A 90 day check in can clarify expectations in executive assistant jobs Chicago.

Starting a new assistant role means learning more than the software and office routines. You are also getting a feel for how your executive likes to work, what needs a quick response, and which details matter most to the wider team. Those preferences are not always written down.

A check in around the three month mark gives you and your manager a quiet moment to compare notes. You can share what is going well, ask about anything that still feels unclear, and find out whether your work matches what the role needs. It is a normal working conversation, not a test you have to pass.

In executive assistant jobs chicago, responsibilities can differ a lot from one employer to another. The same job title might mean calendar management in one office and project coordination in another. Use the conversation to learn what success looks like in your particular role, rather than guessing from a general job description.

Before the meeting, take a few minutes to look back at your first weeks. Note tasks you now handle smoothly, situations where you needed more direction, and work that took longer than expected. Keep your notes factual and brief. You do not need to create a formal presentation.

It also helps to look at your calendar, task list, or project notes so you can bring a few specific examples. If you have managed a busy scheduling change or improved a handoff, mention what you did and what changed for the team. Examples make it easier to talk about your contribution without overselling it.

A useful question is, “What would you most like me to be doing consistently by now?” It invites a specific answer and helps you see whether your manager has a different priority in mind than you do. You can follow up by asking what to focus on over the next month.

You can also ask which tasks are most time sensitive, how much independence your manager expects, and what they would like you to flag sooner. These questions help turn broad feedback into choices you can make during an ordinary workday.

The details matter. If your manager says communication should be more proactive, ask what that means for them. They may want a short update before a deadline, a message when a decision is needed, or fewer routine check ins. Confirming the preferred approach can prevent avoidable misunderstandings.

Many assistants become the person everyone asks for help. That trust can feel good, but it can also leave you switching between requests without knowing what matters most. Use the check in to review your current responsibilities and ask whether anything should be handled differently.

When you discuss executive assistant job duties, bring up the work you do regularly as well as tasks that appear only now and then. You might ask which requests you can accept independently, which ones need your executive’s approval, and how to handle two urgent demands at once. Clear boundaries help you support people without making promises you cannot keep.

If your manager wants you to take on a new project, ask what should move down the list to make room. This is not refusing work. It is making the tradeoff visible so you can deliver well on the most important tasks instead of quietly stretching your day too far.

If something has been difficult, describe the situation plainly and explain what you are trying. For example, you might say that meeting changes are sometimes reaching you after invitations go out, then ask how the team would like those changes shared. A specific issue is easier to solve than a general feeling that you are falling behind.

If you have made a mistake, be direct about what happened and what you have changed. Perhaps you added a reminder to a planning process or started confirming an important detail in writing. Showing the adjustment helps your manager understand that you are learning and taking responsibility.

You can also ask for training or context if a task depends on knowledge you have not yet had a chance to build. In assistant jobs office teams, that might mean learning a booking system, understanding an internal approval process, or getting more background on a project. Ask who can help and when you can practice.

Before you wrap up, repeat the main priorities in your own words. For example, confirm that you will focus first on calendar accuracy, then take on more travel planning once the new process is clear. This gives your manager a chance to correct anything you have misunderstood.

Agree on a simple way to check progress. You might set a date for another short conversation, or decide to share a brief update after a new responsibility has been in place for a few weeks. Keep the plan manageable so it supports your work instead of becoming another task to maintain.

Afterward, write down the decisions and any follow up you promised. A short, friendly note can help both of you remember what you agreed. Then give yourself time to put the feedback into practice. You do not need to perfect every part of the role at once. A clear next step is a strong result from the meeting.