The CTO’s Missing Partner

The one thing I want for you in 2026

I want to share three quick stories with you.

Marcus runs engineering for a fintech company. He has an executive assistant. He also reviews every calendar invitation she sends, rewrites half her emails, and spends Sunday nights reorganizing his week because he doesn’t trust anyone else to get it right. He tells me he’s exhausted. He tells me his EA “helps a little.”

Sarah leads a 60-person engineering org. When I ask about her EA, she tells me about the project coordinator she shares with two other directors. This person schedules her meetings and sometimes books her travel. Sarah still manages her own inbox, still tracks her own action items, still spends four hours every weekend preparing for the week ahead. She doesn’t have an EA. She has occasional administrative support.

David automated everything. Calendly for scheduling. Zapier for workflow triggers. Notion databases for tracking. Superhuman for email. He spent eight months building the perfect productivity system. He still works 65-hour weeks because software can’t call his CEO’s assistant to negotiate a better meeting time, can’t sense when he needs a buffer day after a board presentation, can’t tell him that the vendor demo he agreed to is a waste of time based on a conversation she had with his head of infrastructure.

Three CTOs. Three versions of the same problem. None of them have what they actually need going into 2026.

The Partnership You’ve Never Experienced

Here’s what I want for every CTO I coach in the coming year: a real executive assistant partnership.

Not a task executor. Not a calendar manager. Not a shared resource. A professional whose entire purpose is making your week work.

I know your brain just went to automation. Mine did too, for years. We’re CTOs. We solve problems with systems. When something is inefficient, we build a better process. When something is repetitive, we script it away.

But here’s what I’ve learned from coaching hundreds of technology leaders: the time problem isn’t a systems problem. It’s a judgment problem. It’s an anticipation problem. It’s a “someone needs to protect you from yourself” problem.

Software doesn’t have judgment. Software can’t look at your calendar and realize that back-to-back-to-back meetings on Thursday will leave you worthless for the board prep you need to do Friday morning. Software can’t tell your product lead that no, you’re not available for a “quick sync” because she knows you’ve been in reactive mode all week and need deep work time. Software can’t read the room.

A skilled EA can.

Why Most CTO-EA Relationships Fail

I’ve watched this pattern play out dozens of times. A CTO hires an EA, gives them tasks, wonders why they still feel overwhelmed, and eventually concludes that having an EA “isn’t worth it” for their working style.

The relationship fails. The CTO goes back to doing everything themselves or automates what they can. Another EA gets hired eighteen months later. The cycle repeats.

I coached a CTO last year who had been through four EAs in three years. Four. He was convinced the problem was finding the “right fit.” During our sessions, I started asking questions about how he worked with each of them.

He approved every expense before they could submit it. He wanted to see every email before it went out under his name. He provided detailed instructions for tasks and then revised the output because it wasn’t quite how he would have done it. He kept his own calendar “just in case” and often scheduled meetings directly, creating conflicts his EA would have to untangle.

He didn’t have an EA relationship. He had a very expensive mirror.

The warning signs are consistent across almost every failed EA partnership I’ve seen:

You review everything. If you’re checking every calendar invitation, every email draft, every expense report, you’re not delegating. You’re creating a approval bottleneck with extra steps.

You provide solutions, not outcomes. There’s a difference between “I need you to call the Marriott and book the corner room on the third floor” and “I need a quiet room for focused work during the conference.” The first is task execution. The second allows for judgment.

You feel the need to explain every decision they’ve made. When your EA moves a meeting, do you ask why? When they decline something on your behalf, do you need a debrief? That’s not partnership. That’s surveillance.

Your EA asks permission for everything. This one cuts both ways. If they’re asking before every action, either you’ve trained them to be afraid of your reaction, or they don’t have the context to make decisions. Both are your responsibility to fix.

You secretly keep your own systems. A shadow calendar. A private task list. A personal inbox triage. If you’re duplicating their work “just to be safe,” you’ve signaled that you don’t trust the partnership.

The Joy You’re Missing

I want to talk about something that doesn’t get discussed enough: the joy of this partnership when it works.

There’s a CTO I’ve been coaching for two years. When she first came to me, she was classic startup-scale burnout. Sixty-plus hours a week, constantly in reactive mode, couldn’t remember the last time she had a week that felt like her own.

Six months into our work together, she hired an EA. Not a part-time admin. A professional who had supported C-suite executives for fifteen years.

The first three months were rough. She fought every instinct to control. She bit her tongue when meetings got rescheduled without her input. She felt anxious not knowing exactly what was on her calendar until she looked at it in the morning.

And then something shifted.

She told me about a Thursday when she walked into the office and realized she had two hours blocked for thinking. She hadn’t asked for it. Her EA had noticed the pattern—noticed that she was sharper in meetings when she had prep time, noticed that her Thursdays had become a gauntlet of back-to-backs, and made a decision.

She told me about a conference where her EA had booked her a hotel room on a different floor from the rest of her team. She was initially annoyed until she realized it meant she could actually rest between sessions instead of fielding hallway conversations.

She told me about the vendor meeting that never happened. A sales pitch her EA declined on her behalf because “it didn’t align with your current priorities.” The vendor had gone around her EA to email her directly. Her EA intercepted it, responded professionally, and she never had to spend a calorie on it.

She told me about something else too. Something that surprised her. She started using her EA as a sounding board before difficult conversations. A quick five minutes to vent about a frustrating product decision before walking into the executive meeting. A chance to process her irritation about a missed deadline before her 1:1 with the engineering manager responsible. Her EA became the person who absorbed the emotional weight so she could walk into rooms clear-headed.

And there’s a simpler joy too. The relief of saying “I need Friday afternoon free” and having that be someone else’s problem to solve. Not your problem. Not a puzzle you have to untangle between meetings. Just a statement of what you need, handed off to someone whose job is to make it happen.

That’s not task management. That’s someone thinking about her week more strategically than she has time to think about it herself.

That’s joy.

The Rules of Engagement

If you’ve never had a real EA partnership, there are things you need to understand going in.

The math works in your favor. Dan Martell, in his book Buy Back Your Time, offers a simple formula: take your annual income, divide by 2,000 working hours to get your effective hourly rate, then divide by four. That’s your “Buyback Rate”—the threshold below which you should be paying someone else to do the work. If you’re a CTO earning $400,000, your effective rate is $200/hour. Your buyback rate is $50/hour. Every hour a skilled EA works on your behalf at $75/hour creates $125 in recovered value.

Now think about what that means for you specifically. Every hour you spend on calendar management, expense reports, travel logistics, or inbox triage is an hour you’re not spending on technical strategy, coaching your engineering leaders, aligning with your CEO on product direction, or recruiting that senior architect you desperately need. The EA doesn’t just give you time back. They give you back the right time, the hours you should be spending on the work that only you can do.

You are hiring judgment, not labor. A professional EA isn’t expensive because they can manage calendars. They’re expensive because they can anticipate, prioritize, and protect. You’re paying for the meeting that never got scheduled, the email you never had to write, the decision you never had to make.

Decisions will be made that you don’t understand. This is the hardest part for CTOs. We like to understand systems. We like to know why things work the way they work. In a real EA partnership, you have to accept that sometimes a meeting moves and you don’t know why, and that’s okay. You hired judgment. Let it work.

You cannot control the outcome. If you’re specifying exactly how every task should be done, you’re not getting the value of partnership. You’re getting task execution at partnership prices. Define outcomes. Define boundaries. Then get out of the way.

It takes longer than you think. A real EA partnership takes 6-12 months to mature. The first 90 days are about building context. The next 90 are about building trust. After that, you start to see the leverage. If you’re evaluating at 60 days, you’re measuring the wrong thing.

This is not a part-time job. I cannot stress this enough. A shared admin resource, a project coordinator who “also does EA stuff,” a part-time contractor who manages your calendar—these are not EA partnerships. They might be useful. They are not the same thing. A professional EA needs to be in your context full-time to build the judgment that makes the partnership valuable.

Your 2026 Resolution

Going into the new year, I want you to consider that you might be the reason you don’t have the support you need.

Not because you’re bad at your job. Because you’re too good at it. You’ve survived this long by being the person who handles everything, knows everything, controls everything. That’s how you got here.

It’s also what’s keeping you stuck.

According to a ServiceNow State of Work report, executives spend an average of 16 hours per week on manual administrative work. The equivalent of two full days every week. A Unit4 study across 11 countries found that office workers lose roughly one-third of their working year to administrative and repetitive tasks. That’s 69 work days annually, gone. And research consistently shows that a skilled EA can reclaim 15-20% of an executive’s working hours.

But “skilled EA” is doing a lot of work in that sentence. Most executives don’t have one.

So here’s what I want you to do.

Start by asking yourself an honest question: do you actually want a partner, or do you want an assistant? If the answer is assistant, someone to execute tasks you’ve defined, fine. But stop wondering why you’re still exhausted.

If you want a partner, start with trust. Not trust that’s earned over months of proving competence. Trust that’s given because you’ve decided to give it. Trust that says “I’m hiring you to make decisions about my time, and I’m going to let you make them.”

Find someone who has done this before. A professional EA is not an entry-level role. You want someone who has supported executives, who understands the pace and complexity of C-suite life, who has developed the judgment to know when to protect you and when to push back.

Then give it time. Real time. Not 60 days. Not 90 days. At least six months before you evaluate whether the partnership is working.

And when they make a decision you don’t understand, resist the urge to ask why. Resist the urge to “provide feedback.” Just notice. Notice whether your week worked. Notice whether you had the time you needed. Notice whether you felt protected.

Because that’s what a real EA partnership gives you. Not just time. Protection. Anticipation. Someone whose entire professional purpose is making your week work so you can make your company work.

That’s my wish for you in 2026. Not another productivity system. Not another automation tool. A partner.

I know many brilliant EAs—professionals who have transformed the working lives of the CTOs I coach. If you want help finding your perfect match, send me an email at etienne@7ctos.com.

It might be the most important introduction I ever make.