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CTO Hiring Checklist

January 19, 2021  |  Posted By: Marty Abbott · 6 min read

Interim CTO, Fractional CTO, Full Time CTO Hiring Checklist Image

Whether you are considering a fractional CTO, an interim CTO, a full time CTO, or you just want to “coach up” your current CTO this list is a good place to start to help you define expectations, create your job description, coach up your current CTO and land a great future CTO.

Business and Financial Acumen

In our experience, the top reason for CTO turnover is a lack of business acumen and an inability to speak the language of business.  This is the one area that you should be uniquely qualified to evaluate to avoid the pitfalls of hiring a colleague who does not understand business broadly, and your business specifically.  Here are some of our favorite questions to ferret out candidates who “don’t get” business or do not speak the language of business.

What you are seeking

  • Look for candidates who have sought an academic understanding of business through an MBA.
  • Identify candidates who are conversant in common business topics and can engage in thoughtful discussion and debate.

Example questions

  • What are the financial statements required under GAAP?
  • How do those financial statements relate to each other (give some examples) and what stories do they tell?
  • What is the value of EBIT/EBITDA?  For what is an investor looking when evaluating it?  When does it not make sense as one measure of evaluating a business?
  • What is the difference between amortization and depreciation?  How do they relate to the principle of matching?
  • How do you think about the capitalization of effort?  When is it appropriate, and what are the pitfalls?
  • What are some of the biggest pitfalls with respect to common budgeting and forecasting processes, and how can they be fixed in your experience?
  • What are the benefits and liabilities associated with the “as a service” delivery model?  How does it effect gross margins, operating margins and profit margins?  In your estimation, has the market reacted properly, over-reacted or under-reacted to the introduction of this model?
  • What are some of the sources of capital for a company, and what are the pros and cons of each source?

Technical Depth and Breadth

Your candidate may be more technical than you.  It may be easy for them to “fool” you with their answers.  As such, you may want to consider an outside firm to help with technical assessment.  That said, you can still evaluate how they present answers.  Look for candidates that explain technical issues in business terms and give balanced answers free of hyperbole.

What you are seeking

  • Candidates who discuss technology in business related terms.
  • Candidates who understand that there is rarely a single correct answer (e.g. “Everything should be Agile” or “The answer is always Java”)
  • Candidates who evaluate the forces and trends that lead to an answer, not just give an answer.
  • Candidates who are broad across the technical spectrum and can engage deeply in all areas (architecture, quality, engineering, operations, infrastructure)

Example questions

  • What are the limitations of relational (ACID) based systems?  What are the limitations of non-relational (BASE) systems?  How do you think about when to employ each?
  • What are the most significant developments in product development lifecycles over the last few years?  How do those effect how you think about the development of solutions?
  • How do you think about what programming languages to use in software development?  What are 3 to 4 key attributes you use to determine which language should be used?
  • How do you think about polyglot (multiple language usage) within a development group?  Should there ever be more than one?  Why or why not?
  • What are the most significant infrastructure developments over the last two decades, and how do those effect critical elements like time to market, cost of operations, etc?

Strategy Development

What you are seeking

  • Candidates who can contribute to an effective company and product strategy, while also creating an appropriate technology strategy.
  • Candidates who look for patterns (induction) to form hypothesis (actions) that are then tested through execution.

Example questions to ask

  • How do you go about contributing to a company and product strategy?  What is your role in both of those?
  • How do you go about creating a technology strategy, what are the critical elements of that strategy?  How do you “test” it for correctness and seek alignment with other executives?
  • What is the role of an “N-Forces” analysis in informing a strategy?  How have you used it before?

Team Development and Construction

What you are seeking

  • Candidates who understand that organizational structure impact time to market, cost of development and cost of operations.
  • Candidates who value team autonomy, but primarily in its relationship to business related outcomes.
  • Candidates who understand that accountability can only be achieved through empowerment, and that empowerment without accountability for results is at best risky and at worst dangerous.

Example questions to ask

  • What is most important in your mind – what a team does or how it does those things?  [valuable to recognize that both are important – but make the candidate choose one as being MORE important and explain why]
  • How does your answers of “what vs. why” inform how a team should be constructed?
  • What is your perspective on the topic of services decomposition (sometimes known as microservice architecture)?  How should those services relate to an engineering organization structure?
  • Where do you stand on the notion of both empowerment and accountability?  Are those terms in conflict with each other?  How do you create both empowerment and accountability?


What you are seeking

  • Passionate and compassionate leaders who are vulnerable, empathic, and driven.
  • Candidates who understand the value of a compelling vision, and how to nest a technical and/or product vision to a company vision.

Example questions to ask

  • What are the elements of an effective vision, and how do you go about creating one that drives a team to higher levels of success?
  • How do you get your teams aligned with a vision?  What do you do when someone on your team disagrees with the vision?


What you are seeking

  • Candidates that understand measurement is a critical component of managing teams.
  • Candidates willing to set high standards and hold teams accountable to those standards.
  • Candidates who value creating high performing teams.

Example questions to ask

  • What metrics do you employ to measure productivity?
  • How do you use those metrics to continuously improve your organization?
  • How do you engender loyalty within the teams you manage? (can also be asked under vision above)
  • How do you go about setting high standards and holding teams accountable to them?
  • Give me examples of how you have identified underperforming individuals and teams and how you go about correcting their performance?
  • Have you ever removed someone from a team for underperformance?  Describe the path you took to determine someone was not performing?  Did you wait too long to remove them?
  • How do you go about rewarding superior performance within a team?
  • What is a “self-organizing” team?  What does it mean?  What does it NOT mean?

Drive and First 100 Days

What you are seeking

  • Leader who can quickly assess the strengths, weakness, opportunities, and threats of the technology teams and company – and do so quickly.
  • Candidates who understand how to determine which individuals and/or roles need to be coached, replaced, added, or deprecated.
  • Candidates who know how to move fast, likely faster than the organization moves today.

Example questions to ask

  • What are your plans for your first 10 days when you lead a new organization?
  • What are your plans for your first 100 days?
  • How would you do a SWOT analysis for your organization?
  • How would you determine who needs to be coached up or out?  How would you determine what roles are missing?  What typical roles do you see missing in organizations similar to ours? 

Change and Transformation Agent

What you are seeking

  • Candidates with demonstrable experience on how they affected change in previous organizations
  • Candidates with a bias for action and execution
  • Candidates who understand the need to work with a broad set of stakeholders

Example questions to ask

  • Describe how you approach affecting change?
  • Describe where your change efforts failed in the past. What you would do differently now?
  • How do you ensure everybody is aligned when implementing change?

Need More Help?

AKF Partners can help you with your CTO evaluation and search in a number of ways:

  • Provide part time coaching for a CTO you want to keep but have improve over time.
  • Fractional CTO for companies that do not believe they need a fulltime CTO.
  • Interim CTO for companies that are between full time CTOs.
  • Interview assistance and evaluation assistance for new CTO candidates.

Next: CEO Guide: How to hire a great CTO


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