The Hardest Lessons in Leadership (And Why They Matter More Than Ever)

Hey ,

This week hit hard.

Krystal’s dad passed away unexpectedly. One of those gut-punch moments that puts everything in perspective. It’s been a whirlwind of flights, family, grief, and trying to be present while still holding space for the things we’re building. One minute she was with Zachary at a CT scan, the next she got the call every child fears. Gone. No warning, no time to prepare. Just a punch to the chest that knocks the wind out of you.

Everything else took a backseat. As it should. We flew to Chicago that same day to be with family. And in moments like this, you see clearly: what matters, who shows up, and how you lead when life blindsides you. That’s what this week’s newsletter is about. Not AI. Not outbound. Not playbooks. Leadership. Real leadership.

And despite the heaviness, we’re still building. Our AI agents are coming to life. Event planning is in motion. But this edition is personal. Because some things are just bigger than business.

Oh yeah, and I finally “made it.” I was the “Guest of the Day” at the Fairfield Inn in Pleasant Prairie, Wisconsin.

Estimated reading time is 4.5 minutes. Feel free to hit reply and share your takeaways or questions.

On Deck:

• Leadership Isn’t Easy: A Guide to Being a Good Leader

• Marketing Tip of the Week - Powered by Decoded Strategies

• Episode #99 - The Hottest Takes Guests Have Had Over the Years on A.I., GTM, and More

The Hard Truth About Good Leadership

Leadership isn’t title-deep.

It’s not charisma. It’s not confidence. And it’s definitely not about cloning yourself and expecting everyone to operate the same way you do.

Real leadership is rare.

And we’re seeing more and more companies suffer because the people at the top are mistaking control for clarity, and busyness for effectiveness.

Here’s the truth. You don’t need more people doing what you would do. You need leaders who bring out the best in others, people who know how to recognize strengths that don’t look like their own.

The best leaders aren’t the smartest in the room.

They’re the ones who make the room smarter.

But here’s what I’ve seen go wrong, especially in early and growth-stage startups:

• Founders promote someone who reminds them of themselves.

• That person rewards others who mirror their strengths.

Suddenly, the company is filled with clones… same thinking, same skills, same blind spots.

And what happens?

• Innovation dies.

• Diversity of thought shrinks.

• Burnout rises because everyone’s trying to be someone they’re not.

Good Leaders Do This Differently

If you’re a CEO or founder reading this, here’s your wake-up call:

Leadership is not replication, it’s amplification.

The best leaders do three things exceptionally well:

1. They treat humans like humans, even when it’s inconvenient.

Last week, I shared something deeply personal on LinkedIn. Krystal was with Zachary at a CT scan when she got the call we all fear most: her dad had suffered a massive heart attack. The paramedics tried everything. He didn’t make it.

I was in the middle of a webinar on AI when I got the news. I wrapped up the session, booked the flights, cleared my calendar, and ensured my wife had nothing to worry about but being with family.

Her leader? Told her to take as long as she needed.

Me? I work for myself, but I have two amazing partners who said, “We’ve got it. Go.”

But two of her siblings weren’t as lucky:

• One got just three days off, including the day they found out, only with a death certificate.

• One couldn’t take time off at all—because “no one could cover for her.”

Three days to grieve your dad.

Zero days because you had customers.

If that doesn’t make your blood boil, read it again. Leaders, this is where culture is built or broken. You either protect your people or you protect your policies.

Which one do you think builds loyalty? Which one do you think builds long-term performance?

2. They multiply, not manage.

A good leader doesn’t just get the job done. They make everyone around them better. That looks like:

• Giving stretch opportunities to people who aren’t the obvious choice

• Investing in coaching, not just KPIs

• Holding people accountable and helping them grow

One of the first-time VPs we worked with last year learned this the hard way.

At first, she tried to brute-force her way to results… overcommitting, ignoring process, and flying blind on data.

Board meetings were a mess. The founder lost confidence. She lost her job.

When we debriefed later, she said, “I wish someone had taught me what it actually meant to lead.”

Now she’s thriving because she learned to lead by building others, not just delivering for herself.

3. They recognize the invisible work.

Here’s something most execs forget: Not all impact is measurable in a spreadsheet.

• The team member who quietly defuses tension after a brutal standup

• The manager who checks in when someone’s off their game

• The AE who mentors the new hire without being asked

These moments build trust, resilience, and performance. Ignore them, and you’ll miss your next generation of leaders.

Pro tip:

In your next 1:1, ask your leaders:

“What’s something you’ve done recently that no one saw but made a difference?”

If they can’t answer, they’re not looking hard enough.

And if you don’t care enough to ask, they’ll stop doing it.

Real Leadership in Action

Great leaders:

• Build systems that outlast them

• Embrace discomfort to unlock better thinking

• Protect their team’s humanity, not just their output

• Invest in different, not just “more” of the same

• Own their mistakes, and make it safe for others to do the same

If you’re not doing these things, you’re not leading. You’re just running fast and hoping no one catches on.

Want Better Leaders? Start With You.

If your team isn’t stepping up, ask yourself:

• Have I modeled the behavior I expect?

• Have I created space for leadership to emerge, or just handed out titles?

• Have I rewarded performance and growth?

If the answer is no, the good news is you can change that. You don’t need perfect leaders. You need intentional ones. So give them the tools. Give them the grace. And for the love o fall things, give them more than three days when life hits hard. Want to check out our free guide on how to become a LEADER versus a MANAGER? Drop me a reply and I will shoot it over to you.

Thanks ZoomInfo for Keeping This Newsletter Free!

ZoomInfo is the Go-To-Market intelligence platform that empowers businesses to grow faster with AI-ready insights, trusted data, and advanced automation. Our solutions provide a complete view of your customers, making every seller your best seller.

Marketing Tip of the Week - Powered by Decoded Strategies

This week's tip is all about nailing your founder-led thought leadership strategy, not just throwing things at the wall to see what sticks.

Nailing your Founder-Led Thought Leadership Strategy is an incredibly powerful way to amplify your brand marketing. But when it comes to marketing and communications, founders tend to swing to either end of this spectrum: 

• They make everything about them. The brand rests on their shoulders alone. Their voice is the only one we hear from the brand.

• They invisibilize themselves. They stand back because they aren't sure of the place their voice has in the market.

Neither of these extremes is great, but both are solvable. A founder's voice must be out there, loud and clear, but your approach and what you say matter. It's all about the right positioning.

The key is Founder-Led Thought Leadership. With intention and focus.

Founders need to:

→ Identify 3-4 of their core beliefs, unique perspectives, or areas of expertise

→ Create valuable thought leadership content that anchors on these pillars

→ Anchor your thought leadership content in the problem it solves for your customers and communicate empathy throughout

Episode #99: The Hottest Takes Guests Have Had Over the Years on A.I., GTM, and More...

We’ve had a lot of great episodes, but this one might just take the crown for the most brutally honest. We pulled together some of the spiciest takes from past guests. No fluff, no filters on what’s actually happening in GTM, AI, and leadership.

You’ll hear real talk on:

• Why AI won’t kill jobs, but it will kill average

• The death of the SDR role (and whether that’s a good thing)

• Fractional leadership economics that make full-time hires look insane

• Why gifting works when it’s thoughtful, not timed

• And why most sales teams are still training on frameworks that should’ve been buried years ago

One of my favorite clips? A CRO explaining why firing 40% of his team was the hardest thing he’s ever done, and why he’d never make that mistake again.

If you care about building teams, staying ahead of the curve, or just want to hear people say the quiet part out loud… this one’s for you.

Agree? Disagree? Have Questions?

We love engaging with our community—reply to this email with your thoughts, and let’s chat!

Talk soon,

Adam, Dale, & Jake
Helping companies bridge the GTM Gap™.