Practical Tips on How to Successfully Onboard With A New Executive

When it comes to the job searching, the onboarding process isn’t usually first in priority. Expectations typically hinge on benefits, pay range, working setup, flexibility, responsibilities, and all the other factors that impact our financial success and well-being in the organization. And while all of those are important, onboarding impacts one very important facet of your career: functional and relational success.

While onboarding is a relatively short process compared to your years of tenure in a company, its value is in the fact that it will set the direction of your career in any organization. From the pre-onboarding to the end of your 90-day nesting period, you are setting up foundations that will clarify and establish boundaries, relationship dynamics, and expectations with your colleagues and executives.

We know this is easier said than done, that’s why we invited Ebony Belhumeur to the High Performing EA Summit to share her valuable insights into how you can onboard with a new Executive and set yourself up for success in your new EA role. She is a highly-respected and successful Executive Assistant with an incredible track record of supporting CEOs from Protocol Labs, Twitch, and Sephora. We’d even bet to say that she’s lived the corporate dreams that some of us EAs have always wanted.

So, how about we get to it?


The onboarding process is in three different stages: pre-boarding, onboarding, and landing. Ebony emphasizes that regardless of what stage you’re at, learning is essential. You have 90 days to prove yourself in a new role, so the steeper your learning curve is, the more likely you are going to be seen as a high-impact contributor.

When you join an organization, it’s already a moving train. Their operations are moving as usual; there might already be a pile on your desk and the inbox is already full. This makes you feel like you’re already sinking and doesn’t set you up for success. It’s times like these that it can be tempting to neglect onboarding with your Executive to catch up with the tasks. 

In some instances, you might find yourself in a position where your onboarding is more passive. You were simply required to complete a set of documents and then you’ve been given autonomy in your role after. It’s easy to feel like the onboarding is already successful because you went through the motions but it served no intrinsic value to your functional success in the organization.

So, whatever status your organization has, make it a point to proactively manage your own onboarding.

The secret? Onboarding yourself. 

Approaching your onboarding with initiative and an active learner’s mindset will make a big difference in walking aimlessly through your first evaluation versus a strategic position for your role and function. 

If it’s not happening correctly or at all, take control of your growth and trajectory. Initiate your own onboarding.


This starts in the interview and is the best time to be curious. 

As you talk to the organization, be deliberate in discovering more about them. Most people will skip this step because they are so eager to start a new role, but that can be costly in the long run. Here are some things to help guide you:

Questions to Ask
  • Why are they hiring now? The answer you’re looking for is something that allows you to understand what’s going on in the organization and how structured they currently are. Does the organization have a place prepared for you or are they just throwing things against the wall and hoping that something sticks?
  • What set the previous person up for success and what were their gaps? The answer you want is something that allows you to easily replicate successes and avoid gaps and mistakes. Write those things down and make sure you stay away from them.
  • How does the organization handle failure? Do they punish or provide coaching and support in times of failure? If they can’t specifically answer this, you might want to reconsider whether this organization is the right fit for you. 
What to Know
  • Industry information. Opportunity favors the ready, and that is preceded by putting in your due diligence. Come prepared for the interview and absorb the industry landscape as much as possible. 
  • Challenges and company goals. Once you’re hired, be strategic in your contributions. Find out current challenges your team and Executive are facing alongside the company goals. The challenges can serve as your starting point and the goals as the north star in how you can strategically bring value to the organization.
  • Organizational makeup. It’s imperative you know the people you are working with. This is where you learn where is everyone from. Are they all old friends? Who are the people they usually hire? Understanding the organization's makeup can be your secret weapon so you don’t get alienated or surprised because you know the people who you will be working with.
Things You Can Do
  • Connect.  Reach out to everybody who will be in your immediate team on LinkedIn or any professional platform. Relationships are critical to your success.
  • Familiarize yourself with their tech stack. If you aren’t familiar with the tools they currently use, then learn about them as fast as you can.

This is the time when candor will be essential. They say feedback is a gift, but it’s more than that – it’s an asset especially if it’s actionable and timely. So, proactively initiate conversations to ask for it. Getting feedback right away will be instrumental in your growth and calibration to contribute to the organization effectively. There’s no better time to ask for and establish clarity in your role and expectations than at this stage. 

Questions to Ask
  • What are the expectations your lead has for you in this role? You need to understand clearly what they expect of you, so you know the target you’re aiming for with clarity. So, ask your Executive: what does your role look like from their POV? 

You also need to share specifically and succinctly any relevant concerns and feedback that you have during this time to establish clarity from the start. If you cannot communicate this to your executive the right way, your relationship will crumble. No matter how smart or how many problems you solve, if you cannot clearly and succinctly talk about expectations, your relationship can have potential problems.

  • How did we get here? How did the status quo get to be the status quo? The point is to understand the lay of the land. With any operational or behavioral observations, it would help if you first start asking how did it get to be the standard or routine.

What to Know
  • Understand your work scope clearly. You need to understand what you’re accountable for and not.
  • How/why decisions are made. Is it by influence or metric? If it’s by influence, you need to know who is the influential decision-maker in the organization. If it’s by metrics, ask what the metrics they prioritize and value.
  • What’s working well. Things that are already working should be sustained and continually built upon. 

Things You Can Do
  • Sit in meetings. This is critical because it’s important for you to know where the wind blows.
  • Educate your Executive. Sometimes, your Executives won’t know how to leverage your strengths. This is your chance to let them know what you can do and bring to the table.
  • Give upward feedback to your Executive. Learning how to do this effectively and with tact is an incredibly nuanced skill, but if you do it in the right manner and setting, this can prop you up as a reliable partner to your Executive.
  • Listen first before putting into action. You need to strike the right balance between doing, making things happen, and being (observing, learning, and listening). We tend to come in with a bias toward action but this can often get us into trouble because we’re usually operating with partial information. The reality is when we display a genuine desire to learn and to understand things deeply, people trust us more. 

This is where you work toward concluding your 90-day nesting period with flying colors and talk in detail about your growth and development.

Questions to Ask
  • How would your lead like to see you grow and develop in the next 12 months? You should be delivering this information before the period ends because you need to give them nuggets to think about before your 90-day review.
  • What would need to happen? Always ask what-would-need-to-happen questions to identify the pieces you need to build wins. For example:
  • What would need to happen in order for…?
  • What would need to happen so that we could…?
  • What would need to happen in order for me to launch this great project?
Things to Know
  • You need to know every key stakeholder. That means having 1on1s with your Executive’s direct reports. Be deliberate in talking to them, getting to know them, and befriending them. In the process, learn about their backgrounds and fish for helpful information like the pieces that they think are working and successfully being done (and vice versa). People typically will be a bit more candid with the assistant than with the Executive, so position yourself to acquire the information that’s going to provide color and texture to the lay of the land.
  • Protocols and processes. Your goal is to learn how to navigate the unwritten rules that get things done. This is one of the things a lot of people just don’t pay attention to because there are written rules. However, figuring out the delta between these two and what actually happens is the kind of nuance that the best assistants have.
  • Culture. The last thing you want is to execute all your strategic and tactical to-dos well, only to have a bad relationship with someone in the organization or unintentionally make the wrong impression. So, learn the political and social faux pas you need to stay away from.

Things You Can Do
  • Integrate organizational norms. You need to be one of them. Understanding what language and jargon folks are using and then using those in public forums and meetings is essential in making people start to understand that you are one of them.
  • Prioritize strategically. Effective prioritization is more than just a list in the order of what’s due. It requires strategic thinking and the ability to work backward and an understanding of ROI, so you can do the work that matters. Your goal isn’t just to complete a due date list but deliver high-impact work that drives results and supports your corporate goals. Remember that putting out fires all day won’t move you to the next level, strategy will.
  • Engage your community. Join relevant community channels to engage with people on the team. Relationships are important not just for harmony and collaboration in your workplace but also for building a great network.
  • Sustain the success that is already in place. The reason why you have to ask what’s going well in onboarding is that you should make it a point to continually sustain success. People might not recognize your small wins but when things start going wrong that was already going well, that’s when people second guess your value and contribution to the team. You want to be a team member who helps to continually build the momentum of success, not slow it down. 
  • Reset your boundaries in your 90-day meeting. Let your team and Executive know your boundaries; whether that’s related to untimely feedback, personal time, or any other area of your working relationships and dynamics that need to be recalibrated. This is essential in building a healthy and collaborative working relationship with them.