How to Successfully Onboard a Personal Assistant

Hiring a Personal Assistant (PA) is a valuable step for any executive or organisation. Whether it’s your first time working with a PA or you are rebuilding support after a gap, a structured and well-prepared onboarding process is essential. It sets the tone for the relationship, ensures clarity from the start, and gives your PA the best possible platform to thrive.

At Lily Shippen, we’ve helped hundreds of clients recruit and onboard PAs successfully. Here is our guide to getting it right.

Set Clear Expectations Early

Effective onboarding starts before your new PA has accepted the offer. During the interview process, be clear about what the role involves, what good looks like, and where you see the position evolving over time. This gives candidates the opportunity to assess whether the role is right for them and shows that you’re serious about building a long-term working relationship.

Ask yourself:

• What will success look like in 6 to 12 months?

• What challenges is this role expected to solve?

• How do you ideally want your working day to look once your PA is fully embedded?

These questions help you define expectations clearly and communicate them confidently to your new hire.

Draft a 30/60/90-Day Plan Together

A 30/60/90-day plan gives structure to the onboarding journey and creates alignment from the outset. Drafting it ahead of time and sharing it during the interview stage shows that you are proactive, organised and serious about the hire. Crucially, it also invites the PA’s input. If they are experienced, they may spot opportunities or risks you hadn’t considered.

Below is a more detailed example of how this plan might look:

Days 1 to 30: Learn, Observe and Build Foundations

• Meet key internal and external stakeholders

• Shadow the executive to understand working style, communication preferences and typical challenges

• Review and organise the calendar and inbox, identifying quick wins

• Gain access to all necessary systems and tools

• Understand current administrative workflows and processes

• Begin managing the diary and supporting meeting preparation

• Sit in on team meetings to understand wider business context

• Identify where the PA can take ownership early on

Days 31 to 60: Take Ownership and Add Value

• Manage diary and inbox independently, with regular check-ins

• Begin handling travel arrangements, expenses and meeting logistics

• Prepare briefing materials and follow-ups for key meetings

• Introduce efficiencies across administrative processes

• Set up systems for task tracking, reminders or reporting (depending on the executive’s needs)

• Build relationships with external stakeholders or clients where relevant

• Proactively flag gaps or opportunities to improve support

Days 61 to 90: Embed, Optimise and Begin Driving Change

• Fully embed into the executive’s rhythm and routines

• Take ownership of recurring tasks such as board packs, project timelines or reporting

• Begin implementing improvements to systems or workflows

• Offer solutions to reduce the executive’s time spent on routine admin

• Agree personal development goals aligned with the business

• Conduct a review of onboarding progress and set OKRs for the next quarter

Define Objectives and Areas of Accountability

Alongside the 30/60/90-day plan, set clear objectives and define who owns what. Objectives should be measurable and time-bound. For example:

• Reduce scheduling conflicts by 80 percent in three months

• Respond to all inbound scheduling requests within 24 hours

• Create a centralised filing system for all key documents within six weeks

Accountability is just as important. A lack of clarity can quickly lead to duplicated effort or tasks falling through the cracks. Be explicit about which areas the PA owns fully, such as:

• Travel and accommodation bookings

• Meeting agendas and minutes

• Expenses submission and reconciliation

• Office management duties (where applicable)

Consider the Role Beyond the First 90 Days

A strong onboarding process should not only support the transition into the role but also lay the foundations for growth. Think ahead to how the role could evolve in the next 6 to 12 months. Could your PA take on project coordination, internal communications or office-wide initiatives? Could they become a point of contact for external partners?

Having a long-term view helps you identify potential gaps now and gives your PA the opportunity to develop in a way that aligns with your needs.

Leverage Technology and AI Thoughtfully

As part of the onboarding process, consider how tools such as AI can enhance the role of your PA rather than replace it. Automation can streamline diary scheduling, summarise meeting notes or generate draft communications. When paired with a skilled PA, these tools can free up more time for strategic and relationship-driven work.

Discuss early on what tools you’re already using, what your PA has experience with, and where you might benefit from new solutions. If your PA is confident using AI tools, encourage them to experiment with integrating them into their workflow.

Be Ready Before Day One

A strong onboarding experience begins with being prepared. Too often, executives are excited to bring someone on board but forget the basics. This delays progress and gives the wrong first impression.

Before your PA starts, ensure:

• The equipment is ready and tested

• System access and permissions are in place

• Key documents and processes are shared

• The wider team knows who the PA is and what they will be doing

Whether the onboarding is remote or in person, these steps show respect for your PA’s time and reinforce that they are a valued member of your team from day one.

Effective PA onboarding is about more than just logistics. It’s about clarity, consistency and collaboration. Done well, it sets the tone for a high-impact partnership and builds the trust that is essential to a successful executive-PA relationship.

At Lily Shippen, we go beyond recruitment. We help our clients define roles clearly, set expectations from the start, and build working relationships that last.

If you’re hiring a PA or reviewing how to onboard one effectively, we’d be happy to support you.