Before we begin, I have an exciting announcement!
AI is reshaping your industry. Economic uncertainty is testing your leadership.
If you’re feeling stuck in old patterns, leading in ways that no longer work, and needing space to rethink how you show up—I created something for you:
The Reinvention Lab is a high-impact group coaching experience designed to help you break outdated leadership habits, lead decisively under pressure, and turn uncertainty into opportunity—alongside peers who get it.
Over three months, you’ll build resilience, challenge your thinking, and turn AI-driven disruption into your advantage.
The first cohort starts in May—exclusively for CMOs and VPs of Marketing.
If this sounds interesting, reply to this email or message me in the comments and I’ll send you the details.
Disruption is here. Reinvention starts now.
There’s a myth in leadership that’s far too persistent: that you have to choose between being kind and being effective. That if you want to be taken seriously, you can’t show too much care. That high expectations and empathy are at odds.
Amanda Malko, Chief Revenue & Marketing Officer at Thinkific, is living proof that this thinking is outdated—and ultimately, harmful. In our conversation on On Influence & Impact, she offered a refreshing and deeply honest perspective on how to lead with both compassion and conviction.
As a three-time CMO (scroll for full bio), Amanda has learned how to drive results without compromising her humanity—and she’s helping others do the same.
I encourage you to watch or listen to the full episode but here are some of the most powerful lessons and quotes from our conversation.
Let’s dive in.
“Kindness and performance are not mutually exclusive. They’re connected.”
In the early day of her career, Amanda wrestled with the tension between being “the nice one” and being “the tough one.” She’s had moments where mentors told her she was too nice. And in reflecting on those experiences, she realized something many leaders overlook: kindness and ambition are not in conflict—they’re a power duo.
“Empathy and ambition go very well together,” Amanda shared. “It’s not just that they can coexist. It’s that they actually make each other stronger.”
But that doesn’t mean it’s easy. In fact, she says it’s one of the hardest leadership practices to master. It’s not twice as hard—it’s infinitely harder to hold both care and clarity, empathy and execution. But the leaders who do? They’re the ones creating real impact.
Why the Old Narrative Persists
So why does this false dichotomy continue to show up?
Amanda pointed to two key reasons: fear and laziness.
“I think some people are afraid it can’t be done. Others just aren’t convinced the extra effort is worth it.”
But she’s clear: the extra effort is worth it. When leaders show up with both care and high standards, it unlocks deeper trust, stronger alignment, and more sustainable performance.
Redefining What Kindness Actually Means
Kindness, Amanda explains, has gotten a bad rap. Too often, it’s equated with being a pushover or avoiding hard truths. But real kindness is something else entirely.
“Kindness means understanding the person first—what their strengths, gaps, and interests are—and aligning that with what the business needs. It’s not about over-indexing on comfort. It’s about being human and honest.”
And that includes making hard decisions. Letting someone go when they’re not meeting the bar isn’t unkind—it’s actually a form of compassion.
The Hardest Moments Require the Most Humanity
Amanda didn’t just share philosophies—she shared stories.
One moment that stuck with me was when she talked about how she approaches performance exits. She recounted helping a fellow leader through a tough decision to let someone go, reminding them that feeling sadness and making the right business decision can both be true at the same time.
“The trick is to feel the feelings and also lead with conviction. You can be sad and also make the right call.”
This duality is what makes leadership human. And Amanda’s willingness to embrace it is what makes her leadership not only effective—but deeply respected.
When the Bar Gets Lowered, Everyone Feels It
Amanda also shared an experience from a high-performing organization she helped scale, where expectations were crystal clear—and consistently upheld.
“We never lowered the bar. And because of that, we built the highest performing team I’ve ever worked with.”
Now, when she advises companies, she can spot it immediately: when the bar has quietly dropped. And climbing back up that hill? It’s always harder.
“Letting the bar slip doesn’t just impact performance. It’s actually unfair to the high performers who want to be surrounded by excellence.”
If You’re Struggling to Be Clear, That’s the First Problem
One of the most practical pieces of advice Amanda offered was around clarity. Leaders who struggle with performance conversations often haven’t actually defined what success looks like.
“If you haven’t been clear about the bar, the rest of the conversation is going to be 10 times harder.”
Before tough conversations, Amanda writes down what she wants the outcome to be—and how she wants to show up. It’s a simple but powerful practice, especially when paired with another one she recommends: role-playing with a trusted peer, coach, or mentor.
Your Voice Comes From the Hard Places
We ended our conversation by talking about voice—how Amanda found hers, and how others can find theirs, too.
She didn’t sugarcoat it: her confidence and clarity came through discomfort. Taking on roles that stretched her, pushing through self-doubt, and learning from past missteps.
“Be ambitious in your tolerance for discomfort,” she said. “That’s where the growth is.”
Amanda’s Three Takeaways for Leading with Kindness and Driving Results
1. Know your why
Be clear on what success looks like for the business and how you want to show up as a leader. Clarity of purpose is your compass.
2. Prepare for hard conversations
Write out what you want to say, how you want to feel, and what you want the other person to take away. Don’t wing it.
3. Reflect and revise
If there are conversations you wish you’d handled differently, learn from them. Decide how you want to lead the next time.
If you’re a leader who’s been told you’re too soft—or one who’s been too tough for too long—this conversation is for you. You don’t have to choose between being kind and being effective.
As Amanda Malko shows us, the most influential leaders are the ones who choose both.
— Amanda
In case you missed it
Uber Head of Customer Operations Mariano Fiscella on Trust
Mariano Fiscella shares his wisdom on trust—how to earn it, regain it, and leverage it across functions, geographies, and cultures.
Lattice CEO Sarah Franklin on Courageous Leadership
Sarah Franklin shares her experience on breaking the mold and moving beyond traditional leadership styles.
Glassdoor CEO Christian Sutherland-Wong: From Achievement To Connection, Vulnerability, Trust, & Community
Christian Sutherland-Wong highlights his leadership journey, shifts in perspective, and the key to building high-performing teams.
Interested in exploring my executive coaching practice?
I work with Founders & C-Suite executives on three key levels:
Strategic: I help you gain clarity, decisiveness, and new pathways of thinking to address the strategic challenges of the business.
Leadership: I enable you to evolve and scale your leadership capabilities in line with what the business needs.
Inner Work: I guide you through the inner work that allows you to truly thrive as a human being.
I offer a complimentary discovery session to assess fit. I’d love to hear from you.
Chapters
00:00 Introduction and Guest Welcome
00:30 Debunking Leadership Myths: Kindness and Results
01:10 Balancing Empathy and Ambition
02:31 Gender Dynamics in Leadership
04:55 Personal Leadership Journey
10:19 The Importance of Empathy in Leadership
19:37 Clarity and High Performance
25:03 Advice for Aspiring Leaders
27:19 Conclusion and Final Thoughts
Amanda Malko
Amanda is a go-to-market leader who thrives on leading cross-functional teams to grow revenue and improve the customer experience.
She’s a three-time CMO with experience growing software and marketplace companies between $30M-$1B. With nearly two decades of experience leading marketing for B2B SaaS businesses, she was most recently G2’s CMO (and is still an Advisor). She led the partner program at Mailchimp (acquired by Intuit), and also helped build 360i, one of top digital agencies in the world as named by AdAge and Forbes. She has contributed to the acquisitions of 4 companies (by Microsoft, Dentsu, & Intuit respectively) with a combined value in the $ billions.
Along the way, she’s seen what it takes to scale from $20M to upwards of $1B, how to build an exceptional brand, how to lead marketing teams at different sizes/stages, and more.
Share this post