For those who have transitioned into design leadership roles, what were the most unexpected or difficult challenges you faced? How do you balance hands-on design work with team management, strategy, and advocating for design within the broader organization?

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For many years leading the global team from the top company, the challenges are always trust your gut or follow executive direction and balancing the good for the work or the good for company.
When you become a director, its depended on the size of your company. If you have small team and few designers, you can pick a project and be hands-on on that. But if you are leading big team with 40+ designers, hands-on is not a thing. You will be in meetings all day and even have minimum time to review works.
The position and responsibilities came with price. You gain something and you have to lose something. Depended on what you choose. If you like to do the work, go individual contribution path. Be design principle. If you like to manage and solve problem, go management path. Be design director.

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That's fair. It's always a trade off and context matters! I'm sure that depending on the organization you're part of you'll always have to balance a mix of those things (some more then others depending on the role and the company)

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