Ten Questions You Should Be Asking Your CTO

Your Chief Technology Officer is leading your company’s technology initiatives and development.

They interact with the business to plan strategy roadmaps and turn them into development roadmaps.

They then act as the product owner and manage the engineering departments, functioning as the responsible party for all of your organization’s technology efforts.

If you want to understand how effective your CTO is, the following are ten questions you should ask them:

1. How does our technology stack effect infrastructure cost?

Some technologies require more infrastructures to support business operations, while others require less.

Your CTO should be able to explain the cost associated with the current technology stack used in your organization and compare it to other leading technologies.

2. How does our technology stack effect resources cost?

Market rate for each technology is different.

For example: A JAVA engineer might be more expensive than a .NET engineer and a Ruby engineer might be more expensive then both!

Breaking down the cost of resources by different technologies, might help you budget better.

3. How does our technology stack effect licensing cost?

Workstations, Servers, Databases and IDEs all require licensing at the enterprise level, and while working with Microsoft’s .NET might require you to purchase costly MSDN subscriptions, PHP, for example, will have you working with Eclipse or NetBeans for free.

4. How does our technology stack effect productivity?

Free or cheap technology, might have you scrambling for costly solutions for problems that do not exist in better and more expensive technologies.

If you prefer to spend your money on better technology, not more development hours, you might benefit from a strategic exercise where you compare and contrast diffrent technologies’ productivity.

5. What percent of the quarterly roadmaps reflect new development vs. bug fixes?

If your technology department is spending more time fixing bugs then developing new software ask yourself why.

Then ask your CTO how to get back on track.

6. What is our level of outsourcing vs. in house development?

If you are doing everything in house you might be over staffed.

Consider asking your CTO which tasks can be effectively outsourced.

7. What is our engineering turnover level?

Recruiting and training engineering resources is expensive.

Making sure your engineers are happy and productive is the responsibility of your CTO.

High turnover might be a sign a correction is needed.

8. Are we cloud ready?

Your CTO should be able to effectively explain how to migrate all of your systems to the cloud.

I have wrote about the cloud and all of its benefits here.

9. Write a Fibonacci sequence in your favorite language.

I have said it in the past and I will say it again, a non-technical CTO is not an effective CTO.

I have seen many CTOs at large companies that cannot code their way out of a paper bag.

How can a non-technical person effectively lead a group of engineers?

Ask your CTO to write a Fibonacci sequence in their favorite technology.

If they are unable to do so, will you feel comfortable taking technical recommendations from them again?

10. Where will technology be in five years?

A good CTO will have a profound understanding of industry trends and will be able to answer the question without over estimating the advancements ahead.

They will look at the last ten years of development, factor in the exponential growth in technology and then deduct the outcome.

They should be able to follow up with tangible actions, a game plan designed to prepare your organization for the future.


Getting a better understanding of how your company runs its technology efforts can give you better synergy between the business, sales, marketing and engineering and is almost guaranteed to make for a better and more productive organization.

Need development help?

Check us out at: http://invertedsoftware.com

Join the American CTO Forum here: https://www.linkedin.com/groups/13567967

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s