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EP 17

Jeff Teper on Taking More Shots on Goal and Staying in the Game

Jeff Teper
Executive LeadershipTechnology

Jeff Teper has spent more than three decades at Microsoft, helping build products including SharePoint and Teams and repeatedly reinventing his work as technology moved from the PC to the internet, the cloud and now AI. In this conversation, Jeff reflects on taking a 50% pay cut to join Microsoft, choosing opportunities over titles, learning from failed products, and the leaders who continued to bet on him before success was obvious. He also explains why taking more "shots on goal" matters, why grit and humility can coexist with fierce competitiveness, and why, at a stage when many of his peers have stepped away, the arrival of AI has given him another reason to stay in the game.

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Featured Guest

Jeff Teper
Jeff Teper
Executive Vice President of Apps and Agents at Microsoft
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Jeff Teper on Taking More Shots on Goal and Staying in the Game
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Key Business Lessons

Taking more shots on goal rather than waiting for certainty before trying again
Choosing opportunity over title, even when it looks like a step backwards
Treating failed products as usable information that shapes the next success
Recognizing the leaders who bet on you before you have proven yourself, and returning that trust
Making career-defining decisions as an honest 51/49 call rather than pretending certainty
Staying in the game by seeking out the next reset instead of coasting on past wins
Episode Highlights
4:09
Why reaching a point where you work because you want to can be incredibly freeing
7:08
Learning to program as a child and discovering the creative power of software
8:37
Being put in charge of software development at 19 and learning through mistakes
11:59
Why asking someone about their biggest career mistake can reveal their character
13:06
Wanting to prove to himself that he could get into Harvard Business School
16:00
Taking a 50% pay cut to join Microsoft and be part of the next computing wave
21:47
Choosing to become a small fish in a big pond
23:11
Giving up a management role to restart as an individual contributor in Microsoft's internet business
24:36
How the failure of Site Server eventually helped lead to SharePoint
27:58
Why successful careers often hide all the unsuccessful shots on goal
29:33
The pricing mistake from Site Server that shaped how Jeff approached SharePoint
31:55
The leaders who kept betting on Jeff before he had a major product success
35:25
Why Jeff considers grit one of the qualities he is most confident about
39:56
Being moved out of SharePoint and wondering whether his Microsoft career was over
41:00
The 51/49 decision that brought him back to reinvent SharePoint
42:05
Taking on the challenge of making Microsoft relevant in the cloud era
43:21
Why reinventing something successful sometimes requires harder people decisions
44:00
Leading Teams through its explosive growth during the pandemic
46:37
Why mixed signals from your management should make you reconsider where you are
49:37
Why AI has given Jeff another reason to remain fully engaged
51:39
Leading Microsoft's Apps and Agents organisation into a new era of business software
55:33
Why AI is changing both what software gets built and how it gets built
58:53
Learning to look outside Microsoft for the breakthroughs happening elsewhere
1:02:51
Why retirement should not become a cliff
1:04:48
Looking forward instead of spending the next phase of life replaying old accomplishments