Create Your Own Leadership Path: A Conversation with Kaitlin Liston

I had the pleasure of speaking with Kaitlin Liston for the Kim Coaching Group Interview Series, and I’m so excited to share her story and insights.

Kaitlin is a demand generation manager at RingCentral who has built an impressive and intentional career in tech marketing. She started at a small startup while still in college, held almost every type of marketing role you can imagine, and along the way co-founded a nonprofit and helped more than 100 students with their college applications. But what stands out most is how she consistently created leadership opportunities for herself and brought others along with her.

Here are some of the key takeaways from our conversation, in Kaitlin’s own words, with reflections and examples you can use right away.

Rethink What Leadership Means

“Being a leader is more leading by example… All of the best leaders that I’ve worked under have enabled us to be our best selves. It’s more of a collaboration, allowing for an environment where everyone feels like they have the abilities to do their best.”

Kaitlin grew up playing sports and described how the best team captains were the ones who led by how they showed up, not by barking orders. That same approach shaped her view of leadership at work. She’s not waiting to be given authority, she shows up with it.

We talked about how people often tune out during all-hands meetings or skip team calls because they feel too busy. But leadership means showing up anyway, asking questions, and treating those meetings like they matter, because they do. That’s where you get context, build trust, and show you care about more than just your own tasks.

Decide What Kind of Leader You Want to Be

“I love this quote that you are the sum of the five people closest to you. I started thinking about the kind of people I wanted around me and the kind of leader I wanted to be to them.”

Kaitlin discovered her leadership style by observing others. Some made people feel empowered. Some didn’t. That helped her reflect on what kind of leader she didn’t want to be and she built her own version from there.

You don’t have to pick from the leadership styles already out there. You get to define your own. Kaitlin leads by building trust, giving credit, and making people feel like they belong. That’s what people remember and follow.

Ask yourself: who are the people you admire most in your life and work? What do they do that makes you feel seen and supported? Start modeling those behaviors.

Build a Real Network, Not Just a List of Contacts

“Your network is your net worth.”

Kaitlin believes in building meaningful relationships that go beyond LinkedIn connections. When she joins a new company, she asks her manager to introduce her to 10 people across the org. She reaches out to new hires. She gets curious about what people do and who they are.

We talked about how real networking isn’t about keeping score, it’s about being generous. When you offer help without expecting anything back, you build reputation and trust. And over time, those people remember what you’re great at and want to work with you again.

If you’re wondering how to start, Kaitlin’s advice is simple: send a message that shows genuine interest. Tell someone what you admire about their work, ask one thoughtful question, and offer something specific you can help with.

Create the Opportunities You Want to See

“I didn’t wait for a promotion. I started leading book clubs, organizing events, and building community.”

At RingCentral, Kaitlin helped launch WISE, the Women in SaaS Empowerment group. She began by volunteering to run small programs like book clubs and lunch-and-learns. Eventually, she became the event chair, helping others grow their skills and confidence too.

Outside of work, she co-founded a nonprofit during the pandemic and continues to support students through college counseling. All of this started with small decisions to raise her hand.

We talked about how creating leadership opportunities doesn’t have to be big. You can volunteer to lead a 30-minute discussion. You can offer to review someone’s document. You can step in on something that fits your time and energy, and still have an impact.

Leadership grows with every action. Start where you are.

Think Like a Leader Before Anyone Calls You One

“When something doesn’t feel right, I don’t just let it go, I try to be part of the solution.”

Kaitlin once noticed something in the marketing org that didn’t sit right with her. She was a manager at the time, and it wasn’t her responsibility to weigh in on org-wide strategy, but she cared deeply about where the team was headed. So she sent a thoughtful Slack message to her VP, sharing her perspective.

Leadership often starts like this, not with a formal role, but with a mindset. Leaders treat everything like it’s their problem. When you care enough to speak up, offer ideas, or take initiative, even when it’s not in your job description, you’re already leading.

What’s something that’s been bothering you at work? Instead of venting about it, what would it look like to take action? You don’t have to fix everything. But you can start the conversation.

What’s One Thing You’ll Try?

Kaitlin’s story is full of small, intentional actions that added up to real leadership. She didn’t wait to be chosen. She chose herself.

What’s one thing from her story that you’ll try this month?

Pick something simple. Reach out to someone new. Offer to help. Show up differently.

And if you’re ready to take your leadership to the next level, check out the Women Leaders Club. We go deep into topics like these and support each other through every stretch and leap.

When Everything Feels Like Too Much: A Gentle Way to Shrink the Fear

I hear from so many people lately that they’re feeling heightened anxiety and stress. They can’t sleep. They wake in the middle of the night worrying. They can’t relax. They stay relentlessly busy, trying anything to avoid the discomfort.

And it makes sense—look at what’s happening around us.

Mass layoffs. A brutally tough job market. DEI departments being dismantled. Federal employees let go without warning. Uncertainty is everywhere.

For high-achieving professionals who’ve worked so hard to build meaningful careers, it can feel especially disorienting.

When the world feels shaky, fear starts to grow louder.

What if I lose my job? What if everything I’ve worked for over the last 10 years was for nothing?

Black Dog

This reminds me of a beautifully illustrated children’s book called Black Dog by Levi Pinfold.

In the story, a family wakes one morning to find a terrifyingly large black dog outside their home. Each family member sees it and becomes more afraid than the last. They hide. They panic. And every time someone looks again, the dog seems even bigger.

But the youngest member of the family—Small Hope—does something different.

She walks outside. She meets the dog. She leads it through tight spaces and playful paths. And with each step, the dog gets smaller. By the time they return home, the massive creature is no longer frightening. It’s just a dog.

It’s a powerful metaphor. Fear grows when we avoid it. It shrinks when we face it.

But here’s the real question: How do we face the fear in our own lives?

Here’s a powerful exercise you can try on your own, especially when you feel overwhelmed:

“If That Happens, Then What?” Exercise

When you feel fear rising, 

1. Name it. Write it down.
2. Then ask: If that happens, then what?
3. Write the answer.
4. And ask again: Then what?
5. Repeat at least five times.

Example:

• I’m scared I won’t get a job I like soon.
• If that happens, then what?
• I might have to take a lower-paying job.
• Then what?
• I might not be able to cover all my expenses.
• Then what?
• I’d have to cut back, ask for help, or use savings.
• Then what?

Most people find that after this exercise, their fear shrinks. Sometimes it even disappears. Try it the next time things feel too big to handle.

At Women Leaders Club, we create space for high-achieving women to do exactly this: To shrink fear. To find clarity. To reconnect with what they truly want and go after it. If this resonates with you, I invite you to join us.

Outreach Tips for Building New Connections

Networking is more important than ever when it comes to creating opportunities. But reaching out to someone you don’t know can feel intimidating.

The key question to ask yourself is: Why would this person make time for me?

If your request feels too big or unclear, it can create discomfort. If they don’t know what you want to talk about, they may hesitate to respond. Make your request clear and specific so they can easily imagine what the conversation will be about. When people know what to expect, they’re much more likely to say yes.

• Keep it short—ask for 20 minutes. It’s long enough to have a meaningful conversation but short enough to feel like a small ask. And if things go well, it can naturally extend to 30 minutes, as most meetings start on the hour or half-hour.
• Make it easy to say yes. Most professionals are happy to help, but asking for a referral, resume review, or introduction right away can feel like too much. Instead, start by asking for insights and advice—this makes the conversation feel lighter and more enjoyable.
• Be upfront about your topic. If you say you want to talk about their career journey, stick to it—don’t surprise them with a request for a job. However, if the conversation naturally flows into that, great!

Think of this as opening a relationship, not just a one-time conversation. The most important thing is leaving a strong impression—that you’re smart, capable, and great to work with. That way, when opportunities come up in the future, they’ll think of you.

Here Are Some Ways You Can Request a Chat

Now that you know how to approach these conversations, here are six ways to phrase your request depending on the situation. Try the approach that feels right for you, and test it out. If you’re reaching out to multiple people, track what works best across industries, functions, and company sizes—you might notice interesting patterns!

1️⃣ Interest in Their Role/Experience

👉 “I’m interested in a role similar to yours at [Company] and would love to hear about your experience. What do you enjoy most, and what challenges have you faced? I have a few questions and would appreciate your insights. Would you be open to a 20-minute chat?”

2️⃣ Reference Their Work or Thought Leadership

👉 “I read your work on [topic] and found it really insightful. I have a few questions about your approach and some ideas I’d love to get your thoughts on. Would you be open to a 20-minute chat?”

3️⃣ Mutual Connection or Common Interest

👉 “I was speaking with [mutual connection], and they mentioned you’d be a great person to learn from about [topic]. I’d love to hear how you approached [specific challenge or transition] and ask a few quick questions. Would you be open to a 20-minute chat?”

4️⃣ Specific Career Transition or Advice

👉 “I’m transitioning into [industry/role] and noticed you made a similar move from [previous role] to [current role]. I’d love to hear what helped you the most during that transition and ask a few questions. Would you be open to a 20-minute chat?”

5️⃣ Company or Team-Specific Interest

👉 “I’ve heard great things about [Company], especially [specific aspect—e.g., its reputation, culture, or innovation in X]. I’d love to learn more about what it’s like to work there and how your team approaches [relevant topic]. Would you be open to a 20-minute chat?”

6️⃣ Direct & Concise Approach

👉 “I admire your work in [industry/field] and would love to learn from your experience. Specifically, I’d love to ask about [topic, e.g., how you navigated leadership growth in tech]. Would you be open to a 20-minute chat?”

Build Relationships That Open Doors

Networking isn’t just about one conversation—it’s about building long-term relationships. Every great career opportunity starts with a connection, and the more conversations you have, the more doors you open.

If you need help crafting the right message or navigating networking conversations, feel free to reach out—I’d be happy to help! 

Navigating Career Challenges: Lessons from Jackie Santayana’s Journey

Ever feel like you’re doing everything right, but the job search—or career growth—still isn’t working out?

Jackie Santayana knows that feeling well. She graduated during a financial crisis, faced multiple rejections, and had to take roles that weren’t quite what she envisioned. But instead of getting stuck in frustration, she focused on what she could do—one step at a time.

I had the chance to sit down with Jackie to talk about her journey—how she navigated uncertainty, built resilience, and ultimately grew into a leadership role in tech. If you’ve ever wondered “Should I just settle for this job?” or “How do I actually get to the role I want?”—you’ll want to hear her story.

📺 Watch the full interview here.

Every Job Has Something to Offer—Even If It’s Not “The One”

Jackie’s first few jobs weren’t ideal. She worked as a cashier and in a nonprofit before transitioning into tech. At first, it felt frustrating—like she was falling behind while others were moving forward.

But instead of dismissing those experiences, she asked, “What skills can I take from this?” She learned to manage different stakeholders, handle unexpected challenges, and communicate effectively—all of which later helped her stand out when applying for leadership roles.

I see this all the time with my coaching clients—women who feel like their experience “doesn’t count” because it doesn’t follow a perfect, linear career path. But leadership isn’t about checking off the right boxes. It’s about how you use what you’ve learned to create impact.

The Power of Conversations (Not Just Resumes)

One of Jackie’s biggest turning points came from talking to people who were just a few years ahead of her. She reached out, listened to their experiences, and gained valuable insights on what actually helps in a job search.

She wasn’t just trying to network in the traditional sense—she was building relationships and learning from others’ journeys.

If you’ve ever felt like networking events are a waste of time, here’s something to consider: Instead of trying to “sell” yourself or ask for a job, start with curiosity. Who’s doing work that interests you? What did their path look like? What advice would they give? You never know what doors might open from a genuine conversation.

Mindset Matters More Than You Think

At one point, Jackie was applying for jobs and not getting the results she wanted. She started to wonder, “Am I just not good enough?”

But then she flipped the script. Instead of seeing every rejection as proof she wasn’t qualified, she saw them as data points:

• Where am I getting stuck?

• What patterns am I noticing in feedback?

• What adjustments can I make next time?

This shift made a huge difference—not just in her job search, but in how she showed up in interviews. She stopped trying to prove herself and started owning her value.

I see this transformation happen with my clients all the time. The moment they shift from “Am I good enough?” to “Here’s what I bring to the table,” everything changes—how they speak, how they carry themselves, and ultimately, how others see them.

Taking Action—Even When It’s Not Perfect

One thing that stood out in Jackie’s story is that she didn’t wait until she felt “100% ready” to take the next step. She applied before she felt fully qualified. She reached out before she knew exactly what to say. She tried different things to see what worked.

Too many talented women hold themselves back, waiting until they feel completely prepared before they take action. But clarity comes from doing, not just thinking.

If you’re feeling stuck in your job search or career, ask yourself: What’s one step I can take today—even if it’s small?

Final Thoughts

Jackie’s journey is a powerful reminder that career success isn’t about luck—it’s about taking intentional steps, learning from every experience, and staying open to opportunities in unexpected places.

If her story resonates with you, I’d love to hear—what’s your biggest takeaway? And if you’re feeling stuck and want support in navigating your own career transition, let’s chat. Sometimes, the shift that changes everything is closer than you think.

📺 Watch the full interview here.