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Jan 2, 2019 · 23m · a16z

a16z Podcast | Engineering a Revolution at Work

Steven Sinofsky · 16m spoken Benedict Evans · 6m spoken
0:00 / 0:00
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In this episode of the a16z podcast, Benedict Evans and former Microsoft executive Steven Sinofsky analyze the evolution of workplace productivity tools. They discuss how the shift from legacy desktop suites and paper-heavy corporate hierarchies to unbundled SaaS, mobile form factors, and real-time telemetry fundamentally reshapes modern business operations.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →

The host as informed peer 5.3 Guest teaching 4.5 Guest disagreement 2.0 The host pushing back 1.0
05100:0010:0020:004:18–9:52 · The host as informed peer 6/10 The Evolution from Software Bundling to SaaS Unbundling Evans demonstrates strong domain expertise by discussing early SaaS paradigms like Bloomberg and detailing how corporate workflows repurpose tools like Excel and PowerPoint. Sinofsky adds historical enterprise context regarding desktop bundling and Excel functioning as a word processor in Japan, maintaining a highly collaborative dialogue.9:52–13:07 · The host as informed peer 5/10 Modern Meeting Dynamics and Real-Time Workplace Telemetry Evans offers insightful observations on SaaS unbundling, noting how new file templates function as templates for standalone mobile apps. Sinofsky expands on modern startup meeting culture, highlighting how live telemetry replaces printed static presentations, leading to complete alignment between host and guest.13:07–21:53 · The host as informed peer 6/10 Mobile Form Factors, Changing Workflows, and Bottom-Up Adoption Evans challenges traditional skeptics who claim mobile devices cannot support real work by comparing the debate to historical doubts about laptops replacing desktops. Sinofsky slightly pushes back on the device capability framing, redirecting the discussion toward how underlying business workflows themselves are fundamentally changing.21:53–23:57 · The host as informed peer 4/10 Ecosystem Discontinuity, Innovation, and Future Outlook Evans asks whether SaaS ecosystem fragmentation will eventually consolidate back into a smaller set of dominant software suites. Sinofsky directly takes a different view, arguing that technological discontinuities continuously spawn specialized tools rather than consolidating in the near term.4:18–9:52 · Guest teaching 4/10 The Evolution from Software Bundling to SaaS Unbundling Evans demonstrates strong domain expertise by discussing early SaaS paradigms like Bloomberg and detailing how corporate workflows repurpose tools like Excel and PowerPoint. Sinofsky adds historical enterprise context regarding desktop bundling and Excel functioning as a word processor in Japan, maintaining a highly collaborative dialogue.9:52–13:07 · Guest teaching 3/10 Modern Meeting Dynamics and Real-Time Workplace Telemetry Evans offers insightful observations on SaaS unbundling, noting how new file templates function as templates for standalone mobile apps. Sinofsky expands on modern startup meeting culture, highlighting how live telemetry replaces printed static presentations, leading to complete alignment between host and guest.13:07–21:53 · Guest teaching 6/10 Mobile Form Factors, Changing Workflows, and Bottom-Up Adoption Evans challenges traditional skeptics who claim mobile devices cannot support real work by comparing the debate to historical doubts about laptops replacing desktops. Sinofsky slightly pushes back on the device capability framing, redirecting the discussion toward how underlying business workflows themselves are fundamentally changing.21:53–23:57 · Guest teaching 5/10 Ecosystem Discontinuity, Innovation, and Future Outlook Evans asks whether SaaS ecosystem fragmentation will eventually consolidate back into a smaller set of dominant software suites. Sinofsky directly takes a different view, arguing that technological discontinuities continuously spawn specialized tools rather than consolidating in the near term.4:18–9:52 · Guest disagreement 1/10 The Evolution from Software Bundling to SaaS Unbundling Evans demonstrates strong domain expertise by discussing early SaaS paradigms like Bloomberg and detailing how corporate workflows repurpose tools like Excel and PowerPoint. Sinofsky adds historical enterprise context regarding desktop bundling and Excel functioning as a word processor in Japan, maintaining a highly collaborative dialogue.9:52–13:07 · Guest disagreement 0/10 Modern Meeting Dynamics and Real-Time Workplace Telemetry Evans offers insightful observations on SaaS unbundling, noting how new file templates function as templates for standalone mobile apps. Sinofsky expands on modern startup meeting culture, highlighting how live telemetry replaces printed static presentations, leading to complete alignment between host and guest.13:07–21:53 · Guest disagreement 3/10 Mobile Form Factors, Changing Workflows, and Bottom-Up Adoption Evans challenges traditional skeptics who claim mobile devices cannot support real work by comparing the debate to historical doubts about laptops replacing desktops. Sinofsky slightly pushes back on the device capability framing, redirecting the discussion toward how underlying business workflows themselves are fundamentally changing.21:53–23:57 · Guest disagreement 4/10 Ecosystem Discontinuity, Innovation, and Future Outlook Evans asks whether SaaS ecosystem fragmentation will eventually consolidate back into a smaller set of dominant software suites. Sinofsky directly takes a different view, arguing that technological discontinuities continuously spawn specialized tools rather than consolidating in the near term.4:18–9:52 · The host pushing back 1/10 The Evolution from Software Bundling to SaaS Unbundling Evans demonstrates strong domain expertise by discussing early SaaS paradigms like Bloomberg and detailing how corporate workflows repurpose tools like Excel and PowerPoint. Sinofsky adds historical enterprise context regarding desktop bundling and Excel functioning as a word processor in Japan, maintaining a highly collaborative dialogue.9:52–13:07 · The host pushing back 0/10 Modern Meeting Dynamics and Real-Time Workplace Telemetry Evans offers insightful observations on SaaS unbundling, noting how new file templates function as templates for standalone mobile apps. Sinofsky expands on modern startup meeting culture, highlighting how live telemetry replaces printed static presentations, leading to complete alignment between host and guest.13:07–21:53 · The host pushing back 2/10 Mobile Form Factors, Changing Workflows, and Bottom-Up Adoption Evans challenges traditional skeptics who claim mobile devices cannot support real work by comparing the debate to historical doubts about laptops replacing desktops. Sinofsky slightly pushes back on the device capability framing, redirecting the discussion toward how underlying business workflows themselves are fundamentally changing.21:53–23:57 · The host pushing back 1/10 Ecosystem Discontinuity, Innovation, and Future Outlook Evans asks whether SaaS ecosystem fragmentation will eventually consolidate back into a smaller set of dominant software suites. Sinofsky directly takes a different view, arguing that technological discontinuities continuously spawn specialized tools rather than consolidating in the near term.

speaking balance: gold is the host, purple is the guest (3 minute bins)

0:00 · the host 0% · guest 100%0:00 · the host 0% · guest 100%3:00 · the host 0% · guest 100%3:00 · the host 0% · guest 100%6:00 · the host 0% · guest 100%6:00 · the host 0% · guest 100%9:00 · the host 0% · guest 100%9:00 · the host 0% · guest 100%12:00 · the host 0% · guest 100%12:00 · the host 0% · guest 100%15:00 · the host 0% · guest 100%15:00 · the host 0% · guest 100%18:00 · the host 0% · guest 100%18:00 · the host 0% · guest 100%21:00 · the host 0% · guest 100%21:00 · the host 0% · guest 100%
Sharpest disagreement ▶ 22:28 Sinofsky Disagrees on Consolidation

Sinofsky explicitly rejects Evans' premise that SaaS will re-consolidate into a small set of dominant vendors, taking a clear counter-position.

 Hardest push from the host ▶ 13:07 Evans Challenges Mobile Skeptics

Evans directly refutes the skeptic argument that real work cannot be done on mobile form factors, comparing it to early doubts surrounding laptop utility.

 Biggest teaching moment ▶ 6:15 Sinofsky Reveals Excel's Dominance in Japan

Sinofsky educates Evans on how Excel unexpectedly became Japan's primary word processor in the 1990s due to local document grid preferences.

 The host holds their own ▶ 4:18 Evans Cites Bloomberg and Unintended Tool Use

Evans demonstrates deep industry expertise by highlighting Bloomberg as an early SaaS benchmark and explaining how enterprises bent legacy Office tools into makeshift databases.
the scores for every segment, with the reasoning behind each
ChapterTopicThe host as informed peerGuest teachingGuest disagreementThe host pushing backWhy
The Evolution from Software Bundling to SaaS Unbundling 6411 Evans demonstrates strong domain expertise by discussing early SaaS paradigms like Bloomberg and detailing how corporate workflows repurpose tools like Excel and PowerPoint. Sinofsky adds historical enterprise context regarding desktop bundling and Excel functioning as a word processor in Japan, maintaining a highly collaborative dialogue.
Modern Meeting Dynamics and Real-Time Workplace Telemetry 5300 Evans offers insightful observations on SaaS unbundling, noting how new file templates function as templates for standalone mobile apps. Sinofsky expands on modern startup meeting culture, highlighting how live telemetry replaces printed static presentations, leading to complete alignment between host and guest.
Mobile Form Factors, Changing Workflows, and Bottom-Up Adoption 6632 Evans challenges traditional skeptics who claim mobile devices cannot support real work by comparing the debate to historical doubts about laptops replacing desktops. Sinofsky slightly pushes back on the device capability framing, redirecting the discussion toward how underlying business workflows themselves are fundamentally changing.
Ecosystem Discontinuity, Innovation, and Future Outlook 4541 Evans asks whether SaaS ecosystem fragmentation will eventually consolidate back into a smaller set of dominant software suites. Sinofsky directly takes a different view, arguing that technological discontinuities continuously spawn specialized tools rather than consolidating in the near term.

Statements from this episode (7)

Insight
Sinofsky: Productivity tools define work culture, not just efficiency
“And so now we've got this, we got to this world where these tools were democratized and it didn't just make things more efficient. It also defined a work culture.”
Steven Sinofsky Jan 2, 2019 ▶ 3:11
Insight
Evans: Only Outsiders Who Have Never Seen Bloomberg Can Disrupt It
“The only people who can disrupt Bloomberg are people who've never seen it and have no idea what you use it for.”
Benedict Evans Jan 2, 2019 ▶ 4:59
Assertion Supported
Sinofsky: Excel Was the Preferred Word Processor in Japan During the 1990s
“One of these eyeopening experiences I had was to find out at one point in the nineties that Excel was the preferred word processor in Japan because the documents in Japan are all highly structured.”
Steven Sinofsky Jan 2, 2019 ▶ 6:28
Insight
Sinofsky: Low Installation Friction Enables Unbundling of Productivity Software
“Today's model where everything is sort of a click away, even apps, which everybody can talk about the headaches of getting all the different apps and stuff, but the friction is very, very low. And your ability to put it on the machine, to get it off the machin…”
Steven Sinofsky Jan 2, 2019 ▶ 8:52
Assertion Not checkable as stated
Sinofsky: Companies under 1,000 employees do not use printed meeting materials
“If you think about the average large kind of company meeting, even today, the vast majority of meetings are start off with somebody showing up and passing out like a printed version of a work product. You just don't see that in a company of less than, you know…”
Steven Sinofsky Jan 2, 2019 ▶ 11:10
Insight
Sinofsky: Managers should use meetings for action, not receiving status reports
“Like, what your role as a manager is in a meeting is no longer to be reported to, because frankly, if you want to know, you should just go visit the place that everybody on the team is already using to keep track of their information. And when you get everybod…”
Steven Sinofsky Jan 2, 2019 ▶ 12:34
Assertion Not checkable as stated
Evans: Desktop computers are now only necessary for hardcore video editing
“And that line has kind of moved steadily of the stuff that you actually needed a desktop for. It shrunk and shrunk and shrunk and shrunk. And now it's really only, like, hardcore video editing or something you need an enormous screen for.”
Benedict Evans Jan 2, 2019 ▶ 13:48
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