A CEO's Guide to Working with CTOs and CPOs

I have worked closely with CEOs for most of my career. Some of them were excellent partners who created the conditions for me and my team to do our best work. Others were not, despite good intentions. The difference was rarely about technical literacy. It was about how the CEO understood the role of technology and product leadership in the organization.

This is a guide for CEOs, presidents, and general managers who work with CTOs, CPOs, or CPTOs. It is written from the technology and product leader’s perspective, which means it reflects what I have seen work and what I have seen fail from inside the relationship.

What Your Technology and Product Leaders Actually Do

Your CTO or CPTO does five things. Three are visible. Two are not.

The visible work: they set product and technology strategy, they build and manage a team, and they deliver products and platforms that serve your users and your business.

The invisible work is twofold. First, they translate between your world and the engineering world. When you say “we need to grow subscriptions by 30%,” your technology leader converts that into a set of product initiatives, engineering projects, data analysis, and organizational priorities. When the engineering team says “we need to replatform our content management system,” your technology leader converts that into a business case you can evaluate: what it costs, what it enables, and what happens if you do not do it.

Second, they manage the tension between short-term delivery and long-term capability. Every day, your technology leader makes invisible tradeoffs between shipping the feature the business wants this quarter and investing in the platform, infrastructure, and talent that will determine what you can build next year. This portfolio management happens continuously, and when it is done well, you never notice it. When it is done poorly, the consequences show up eighteen months later as a technology organization that cannot move fast enough.

This translation and portfolio work is the most important thing your technology leader does, and it is the thing that most CEOs do not see or value enough. A CTO who can build great technology but cannot explain its business impact is only half as useful as one who can do both. I have written about what it takes to be effective as a CTO, and this translation ability is central to it. Invest in the relationship with the leader who does both.

How to Evaluate Your Technology Leader

Most CEOs evaluate their technology leaders on the wrong things. They focus on whether projects ship on time, whether the technology “works,” and whether the technology team causes problems. These are table stakes, not measures of excellence.

Here is what to actually evaluate:

Are the products getting better? Not “are features being shipped” but “are the products that users interact with measurably improving?” User engagement, retention, satisfaction, and revenue per user should trend in the right direction over time. If your technology leader is shipping features but these metrics are flat, something is wrong with the strategy, the execution, or the measurement.

Is the team strong and stable? Technology talent is expensive and hard to replace. If your CTO has high turnover, difficulty hiring, or a team that is burning out, the organizational cost is enormous even if individual projects are shipping. A great technology leader builds a team that attracts and retains strong people. Check retention rates, time-to-fill for open roles, and employee engagement scores. Talk to people on the team occasionally.

Is the technology strategy coherent? Your CTO should be able to explain, in language you understand, what the technology strategy is and why it supports the business strategy. If you cannot follow the explanation, the problem might be the CTO’s communication skills or it might be that there is no coherent strategy. Either way, it needs to be addressed.

Does your technology leader anticipate problems or only react to them? A CTO who comes to you with “we have a security incident” is doing their job. A CTO who comes to you with “our security posture has gaps and here is our plan to address them before they become incidents” is doing their job well. The best technology leaders are proactive about risk, technical debt, and emerging opportunities.

Working with Your CTO

The CTO owns the engineering organization, the technology architecture, and the technical quality of everything you build. The best CTOs combine deep technical understanding with organizational leadership. They know when to invest in infrastructure, when to take on technical debt deliberately, and when to push back on a timeline because cutting corners will cost more later.

What a CTO needs from you is straightforward: the authority to make technical decisions, the budget to invest in the platform and the team, and the trust to manage technical tradeoffs without having to justify every choice to non-technical stakeholders. In return, they owe you a technology organization that delivers reliably, a platform that can support your business ambitions, and honest communication about risks and constraints.

The most common failure mode with CTOs is treating them as implementers rather than strategists. If your CTO is only brought in after business decisions have been made, you are missing the value they can provide.

Technology decisions are business decisions. The CTO should be shaping strategy, not just executing it.

Working with Your CPO

The Chief Product Officer owns a fundamentally different set of problems than the CTO. The CPO is responsible for understanding users, defining what to build, measuring whether it works, and ensuring that the product portfolio serves both user needs and business objectives. Where the CTO asks “how do we build this well?” the CPO asks “what should we build, and how do we know it is working?”

Evaluating a CPO requires different criteria than evaluating a CTO. The right questions are: Does the CPO deeply understand your users and your market? Are product decisions based on research and data rather than opinions and politics? Is the product roadmap strategic and coherent, or is it a collection of reactive requests from stakeholders? Are product managers empowered to define solutions, or are they taking orders?

What a CPO needs from you is different too. The CPO needs you to believe that product management is a strategic function, not a project management function. They need the authority to say no to feature requests that do not serve the product strategy, even when those requests come from powerful stakeholders. And they need you to evaluate them on outcomes — user adoption, engagement, retention, revenue impact — not on how many features they shipped or how many stakeholders they made happy.

A common mistake CEOs make with CPOs is confusing product management with project management. If your CPO spends most of their time managing stakeholder requests, tracking delivery timelines, and producing status reports, you have hired a CPO but created a project management role. The CPO should be spending their time on user research, market analysis, product strategy, and experimentation.

Keeping Product and Technology Working Together

When you have both a CTO and a CPO, the relationship between them is one of the most consequential dynamics in your organization. When it works, product and engineering operate as a unified team that discovers, builds, and measures together. When it does not work, product and engineering become adversaries: product complains that engineering is slow, engineering complains that product changes requirements, and the CEO spends time refereeing conflicts that should never reach their desk.

Here is what to watch for:

Are product and engineering planning together? If the product team defines requirements and hands them to engineering, you have a waterfall relationship regardless of what methodology you use. Product and engineering should be collaborating from the discovery phase, with engineers contributing to solution design and product managers understanding technical constraints.

Do they share accountability for outcomes? If product owns the “what” and engineering owns the “how” but neither owns the result, you have a structural accountability gap. OKRs are one way to create that shared accountability. Both leaders should be measured on the same outcomes: user engagement, product quality, delivery reliability, and business impact.

Is the CTO-CPO relationship healthy? Talk to both of them, separately and together. If they are aligned on priorities, resolve disagreements directly, and present a united front to the organization, the relationship is working. If they are lobbying you separately, blaming each other for problems, or running parallel planning processes, you have a problem that will get worse.

My strong recommendation to CEOs is to combine product and technology under one leader: a Chief Product and Technology Officer. I have led organizations both ways, and the difference is significant.

When product and engineering report to separate executives, alignment is a constant negotiation. Every decision about what to build, how to build it, and when to ship it requires cross-organizational coordination. Disagreements escalate to the CEO, who must arbitrate tradeoffs they may not fully understand. The overhead is real, and it gets worse as the organization grows.

When product, design, and engineering report to one CPTO, alignment is structural rather than negotiated. The tradeoffs between feature velocity and technical investment are managed internally by someone who understands both. The CEO gets a single point of accountability for the entire product and technology portfolio. And the people doing the work operate as one team rather than two organizations that need to coordinate.

This is not the right structure for every company. Very large technology organizations may need separate leaders at the CTO and CPO level, with strong coordination mechanisms. But for most companies, especially in media and publishing, a single CPTO produces better products, faster execution, and less organizational friction than split leadership.

What Your Technology and Product Leaders Need from You

A seat at the strategy table. If your CTO or CPO learns about major business decisions after they have been made, they cannot align technology and product investments with business priorities. Include them in strategic planning from the beginning, not as an afterthought.

Budget authority. Technology is an investment, not an expense. If your CFO treats the technology budget as a cost to be minimized, your CTO will spend their time justifying every dollar rather than investing strategically. Give your technology and product leaders a budget they can manage with autonomy, with accountability for outcomes, and get out of the way.

Air cover. When your CTO or CPO makes a product decision that a business stakeholder does not like, that stakeholder will come to you.

If you override your technology leader to placate the stakeholder, you have just told the entire organization that the CTO does not actually have authority over product and technology decisions. Do this twice and no competent technology leader will stay.

This does not mean the CTO is always right. It means that disagreements should be resolved through a structured process, not through end-runs to the CEO. If a stakeholder has a legitimate concern about a product decision, the right process is for them to raise it with the CTO or CPO directly. If they cannot resolve it, you mediate. But the default should be that your product and technology leader’s decisions stand unless there is a compelling business reason to override them.

Patience during transitions. If you hired a new CTO or CPTO to transform the technology organization, the transformation will take time. The first six months will involve assessing the team, the technology stack, and the organizational dynamics. The next six months will involve making changes. Results will start to become visible in the second year. If you expect visible transformation in the first quarter, you will be disappointed, and the pressure you put on the leader will cause them to make short-term moves that undermine the long-term strategy.

Common Mistakes CEOs Make

Hiring a CTO to fix a culture problem. If your organization has an IT culture rather than a product culture, hiring a great CTO will not fix that. The CTO will arrive, discover that they have responsibility without authority, spend six months trying to change the culture, and leave. Fix the culture problem first — or at minimum, commit to fixing it alongside your new hire and give them explicit support.

Confusing technical fluency with strategic ability. Some CTOs are deep technologists who can explain every detail of the architecture. Others are strategic leaders who understand technology well enough to make good decisions but spend most of their time on organization, strategy, and stakeholder management. Both types can be excellent, but they are good at different things. Know which one your company needs before you hire.

Treating the technology team as a service bureau. If every department in the company can request features from the technology team, and the technology team is expected to deliver all of them, you do not have a product organization. You have an internal agency. The result will be a reactive roadmap, a demoralized team, and products that reflect the priorities of the loudest stakeholders rather than the needs of users.

Asking for estimates and then treating them as commitments. When you ask your CTO “how long will this take?” and they say “three to four months,” that is an estimate based on current understanding. It is not a promise. Software development involves uncertainty. If you hold your CTO to every initial estimate as though it were a contract, they will learn to pad their estimates by 50%, which wastes resources, or they will cut quality to hit deadlines, which creates technical debt that costs more later.

Splitting product and technology without a coordination plan. If you have a separate CTO and CPO, you need an explicit plan for how they will work together: shared planning, joint accountability, a clear escalation path, and regular alignment meetings. Without this, the split will create more problems than it solves. If you are not willing to invest in the coordination overhead, combine the roles under one CPTO.

Not investing in the relationship. Your CTO and CPO are among the most important people in your organization. Spend time with them. Understand their challenges. Ask what they need. The CEOs who have gotten the best work out of me are the ones who treated the relationship as a genuine partnership, not a reporting line.

The Bottom Line

Your technology and product leaders are not vendors. They are strategic partners who can materially affect the trajectory of your business. Give them the authority, the resources, and the partnership they need, and hold them accountable for results. That is the formula. It is simple to describe and difficult to sustain, which is why the companies that do it well have such a significant advantage over those that do not.