I can teach anyone to be organized. Systems, workflows, calendars, all of it. What I can't put in a training doc is how to make it land with people. That's the secret ingredient, and it's what makes an EA, a Chief of Staff or a COO truly great.
I can teach someone to be incredibly organized.
I can teach systems. I can teach workflows. I can teach how to run a calendar, prep a board meeting, track every commitment and never drop a ball. I can teach all of that with complete accuracy, and the person will do it well.
What I can't teach in a training doc is how to implement it with people. How to read the room. How to know what someone needs before they say it. How to bring a change to a team that's nervous about it.
That's the secret ingredient. And after years as an executive assistant, then a Chief of Staff, then a COO, I've come to believe it's what makes these roles so valuable.
It starts as a calling
Being a great executive assistant is a calling. It's close to being a concierge. Your clients are your CEO, your leadership team, the people you support every day, and your job is to anticipate what they need before they need it.
The hard skills are real and they matter. Knowing who's going to be in the room before every meeting and event. Knowing which VIPs need special care. Tracking the dates that matter to people. Having the briefing ready before anyone asks.
But the hard skills only get you halfway. The other half is emotional intelligence and empathy.
Celebrating people is the example I always come back to. Everyone likes to be appreciated, but not everyone likes it the same way. One person lights up with balloons on their desk and a shout-out in front of the whole company. Another would be mortified by that, and a handwritten note left quietly on their desk means the world to them. One executive wants their birthday celebrated with the team. Another would rather nobody mention it at all.
No system tells you which is which. You learn it by paying attention to people. That's the difference between support that checks the box and support that people remember for years.
Chief of Staff: strong in a different way
When you step into the Chief of Staff seat, the job changes. You still anticipate, but now you also remove barriers.
That's harder than it sounds. Removing barriers means stepping into the friction. Two teams that don't agree. A project stuck between departments. A decision that's stalled because someone is uncomfortable. A lot of the time, you become the person who manages conflict and gets people unstuck.
To do that well, you need real insight into people. What's actually driving the disagreement. Who needs to be heard before they can move. Who needs a direct conversation and who needs a softer one. You have to be very human about it, and very steady at the same time.
COO: carrying your own authority
Then comes the COO seat, where you carry the authority yourself.
This is where the two roles before it pay off. Being an EA teaches you to see situations from every angle. Being a Chief of Staff teaches you how to approach people, how to talk to them, and how to move a group that doesn't want to move. By the time you're a COO, you've spent years learning how your words land. That makes you a better leader, because you know authority alone doesn't bring people with you.
The piece most roles are missing: change management
If there's one place the soft skills matter most, it's change.
When a company brings in new software, changes a process, or restructures how work gets done, it can feel threatening to the people living through it. Even good changes can feel intimidating.
If you want a change to go well, you need transparency. Not just a memo, but transparency shared in a way that actually reaches people. Why we're doing this. What it means for you. What isn't changing. Where you can ask questions.
That's the work EAs, Chiefs of Staff and COOs do every day, often without anyone calling it change management. It's also exactly why so many rollouts stall when nobody owns that part.
The balance is the magic
Hard skills build the system. Soft skills make it work with real people.
You need both. A beautifully organized calendar doesn't help if the executive doesn't trust the person running it. A perfect process doesn't help if the team resists it. The balance between the two is what turns a capable person in one of these seats into someone a company can't imagine running without.
If you're hiring for one of these roles
Test for the hard skills, but don't stop there.
Ask how they'd handle a delicate moment, like recognizing someone who hates the spotlight, or two leaders who won't agree. Ask about a time they had to bring a team through a change. Listen for how they think about people, not just process.
And once they're in the seat, give them what they need to do the human part well: regular time with you, the why behind your decisions, a seat in the rooms where things get decided, and a few months to learn how your organization really works.
The systems can be taught. The secret ingredient is what you're really hiring for.
If you're a founder deciding whether you need an EA, a Chief of Staff or a COO, let's talk.
