Rising Team CCO Jami Zakem on the Power of Questions

There’s one leadership skill that might be more powerful than any other: the ability to ask better questions.

In this episode of On Influence & Impact, I sat down with my brilliant friend and longtime leadership partner, Jami Zakem, to explore a wide range of leadership topics—and how asking thoughtful, well-timed questions is at the center of it all.

Over her 25+ year career—leading high-performing teams at Yelp, Eventbrite, and now as Chief Customer Officer at Rising Team—Jami has developed a rare ability to blend deep care and drive results. We trace her evolution as a leader, how growth often happens in steps, why the basics still matter, and how to lead senior talent.

Our conversation is full of stories, practical wisdom, and insights you can apply now.

I encourage you to watch or listen to the full episode—but I’ve pulled out some of the most valuable takeaways and quotes from our conversation below.

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But first—a quick announcement.

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If you’re a Marketing Leader, I hope you’ll apply.

AI is reshaping everything. Economic uncertainty is testing even the strongest leaders. And the pressure to keep up is relentless.

Reinvention Lab is a high-impact group coaching experience designed to help you break old patterns, lead more decisively under pressure, and turn uncertainty into opportunity—alongside a community of peers who get it. If you’re ready, now is the time to apply.

Okay—let’s dive in.

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Mindset, Skillset, Toolset

Jami brought up these success factors as she’s reading The Only Sales Guide You’ll Ever Need by Anthony Iannarino—and applied them to her own evolution as a leader.

• Mindset is your internal orientation—your beliefs, values and desires about leadership.

• Skillset is your ability—how well you lead people.

• Toolset is your system—repeatable frameworks and templates that make your skills scale.

“I had the mindset early on—I cared deeply about people. But I needed to build the skillset and the toolset to match.”

What I appreciate about this perspective is how it maps the arc of leadership growth.

We often start with a belief (I can lead) and a desire (I want to help others thrive). Then comes the work of building the skills—and eventually we create the systems that turn intentions into impact.

But here’s the key insight: the inner game powers it all.

If your mindset is off, the best tools and systems can miss the mark.

But if your mindset is strong—growth-oriented, curious, resilient, open—you can amplify everything else.

It’s a reminder to not just focus on what you do, but continually tend to how you think.

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Growth Happens in Steps

Jami described her leadership journey as a upward staircase—full of learning curves, inflection points, and the humility to say, “I haven’t done this before.”

“You’re pulling yourself up to the edge again and again.”

The image Jami paints is a well-known framework: The Five Stages of Learning.

When applied to leadership, it helps normalize the discomfort of growth and gives language to the journey many of us are on.

Here’s how the stages work—explained through a leadership lens:

1. Unconscious Incompetence

You don’t know what you don’t know.

You’re unaware of gaps in your leadership because they haven’t surfaced yet.

2. Conscious Incompetence

You realize you lack a skill—and it stings.

You’ve hit a growth edge and know it’s time to evolve, but you don’t yet know how.

3. Conscious Competence

You’re building the skill, but it still takes effort.

You’re practicing new behaviors—like shifting from reactivity and control to empowering your team with autonomy and trust—and starting to feel more capable.

4. Unconscious Competence

You’ve internalized the skill.

It becomes second nature—you can delegate and inspire ownership and accountability with ease.

5. Conscious Unconscious Competence

You’ve mastered the skill and can teach others.

You understand what works, why it works, and how to help others do it, too.

The real power is in knowing where you are on it.

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Jami’s 5 Questions for New Direct Reports

When onboarding someone new, Jami always starts with the same five questions—simple, open-ended prompts that surface meaningful context and lay the foundation for a strong working relationship.

They’re deceptively powerful. Not only do they build trust, they help leaders manage with more precision, empathy, and awareness.

Here they are:

1. Tell me your story.

Not just your resume—who are you? Where are you from? What shaped you?

“I want to hear it all—whatever they’re comfortable sharing. That’s usually where I get the really rich, unexpected details.”

2. What are your goals?

Personally or professionally, short-term or long-term. The better you understand their aspirations, the more you can support them.

3. How do you like to be managed?

This question surprises people—but it opens up a vital dialogue early about communication preferences and expectations.

“Some people thrive with autonomy. Others want daily touchpoints. Just talking about it creates clarity.”

4. What motivates you?

This changes over time. Ask again and again.

“When I was 24, it was praise—all the praise. Now it’s about impact, growth, and flexibility.”

5. What else should I know?

This is the magic question. It often unlocks the deepest insights.

“It’s the third, fourth, or fifth thing they say that reveals the truth. That’s why ‘What else?’ is my favorite coaching question ever.”

Come back to these questions often. People’s lives and needs change.

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Leading Senior Leaders

As you grow as a leader, so does the complexity of who you lead.

Managing senior talent—especially those with deep expertise or strong points of view—requires a shift in mindset and strategy.

Jami offered thoughtful, grounded guidance on how to navigate this transition with confidence and care:

1. Remember: They’re making it up, too.

Even the most seasoned executives are facing new challenges, learning in real time, and adapting as they go. If you find yourself feeling insecure or wondering, How do I add value here?—remember that leadership isn’t about knowing more than your team. It’s about unlocking their potential and being a partner in their growth.

2. Expand how you add value.

As Jami put it, “It’s not just about oversight anymore.” When you’re leading other leaders, value comes from:

• Creating clarity around vision and priorities

• Sharing your network and making strategic connections

• Advocating for their growth internally

• Providing exposure to new experiences (like board meetings or cross-functional initiatives)

• Offering thoughtful support, feedback, and stretch opportunities

3. Keep the career growth conversation going.

One book Jami recommends for supporting the development of senior leaders is Help Them Grow or Watch Them Go by Beverly Kaye and Julie Winkle Giulioni. It reframes career conversations not as “once-a-year promotion talks” but as ongoing opportunities to help people grow where they are.

The book outlines three types of conversations every leader can have:

• Hindsight Conversations
  Invite reflection. Ask questions like:
  → When have you felt most fulfilled in your career?
  → What past experiences energized you the most?
  → What did you love doing as a kid?

These conversations often uncover forgotten passions and values that still hold power today.

• Foresight Conversations
  Help them look ahead. Explore future industry shifts, economic trends, or skill gaps:
  → How do you think AI will impact your role and function?
  → What new areas of expertise would you like to explore?
  → What roles might not exist yet—but excite you to imagine?

This kind of conversation fuels curiosity and keeps leaders adaptable.

• Insight Conversations
  Reveal blind spots, patterns, and potential. This is where coaching comes in:
  → Have you noticed you light up when talking about X?
  → You’ve mentioned this goal a few times—what do you think is really driving it?
  → I’m seeing a strength in you that you might be underestimating.

These moments build self-awareness—and often unlock unexpected growth.

“Your job isn’t to get them their next promotion. It’s to help them grow—constantly.”

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Back to the Basics

With all the frameworks, theories, and optimizations out there, it’s easy to forget the fundamentals.

But Jami reminded us that leadership is built on core practices—ones that never go out of style.

“How do you kick off a management relationship? How do you build trust? How do you inspire people? How do you set expectations and hold them accountable? How do you give coaching and feedback? To me, those are the basics. And I would say for any leader—go back to the basics.”

This guidance came from a popular training Jami created called Manager Essentials, inspired by a surprising moment: taking a yoga basics class after 20 years of practice. It was refreshing—almost revolutionary—to return to the fundamentals and remember why she started.

If you’re feeling stuck in your leadership, start by returning to the basics.

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One Thing You Can Do Now

Jami’s favorite low-lift practices?

• Say good morning. It builds connection—especially in remote settings.

• Give appreciation. Not praise, but specific acknowledgment of effort.

“Thanks for your hard work this week” goes a long way.

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What will you apply?

Being a great leader isn’t about having all the answers. It’s about asking better questions—the kind that reveal what your team really needs to do their best work.

It’s about listening. Slowing down. Get curious. And caring deeply.

Because when people feel seen, supported, and challenged in the right ways, they don’t just perform.

They grow. They thrive. And that’s when the real impact begins.

— Amanda

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Chapters

00:00 Introduction and Warm Welcome

00:50 Career Journey and Achievements

01:35 Defining Leadership and Influence

02:03 Early Leadership Influences

03:19 Balancing Care and Results

04:49 Developing Leadership Skills

06:31 Growth and Learning in Leadership

13:18 The Power of Asking Questions

22:19 Managing Senior Leaders

27:58 Final Thoughts and Appreciation

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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.

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In case you missed it

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