Climb On

Ella Hassan left medical school in Jordan with a lot to prove. She joined Microsoft as a 19-year-old testing intern and has been there for more than twenty years, reinventing herself from tester to engineer to product.

Some of those changes she chose. Some she didn’t. And one of the best things she ever did for her career was step away from it for a while.

In this conversation, we talk about:

• The role change she didn’t ask for, and why her career did better because of it
• Why taking time away can change your trajectory
• How being authentic “filtered” the people around her, instead of costing her
• What she’d tell her younger self about people who say yes in the room and no elsewhere
• How to stay steady while AI reshapes the industry
• A story about kindness, and why it pays off at work

If you’re anxious about what’s next in your career, or wondering whether you can reinvent yourself without leaving, this one is for you.

Connect with Ella

• LinkedIn: https://www.linkedin.com/in/ella-h-7915456/

Next time: Kundana, author of The Things We Remember, on leaving tech after twenty-six years.

Find us at Climboncoaching.com

Claire Oliveros didn’t choose higher education. It found her during a morning workshop in her senior year of high school in Portland. She was the first in her family to go to college.

She went on to build multicultural centers, move across the country twice, and apply to more than a dozen college presidencies before landing one. She became the first Filipina American president in her district’s hundred-year history. Two years later, the role ended, and she turned that ending into the start of her own leadership coaching practice for women of color.

In this conversation, we talk about:

• How a pause can give you the focus to keep going
• What a dozen rejections teach you about wanting something
• Why a diverse leadership team doesn’t automatically change the system
• Ingat Ka, Claire’s practice of micro-meditations for leaders with no time
• Why your title doesn’t define your leadership or your worth

If you’re in a pause right now, or questioning what you’re worth without a title, this one is for you.

Connect with Claire

• Website and newsletter: drclaireoliveros.com
• Podcast: Ascend with Claire Oliveros

Next time: Ella, who joined Microsoft as a 19-year-old intern and reinvented herself without leaving.

Find us at Climboncoaching.com

n 2013, Gustavo left Microsoft for what he planned as a six-month break to help his wife’s real estate team. He never went back. He became a top-performing agent, kept the career change secret for two years in case he needed a way back, then moved his family to Mexico and built a service business for U.S. real estate agents. It nearly failed in 2019, until a brother-in-law with a pencil and a P&L showed him what he couldn’t see.

Gustavo was G’s first manager at Microsoft, Redmond. In this conversation, they talk about leaving the security of a corporate job, why it took ten years to get where he expected to be in three, the two days a month he still misses Microsoft, and why the exploration phase is seductive, but giving up too soon is the real mistake.

Find us at Climboncoaching.com

After five months away, I went back to work with a written plan. The boundaries held. The freedom didn't. A solo episode on what returning really costs, and why slow doesn't mean not growing.

Find us at Climboncoaching.com

Eighteen years at Microsoft, all in engineering. Natasha made it to M2 — and then went back to M1, because that's the work that fills her up.

A conversation about building a network before you need it, the mistakes worth making, and what she calls balance. On taking your shot, learning what fulfillment actually feels like for you, and slow ambition.

Find Natasha @ inkedin.com/in/natasha-gaitonde-7035512

Find us at Climboncoaching.com

Rekha turned down a job at the IBM lab that built the computer that beat Jeopardy — and she's never called it a mistake. Twenty-five years into her career, she's asked herself three different questions about what to do next. This episode is about how you know when the one you're using has expired.

Rekha Raghu is a fractional executive, a coach, and my co-founder at Climbon Coaching.

Contact Rekha: linkedin.com/in/rekharaghu

Find us at Climboncoaching.com

Earlier this year I stopped working for five months. Ten years ago I couldn't have done that — and this episode is about why.

Next episode: Rekha Raghu, fractional executive and my co-founder at Climbon Coaching.

Find us at Climboncoaching.com

When Microsoft laid me off in 2014, it felt like being jilted by a lover. There were no boundaries between me and my work — I didn't have a job at Microsoft, I was my job at Microsoft. So when the job ended, I couldn't tell you what was left.

In this first episode I tell the story of the two coaches who split my career in half. The first one, in 2014, was handed to me after the layoff. She worked on my strengths and told me something I'd known my whole working life without ever saying out loud.

The second one, in 2022, I found and paid for myself — while I still had the job, the title, and the stock package. She worked on my values. That conversation is why I walked away from two million dollars at Broadcom before the golden handcuffs closed.

Strengths tell you what you're good at. Values tell you what to do when the good option and the right option aren't the same option.

Find us at Climboncoaching.com