Great executives don’t scale alone; they scale with support. A skilled executive assistant (EA) is the operational backbone behind fast-moving founders and business leaders, handling communication, scheduling, follow-ups, research, documentation, and the dozens of tasks that keep work flowing smoothly.
But as the demand for high-performing remote support grows and U.S. hiring costs rise, more companies are turning to nearshore talent in Latin America to hire full-time executive assistants who are reliable, proactive, and aligned with U.S. working hours.
Nearshore hiring brings together what busy executives need most: cost-effective staffing, strong English communication skills, cultural alignment, professional tech-savvy talent, and real-time collaboration (no middle-of-the-night message delays).
Still, not every EA you find online is equipped to operate at an executive level, and hiring the wrong person can lead to missed deadlines, communication gaps, and costly inefficiencies.
In this article, you’ll learn five proven tips to help you identify, evaluate, and hire the right nearshore executive assistant, someone who can help you stay organized, keep priorities moving, and protect your time so you can focus on high-impact work.
Why Nearshoring for Executive Assistants Makes Sense
Nearshoring enables companies to assemble high-quality support teams without compromising collaboration, professionalism, or productivity. Unlike offshore talent located in Europe, Africa, or Asia, nearshore executive assistants in Latin America share overlapping working hours with U.S.-based founders, resulting in faster responses, real-time problem-solving, and smoother communication.
Beyond timezone alignment, Latin America offers a strong pool of experienced administrative and operational talent with backgrounds in startups, tech companies, customer service, project coordination, and executive support roles. Many speak excellent English, are familiar with Western business etiquette, and already work comfortably with U.S. tools such as Google Workspace, Slack, Notion, HubSpot, Trello, Asana, Zoom, and AI productivity apps.
Companies also benefit from significantly lower hiring costs without compromising on professionalism, reliability, or ambition. In other words, nearshore hiring isn’t just about saving money; it’s about expanding access to top-tier talent while improving operational capacity.
Tip #1: Clearly Define Your Support Needs and Work Style
Before reviewing candidates, take time to map out the specific responsibilities, expectations, and working preferences for your executive assistant. The role can vary widely depending on the leader and business stage, so clarity is crucial, not only to attract the right candidate, but also to evaluate them fairly.
Start by listing your recurring tasks and typical bottlenecks. These may include inbox management, calendar coordination, travel planning, meeting preparation, research, document creation, CRM updates, customer follow-ups, vendor communication, or personal-administrative support. Then outline the tech stack your EA will use, such as Notion, Google Workspace, Slack, HubSpot, ClickUp, Trello, or AI copilots.
Next, define your personal working style. Do you prefer asynchronous updates or frequent check-ins? Short messages or detailed notes? Do you want your EA to act only on instructions or to anticipate needs and make decisions with limited guidance proactively?
The more specific you are in writing, the easier it becomes to identify candidates who naturally fit your workflow, communication habits, and expectations.
Tip #2: Verify Skills With Practical, Real-World Competencies
A strong executive assistant is measured by output, judgment, and proactivity, not just a polished résumé. Instead of focusing only on past job titles, evaluate the actual skills the candidate brings to the table and how well they can adapt to your workflow, pace, and level of responsibility.
Look for experience in areas such as calendar and inbox management, document drafting, client communication, project coordination, and executive-level decision support. They should also demonstrate competency with productivity software, scheduling tools, and automation platforms (Calendly, Notion, ClickUp, Asana, Slack, Google Workspace, AI writing and summarization tools, CRM systems, and file-sharing platforms).
The best nearshore EAs go beyond task execution; they can anticipate, structure, and prioritize. During interviews, ask behavioral questions that reveal problem-solving, attention to detail, and situational judgment, for example:
- “Tell me about a time you prevented a scheduling conflict before it happened.”
- “How do you organize an inbox with hundreds of unread emails?”
- “What would you do if a client or vendor asked for something you weren’t authorized to approve?”
Consider adding micro-tests such as:
- drafting an email reply based on a short scenario
- turning raw meeting notes into a structured summary
- building a one-week executive schedule given priorities
- identifying missing deadlines from a sample task list
This approach helps you assess real-world accuracy, communication tone, organization, and initiative, all crucial traits for long-term success.
Tip #3: Evaluate Communication, Professionalism, and Responsiveness
An executive assistant is often the face and voice of the executive they support, which means communication is not just a skill; it’s a core success factor. When hiring a nearshore EA, assess how clearly, confidently, and professionally they communicate across written, verbal, and asynchronous channels.
Consider how quickly they respond, how well they interpret instructions, and how effectively they confirm details before taking action. A strong EA should be able to summarize information, ask clarifying questions when needed, and deliver updates without prompting. They should also communicate in a tone that reflects your leadership style, whether formal, neutral, upbeat, or concise.
During the interview and screening process, pay attention to subtle cues:
- Do they proofread messages before sending?
- Do they confirm next steps after meetings?
- Do they provide solutions instead of waiting for direction?
- Do they accurately record and document decisions?
- Do they communicate confidently in English across email, chat, and video?
Professionalism also matters. Notice punctuality, follow-through after the interview, preparedness, and reliability. If they arrive late to the interview or forget to follow up as agreed, treat it as real-world performance, because it is.
Tip #4: Assess Tools, Digital Fluency & Process Orientation
Modern executive assistants are no longer limited to scheduling and email; they are digital operators who must navigate multiple platforms, automate repetitive work, and structure information in ways that reduce your mental load. When interviewing nearshore talent, look for candidates who are both comfortable with technology and able to create or improve systems, rather than just following them.
Strong EAs should be familiar with business tools like Google Workspace, Notion, Slack, Zoom, HubSpot, Monday.com, Asana, Trello, Miro, and AI productivity tools for drafting, research, and summarization. Equally important is process thinking: how they organize information, streamline communication, document procedures, and build repeatable workflows that reduce your dependency on verbal instructions.
Ask about tools they’ve implemented, workflows they’ve built, and how they handle documentation. A proactive EA might show you color-coded workflows, SOP templates, naming conventions, dashboards, or automation shortcuts. The best candidates think like systems designers; they don’t just complete tasks, they future-proof them.
Tip #5: Start With a Paid Trial to Validate Real-World Fit
Even the most impressive interview and résumé can’t fully guarantee long-term fit, which is why a short, structured paid trial is one of the most effective ways to validate performance, communication style, responsibility levels, and chemistry.
A trial can last anywhere from one to four weeks, depending on your workflow and the urgency of the matter. During this period, assign real tasks that reflect the complexity and pace of the role, rather than just simple administrative duties. Examples include:
- managing your inbox using agreed-upon filters and categories
- coordinating upcoming meetings and preparing agendas
- drafting follow-up messages after calls or events
- building or improving a productivity dashboard or weekly report
- documenting processes or SOPs you’ve never written down
Don’t just observe what they deliver; observe how they manage priorities, clarify details, track actions, handle ambiguity, and communicate progress.
By the end of the trial, you should clearly know whether this person:
- makes your workload lighter rather than heavier
- requires less supervision over time
- shows initiative rather than waiting for instructions
- communicates with clarity, accuracy, and accountability
If the trial proves successful, you can move into a long-term agreement with confidence. If not, you can exit respectfully and continue your search without costly misalignment.
Red Flags to Watch Out For
Not every candidate who markets themselves as an executive assistant has the right mindset or operating discipline for executive-level support. To avoid costly mismatches, watch for signals that indicate a lack of structure, limited judgment, or low ownership. Common warning signs include:
- Slow or inconsistent communication — long response times, vague updates, or unclear messaging are major risks in a role built around urgency and clarity.
- No examples of systems or processes — strong EAs can demonstrate how they organize work, track deadlines, or document procedures.
- Needs constant supervision or instructions — if they can’t move a task forward without hand-holding, you’ll become the bottleneck.
- Unfamiliar with modern productivity tools — even if they learn quickly, this creates early friction and slows execution.
- Uncomfortable asking clarifying questions — high-level support requires proactive alignment, not guesswork.
- Focuses on tasks, not outcomes — an EA should understand why a task exists and how it ties to the executive’s goals.
- Lack of discretion or professionalism — oversharing, informal communication, or mishandled confidential info are critical red flags.
A great executive assistant makes you faster and more effective. A misaligned hire creates more work, more risk, and more stress; the opposite of what you need.
The Takeaway
Hiring the right nearshore executive assistant is all about finding a trusted partner who can help you operate with clarity, stay organized, protect your priorities, and reduce the friction that slows leadership down.
With clear expectations, skill-based evaluation, strong communication standards, modern tool fluency, and a structured trial period, you can confidently select an EA who adds long-term value and becomes an extension of your leadership style.
If you’d like help finding pre-vetted, English-speaking executive assistants in Latin America who are ready to work U.S. hours and integrate seamlessly into your workflow, South can help. We match you with vetted professionals based on your needs, tools, pace, and leadership preferences, without hidden markups or hiring headaches.
Build your executive support the smarter way. Book a call with South today!
