Think Like a CTO 1st Edition by Alan Williamson 1638351872 9781638351870

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

Summary

Checklist

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

Summary

Checklist

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

Summary

Checklist

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

Summary

Checklist

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

Summary

Checklist

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

Summary

Checklist

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

Summary

Checklist

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

Summary

Checklist

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

Summary

Checklist

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

Summary

Checklist

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

Summary

Checklist

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)

Summary

Checklist

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

Summary

Checklist

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

Summary

Checklist

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

Summary

Checklist

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