How to be Effective as a CTO

Written by Solutions at Scale Managing Partner and former NY Times CTO - Rajiv Pant

A CTO's job combines Culture, Technology, and Operations. Each of the three is necessary; a field of knowledge, experimentation, and learning in itself; and interdependent with the other two. To be successful as a CTO, you need to work on and continually master all three areas. If you’d like to see the responsibilities of a CTO as a picture, here is a mind map illustrating things CTOs are responsible for.

Culture

Culture, as the first part of a CTO's job is the answer to who you are you as a team. A CTO's role starts with the culture they develop, evolve, and lead by example.

Culture can be described as peopleknowledge, and behaviors in a community connected by relationshipsnorms, and purpose

The people in a CTO's job include internal stakeholders and colleagues, engineering and product teams, partners, and external customers. As CTO, it is your job to foster constructive collaboration among them. 

Regular sharing of knowledge among members and teams is essential for a culture to be developed, sustained, and evolved. As CTO, you are accountable and responsible for compiling, updating, and sharing knowledge among your teams, stakeholders, and customers.

Observed behaviors describe your culture as it really is. Talk is hollow if you and your teams don't walk the walk. If you are in a leadership role, people observe what you do, and learn from and emulate what you do, far more than from what you say. 

As CTO, you need to appreciate, learn, and apply cognitive science, behavioral psychology, and social science with integrity and in ethical ways to develop a culture of excellence. You must not let a mentality of us-versus-them take root between technology staffers and other parts of the company. Remind yourself and your team members that your allegiance to your whole organization is not less than that to your department or team.

For example, if as CTO, you are resentful of the marketing department and you mock the Chief Marketing Officer and her team, then your team will absorb this poisonous behavior from you. If you disparage your boss behind her back while pretending to be loyal in front of her, your team will learn to do the same to you. If you put the needs and desires of the technology organization ahead of those of the overall organization, then the teams that report in to you are going to act similarly towards your overall technology team. To be a good corporate citizen and team player with your peers is not only the right thing to do, but is also in your self-interest. 

A mistake that CTOs sometimes make is that they organize their team and prioritize their work based too much on what they think is best for the company mainly from the perspective of technology. This results in their stakeholders not seeing eye to eye with the tech team, and stakeholders complain that “things here take forever to get done.” Whenever you hear something like “work takes ages to complete,” there is a deeper problem underneath: The real problem is that engineering and stakeholders are not on the same page about priorities and are not communicating sufficiently with each other about value, progress, problems, and risks.

You can implement the most suitable rapid development practices (e.g. continuous delivery, agile, and lean startup methodologies) and use the best modern techniques, tools, and technologies (e.g. microservices, machine learning, and magic :-) ), that deliver projects with great speed, scalability, and success, but if you and your stakeholders are not in sync, things will be perceived as too slow, stubborn, and substandard. 

Without a good culture, technologies and products decay and operations fail because people do not do the right things towards the shared mission. 

Technology

Technology, as the core part of a CTO's job, is the answer to what you do as a team.

Technology includes engineering, architecture, data, infrastructure, scalability, reliability, trust, security, privacy, and other ingredients. The specific areas of technology in a CTO's purview vary based on the organization, its scale, and condition. Here is an example of an organizational structure that worked well for a smaller media company and another that helped a larger media company be successful. 

Even though most CTO's job duties do not include writing code yourself, to be a credible CTO, you need to not only know how to write good software code, but you should also enjoy doing it as a hobby. You must have a passion for many areas of technology combined with a perpetual desire to keep learning as technologies progress.

As CTO, you are the head coach, mentor, and guide to the technology staff. You preside and govern, not dictate or micromanage. You are not a middleman requiring every communication, decision, or solution to go through you. You are sincerely interested, engaged and involved in the work your teams do but you are not an obstacle. You are a connector who links the technology staff with other members of the organization.  You remember that you have two ears and two eyes but only one mouth, so you listen and observe more than you talk. You respect the makers and the managers who report in to you because you are both their teacher and their student. 

Without good technology, operations are inefficient and have trouble overcoming roadblocks, resulting in undesirably slow progress and heavy costs. With good technology, there is a strong sense of pride and that helps develop a culture of excellence where recruiting, retention, and productivity flourish.

Operations

Operations, as the integrating part of a CTO's job, is the answer to how you do your job as a team. 

Operations can be described as how and how well things get done and are delivered. Operations span how resources (including costs) are allocated and managed, how processes and systems work, and how trade-offs should be made. They involve managing the portfolio of projects, products, and services; prioritization; and decommissioning and letting go of products and projects.

Any team that does product development, infrastructure engineering, or provision of services needs to be operationally effective. For this, you and your team need to track progress, record data, measure results, report results, compile lessons learned, and implement improvements. Continuously. 

Operations are critical to every organization's success. This is where the rubber hits the road. You can have a wonderful culture and innovative technologies, but if you don't get projects done successfully, you won't have the other two for long.

To put the above in context, I am sharing some tips from my recent talk at the Fastly 2016 Summit.

5 Lessons I learned as a CTO in major media companies

To succeed as a CTO or head of engineering, you need to work with the APIs of your fellow human beings 

1. Instead of trying to be salesperson, be a friend

  • It is better to win people over, than to sell them your idea
    • Don’t push your solution. Draw others to your solution
    • Don’t pander either. Win over
  • Don’t make B.S. claims about future benefits of the project. Instead, emphasize the purpose and passion
  • Don’t try to falsely attach your infrastructure project to a product development the business has asked for. Present it on its own merit
  • Don’t spend your time as a technologist writing a business justification. Partner with a finance or business analyst to do that
  • Empathize with your business colleagues and help them empathize with you 

2. Speak to the heart, not just to the brain

  • Go beyond making a rational business case. Generate excitement about the engineering work
    • Getting true buy-in requires evoking emotion and passion
    • Identify an external enemy
  • Share your genuine fears about potential losses resulting from getting hacked or systems crashing.
    • We are all averse to losses
  • Make it “our” project instead of “my” project. Request business stakeholders to talk about the project to their colleagues’ stakeholders, and bosses. Encourage them to include it in their presentations.
    • By doing this, they make a public commitment to it 

3. Leverage reciprocity

  • Deliver successes to the business to build credibility first
    • Before you pitch a major infrastructure project
    • As a new employee, don’t use up your honeymoon credits on a project whose benefits to your stakeholders aren’t as clear
  • When your colleagues ask for something that you don’t value as much, be open minded to them
    • Your colleagues will reciprocate by embracing your ideas if you embrace theirs

4. Don’t be a “middleman.” Be a connector

  • If you are a CTO or senior manager, it is in your interest that your business colleagues know, appreciate, and have direct connections with your teammates
    • Their expertise supports and complements yours
    • They bring additional credibility
    • You make a stronger case as a team

Invite business colleagues to select gatherings of the product engineering teams 

5. Regularly discuss your projects and their value with your colleagues

  • Never assume that your business colleagues won’t understand or appreciate technical stuff. Be a translator
  • A critical part of your job as a technologist is to regularly describe what you do and its value to your colleagues
  • …and vice versa. Take an interest in what they do

Where to go from here

So you are about to or have just started as a CTO or other technology leadership position. What’s a practical way to proceed? Here is a template for a 90 Day Plan for a CTO in a New Job.