liveBook · Manning

What you will learn in Think Like a CTO

by Alan Williamson

Chapter by chapter

Chapter 1: The Chief Technology Officer (CTO)

1.1 What makes a Chief Technology Officer · 1.2 Different types of CTOs · 1.2.1 Prestartup, in name only · 1.2.2 Funded startup: The technology expert with money · 1.2.3 Established company: Their first CTO · 1.2.4 Established company with CTO · 1.3 Determining whether we need a CTO · 1.4 Evolution from engineer · 1.4.1 The first 100 days · 1.5 Top 10 qualities for a CTO · 1.6 Summary · 1.7 Checklist

What you learn in chapter 1 →

Chapter 2: Managing up

2.1 Partnering with your CEO · 2.1.1 The office of the CEO · 2.1.2 Types of CEOs · 2.1.3 Setting the tone · 2.1.4 Tips for a successful partnership · 2.2 Counting on your CFO · 2.2.1 Getting a handle on your expenditures · 2.2.2 Reaching out · 2.3 Working with peers · 2.3.1 Know your company · 2.3.2 Speak their language · 2.3.3 Find their pain · 2.3.4 Think strategically · 2.4 Taking over from another CTO · 2.4.1 Celebrate, not disparage · 2.4.2 Speak to the outgoing CTO · 2.4.3 Discover the team · 2.5 Presenting to the board · 2.5.1 Know your audience · 2.5.2 Format of the meeting · 2.5.3 Your role · 2.5.4 The dos and don’ts · 2.6 Communications · 2.6.1 Internal · 2.6.2 External · 2.7 Internal politics · 2.7.1 The major types · 2.7.2 Mitigating politics · 2.8 Change management · 2.8.1 Boiling the frog · 2.8.2 Excitement committee · 2.8.3 Valley of anguish · 2.8.4 Consequences · 2.9 Summary · 2.10 Checklist

What you learn in chapter 2 →

Chapter 3: Visionary planning

3.1 The grand vision · 3.1.1 The “what”/“why” part · 3.1.2 The “how” part · 3.1.3 Define success · 3.2 Engaging with clients · 3.2.1 Know your client · 3.2.2 Your counterpart · 3.3 Long-term planning · 3.3.1 Timing is everything · 3.3.2 Keep in mind · 3.4 Incorporating seismic shifts · 3.4.1 Decision paralysis · 3.4.2 Identify the pillars of your vision · 3.4.3 Watching the pillars · 3.4.4 Looking for simplicity · 3.5 Elevator pitch · 3.5.1 Creating your pitch · 3.5.2 Practicing and honing the pitch · 3.6 Putting together a budget · 3.6.1 What to include · 3.6.2 Lay out the budget · 3.6.3 Keeping track · 3.6.4 Return on investment (ROI) · 3.7 Near-term planning and expectations · 3.7.1 Communication · 3.7.2 Controlling the narrative · 3.8 Summary · 3.9 Checklist

What you learn in chapter 3 →

Chapter 4: Building a team

4.1 Different types of resources · 4.1.1 Full-time employee (FTE) · 4.1.2 Contracting individuals · 4.1.3 Outsourcing to vendor · 4.1.4 Onshore resourcing · 4.1.5 Offshore resourcing · 4.1.6 Comparison review · 4.2 Knowing when to hire · 4.2.1 Hiring events · 4.2.2 Discipline matrix · 4.2.3 Impact of not hiring · 4.3 Sourcing candidates · 4.3.1 Referrals · 4.3.2 Recruitment agency · 4.3.3 Headhunting · 4.3.4 Graduate fairs/internships · 4.3.5 Self-serve online · 4.4 Creating the job description · 4.4.1 Basic structure · 4.4.2 Title · 4.4.3 Description · 4.4.4 Minimum requirements · 4.4.5 Required skills · 4.4.6 About/legal information · 4.5 Summary · 4.6 Checklist

What you learn in chapter 4 →

Chapter 5: Interviewing, choosing, and onboarding

5.1 The interview · 5.1.1 Getting into the right mindset · 5.1.2 Your objectives · 5.1.3 Phone interview (or preinterview) · 5.1.4 In-person interview · 5.1.5 Video interview · 5.2 Scoring candidates · 5.2.1 Defining your criteria · 5.2.2 Marking the candidate · 5.3 Saying no · 5.3.1 Definitely not · 5.3.2 Definitely maybe · 5.4 Onboarding · 5.4.1 Bringing them up to speed · 5.4.2 Your expectations · 5.4.3 Getting to work · 5.5 Summary · 5.6 Checklist

What you learn in chapter 5 →

Chapter 6: Team management

6.1 Charter · 6.1.1 Knowledge · 6.1.2 Sample charter · 6.2 Team structure · 6.2.1 Product centric · 6.2.2 Lifecycle centric · 6.2.3 Customer/vertical centric · 6.2.4 Hybrid approach · 6.3 Titles · 6.3.1 What is in the title? · 6.3.2 Ladder to improvement · 6.3.3 Common mistakes with titles · 6.4 Team reporting · 6.4.1 Define autonomy · 6.4.2 Reporting metrics · 6.4.3 Accountability · 6.5 One-on-one meeting · 6.6 Education and training · 6.6.1 Online libraries/resources · 6.6.2 Platform/software certifications · 6.6.3 Bootcamps · 6.6.4 User groups · 6.6.5 Internal training · 6.6.6 Conferences · 6.6.7 University/college courses · 6.7 Communication · 6.7.1 Email · 6.7.2 Meetings · 6.7.3 Feedback · 6.8 Summary · 6.9 Checklist

What you learn in chapter 6 →

Chapter 7: Annual reviews

7.1 Skill matrix · 7.1.1 Basic matrix structure · 7.1.2 Filling out the grid · 7.1.3 Logistics · 7.2 Handling failure · 7.2.1 Initial reaction · 7.2.2 Investigation · 7.2.3 Learning · 7.3 Termination · 7.3.1 Downsizing the department · 7.3.2 Skills no longer required · 7.3.3 Poor performance · 7.3.4 Logistics · 7.3.5 The exit interview · 7.4 Remote working · 7.4.1 Setup · 7.4.2 Managing expectations · 7.4.3 Preventing abuse · 7.5 Summary · 7.6 Checklist

What you learn in chapter 7 →

Chapter 8: Technology decisions

8.1 Avoid lock-in · 8.2 Build vs. buy · 8.2.1 Buy · 8.2.2 Build · 8.2.3 Considerations · 8.2.4 Checklist · 8.3 Cloud vs. on-prem · 8.3.1 Cloud · 8.3.2 On-prem · 8.4 Disaster recover · 8.4.1 Downtime tolerance · 8.4.2 Full or partial service · 8.4.3 Fail forward vs. bounce back · 8.4.4 Managing the event · 8.4.5 Cloud and DR · 8.5 Data management · 8.5.1 Storage · 8.5.2 Data types · 8.6 Microservices vs. monolithic · 8.7 Open source · 8.7.1 License types · 8.7.2 Usage guidelines · 8.7.3 Publishing open source · 8.7.4 Using code from the web · 8.8 Languages and frameworks · 8.8.1 Legacy language · 8.8.2 Choosing the next one · 8.9 Summary · 8.10 Checklist

What you learn in chapter 8 →

Chapter 9: Development

9.1 Project planning · 9.1.1 Project manager · 9.1.2 Defining projects · 9.2 Development standards · 9.3 Version control · 9.4 Quality assurance (QA) · 9.4.1 Manual testing · 9.4.2 Automated tests · 9.5 Cl/CD · 9.6 Technical debt · 9.7 Release · 9.7.1 Outage release · 9.7.2 Blue-green release · 9.8 Client requests · 9.9 Summary · 9.10 Checklist

What you learn in chapter 9 →

Chapter 10: Contract management

10.1 Service agreement · 10.1.1 Statement of work · 10.1.2 Service-level agreement · 10.2 Evaluating vendors · 10.3 Software licensing · 10.4 Support contracts · 10.5 Summary · 10.6 Checklist

What you learn in chapter 10 →

Chapter 11: Documentation

11.1 Why document? · 11.1.1 Audience · 11.1.2 Format · 11.1.3 Validation · 11.2 Documentation types · 11.2.1 Meeting notes · 11.2.2 Walk-throughs demos · 11.2.3 Owner’s manual · 11.2.4 Backing up and restoration · 11.2.5 Deployment process · 11.2.6 Source/code comments · 11.2.7 Architectural diagrams · 11.2.8 Process diagrams · 11.2.9 Network diagrams · 11.2.10 Data schemas · 11.2.11 Compliance documentation · 11.2.12 License and audit tracking · 11.3 Whitepapers · 11.4 Best practices · 11.5 Summary · 11.6 Checklist

What you learn in chapter 11 →

Chapter 12: Security

12.1 Patching · 12.1.1 Identify patches · 12.1.2 Scheduling · 12.1.3 Special considerations · 12.2 Penetration testing · 12.3 Social engineering · 12.4 Data leakage · 12.4.1 Logging · 12.4.2 Application errors · 12.4.3 Data exports · 12.4.4 Version control · 12.5 Password rotation · 12.5.1 System credentials tracking · 12.6 Secure environment · 12.6.1 Identify · 12.6.2 Protect · 12.6.3 Monitor · 12.7 Developing with security · 12.7.1 Creating secure code · 12.7.2 Securing the build process · 12.8 “We are under attack” · 12.8.1 Kill switch · 12.8.2 Communication · 12.8.3 Managing a security breach · 12.9 Chief Information Security Officer (CISO) · 12.10 Summary · 12.11 Checklist

What you learn in chapter 12 →

Chapter 13: Housekeeping

13.1 Managing hardware · 13.2 Support contracts · 13.2.1 Providing support · 13.3 Monitoring · 13.3.1 Outside looking in · 13.3.2 Inside looking in · 13.4 Backup and restoration · 13.4.1 Frequency/retention · 13.4.2 Archive security · 13.5 Budget oversight · 13.6 Summary · 13.7 Checklist

What you learn in chapter 13 →

Chapter 14: Company growth

14.1 Investment groups · 14.2 Impromptu pitch · 14.3 Investment cadence · 14.4 Preparing for integration · 14.5 Due diligence · 14.5.1 Performing due diligence · 14.5.2 Conducting due diligence · 14.5.3 Presenting your findings · 14.5.4 Answering due diligence · 14.6 Handing over the reins · 14.7 Taking the reins · 14.8 Summary · 14.9 Checklist

What you learn in chapter 14 →

Chapter 15: You, Inc.

15.1 Reviewing yourself · 15.2 Mentor · 15.3 Keeping pace · 15.4 Monitoring change · 15.5 Succession planning · 15.6 Career success · 15.7 Stepping up · 15.8 Summary · 15.9 Checklist

What you learn in chapter 15 →

Concepts explained in this book

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