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5 conversations every CEO & CTO should have

Ashley Streb
Ashley Streb
Chief Client Officer, DEPT® Americas
5 min read
7 January 2021

While CEOs have guided companies for decades, the abundance of technology has driven the need for a new executive leader: the CTO.

As CTOs become more essential for driving the business forward, the CEO-and-CTO relationship needs to be collaborative and equitable.

Our CEO and I, as CTO, have worked in a number of product organizations over the years and in 2015, we switched gears and began serving product teams. Since then, we’ve seen firsthand how CEO and CTO leadership affects the success of a product.

Based on these experiences, here are top scenarios where CEOs and CTOs should be on the same page. For most of these conversations, a balance between technology and business is key.

How Does Our Technical Debt Affect Our Agility?

Technical debt is never a fun conversation to have. However, it becomes even less enjoyable when you realize that your product or engineering team has accumulated a lot of technical debt in the name of new features.

A CEO is likely to care more about creating ROI-positive product features. A CTO will want to create a bank of time devoted to technical debt. Therefore, this conversation needs to find a balance between the two so you maximize revenue and keep technical debt at appropriate levels.

There’s the right time to accumulate tech debt to move quickly and there’s the right time to pay that debt down (refactor). If you do only one or the other too often, you’ll fail.

How Do We Balance Short-Term And Long-Term Product Needs?

All digital products need to keep current clients happy and attract future clients. If you focus too much on keeping current customers pleased, you won’t have the resources to innovate and stay competitive. However, if you ignore your clients to push the product, you risk cancellation.

A CTO and a CEO must find a balance between these initiatives. Where are you spending development resources? Are your current clients satisfied? On average, how much technical debt do we have? Understand available resourcing and agree on current versus future product needs.

Consider a set number of hours per month to work on client requests and let customer success and sales control what occurs in those hours. This can be a win-win. It gives customer success and sales agency to keep customers happy and limits the time product and engineering spends on those requests.

How Much Will Sales Guide Our Product?

To some extent, sales will always help guide a product’s evolution. Both of you should be tuned into your sales team’s strategy for winning business.

By nature, salespeople are incentivized to close the deal in front of them — not to look at the market in the long term. If you let your sales folks control too much of your product direction, they’ll likely close a few things in the short term, but create a Frankenstein product that nobody wants in the long term.

However, if you let your sales folks control none of your product decisions, you’ll likely make a “perfect” product for long-term market fit, while failing to land any customers in the short term.

Every organization needs to find the middle ground that works for them and this usually starts with conversations between CEOs and CTOs.

Are Our Product And Non-Product Teams Aligned?

It’s easy for product and technical teams to silo themselves from other departments and this behavior often starts at the top. Therefore, it’s essential for CEOs and CTOs to align goals and then communicate those goals downstream.

A follow-up question might be, how much time do we account for customer requests? Knowing this feeds into customer success, which feeds into retention rates and revenue.

Only when the CEO and CTO are in agreement can you properly incentivize and hold teams accountable.

What’s Your Work Style?

I don’t like to generalize, but in most cases, CTOs and CEOs have different communication and work styles.

A CTO will likely have an engineering mindset in which details matter. A CEO will likely have a visionary mindset and want to keep moving forward.

There is space for both of these people in executive leadership. In fact, it’s often mandatory to have both of these leaders, but if personalities clash without setting proper expectations, it can cause trouble. Have conversations around work style and personality so you can figure out how to work together and complement each other’s skills.


Overall, CEOs and CTOs need to frequently converse around technology and business goals. Balancing current and future product needs, team expectations and technical debt are some of the most important areas on which to focus.

My advice is to establish two types of meetings: vision meetings and implementation meetings.

During a vision meeting, CTOs need to shut off their pragmatic and skeptical side. During an implementation meeting, CEOs need to focus on immediate, concrete things. This helps create space for both personalities to contribute in an equitable way.

This article isn’t to say that CTOs and CEOs need to agree on everything. That likely won’t happen. But knowing your counterpart’s philosophy on these core functions is always beneficial to your business’s bottom line.

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Chief Client Officer, DEPT® Americas

Ashley Streb