Books I regularly recommend to engineering leaders, by level

For individual contributors

• Design Patterns: Elements of Reusable Object-Oriented Software by Erich Gamma, Richard Helm, Ralph Johnson, & John Vlissides
• User Interface Design for Programmers by Joel Spolsky (Author)
• Agile Development using Scrum by Ken Schwaber & Mike Beedle
• Refactoring: Improving the Design of Existing Code by Martin Fowler, Kent Beck, John Brant, William Opdyke, & Don Roberts
• The Mythical Man-Month: Essays on Software Engineering by Frederick Brooks

For engineering managers

• Extreme Ownership by Jocko Willink
• Managing Humans by Michael Lopp

For senior individual contributors

• Extreme Ownership by Jocko Willink
• Staff Engineer by Will Larson

For senior engineering managers

• Extreme Ownership by Jocko Willink
• An Elegant Puzzle by Will Larson

For directors of engineering, VPs of engineering, and above

• Extreme Ownership by Jocko Willink
• Team of Teams by Gen. Stanley McChrystal
• An Elegant Puzzle by Will Larson