All Aboard The Onboarding Train!
Fun Fact: This is a picture I took about a decade ago, in the now ghost town of Hinkley, California.
So, you’ve met with a potential new client, and things seem like a good fit… now the real work begins!
I want to share a bit about my approach to onboarding and how to make the most of this formative time together. By this point, you should know your client’s major priorities, the gaps they’re looking to you to fill, and the logistics that make your work possible and supported. You’ll want to keep all of this front-of-mind as you develop a new working relationship, so you can stay focused on what really matters.
I’m going to share some of my favorite questions to help start a new partnership on the right foot.
⭐️ Identify Your Client’s Priorities
These questions help you understand the core essence of your client’s work and goals:
What are the most important aspects of your work right now?
What are your favorite aspects of your work?
What does success look like for you in the next 30, 60, and 90 days?
What are your top three goals for the next quarter?
What immediate deadlines or priorities would you like support with?
What responsibilities or projects must stay on your plate, and what can be delegated?
What are your biggest current challenges or pain points?
What does your daily/weekly routine look like, and is it working for you?
⭐️ Identify the Gaps They Want You to Fill
These questions will reveal your North Star when it comes to prioritizing your time and efforts:
What made you decide to bring on Executive/Admin support or a consultant?
What are your biggest current challenges, pain points, or bottlenecks?
What does your daily/weekly routine look like, and is it working for you?
Imagine a great workday three months from now: what does it look like, and how is it different from your current reality?
⭐️ Logistics
These questions will ensure you have access to the tools and resources you need to get started right away:
What accounts, programs, software, and permissions do I need access to in order to work effectively?
Who should I talk to about setting up access?
Do you use a preferred or organization-wide password manager?
What is your preferred communication cadence for check-ins?
How do you prefer I communicate questions—one-off as they arise, or batched?
Are there specific office hours you’d like me to keep?
What time of day or week do you need me to be most available?
While these three categories cover a lot of ground, I’ve also gathered some questions related to certain scopes of work that I find especially helpful. If any of the categories below pertain to you and the services you offer, I recommend reviewing these lists as well.
⭐️ Daily Rhythm & Working Style
When are you most productive? Are there times you prefer to block for focus?
Are there times you prefer to avoid meetings?
What do you want to be notified about immediately vs. in a daily/weekly digest?
How do you prefer updates—Slack, email, Teams, text, or something else?
What level of detail do you appreciate in updates?
⭐️ Calendar & Scheduling Expectations
What are your non-negotiable weekly commitments?
What is your ideal scheduling buffer between meetings?
Do you prefer meetings stacked back-to-back or spaced out?
Are there recurring personal or wellness blocks I should protect?
What are your preferences around travel time, commute windows, or in-person vs. virtual meetings?
⭐️ Inbox & Information Management
What’s your current system for managing email?
What types of emails would you like me to draft, send, or manage?
What should always stay in your inbox for personal review?
Are there communication threads you want me to monitor or flag automatically?
⭐️ Delegation & Boundaries
What tasks drain you the most that you’d love to offload?
What tasks give you energy and you’d like to keep?
What is fully within my authority to decide on your behalf?
When should I loop you in before proceeding?
How do you prefer I handle unclear requests—check in first, or use my best judgment?
⭐️ Projects, Deliverables & Workflows
What major projects are coming up in the next 90 days?
Any grants, events, deadlines, or reports we should track from day one?
What tools or systems are we using (e.g., Google Workspace, Microsoft 365, Asana, ClickUp, CRM)?
What workflows currently feel clunky or inefficient?
⭐️ Relationship Management
Who are the key stakeholders I should know and understand?
Any important partnerships, donors, clients, or boards I should be mindful of?
How do you like me to represent you in communications?
Is there anything politically sensitive within the organization I should be aware of?
⭐️ Personal Preferences
What is your decision-making style—quick and intuitive, or thoughtful and deliberate?
How do you prefer documents formatted?
Any tone or writing style preferences?
What constitutes an emergency or urgent request for you?
Any personal preferences that help things run smoother (commute considerations, focus needs, etc.)?
Oh! And don’t forget to add a personal touch with … 🪄✨
⭐️ Casual Introductions
When it comes to Executive Support, I love knowing that I’m helping people thrive in their roles—and I also find it rewarding to know that the support I provide helps them enjoy their life outside of work as well. I encourage you to get to know the people you work with. Learn how they spend their time so you can help encourage the work–life balance we all crave.
When you’re not working, how do you like to spend your time?
Who do you spend time with outside of work? (This opens the door for people to talk about family if they want to—without assumptions.)
What does work–life balance look like for you?
Are there ways I can support healthy boundaries for you during your off-time?
I recognize that this list includes a lot of questions. I don’t expect—or necessarily recommend—asking all of them at once. But as someone who genuinely loves starting new projects and bringing on new clients, I’ve found these questions incredibly insightful when tailoring my services. I view onboarding as an exciting opportunity to align on goals, strategize, and organize my starter routine with a new client. Every time I onboard someone, I learn more about the process and find new ways to streamline my approach.
Did I miss one of your favorite onboarding questions? Share below! I’m always refining this list and learning how to ask the right questions to make onboarding as effective as possible.
