How to Get Past the First Mistake With Your Executive Assistant

Let’s put this out there – we’ve all made a mistake at work at some point!

It’s part of the human condition that we’re bound to forget something, or mess something up from time to time. For most, it leaves you with that horrible, sinking feeling. You worry that it’s going to lead to severe fallout, for your company, your boss, and yourself.

We’ve been thinking about mistakes and how to get past them when working with executive assistants. After all, while executive assistants tend to be part magician, they’re also human! 

As a manager or employer, it’s easy to be frustrated in the moment, but it’s also important to think about the outcome you’d like. Is one mistake a total deal-breaker?

As an executive assistant, you’re probably feeling mortified and want to know how you can make up for your mistake.

We’re taking a look at both sides of the coin here, with a section for employers and another for executive assistants on getting past that first mistake.

For employers…

First, it’s a good idea to pause for breath, especially if you want to preserve the relationship with the executive assistant (or other employee for that matter). Employees will join companies that they’re enthusiastic about working for, but quit managers. This often happens if they feel they’ve been treated unfairly or demoralized in some way.

Something like being harshly berated might fall under “unfair treatment” in the eyes of the employee. While your gut reaction might be to show anger or frustration, you tend to get further if you can keep a more even-tempered approach.

With that said, some steps to get past that mistake might include:

Check that anything urgent is done

Does the mistake mean that something needs urgently correcting? A good executive assistant will immediately take responsibility and be doing what they can to rectify the mistake, but you could still check whether there’s anything they need your help to fix. (For example, whether your influence is needed in contacting someone else).

Identify what led to the mistake

Asking open-ended questions can help, as well as encourage the EA to speak up. “What could we have done differently” or “how can we make sure that the instructions are clear?” are good examples of questions that encourage discussion without assigning blame.

Consider whether anything outside of the EA’s control could have contributed too. For example, if information was missing that they were unaware of, or if they were hampered by a lack of response from someone else. 

Another thing to look at is whether workload is a factor at all. If they simply have too much on their plate, then error is made more likely.

Work through the mistake

Make sure that both you and the EA have a good understanding of how the mistake happened and what can be done to prevent a similar episode from happening again. Make a plan so that everyone is on the same page next time and mistakes are avoided.

Give timely feedback

As a general rule, giving feedback early and often can help. If there is an action or behavior that has been bothering you, communicate sooner rather than later to prevent issues building up. (Of course, give regular feedback on the positives, too!).

It’s common for employees to say “I only hear from my boss if I’ve done something wrong,” but it shouldn’t be this way. Your employees can be more productive, more quickly if they receive regular feedback.

For executive assistants…

We know first-hand that if you’ve made a mistake, you’re feeling awful! There’s the moment where you have that sick feeling, knowing that it’s on you. First of all, know that a mistake doesn’t have to be the end – how you proceed from here matters.

Just like our advice for employers, we advise that you pause and take a breath. Sometimes people overreact in the moment, acting too quickly and perhaps even making a bigger deal than is necessary. It’s important to maintain poise and professionalism, and think the situation through rationally. 

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Here are a few steps:

Take ownership of the mistake

Taking responsibility is part of the professional expectations of the executive assistant role. You need to own what has happened and immediately look to make it right. That might mean taking quick action that fixes it on the spot, or it might mean having to go to your boss first and explain what has happened.

Keep it simple – “Here is what happened, this is what I’ve done/am doing/need help with doing to fix it.”

Going to your employer with solutions is always preferable (and more professional) than going into a panic and simply unloading the problem. The executive assistant role is more like a business partner – one who is expected to have ideas and solutions, rather than stand on the sidelines.

It’s also important to remain calm. Sometimes people react by dramatically rushing out to let everyone know they’ve made a mistake and apologize profusely. In their minds, that’s taking ownership and showing that they care, but to other people, it can seem like an over reaction. Chill!

Take whatever action you can immediately

Is there something that you can do right away so that you’ve either already fixed the mistake or you’re part-way there before having to let your boss know? For example, what if you accidentally hit send on an email that was meant to be saved in draft instead? Your immediate action could be to recall the email. Depending on the circumstances, your next action might be to tell your boss – perhaps they need to speak up if anyone has already seen the email.

Being proactive is part of the EA job description, but it’s also something of a relief to managers that a solution is already underway. 

Learn from your mistake

What led to the mistake? Analyze the situation so that you can learn from it. Most of the time we’ve found that mistakes only have to happen once – it’s usually enough to give you a jolt so that you’re never going to let it happen again.

Deal with it and move on is a good mantra to take. There’s no sense in dwelling on it, no matter how much you want to beat yourself up. You’ll be more efficient and productive if you can learn the lesson and move on.

Some examples…

Wondering what sorts of mistakes executive assistants have dealt with? Here’s a handful of real-world problems and solutions:

  1. The executive assistant thought she was supposed to be confirming travel arrangements already made but quickly learned she was supposed to make the travel arrangements herself. This almost caused the executive to miss a very important client meeting. She immediately found options to get him where he needed to be on time. This happened on her FIRST day.
  2. An executive was sent to the wrong airport. The executive assistant arranged for a town car to pick them up and deliver them to the correct airport at her own expense.
  3. The EA forgot to put a board meeting on the calendar and the executive was out of the office. She called the executive and connected him to the call from her own phone via three-way to ensure he didn’t miss the meeting, since there was no way for her to transfer him into the call.
  4. The EA sent a proposal to the wrong client, but through the relationships she built within the organization, she was able to pull the team together to make sure the proposal was recreated and delivered on time to the correct client. At the same time, she contacted the client to whom the wrong proposal was sent to ensure the proposal was destroyed upon receipt.
  5. The EA forgot to make hotel reservations for a conference her executive was scheduled to attend. She was able to use her connections in a hotel chain to get him a room within walking distance to the conference.

Everyone makes mistakes at some point. The important thing is how you deal with them. Executive assistants are expected to take ownership immediately and maintain a strong sense of professionalism. Most of the time, they’re able to fix the issue themselves.

From a management perspective, how you react to any mistake plays a role in your overall success with your EA, or with any other employee. Giving timely feedback and getting to the bottom of why the mistake happened can help. 

Together, you can get past that first mistake and have a successful, productive working relationship.

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