The search for an incomplete CTO

By Anujah Bosman, CEO of Chillisoft

Johannesburg, 14 Sep 2023
Anujah Bosman.
Anujah Bosman.

A CTO (chief technology officer) has long been lauded as a critical business role that straddles technical and business strategy. A CTO is as critical as a CEO if technology is the core business. It is therefore surprising that when recruiting for a CTO, the criteria is often equated with choosing a CIO, or another Team Lead or a Senior Developer.

While all of these roles require a high level of technical competency, a CTO is required to lead and to listen to business, customers and developers. If you choose a CTO who is misaligned to your business, customer and/or development team needs, there are expensive long-term business, culture and financial consequences. 

Chillisoft has operated in the technical software development leadership and consulting role for 18 years. During this period, the company has engaged with businesses from various sectors, team cultures, business maturity and team sizes. Chillisoft has noticed that there are common assumptions and generalisations made by business when choosing a CTO. How do you decide if an individual is a correct CTO fit for your business?

It starts with the business or the board preparing an honest assessment of where they are and how they envision technology helping them to grow, expand or sustain their business. What has prompted the recruitment of a CTO? Is it just due to a vacancy having to be filled or are there tangible business expectations of what the CTO must accomplish? If there is an existing crisis, what factors may have caused the crisis ? In summary, what are the real business expectations of the CTO in the next six months? What customer and or business value drives these expectations? How would you know if the CTO has correctly translated the business and development needs? What qualities should such a CTO have?

In taking stock of the business's needs, the focus areas and priorities must be identified. All potential scenarios and the range of consequences affecting the following areas must be considered, such as:

  • Business continuity
  • Technical availability
  • Company reputation
  • Customer relationships
  • Employee retention
  • Market penetration
  • Market share
  • Data and security
  • Access to expertise
  • Executive team’s knowledge of IT and software development

What are the immediate goals? What is the current state of the development team regarding:

  • The chosen technology stacks
  • Domain knowledge of business systems
  • Security and data
  • Development processes
  • Development team retention

These are a just a few of the high-level questions to guide the thinking process to determine the type of CTO that you will need.

All CTOs must be technically competent and must have led and worked in and with software teams. It is unlikely that a CTO will manage to lead a team of senior developers if he or she is not technically competent. All CTOs must understand how to build, shift and/or maintain an existing development culture. They must understand business value and how to make technical trade-offs.

A potential CTO must be able to:

  • Actively listen.
  • Justify a decision based on value.
  • Ask questions and problem solve.
  • Inspire a team.
  • Understand what the business values.
  • Understand how to deliver value as soon as possible, while ensuring long-term sustainability.
  • And willing to work alongside his or her peers.
  • Speak of development practice systems, methodologies and processes to ensure sustainability and prevent key man dependencies.

The pace of change that a CTO is required to have in order to drive and implement change, their required level of resilience and the depth of business acumen that is required depends on the business needs, process or product maturity and immediate business priorities. A CTO for a start-up requires a very different set of competencies compared to a CTO of a senior development team. A CTO who is required to rescue a product or capture market share works at a different pace and scale to a CTO who is required to maintain a mature business product.

The interviewing process for CTOs is fraught with contradictions. If an executive team is interviewing a CTO, they are using an executive lens to filter the candidate’s responses and may favour qualities such as excellent communication and charisma. If a set of senior developers are interviewing for a CTO, they are most likely judging the candidate by technical proficiency in a stack that they favour. Both of these approaches are “blunt” and do not necessarily check for alignment in CTO fit and business needs.

Through the years, Chillisoft has assisted several company executives to choose CTOs. Some of the warning signs of unsuitable qualities in a CTO are:

1) Believes that he or she is a rockstar and must be on top of everything.

2) Badmouths or throws out the existing architecture completely.

3) Favours individuals who defer to his or her expertise or tells you what you want to hear.

4) Creates a divisive culture and speaks about the business or the board and us “devs”.

5) Believes that culture just happens.

6) Does not release early or often or believes in big upfront design.

7) Individuals who do not have experience in leading any team.

8) An individual who cannot explain technology decisions in business terms.

9) An individual who cannot explain a customer’s needs and or the quality of the solution relative to the needs of a customer.

10) Does not understand the need to build a learning culture.

11) Is not prepared to sell or pitch the software development service or product

12) An individual who has not asked the business questions about the pace of delivery, customer value, methodology, communication structures or approach to quality.

13) An individual who cannot discuss the pros and cons of various methodologies

14) An individual who only considers the happy path scenario and does not highlight what if scenarios.

15) An individual who believes that the business does not need to be consulted.

Chillisoft understands that a CTO is not a silver bullet! However, you have a higher chance of hiring a pragmatic CTO if he or she understands that he or she is incomplete and knows how to harness and leverage off a team and suppliers.

A CTO is fulfilling a critical role in strategy and makes long-term decisions that commits the business to a methodology and path, yet often, CTOs have just a month’s notice period, no restraint of trade and no performance metrics or targets. If you are depending on a CTO, and you are not technically knowledgeable, how do you know that the path that he or she has advised is the best suited path? Were the other options evaluated? Chillisoft believes that leadership requires trust, but trust is earned over time, so how do you know that your recently hired CTO will stay the course, or that he or she is giving you pragmatic advice? Why are there no audits and control checks to audit strategic technical decisions and sustainability?

Chillisoft understands that the path to choosing a CTO is difficult and treacherous. The company also understands that the blistering competition, increasing disruption to markets, the escalating software development skills shortage and international markets exacerbates this problem and requires businesses to act quickly and sometimes with haste. It is for this reason that Chillisoft has responded to a flood of customer requests and the company is now providing technical consulting by:

  • Conducting an objective technical due diligence.
  • Stepping in to maintain and support your system during a crisis.
  • Salvaging projects with project rescue.
  • Providing software development workshops and coaching for executives.
  • Team coaching.
  • CTO leadership and coaching.
  • Assisting business with prioritising business value and quick wins.
  • Assisting the business with CTO assessments and interviews.

Please contact if you would like to discuss these options further.


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