This week on the GeekWire Podcast: Executive coach and former Microsoft leader Sabina Nawaz talks about her book, You’re the Boss: Become the Manager You Want to Be (and Others Need) — and why she believes pressure, not power, is what truly corrupts leaders.

We discuss the thinning layer of middle management, how AI tools are changing the landscape, and why many younger workers no longer aspire to lead. Sabina shares actionable strategies from the book, including Micro Habits, the power of Blank Space, and how managers can stop micromanaging and start serving as the “container, not the content.”

She also reflects on her time advising Bill Gates and Steve Ballmer — including a memorable moment involving an umlaut — and explains why getting promoted might be the riskiest moment in your career.

Topics Covered:

• Why pressure is more dangerous than power
• Managing when the middle layer disappears
• The double-edged sword of AI-powered management
• Tools: Micro Habits, the Yes List, Blank Space
• Communication fault lines and “sage speak”
• Leadership lessons from Gates and Ballmer
• How to lead without burning out

With GeekWire co-founder Todd Bishop; edited by Curt Milton.

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This week on the GeekWire Podcast, our guest is Hanson Hosein — an Emmy Award-winning journalist, filmmaker, and communication strategist who has spent his career making sense of the world in times of change.

His latest project is American Dignity, a short documentary that follows the legacy of the Civil Rights Movement from Seattle to Selma to Washington D.C., and considers what those lessons mean for America today.

He started out as an NBC News correspondent, reporting from conflict zones in the Middle East and the Balkans. Later, he founded the Communication Leadership program at the University of Washington and became an early voice for digital storytelling, using technology to find new ways of reaching audiences.

We visit his self-contained studio on the former site of a chicken coop, and talk about how he made this film as a one-person operation, what he learned along the way, and where he thinks media is headed. We also dig into how AI is changing the creative process and what it takes to tell meaningful stories in this new world.

With GeekWire co-founder Todd Bishop. Edited by Curt Milton.

See omnystudio.com/listener for privacy information.

This week on the GeekWire Podcast, we discuss how AI is transforming our local tech giants, changing the fundamental nature of work, and blurring the lines between human and machine.

We dive into the memo that has Amazon employees either signing up for AI training or updating their resumes; unpack why you're answering emails at 10 p.m.; and explain how one of us ended up quizzing his dentist's office assistant (or was it an AI chatbot?) about whether he or she (or it?) was human. Then we ask the new Alexa+ what it (she?) thinks about the exchange.

Related stories

• Andy Jassy’s long game: Amazon’s reinvention enters its 5th phase as AI upends the workforce
• Amazon CEO: AI will shrink corporate workforce in coming years
• The ‘infinite workday’ is here — and Microsoft says AI will make it worse if we’re not careful

With GeekWire co-founders Todd Bishop and John Cook.

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A message from GeekWire co-founder Todd Bishop: This episode of the GeekWire Podcast is unlike any we’ve done before. It touches on some of the most contentious and disputed issues in the tech industry, and in the world more broadly.

It started with my curiosity and desire to understand something that happened in March, at GeekWire’s independent Microsoft @ 50 event. I was on stage interviewing Microsoft Vice Chair and President Brad Smith when the conversation was interrupted by a protester.

The group behind the protest, called No Azure for Apartheid, represents current and former Microsoft employees who want the company to end its cloud computing and AI contracts with the Israeli military. They cite concerns over how they believe their work is being used by Israel.

Addressing the larger issues raised by the group, Microsoft said in a May 15 post that it conducted internal and external reviews and “found no evidence to date that Microsoft’s Azure and AI technologies have been used to target or harm people in the conflict in Gaza.”

After covering Microsoft’s statements and the group’s response — and seeing the continued protests unfold at Microsoft events — I decided to dig deeper and learn more.

As part of that, I invited one of the organizers of No Azure for Apartheid to join me on this podcast, for a conversation about the motivations behind the group, their views on Microsoft’s responsibilities, and how the tech industry intersects with international conflicts.

Our guest is software engineer Hossam Nasr, who was fired by Microsoft last year related to protests on the Microsoft campus. In fact, he was the first to protest inside the GeekWire event.

What followed was a complex conversation — one that at times went beyond Microsoft’s role into broader political and ethical criticisms of Israel’s actions in Gaza.

These are deeply polarizing issues, and we know there are strong, divergent opinions about them. I’ve added context conveying Microsoft’s responses, and noting areas where statements and characterizations about Israel, Palestine, and Gaza are the subject of dispute.

The conversation includes detailed descriptions of the ongoing conflict in Gaza and some historical comparisons that some listeners may find disturbing or offensive. And lastly, we recorded this conversation in late May, before the latest developments in the Middle East.

Related Links:

• Microsoft: Statement on the Issues Relating to Technology Services in Israel and Gaza
• Associated Press: As Israel uses US-made AI models in war, concerns arise about tech’s role in who lives and who dies
• AP: Microsoft fires employees who organized vigil for Palestinians killed in Gaza
• +972: Leaked documents expose deep ties between Israeli army and Microsoft
• The Verge: Microsoft blocks emails that contain ‘Palestine’ after employee protests
• Guardian: Microsoft deepened ties with Israeli military to provide tech support during Gaza war

Editing by Curt Milton. Read more at GeekWire.com.

See omnystudio.com/listener for privacy information.

Fifteen years ago, Steve Jobs and Apple had just introduced the first iPad, Steve Ballmer’s Microsoft had been left for dead, and nerdy online bookseller Jeff Bezos was still getting Amazon settled into its South Lake Union HQ. That’s when we started this podcast.

This week, we’re going back to 2010, revisiting clips from the earliest days of the show. We remember what was happening with Amazon, Microsoft, and Seattle’s startup scene, and try to wrap our heads around all the things that have changed since then.

With GeekWire co-founders Todd Bishop and John Cook.

Audio editing by Curt Milton.

See omnystudio.com/listener for privacy information.

This week on the GeekWire Podcast, we discuss Amazon's new licensing deal with The New York Times for AI content training, and go behind the scenes at two different office spaces: Microsoft's redeveloped Redmond campus and Remitly's new Seattle HQ.

• Amazon inks deal with New York Times to license newspaper’s content for AI platforms

• Rebooting Redmond: Microsoft’s new campus reflects ongoing transformation, uncertain future

• A world away in the heart of Seattle: Remitly’s new HQ provides more room to collaborate — and grow

With GeekWire co-founder Todd Bishop and reporter Kurt Schlosser.

See omnystudio.com/listener for privacy information.

Satya Nadella’s offhand remark at Build, about Elon Musk once interning at Microsoft, sparked a mystery that sent us digging through biographies and transcripts in search of confirmation.

We also break down Microsoft’s new AI moves, and consider what its agentic ambitions mean for tech jobs and the economy. Plus, a sharp warning from Microsoft President Brad Smith on Washington state’s fading focus on innovation.

RELATED STORIES

• Elon and Satya, together again: Microsoft brings Musk’s xAI models to Azure, despite OpenAI feud
• Microsoft expands AI roster with Anthropic and xAI integrations, looking beyond OpenAI alliance
• Businessweek: Microsoft’s CEO on How AI Will Remake Every Company, Including His
• Washington state cuts back economic development program amid criticism of innovation approach
• ‘We better wake up’: Microsoft’s Brad Smith sounds alarm as state enacts controversial tax plan
• Washington governor approves new business taxes, acknowledges potential ‘unintended consequences’

With GeekWire co-founders Todd Bishop and John Cook. Edited by Curt Milton.

See omnystudio.com/listener for privacy information.

Box CEO and co-founder Aaron Levie joins the GeekWire Podcast to talk about the company’s latest AI initiatives, including a new integration with Microsoft 365 Copilot and a suite of Box AI agents designed to help businesses analyze content, extract data, and generate insights.

Levie shares how AI is changing the way he and his team work, explains why he believes 2025 is still “day one” for enterprise AI agents, and offers a realistic take on what AI can — and can’t — do today. He also reflects on Box’s evolution, the shifting role of content in the enterprise, and why he thinks AI is creating more work, not less.

RELATED LINKS

• GeekWire: Box tightens Microsoft ties with new Copilot integration, builds out its own suite of AI agents
• Aaron Levie: How AI is changing my work as CEO at Box

With GeekWire co-founder Todd Bishop

See omnystudio.com/listener for privacy information.