When habits forged in one workplace clash with the culture of the next, even seasoned professionals can trip up.
When Bob Baxley left Apple, he did what many in tech do, he jumped straight into his next role, wasting no time between jobs. But in hindsight, that decision tripped him up. After a Friday farewell at Cupertino, he walked into Pinterest the following Monday, expecting to carry on as usual. What he hadn’t expected was to collide with a different kind of company rhythm.
At Apple, work was intense but clean-cut, Baxley explained this in a recent Lenny's Podcast. Disagreements were normal, even welcomed, so long as the end goal was clarity and excellence. The culture was sharp, well-oiled and quietly unforgiving. It didn’t just shape how people worked, it soaked into their thinking, their timing, even how they spoke in meetings. That way of doing things, honed over years, had become second nature for Baxley.
But Pinterest wasn’t Apple, and it didn’t want to be. The atmosphere there was softer, slower, more reflective. Baxley, still wired for Apple’s pace, quickly found himself out of step. He didn’t fail in the traditional sense, but as he put it, he “bounced off the culture”. He had brought along too much of his old self and hadn’t given the new place enough space to breathe.
It’s a problem that crops up often in tech, especially when people jump from one high-pressure company to another. Cultures at big firms like Apple, Google or Meta aren’t just guidelines, they’re deeply ingrained habits. After a few years, you don’t even realize how much you’ve adapted. You’ve soaked up the norms, how to give feedback, how to push an idea, how to read a meeting room, and those instincts can clash hard with a new environment.
Some people, Baxley noted, manage the switch better than others. One example he pointed to was Hiroki Asai, a former Apple executive who took a break of several years before stepping into his next big role. That pause, deliberate or not, gave him time to unwind old patterns and tune in to a different kind of workplace. It acted, in Baxley’s words, like a second "car wash", a way of rinsing off the mindset of the previous company before taking on something new.
The lesson here isn’t that people should forget what they’ve learned, only that they need to carry it differently. What made someone valuable at one firm might still be an asset, but not if it’s wrapped in the same packaging. Apple, for instance, thrives on detail, polish and a refusal to settle for “good enough”. Those values can serve someone well elsewhere, but only if they’re expressed in a way the new team can hear.
By the time Baxley landed at ThoughtSpot, a later role in his career, he had learned to hold on to the values but leave behind the tone. That meant aiming for excellence but not insisting it arrive in an Apple-shaped box. It meant asking not just “What would Apple do?” but “How do these people work, and how can I meet them where they are?”
For anyone moving between roles, especially in tech where the ground shifts quickly, that kind of recalibration can be the difference between fitting in and falling flat. The temptation to jump straight into the next big thing is strong, but it comes with risk. If you don’t pause and watch, you might miss what’s really going on around you.
Careers rarely unfold like neat ladders. More often they twist and turn, with moments of clarity followed by long spells of trial and error. One role might stretch you, another might humble you. But each stop along the way leaves a mark, and if you're not careful, that mark might shape more than just your resume.
In the end, what matters most is not just where you go, but how well you listen when you get there.
Image: DIW-Aigen
Read next:
• When Machines Compete, People Trust Their Creative Side More
• TikTok Shop Sees Surge in U.S. Activity but Still Trails Its Vision
When Bob Baxley left Apple, he did what many in tech do, he jumped straight into his next role, wasting no time between jobs. But in hindsight, that decision tripped him up. After a Friday farewell at Cupertino, he walked into Pinterest the following Monday, expecting to carry on as usual. What he hadn’t expected was to collide with a different kind of company rhythm.
At Apple, work was intense but clean-cut, Baxley explained this in a recent Lenny's Podcast. Disagreements were normal, even welcomed, so long as the end goal was clarity and excellence. The culture was sharp, well-oiled and quietly unforgiving. It didn’t just shape how people worked, it soaked into their thinking, their timing, even how they spoke in meetings. That way of doing things, honed over years, had become second nature for Baxley.
But Pinterest wasn’t Apple, and it didn’t want to be. The atmosphere there was softer, slower, more reflective. Baxley, still wired for Apple’s pace, quickly found himself out of step. He didn’t fail in the traditional sense, but as he put it, he “bounced off the culture”. He had brought along too much of his old self and hadn’t given the new place enough space to breathe.
It’s a problem that crops up often in tech, especially when people jump from one high-pressure company to another. Cultures at big firms like Apple, Google or Meta aren’t just guidelines, they’re deeply ingrained habits. After a few years, you don’t even realize how much you’ve adapted. You’ve soaked up the norms, how to give feedback, how to push an idea, how to read a meeting room, and those instincts can clash hard with a new environment.
Some people, Baxley noted, manage the switch better than others. One example he pointed to was Hiroki Asai, a former Apple executive who took a break of several years before stepping into his next big role. That pause, deliberate or not, gave him time to unwind old patterns and tune in to a different kind of workplace. It acted, in Baxley’s words, like a second "car wash", a way of rinsing off the mindset of the previous company before taking on something new.
The lesson here isn’t that people should forget what they’ve learned, only that they need to carry it differently. What made someone valuable at one firm might still be an asset, but not if it’s wrapped in the same packaging. Apple, for instance, thrives on detail, polish and a refusal to settle for “good enough”. Those values can serve someone well elsewhere, but only if they’re expressed in a way the new team can hear.
By the time Baxley landed at ThoughtSpot, a later role in his career, he had learned to hold on to the values but leave behind the tone. That meant aiming for excellence but not insisting it arrive in an Apple-shaped box. It meant asking not just “What would Apple do?” but “How do these people work, and how can I meet them where they are?”
For anyone moving between roles, especially in tech where the ground shifts quickly, that kind of recalibration can be the difference between fitting in and falling flat. The temptation to jump straight into the next big thing is strong, but it comes with risk. If you don’t pause and watch, you might miss what’s really going on around you.
Careers rarely unfold like neat ladders. More often they twist and turn, with moments of clarity followed by long spells of trial and error. One role might stretch you, another might humble you. But each stop along the way leaves a mark, and if you're not careful, that mark might shape more than just your resume.
In the end, what matters most is not just where you go, but how well you listen when you get there.
Read next:
• When Machines Compete, People Trust Their Creative Side More
• TikTok Shop Sees Surge in U.S. Activity but Still Trails Its Vision
