How to upskill your executive assistant for long-term success

Learn how to upskill your asisstant

Most startup executives have ever-changing responsibilities. Hiring for a new role was last week’s focus, but this week it’s all about OKR planning for the new quarter. That’s why executive assistants to startup execs can’t be limited to calendar management or team engagement; they must constantly master new skills. How can you upskill your assistant to match the demands of your role and your organization? Here’s how you do it.

Table of contents:

• Identify growth opportunities
• Access training resources and tools
• Measure upskilling success
• Define growth paths for your EA
• Delegate EA training if you’re short on time

1. Identify growth opportunities

The first step in upskilling your assistant is identifying their strengths, weaknesses, and potential for growth. This starts with assessing the current demands of their role and predicting how needs will evolve as your company scales. By spotting growth opportunities for EAs, you can ensure your executive assistant is constantly developing the skills that will help them succeed over the long-term.

Examples by role and industry:

• Series B CEO of a logistics startup
  Emma’s EA, Ana, was initially responsible for managing Emma’s calendar and taking notes during leadership meetings. Over time, Emma noticed that Ana’s impeccable organizational skills and standardized processes in an everchanging business made her a strong candidate for project management. She began delegating more responsibilities to Ana, who took on handling follow-ups on freight logistics. After completing an introductory project management course on Coursera, Ana then began overseeing vendor contracts and shipment KPIs.
• Series E CTO of a cybersecurity SaaS company
  Daniel’s EA, Maria, excelled in managing his email and prioritizing technical communication. As the company grew, Maria assumed responsibility for coordinating engineering and product team workflows. After earning a Scrum Master certification, Maria organized sprint reviews, managed project timelines, and facilitated communication between teams.
• Series C COO of a biotech startup
  Marissa’s EA, Gabriela, initially handled operational tasks like coordinating lab schedules and managing equipment procurement. Recognizing Gabriela’s organizational skills, Marissa encouraged her to complete a data analysis course, which equipped her to assist in tracking clinical trial timelines and budgets.

How can you upskill your EA?

• Conduct monthly check-ins: Regularly discuss your EA’s professional goals and how you can support them to achieve those goals. Use these conversations to evaluate whether their responsibilities align with their interests and strengths, providing consistent executive assistant training along the way.
• Use tools like the Skill/Will matrix: This framework helps map your assistant’s strengths and areas for development. You can assess their current abilities (Skill) and motivation levels (Will) to determine where to focus your efforts.
• Start small: When assigning new tasks, ensure they challenge your EA without overwhelming them. Providing a gradual increase in responsibility ensures they’re not only prepared but also empowered to take on startup executive assistant tasks that support your business’s growth

And if you don’t have the time to do any of the above, hire Viva, a remote executive assistant subscription service that would make the whole process much easier. A dedicated customer success manager will onboard, train, coach, and upskill your EA so you don’t have to worry about it.

2. Access training resources and tools

Once growth opportunities are identified, you need to provide the right resources to support your EA’s development. If they’re the right EA for you, they will use these resources as a starting point, and constantly find new ways to expand their skill set. Upskilling doesn’t have to be expensive or time-consuming; it simply needs to be relevant to your company’s needs and tailored to your assistant’s strengths.

Suggested training resources:

• Coursera and LinkedIn learning: These platforms offer a wide range of affordable, industry-relevant courses that can suit the diverse needs of your assistant. For example, Coursera’s leadership training can help EAs transition into roles like chief of staff, which is crucial as they continue their journey toward long-term EA success.
• Pluralsight: This platform is perfect for technical upskilling. With an abundance of resources focused on software development, cybersecurity, and technical communication, Pluralsight is ideal for EAs in tech-focused startups who need to build startup executive assistant skills.
• Mentorship programs: Pair your EA with senior team members for mentorship. These relationships help them gain hands-on experience and access to more strategic decision-making processes.
• On-the-job shadowing: Allow your EA to shadow you or key decision-makers. This exposure is invaluable for understanding high-level workflows and decision-making processes.

Examples by role and industry:

• Logistics startup (Emma and Ana):
  Ana attended a webinar series on supply chain management and used Asana tutorials to master advanced task tracking. Over time, Ana learned how to coordinate logistics teams and manage shipment KPIs more effectively.
• Cybersecurity SaaS (Daniel and Maria):
  Maria leveraged Pluralsight to learn technical communication skills, ensuring she bridged gaps between engineering and product teams. Daniel also paired Maria with the Head of Engineering for mentorship, where she learned how to facilitate cross-functional meetings.
• Biotech startup (Marissa and Gabriela):
  Gabriela completed a LinkedIn learning program on regulatory compliance, which helped her manage documentation for clinical trials more efficiently. With this knowledge, she improved the accuracy of regulatory submissions and mitigated risks related to non-compliance.

3. Measure upskilling success

If you want to upskill your assistant, keep in mind it’s not just about adding skills—it’s about seeing measurable impact in the areas that matter to you. Think of the upskilling process for your EA in the same way that you’d think about developing a prototype into a scalable product:

1. Foundation building (1-2 months): This is when you identify growth areas for your EA and set clear objectives for their development. The initial stages focus on executive assistant training in core areas that align with their existing strengths.
2. Skill enhancement (3-6 months): During this phase, you assign new tasks that test your EA’s ability to execute. The goal is to ensure they can handle more responsibility and gain proficiency in startup executive assistant skills.
3. Optimization and feedback (6-9 months): By now, your EA should be taking on more significant responsibilities. Measure their efficiency and accuracy as they tackle more complex tasks and build confidence in their new skills.
4. Scalability and autonomy (9-12 months): This is when you evaluate whether your EA is ready for a promotion. Consider moving them into a leadership role, such as Senior EA or Chief of Staff, that will allow them to fully unlock growth opportunities within your organization.

Define benchmarks for success and track progress over time. By setting clear expectations and regularly assessing performance, you can ensure the upskilling process remains on track, ultimately setting you and your assistant up for success. 

Examples by role and industry:

• Logistics (Emma and Ana):
  Ana tracks freight delivery metrics and reduces delays by improving communication with vendors. By using advanced tools, she helps simplify the logistics process, cutting delivery times by 15%.
• Cybersecurity (Daniel and Maria):
  Maria introduced a new workflow for sprint planning that reduces wasted time by 20%, an outcome that helps the engineering team meet deadlines more consistently. She also refines communication protocols, ensuring fewer miscommunications between technical teams.
• Biotech (Marissa and Gabriela):
  Gabriela created a new tracking system for clinical trials, which improves visibility into trial progress. This system reduces errors in regulatory submissions, helping the company avoid costly delays and compliance issues.

Key metrics to track:

• Task completion time: Has the EA’s ability to complete tasks with less oversight improved? This is a critical indicator of the value added through executive assistant training.
• Error reduction: Is the EA’s work becoming more accurate as they gain more skills and responsibilities? This shows growth in their ability to manage complex tasks effectively.
• Feedback from stakeholders: What feedback are you receiving from team members, executives, and other stakeholders about your EA’s work?
• Task complexity: Is the EA taking on more complex and strategic tasks as they upskill? This demonstrates their ability to tackle more leadership-level challenges, enhancing long-term EA success.

4. Define growth paths for your EA

As your EA continues to develop, there are several growth paths they can pursue within your company, helping them stay engaged while contributing even more to you and your team.

Senior EA: For startups where high-level support remains crucial. This role involves providing executive-level support with a focus on strategic initiatives and long-term planning. Senior EAs also manage other administrative staff and mentor newer assistants.

Chief of staff: If your EA has developed strong organizational and leadership skills, they may be a good fit for the Chief of staff role. This role involves overseeing internal projects, managing inter-departmental communication, and ensuring executive priorities are aligned across the company.

Operations lead: EAs with a passion for process creation and execution may transition into an operations role, where they manage workflows, optimize team efficiencies, and oversee day-to-day business functions.

5. Delegate EA training if you’re short on time

Your desire to upskill your assistant speaks volumes about your leadership. But what if you simply don’t have the time to assess their skills, arrange mentorship sessions, or provide tailored training? You’re not alone—many startup executives face the same time constraints. 

At Viva, we understand that while personal growth is crucial, time is the most valuable resource for busy leaders like you. That’s why our customer success team takes on the responsibility of EA upskilling for you. Just share your expectations with us, and we’ll ensure your executive assistant evolves in sync with your needs, providing proactive, flexible, and adaptable support as your business grows.

Are you looking for an executive assistant who can adapt to your company’s needs? Let us match you with the perfect EA to support your startup’s journey. Book a call today.