Tim O’Reilly – How I failed:
“As a management team, you aren’t just working for the company; you have to work on the company, shaping it, tuning it, setting the rules that it will live by. And it’s way too easy to give that latter work short shrift.
[…] I was always pretty good at finding the sweet spot where idealism and business reality meet, but I didn’t spend enough time teaching that skill to everyone on my team. […] If I were starting O’Reilly all over again, I’d spend a lot more time making sure the culture I was trying to create was the one that I actually did create.
[…] Every manager — in fact, every employee — needs to understand the financial side of the business. One of my big mistakes was to let people build products, or do marketing, without forcing them to understand the financial impact of their decisions.
[…] Looking back, I wish we’d worked harder early on to build an organization in which human potential isn’t just expected and taken for granted, but is also nurtured — if necessary, with tough love. […] We ended up building a culture where managers too often compensated for the failings of employees by working around them, either working harder themselves, hiring someone else to fill in the gaps, or just letting the organization be less effective.
[…] I never regretted raising the bar […] but I look back at the many times I let something go by that I shouldn’t have because the team would be upset, and I regret every one of them.”