Every assistant offers help, but not every kind of assistant delivers the same partnership.
By the time most executives reach out to us, they’re not wondering if they need support, they already know they do. The real question is: What does great support actually look like in practice?
We sat down with four business leaders and their Boldly Executive Assistants to find out. Each pair joined us on a video call to talk about their working relationship, and what emerged wasn’t just a collection of task lists or efficiency metrics.
What we heard was partnership.
The kind where an EA anticipates needs before they’re voiced. Where trust runs deep enough that decisions get made with confidence. Where both people bring their best to the table because they genuinely want to see each other succeed.
Here’s what these business leaders and their executive assistants had to say about working together.
When You Know, You Know
For Tracy, a business leader who connected with her EA Erica, the match felt right from the start.
“I had a conversation with Erica, and in the first 15 minutes, I was like, ‘Yep, I love her. She’s the one.’ And we’ve been inseparable ever since.”
That instant connection wasn’t one-sided. Erica felt it too.
“I loved her. I wanted to support her. I wanted to help her grow her business. I wanted to be part of her team. We just had synergy from the very beginning. We think a lot alike. We operate a lot alike.”
This kind of connection is what happens when the matching process goes beyond skills and experience to consider personalities, working styles, and values. A great EA partnership is built on mutual respect and shared goals.
Experience That Speaks For Itself
Matt, another CEO in our conversation, had worked with assistants before. But his experience with Natasha, his Boldly EA, was different.
“Every time I think I have a good idea of something, she’s already done it for 10 or 15 years, which I have to say is a major credit to her. But also what Boldly’s been able to do, because I’ve had other assistants in the past that didn’t have that kind of background.”
That depth of experience makes all the difference. A premium executive assistant doesn’t just complete tasks, they bring a toolkit built over years of supporting senior leaders. They’ve seen the patterns. They know the pitfalls. They can anticipate what’s coming because they’ve navigated similar situations dozens of times before.
Natasha’s approach reflects this level of strategic thinking:
“You have to be mindful of what their needs are to make sure that they’re successful. So going in, one of the first things I had said to him was, ‘What can I do to help you succeed and get what you want from your business?’”
Natasha is an excellent example of an EA that does not need to be told what to do. She stepped into her partnership with intention, asked the right questions upfront, and positioned herself to deliver real value.
Thinking Ahead, Not Just Getting Things Done
Thana, a business leader at Gramercy Consulting, pointed to one quality that sets her EA, Jenny, apart from the support she’s worked with in the past.
“There’s a lot of really great folks out there that can provide support to executives, but you have to lay everything out, you know. But Jenny has always been somebody who anticipates my needs. She’s always thinking ahead, and that really helps. She doesn’t just get the scheduling done. She’s thinking about impacts.”
That proactive mindset is the hallmark of a high-level executive assistant.
Anyone can manage a calendar. A premium EA manages it strategically, considering not just availability but priorities, relationships, energy levels, and downstream effects of every decision.
Jenny understands that her role goes beyond execution. She’s representing both her client and Boldly in everything she does.
“I’ve worked for clients before, and sometimes it’s really hard for them to let go of control. With Thana, I have full permission to access her calendar, and she trusts me to make decisions. I’m a reflection of Gramercy Consulting, and I’m a reflection of Boldly.”
That level of trust doesn’t happen overnight. It’s earned through consistent judgment, reliability, and a genuine commitment to doing excellent work.
The Details That Make All The Difference
Kim, our fourth business leader, saw the difference right away when she started working with her EA Stacy.
“She did things that she heard, and I didn’t even ask her to do. And I was just amazed at how on the ball she was. And she actually made my office so organized.”
This is what proactive support looks like in action. Stacy wasn’t waiting for a detailed task list. She was listening, observing, and taking initiative to solve problems before they were even articulated as needs.
For Stacy, the connection was just as immediate.
“Right away, I could tell when I talked to Kim that it was going to be a good match. It’s just the personalities, like she said, that feed off of each other. I didn’t feel nervous. I just felt like there was a good connection.”
When both people feel that connection, the working relationship becomes more than a transaction. It becomes a true partnership where both sides are invested in success.
What Makes These Partnerships Work
Across all four conversations, specific themes emerged that explain why these EA partnerships deliver such strong results:
- Genuine chemistry matters. The best working relationships start with a natural fit. When personalities align, and working styles complement each other, everything else flows more easily.
- Experience creates confidence. Business leaders trust their EAs to make essential decisions because those EAs have years of experience in similar situations. That background translates to better judgment, fewer mistakes, and faster problem-solving.
- Trust goes both ways. These partnerships work because both people respect each other’s expertise. The EA trusts the executive to provide direction and context. The executive trusts the EA to make wise decisions and represent them well.
- Shared investment in success. When an EA genuinely wants to see their executive and their business thrive, it shows in the quality of their work. And when an executive values their EA’s contributions, that appreciation creates a positive cycle of excellence.
The Boldly Difference
These aren’t typical virtual assistant relationships you can find just anywhere. They’re high-level partnerships between experienced professionals.
This is what happens when you match senior executives with premium executive assistants with Fortune 500 backgrounds. You get people who understand not just how to complete tasks, but how to think strategically about business priorities. Who bring emotional intelligence, business judgment, and years of experience supporting leaders at the highest levels.
As Hollie Swofford, Boldly’s Director of Team Operations, explains: “Executive assistants are generally caretakers. They get a lot of energy in their work from making the lives of other people easier, more organized, really showcasing a lot of care for their executives behind the scenes so that their executives can focus on meaningful work to move the organization forward.”
With Boldly’s subscription-staffing model, you get access to this level of premium support for just the hours you need. You work with highly qualified, personally matched remote talent without the hassles of recruiting and employment, at a lower cost than traditional hiring.
The result? Partnerships like the ones you just read about.
Relationships where both people bring their best, where trust runs deep, and where real business impact happens every single day.
Because at the end of the day, the right executive assistant doesn’t just help you get things done.
They allow you to operate at an entirely different level.
