rd ring. Dominate the first before prioritizing the second.

Your strategic AIM informs how you set pricing, packaging, and messaging. It also makes annual goal setting a lot easier. What are the company's top three annual priorities that advance our strategic AIM? Pay special attention to your multi year core bets. These help shape annual goals.

Revisit your strategic AIM at least annually. As your vision evolves, your strategic AIM should evolve. They're joined at the hip. You should always have a company wide strategic AIM, but you could also have one for different products or markets as you get bigger.

If you're a founder or operator and you enjoy my content, you should check out Highland Academy: https://lnkd.in/eAVA5ekz

How to create an unstoppable strategy in 3 simple steps:

In 2017 I was called to my lead investor’s office in La Jolla. 

I had no idea what the meeting was about. 

They wanted me out as CEO after nearly ten years running the company. 

I had missed two quarters and lost their confidence. 

That was enough. 

But they weren’t wrong, I wasn’t yet a great CEO. 

While they tried to push me out, I studied the role like a maniac. 

Determined to be better than anyone that could replace me. 

Ultimately, it worked and the company 5x’d in valuation. 

Now I teach everything I learned through Highland Academy. 

If you’re a founder working to become a great CEO, this is for you.

I'll drop a link in the comments if you want to apply.

Or shoot me a dm.

Don't screw up your annual company kick-off!

Most CEOs don't realize how high-stakes their company kick-off really is. They waste the moment. Why? 

Because they don’t realize how high-stakes it is. They think B- work is ok. Check the box. Get back to the “real work”. I mean, you do have lots of shit going on. Carving out a half-day for a company kick off can feel like a waste of time.

I've been on both sides of this. As a founder, I learned the hard way that the leaders who put their heads down and "get back to work" in January are making one of the costliest mistakes of the year. The annual kick-off isn't a distraction from the real work. It IS the real work.

Andy Grove called this "managerial leverage" in High Output Management. The idea is simple: what you put in is nothing compared to what you get out. A few hours of intentional effort in January can shape the behavior of your entire company for months, if not years. Skip it and you put your team at an information disadvantage you'll be fighting all year long.

The truth is, your kick-off is the highest-leverage meeting of the entire year.
Get it right and your team has the clarity to do their best work all year long. Get it wrong, and you're playing catch-up on culture and alignment for months.

I've worked with hundreds of CEOs on this. The ones who treat their kick-off like the Super Bowl moment it is? They never say die. They show up prepared, energetic, and locked in, and their teams follow suit. The ones who phone it in? They spend the rest of the year wondering why nothing is sticking.

I wrote a guide to follow in a recent newsletter. It includes the one thing your team needs from their leader going into the new year: Purpose, Direction & Progress.

link in the comments to go in depth on this topic 👍

This is where companies quietly fall apart:

Most founders inherit the CEO title before they have any idea what it actually requires. 

You start the company, you get the title. 

No one sits you down and explains what the job is supposed to look like. 

You have to be intentional about learning the role. 

It’s not the same as being a founder. 

Two very different things.

***
Learn what the role of a CEO actually looks like in my recent article (link in comments)

How to speak like the top CEOs on the planet:

Most people communicate: 
- nervousness
- indecision
- selfishness

When they should be conveying: 
- conviction
- thoughtfulness
- partnership

Not all CEOs get it either, but the best certainly do. 

Here’s how 👇 

1/ Keep it clear & simple: Avoid jargon. Use plain English. Be yourself. Don’t over-share or talk in circles. Focus on nailing one main point but never exceed three. Don’t assume understanding. Ask the person if they get it.

2/ Speak with energy: Show enthusiasm & belief in what you say. Avoid fidgeting or whispering. Makes you look nervous. Stay solution-oriented. Don’t be a negative Nancy. You’ll demotivate everyone. Use storytelling to inspire & provide tangible examples.

3/ Talk like a partner: Say “we,” not “I”. Stay relatable to every level of the organization. Create a sense of shared ownership. Ask people: “What do you think?” Take people’s feedback seriously. Even if you make the final call.

4/ Communicate the ‘why’: Tie things back to mission & vision. Always explain reasoning behind major decisions. Help people understand company's progress. Create a sense of urgency when you fall behind. Say “because” more to force yourself to provide context to the team.

5/ Control your emotions: Never let feelings override the message. Stay composed under pressure. Don’t over-share and freak everyone out. But don’t sugarcoat things either. Be realistic & communicate a plan.

6/ Ask the right questions: Don’t pretend to have every answer. Find solutions through thoughtful questions. The best CEOs see themselves as detectives. Practice ‘5 whys’ asking why five times to find root causes.

7/ Guide, don’t dictate: Be a facilitator, not a dictator. Orchestrate debate & discussion. Pre-plan exercises that get people collaborating. Keep the room on track and constructive. Shape the discussion, don’t dominate it.


📌 ps if you want me to teach you how to do this at your company, check out Highland Academy: https://lnkd.in/eAVA5ekz

📌 📌 pps. if you enjoy my content, you'll love my free newsletter. Subscribe here: https://lnkd.in/e6ak5dbP

EOS and OKRs broke at scale. 

Here’s what replaced them.

I spent over a decade building Classy from a scrappy idea into a $100M+ company that processed billions in donations before we sold to GoFundMe.

As we scaled, one problem kept surfacing:
No operating system held up past ~$5M in revenue.

We tried OKRs. The product team loved them. But across the company they became too complex. Too many objectives, too many key results, quarterly resets, confusing grading. The system meant to create focus became a recurring distraction.

We looked at EOS. It was cleaner, but too prescriptive. And I didn’t agree with the idea that the founder should hand off operations to a “professional operator.” 

My belief is simple: The CEO must own the operating system.

There was also a deeper issue.

Classy was an impact company. Our mission wasn’t a slogan on a wall. It was the reason people showed up. We needed an operating system that connected purpose all the way down to daily execution, and not just tactical documentation.

So I built one.

It’s called the Northstar OS.

📌ps. If you want to dive into the Northstar OS framework, check out this article I wrote that breaks it down: https://lnkd.in/eDeRw6D2

pps. Sign up for my free newsletter here: https://lnkd.in/gXCsenmP

"Don't worry, you're gonna do great."

I was frozen in the green room at TEDx San Diego. My body felt like 1,000 pounds. I've only been a founder for a couple of years. Why am I giving a TED talk? People are going to laugh me out of this theatre.

An old man in the corner spoke up. That nudge got my legs working again.

I gave my talk. Came back dripping sweat.

"See, I told you you'd do great. You should be proud."

Then he walked on stage to give his own talk.

⁂

Years later, an advisor sent me a book that changed everything about how I manage people.

The One Minute Manager.

I googled the author. Ken Blanchard.

His face stared back at me.

The old man from my TED talk.

Here was one of the most successful business writers of all time, about to give one of his best talks ever, and he was focused on me.

That night I wrote Ken a thank you. He responded with equal grace.

⁂

The book became required reading for every manager at my company. Here are the 3 lessons that changed how I manage people forever:

1/ Great leadership is a side-by-side relationship. Not top-down. It's a partnership. When the organization wins, the people should win. Get this right and your people start managing themselves.

2/ Catch people doing something right. Positive recognition isn't soft, it's smart. People repeat what's recognized.

3/ Correct the behavior, not the person. Address mistakes quickly and specifically. End with reaffirmation. Every 1×1 becomes an opportunity to help people stay on track.

That night, Ken was demonstrating everything he'd later teach me through his book.

True leadership is the smallest acts of support, delivered at the right moment.

Full story + breakdown here:

Open article: 3 simple rules that changed how I manage people forever: by scotchisholm.com

3 simple rules that changed how I manage people forever:

CEO at C-Serv | Helping high-growth companies build and scale world-class tech teams.

👋 Hi, I’m Amy, CEO of C‑Serv. 

We partner with technology leaders building world-class solutions across networking, cloud, cybersecurity, and AI- delivering expert teams and consulting support in 50+ countries.

From billion-dollar enterprises to ambitious startups, we help high-growth companies scale faster and overcome complex delivery challenges with confidence. Whether you’re launching in a new region, driving transformation, or need embedded delivery support, we bring the technical firepower and operational strategy to make it happen.

What sets us apart: 
-       Partnership-driven approach
-       Specialized tech & consulting expertise
-       End-to-end international workforce solutions
-       Global reach, local insight
 
We built this company on empathy, kindness, and integrity.

I believe in leading with honesty, putting people first, and working with innovative companies that value culture and want to make a difference.
 
Who we are: 
 
💎  A team of A-players who care about exceptional work
🤝  Ethical and kind: no politics, no ego
🚀  Growth-oriented: we move fast and raise the bar
 
Besides being a CEO, I share insights on leadership, business growth, and building high-performing teams.

Amy Gibson

The leaders who changed my life didn't manage me.
They believed in me.

They didn't hover or micromanage. 
They gave me room to grow and trusted I'd figure it out.

And when I stumbled? 

They didn't make me feel small. 
They helped me get back up.

That's what people-first leadership has looked like for me.

Celebrating wins you had nothing to do with. 
Taking responsibility for losses you didn't cause.

It's harder than it sounds.

I've had to hear feedback that stung and say thank you instead of getting defensive.

I've watched people I mentored get the promotion and had to check my ego at the door.

I've been the steady one when everything felt uncertain. 
Even when I was uncertain too.

The truth is, people-first leadership isn't soft.

It can take real strength to stay curious when you want to assume the worst. 
To admit you don't know when you want to pretend you do.

So now I try to remember what my team is working toward beyond their job titles. 

I loop people in before decisions are final. 
I try to make it safe to disagree.

And when I give hard feedback, I do my best to deliver it in a way that builds trust instead of breaking it.

I'm still learning. Every single day.
And I think I always will be. 

But I know this much:

Years from now, your team won't remember the strategy.
They'll remember how you made them feel.

That's the kind of leader I want to be.

One who believes in people the way someone once believed in me.

What's one way a leader believing in you changed things for you?

♻️ If this resonates, repost for your network.
📌 Follow Amy Gibson for more leadership insights.

Mission statements can inspire.
Core values can guide.
But only your daily decisions build real culture.

Eric Partaker's post on healthy company culture got me thinking about what actually builds strong teams.

I've noticed all 7 of these patterns in teams with healthy cultures:

1️⃣ They address toxic behavior, even from top performers

• Talent doesn't excuse toxicity when it harms the team
• One bad person can poison the entire team
  
2️⃣ They promote based on merit, not politics

• Wrong promotions make your best people start looking
• Performance and values should both matter
  
3️⃣ They don't play favorites

• Everyone sees it, even when no one says it
• Favoritism makes trust start to break down
  
4️⃣ They grow people-first leaders

• Technical skills matter but aren't enough alone
• Leaders who can't grow people shouldn't lead them
  
5️⃣ They make it safe to speak up

• When people fear feedback, problems grow
• Feeling safe to speak isn't optional
  
6️⃣ They give recognition regularly

• People don't leave because of the work
• They leave when they don't feel valued
  
7️⃣ They apply values consistently

• Not just to some people but to everyone
• No exceptions for title, time, or revenue
  
Culture isn't built in the big moments.

It's built in the daily decisions about who you protect, who you promote, and what you tolerate.

That's where trust lives or dies.

♻️ If this resonates, repost for your network.
📌 Follow Amy Gibson for more leadership insights.

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The CEO Coach | CEO of the Year | McKinsey, Skype | Bestselling Author | CEO Accelerator | Follow for Inclusive Leadership & Sustainable Growth

Jenny Tod

“A bad workman always blames his tools.”

One of my teachers used to say this constantly to our class. 

Spilled paint? Blame the table.

Bad grade? Blame the exam.

He never let us get away with it.

And honestly, it used to drive us a bit mad.

But here’s what I realise now:

He was teaching me accountability.
Not the harsh kind.

The kind that says: what’s in your control?

That’s the question I bring to my team now.

Not “why did you fail?”
But “what was in your control, and what wasn’t?”

It changes the conversation. 

Blame shrinks.

Ownership grows.

You can still talk with kindness. 

Holding people accountable can feel terrifying.
Here's what I've noticed about doing it well:

It’s not one big talk.
It’s many small ones.

Jonathan Raymond calls this the Accountability Dial.

A series of conversations that gently ramp up:

→ The Mention: 
“I noticed this... is everything okay?”

→ The Invitation: 
“I’ve seen this a few times. What’s the pattern here?”

→ The Conversation: 
“This is affecting the team. Let’s figure it out together.”

Each one is a chance to stay connected, not prove a point.

But before I hold anyone else accountable, I check myself first.

Did I set clear expectations?
Did I give them what they needed to succeed?

Am I calm enough to listen? 

Only once I've answered these questions do I move forward. 

For me, accountability isn’t about catching people out.
It’s about helping them see clearly.

Our teacher knew that.
He just didn’t call it leadership.

♻️ If this resonates, repost for your network.
📌 Follow Amy Gibson for more leadership insights.

Coaching someone who doesn’t see the problem
can test even the most patient leader.

And the harder you push…

The harder they resist.

But I’ve noticed something surprising:

Breakthroughs rarely happen because we explain something better.
But they can happen if we ask better questions.

Here are a few things that have helped me:

1. Shift from telling to exploring

❌ Instead of: “Why did you do that?”
✅ Try: “What were you hoping would happen?”

❌ Instead of: “Don’t you see the issue?”
✅ Try: “How do you think that landed?”

❌ The wrong question triggers defense.
✅ The right one invites reflection.

2. Meet them where they are
↳  Not everyone is ready to change.

Some are in: “I don’t see a problem.”
Others are in: “Maybe something’s off.”

If they’re not ready for action, your role might not be 
to convince.

It might be to plant seeds.

3. Look for quiet signs of awareness
↳  It’s often subtle.
• They pause longer before responding
• They ask more clarifying questions
• They revisit the conversation later
• They stop defending… and start wondering

That’s usually the shift.
Coaching someone into awareness can take a bit of time.

The breakthrough often happens after the conversation ends.

And sometimes…

The person who grows the most in the process
is the leader.

Different paths work for different people.

But holding space, without forcing the moment, has 
rarely steered me wrong.

♻️ If this resonates, repost for your network.
📌 Follow Amy Gibson for more leadership insights.

Kindness matters in leadership.

It’s more powerful than authority.
It’s more lasting than commands.
It’s more effective than pressure.

11 ways effective leaders lead with kindness:

✦ Ask how they're doing, then listen deeply
✦ Find daily reasons to give recognition
✦ Listen for the voices that speak softly
✦ Put the human before the employee
✦ Stand up for your team, every time
✦ Make feedback a tool for growth
✦ Let people be their whole selves
✦ Celebrate small steps forward
✦ Respect the lines others draw
✦ Stay present when storms hit
✦ Reach out before they ask

My biggest lesson as a CEO?

Authority might get tasks done.
But kindness builds loyalty that lasts.

Your team won't recall every meeting.
But they'll never forget:

— How you helped them grow
— The time you defended them
— When you noticed they weren't okay

Because that's what real leadership is about.

Not perfection. Progress.
Not control. Support.
Not power. Partnership.

And a whole lot of heart.

♻️ If this resonates, repost for your network.
📌 Follow Amy Gibson for more leadership insights.

The advice I'd give my younger self in one list:

1 / Don't fear failure, fear staying still. 
→ Staying in the same place might be the bigger risk
→ Moving forward matters more than being perfect

2 / It’s okay to say no to things. 
→ Good opportunities can block amazing ones
→ Every yes should be intentional rather than reactive

3 / Let your calendar reflect what truly matters
→ What gets scheduled, gets your energy and attention
→ Time is one of the clearest signals of priority 

4 / Invest in your network before you need it. 
→ Always offer real value, with no expectation in return
→ The strongest connections are built over time, not at the moment of need

5 / Have honest conversations as soon as possible.
→ Addressing issues early reduces the chance of escalation
→ Avoidance doesn’t make things easier - just heavier

6 / Rest before you're tired, recover before you're broken.
→ Sustainable work starts with steady energy
→ Rest is part of the work, not a break from it

7 / Speak last, listening often reveals more than talking. 
→ Pause so others can contribute fully
→ The best insights can emerge when people feel heard 

8 / Choose the quiet discipline over the pain of regret.
→ Sustainable, consistent effort often beats short-term sprints
→ Success takes longer and more work than you think, but it’s worth it. 

9 / Hire people smarter than you, then listen to them.
→ Feeling threatened hires down, confidence hires up
→ The best teams challenge each other and grow together 

10 / Take responsibility quickly, share credit loudly 
→ Honest accountability earns trust
→ Celebrating others and shared wins build stronger teams

11 / Judge yourself in decades, forgive yourself in days.
→ Long-term growth takes patience, don’t be too hard on yourself
→ A hard day doesn’t define your future journey.

12 / Measure success by how others grow around you
→ Leadership is multiplied through people
→ When you help others rise and succeed? That’s real impact. 

It took me years to learn these.

You just read them in 2 minutes.

If even one of these shifts how you lead, it was worth it.

♻️ If this resonates, repost for your network.
📌 Follow Amy Gibson for more leadership insights.

My company has been building teams for years now.
And we’ve learned to spot high performers early.

(Credit to George Stern for this brilliant infographic.) 

Here's what we've noticed:

It's rarely the loudest person in the room.
It's the one who quietly takes ownership.

The one who asks for feedback, even when it's hard 
to hear.

The one who brings solutions, not just problems.

I remember watching someone on my team handle 
a crisis.

Everything was falling apart.
It was chaotic. 

And this team member was calm.

Clear. Focused. Steady.

It's not just about talent. 
It's about how you show up when it counts.

High performers often show up in similar ways:

⭐ They say what needs to be said, with honesty and care.
⭐ They stretch themselves beyond what's comfortable.
⭐ They ask for feedback, even when it's hard to hear.
⭐ They own their results without making excuses.
⭐ They keep showing up, even on the hard days.
⭐ They stay calm when everything feels chaotic.
⭐ They know when to push and when to rest.
⭐ They bring solutions, not just problems.
⭐ They give more than what's expected.
⭐ They treat failure as data, not defeat.
⭐ They chase impact, not just activity.
⭐ They lift the people around them.


And I've come to believe something about this. 

High performers aren't necessarily born with a secret gift.

They create their high performance through small, daily choices.

Choices to show up.
Choices to care.
Choices to keep going when it gets hard.

If you're reading this thinking, "That's me"?

Keep going.

Your work is being noticed.
Even if no one's said it yet.

♻️ If this resonates, repost for your network.
📌 Follow Amy Gibson for more leadership insights.

Empathy isn't soft.

It's one of the hardest leadership skills to practice. 

Because it’s not just about being kind. 
It’s about choosing curiosity when your instinct is to move on. 

When someone on your team is frustrated or overwhelmed, it’s easy to want to smooth things over quickly.

But instead of solving or softening, try starting with:
“I can see this matters to you.”

That sentence opens the door to the real issue.

The words we choose in tense moments either shut people down or open them up.

When someone's upset, they don't need us to fix it instantly.

They need to feel heard first.

Here are 12 phrase swaps that can transform how leaders communicate:

1. Instead of "calm down," try "I can see this matters to you."

2. Instead of "that doesn't make sense," try "help me understand your perspective."

3. Instead of "it's not a big deal," try "I can see why this is frustrating."

4. Instead of "stop being emotional," try "take your time. I want to hear you."

5. Instead of "I don't have time," try "this deserves my full attention."

6. Instead of "let's just move on," try "I don't want to rush past this."

7. Instead of "you're making this harder," try "what would make this easier?"

8. Instead of "I already explained this," try "let me try saying it differently."

9. Instead of "there's nothing I can do," try "let's explore our options together."

10. Instead of "why are you so upset?" try "something's bothering you. I'm here."

11. Instead of "everyone else is fine with it," try "your experience matters too."

12. Instead of "that's not what I said," try "let me clarify what I meant."

These aren't magic words.

They're tools for creating space when tension runs high.

They help leaders build trust instead of reinforcing hierarchy.

And they turn ordinary managers into the kind of leaders people actually want to follow.

What phrases have helped you navigate difficult conversations?

♻️ If this resonates, repost for your network.
📌 Follow Amy Gibson for more leadership insights.

Years ago, I walked into a meeting ready to defend a decision.

I had my points. My data. My logic.

But the person across from me didn't push back.
She just asked questions.

Not to trap me. 
Not to prove me wrong.

She was genuinely trying to understand what I was seeing.

By the end, I'd actually changed my own mind.

It was a perfect example of what emotional intelligence actually looks like in a leader.

It's rarely loud.

It's more like... awareness.

• Noticing who hasn't spoken.
• Staying curious when things get tense.
• Owning mistakes without spinning them.
• Letting someone feel heard before jumping to fix.
• Reading the room before charging into an agenda.

It's the kind of leadership people don't always name.
But they feel it.

And they remember it. 
Sometimes longer than the work itself.

I'm still learning what this looks like in my own leadership.
Some days I get it right. Some days I don't.

But I keep coming back to that meeting.

And the questions that changed more than any argument could.

It can look different for everyone. What does it look like for you?

♻️ If this resonates, repost for your network.
📌 Follow Amy Gibson for more leadership insights.

You don’t lose great people because you couldn’t 
promote them.

You lose them when they stop growing.

(And growth can look wildly different
from one season to the next.)

Or worse…

When they stop feeling seen.

I’ve promoted people who have still left.

And I’ve retained people without changing their title 
at all.

So, if someone on your team can’t move up right now,
these 8 things often help keep them around:

1. Ask What Would Make Them Stay
↳ The answer is often simpler than we assume.
↳ But only they know what they need.

2. Expand Their Influence
↳ Growth isn’t always vertical.
↳ Visibility and ownership can feel just as meaningful.

3. Recognize Their Impact Publicly
↳ A private thank you matters.
↳ Public appreciation multiplies it.

4. Offer Flexibility Where You Can
↳ Autonomy often communicates trust.
↳ Trust tends to build loyalty.

5. Include Them in Decisions
↳ Invite their thinking early.
↳ Signal that their voice carries weight.

6. Help Them Become Known
↳ Make introductions.
↳ Advocate when they’re not in the room.

7. Connect Their Work to the Bigger Picture
↳ Show how their effort moves the whole.
↳ Meaning sustains momentum.

8. Have Honest Conversations About Their Future
↳ Even when the answer is “not yet.”
↳ Clarity often retains more than vague reassurance.

In my experience, it’s rare to see high performers leave 
over one moment.

More often, it's when growth quietly stalls.

Titles help.

But so does momentum.
Voice.
Recognition.

There isn’t one right way to retain great people.

But when someone feels stretched, trusted, and seen,
they often find reasons to stay.

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Kindness is the most misunderstood leadership trait.

Most people think it means being nice. Being soft. Saying yes when you should say no.

That's not kindness. That's people-pleasing.

Real kindness takes courage.

It's telling someone the truth when a lie would be easier.

It's holding people to higher standards because you believe in what they can do.

It's having the hard conversation on Monday instead of letting someone struggle until Friday.

Kind leaders don't avoid conflict. They handle it with care.

They don't lower the bar. They help people clear it.

They don't ignore toxic behavior to "keep the peace." They protect their team... because that IS the peace.

I'm still in the early part of my leadership journey. But I've learned:

The leaders people like working for aren't the ones who let everything slide.

They're the ones who care enough to be honest.

Who give you the benefit of the doubt but also give you the feedback.

Who see you as a whole person, not just a role to be filled.

They go first. They own their mistakes. They say sorry when they're wrong.

And they never ask you to do something they wouldn't do themselves.

Kindness isn't a weakness. It's a leadership strength.

And honestly? It's the hardest kind of leadership there is.

Because it's easy to be harsh. It's easy to look away.

It takes real strength to lead with both high standards and a full heart.

That's the kind of leader I’m striving to be. Every single day.

How about you?

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Brian Wright

Criticism can hurt, even when it’s well-intended.

But emotionally intelligent leaders respond
differently, despite the sting.

They don’t ignore it.
They don’t shut down.
They don’t let it knock them off track.

Instead…

✅They pause.
✅They reflect.
✅They respond with compassion and care.

Here are 8 ways you can too:

1. Stay Calm and Listen
• Take a breath before reacting.
• Listen to understand, not to defend.
• Reflect back what you heard to show respect.

2. Take Time to Process
• Emotions need space to settle.
• Write down key points before responding.
• Ask for time to reflect before moving forward.

3. Separate Feelings from Facts
• Acknowledge the sting without making it personal.
• Ask yourself, “What part of this could help me grow?”
• View feedback as insight, not identity.

4. Ask Clarifying Questions
• Vague feedback limits learning.
• Ask for examples to deepen understanding.
• Clarify the intent before reacting to the tone.

5. Control the Urge to Justify
• Pause the instinct to explain.
• Start with empathy, not excuses.
• Make space for the other person’s perspective.

6. Respond with Gratitude
• Recognize the courage it takes to give feedback.
• Say thank you, even when it’s hard to hear.
• Let appreciation set the tone for future conversations.

7. Take Action and Follow Up
• Identify one shift you can make.
• Share how you’re applying what you’ve heard.
• Follow up to show integrity and commitment.

Criticism will never feel easy.

But when met with emotional intelligence,
it becomes a bridge to deeper trust.

After all, leadership isn’t about being right.

It’s about being willing to learn.

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Milton Barbarosh

69% of workers would leave a job because of a bad manager.
That number surprised me at first.
Then I thought about it... 

I've had both.

The boss who made me shrink.
And the leader who made me brave.

Same meetings. Same deadlines. Same pressures.

But one made me dread Mondays.
The other made me want to stay.

Self-serving bosses often:

→ Take the credit, share the blame
→ Make time off feel like a favor
→ Pretend to know everything
→ Take pushback personally
→ Ask why you failed

People-first leaders tend to:

→ Ask what got in the way
→ Want you to actually rest
→ Say "I don't know" out loud
→ Thank you for pushing back
→ Take the blame, share the credit


I’ve noticed that the self-serving boss isn't always obvious.

They can be charming. Successful. Even well-liked.
But their team feels it.

In the hesitation before speaking up.
In the relief when they're out of office.
In the quiet decision to start looking elsewhere.

And the people-first leader?

They might not be the loudest in the room.
But their team runs through walls for them.

Not because they have to.
Because they want to.

69% would leave because of a bad manager.

I wonder how many would stay forever for a great one.

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(69% Stat Source: Fortune)

Raises can reward.
Promotions can motivate.
But only empathy builds real belonging.

I’ve noticed something in the teams that work best.

People feel safe.
They speak up.
They stay.

And when I look closer, the leaders in those rooms tend 
to share a few habits. 

Nothing dramatic. 
Just small ways of being present that add up over time.

I think of them as the 7 letters of E.M.P.A.T.H.Y:

E – Engage Fully
↳ Put the phone down. Close the laptop.
↳ Let them feel heard.

M – Mirror Emotions
↳ “It sounds like you’re feeling...”
↳ This alone can shift a whole talk.

P – Pause Before Responding
↳ A breath can change your reply.
↳ It gives space for what they said to land.

A – Ask, Don’t Assume
↳ “Help me know more” beats “I think I know.”
↳ Get curious first.

T – Trust Their Perspective
↳ Their view is real to them.
↳ You don’t have to fix it to honor it.

H – Hold Space
↳ Sometimes people need a person.
↳ Not a plan.

Y – Yield the Spotlight
↳ Wait for the whole thought.
↳ Your turn will come.

Empathy takes practice.
It’s a skill, not a trait.

And honestly, some days you’ll get it right. 
Other days you won’t. That’s okay.

The point isn’t to be perfect at all seven. 

It’s to keep showing up and trying one or two when it 
matters most.

Your version of empathy might look different from mine. 

That’s the beauty of it. 
There’s no single way to make someone feel seen.

But the teams that feel it?
They give it back tenfold.

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4 Reasons EQ Beats Leadership Experience 👇
(And where it shows up every day)

Credit to Dora Vanourek for the brilliant infographic. 

You can have years of leadership experience.
Strong results.
A proven track record.

And still miss key things within your team.

Because leadership isn’t only about what you know.
It’s about what you notice.

That’s where emotional intelligence shows up.

Here’s why EQ can be more important than length of time in a role:

↳ It spots problems early, before they become costly.
↳ It notices emotional tension before it turns into conflict.
↳ It sees disengagement before performance drops.
↳ It adjusts leadership to people, not just plans.

Breaking signs are usually small.

They look like this:

↳ Emotional tension shows up in side conversations
↳ One person becomes the group’s reality check
↳ You find yourself reading between the lines
↳ Stress spreads even when results look fine
↳ Meetings drift without clear outcomes
↳ A normally vocal person goes quiet
↳ Someone stops asking questions
↳ Small frustrations start repeating
↳ Energy drops in meetings
↳ Enthusiasm feels forced

This isn’t about being nice.
Or soft.
Or avoiding hard conversations.

It’s about awareness.

EQ doesn’t replace experience.
It makes experience work.

And like any skill, it can be built:

↳ Pause before reacting
↳ Listen for what’s not being said
↳ Pay attention to how people change under pressure

Over time, people feel it.
Even if they can’t explain why.

That’s emotional intelligence at work.

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When I stepped into my first leadership role,
I knew that respect didn’t come with the title. 

The deafening silence in those early meetings confirmed it. 

I remember trying to figure out how to earn my team’s trust.

I wanted to be someone worth following. 
Someone they could genuinely see as their leader. 

I learned quickly that respect is built in small moments. 

✨ In how you listen.
✨ In how you show up.
✨ In how you treat people when things get hard.

Here are 8 things that helped me earn trust and respect 
as a new leader:

→ Be honest about what you don't know
→ Be the same person every single day
→ Listen before you give direction
→ Share credit often and freely
→ Stay calm when things get hard
→ Ask for feedback and mean it
→ Stand up for your team
→ Be patient with yourself

None of these are loud.
But people notice.

They notice when you admit a gap.
They notice when you stay steady.
They notice when you put them first.

Respect took a long time. 
And that was okay.

There were days I wondered if I was doing it right.
Days when leadership felt heavier than I imagined.

What helped was showing up anyway.
Being patient with my team.
And being patient with myself.

The trust and respect did come.
I can promise you, yours will too.

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Building wealth can feel like a mystery.
But the habits behind it are often surprisingly simple.

There’s so much advice out there.

So many voices. So many strategies.

And if you’re anything like me when I was first learning about this,
it can all feel a bit overwhelming.

But the habits that have truly helped me?

They’re quiet. 
And boring.

Here are the 7 that have allowed me to feel financially secure: 

1. Pay Yourself First
→ Even saving 10% can make a difference over time.
→ Move the % to savings/investments as soon as your salary is paid. 

2. Automate Everything
→ Auto-transfers on payday take the thinking out of it.
→ Bills, savings, investments. All in one go.

3. Live Below Your Means
→ Tracking spending for a month can be eye-opening.
→ Not to judge, just to notice.

4. Know Your Numbers
→ Net worth. Monthly spending. Emergency buffer.
→ Even a rough idea helps.

5. Invest Early and Boring
→ A simple index fund can do a lot of the heavy lifting.
→ Adding a little each month will compound over years. 

6. Avoid Debt That Doesn’t Build Wealth
→ Some debt opens doors. Some just adds weight.
→ Worth asking which is which before signing.

7. Think in Decades, Not Days
→ Markets go up and down. That’s normal.
→ Staying in tends to matter more than timing it right.

Wealth isn’t really about money.

Don't get me wrong, money matters. 

But it’s about buying back your time.
Your choices. Your peace of mind.

And that’s available to more of us than we think.

♻️ If this resonates, repost for your network.
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Experts solve problems.
Great leadership is making space for experts 
to solve problems.

But leading people who know more than you can 
challenge even the most experienced leaders.

Here's what I've seen in those who do it well:

1️⃣ Say "I Don't Know" Out Loud
→ This isn't weakness, it's permission
→ When you're honest, others feel safe to be too

2️⃣ Ask More Than You Tell
→ Newcomers notice what veterans overlook
→ The right question can open doors expertise keeps closed

3️⃣ Trust the People Closest to the Work
→ They're living in the details every day
→ Your role is supporting your people 

4️⃣ Use Your Distance as an Advantage
→ While they navigate the trees, you can see the forest
→ Perspective is its own kind of expertise

5️⃣ Lead the Process, Not the Details
→ Momentum matters more than mastery
→ Keep things moving in the right direction

6️⃣ Be the Buffer
→ Shield your team from the noise they don't need
→ Politics, endless meetings... Absorb what you can

7️⃣ Stay Curious, Not Defensive
→ Someone disagreeing with you is a gift
→ Let the strongest idea win, even when it isn't yours

Leadership isn't about being the smartest in the room.

It's about building rooms where the smartest ideas can win.

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Stephen Peele Sr.

The best teams don’t run on talent alone.
They run on trust.

⚡ Trust that your teammate will follow through.
⚡ Trust that a meeting won’t drain your energy.
⚡ Trust that feedback won’t become a battlefield.

Being someone others want to work with isn't about being liked.

It’s about being reliable, respectful, and real.

5 behaviors that make you the colleague everyone wants on their team:

1/ Respond Like You Care
↳ Acknowledge emails within 24 hours
↳ Even if it’s just “Got it, will review by Friday”
↳ People need to know you’re there

2/ Prepare Before You Show Up
↳ Read the pre-read
↳ Come with questions, not confusion
↳ Respect everyone’s time by being ready

3/ Disagree Without Being Disagreeable
↳ Challenge ideas, not people
↳ Say “I see it differently” not “You’re wrong”
↳ Stay curious about other perspectives

4/ Share Information Freely
↳ CC people who need context
↳ Document your processes
↳ Your knowledge isn’t power if it blocks progress

5/ Clean Up Your Own Mess
↳ Own mistakes quickly
↳ Fix what you broke
↳ Learn without making excuses

The colleague everyone wants to work with?

They make hard work feel easier.
Not because they do it all.
But because they show up ready to do their part.

They turn tension into solutions.
They make Monday mornings feel possible.

And they remind us why we chose this work in the first place.

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Many leaders get empathy completely wrong.

And it costs them their best people.

Credit to Justin Wright for this brilliant infographic.

I used to think empathy meant feeling sorry for someone going through a tough time.

Say something nice. Move on.

But that's not empathy. That's sympathy.

And there's a huge difference.

Real empathy goes so much deeper.

It's listening without rushing to fix things.

It's imagining yourself in their situation before you respond.

It's respecting how someone feels without trying to change their mind.

It's showing up with genuine concern, not just a quick "let me know if you need anything."

Empathy builds trust.

When someone on your team is struggling and you just listen.

When you hold back judgment and sit with them in the discomfort.

When you ask "How are you really doing?" and actually wait for the answer.

Those moments change everything.

Because people don't leave companies where they feel seen.

They don't quit on leaders who make them feel heard.

Empathy isn't a soft skill.

It's the hardest skill to master and the most important one you'll ever develop.

It won't show up on a quarterly report.

But it will show up in your retention, your culture, and the loyalty of the people around you.

The best leaders I've ever worked with didn't have all the answers.

They just made you feel like you mattered.

That's empathy.

And it changes everything.

What's one small way you practice empathy with your team?

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