In a recent survey conducted in the U.K., Hays Recruitment found that 43% of respondents said leaders needed to improve their communication skills—far more than areas like strategy and planning (23%) or remote staff management (13%).
For Assistants working remotely, this isn’t surprising. In fact, even before COVID-19, I wouldn’t have been particularly surprised by this statistic.
Poor communication is the biggest challenge in building an effective relationship between an Assistant and an Executive. Staying in the loop, understanding what’s needed, and managing expectations is difficult with an Executive who can’t communicate clearly. For Assistants working with a poor communicator, the role becomes even more challenging, especially when working remotely.
Does this sound familiar? Is your Executive a poor communicator?
I want to look at how Assistants can work with poor communicators, but first, let’s define what it means to be a poor communicator.

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How Does Your Executive Communicate?
Understanding your Executive’s communication style is incredibly important for Assistants. Knowing when and how to communicate is essential. You have to communicate effectively and strategically to get the most out of every interaction. Assistants can only manage this well if they know their Executive’s communication style and preferences.
Once you understand their preference, it will help you manage those gaps in their communication skills. However, this won’t necessarily make them a better communicator—it just gives you better insight into how to work with them.
So, how do their poor communication skills show up?
Here are a few examples:
- Are they vague in their instructions, leaving you confused about what’s expected?
- Do they go AWOL for long periods, leaving you unsure of their whereabouts or what tasks they’re focused on?
- Do they over-complicate instructions so that you can’t differentiate important information from trivial details?
- Do they hold pointless meetings without objectives or structure, wasting everyone’s time?
- Are they too direct with their instructions, leaving no room for creative thinking or personal interaction?
Some of these might sound familiar, or you might have your own examples. Either way, working with a poor communicator is tough but not impossible if you’re willing to manage up and communicate your needs to work effectively.
How to Work with a Poor Communicator
It’s more important than ever to communicate regularly with your Executive. Even while working remotely, you need to be seen and heard—daily. This might require you to take the initiative, but it’s essential. When times are tough and economies are impacted, employees who are not seen as adding value (or who simply aren’t noticed) may be the ones let go. Right now, you need to prioritize regular communication with your Executive, ideally face-to-face.
I wrote a post about this a few months ago, which is worth another read if you feel out of the loop with your Executive.
That said, there are many tactics you can use to work with an Executive who is a poor communicator.
Seek Clarity
To ensure you understand what’s being asked of you, you must seek clarity. Ask questions to gain the understanding needed to move forward with tasks and projects.
Summarize and Repeat Instructions Back to Your Executive
For example, if your Executive asks you to compile a sales report without much further instruction, reply with something like, “I can get the sales report for this quarter to you by the end of the day. Will that work for you?” They might confirm, or they might reply, “Actually, I wanted the year-end report, and it’s fine if you get it to me by the end of the week.”
Summarizing their request and repeating it back to them ensures you know exactly what’s expected.
Set Clear Goals and Priorities
Working with a poor communicator often means there’s less structure around your role. Set clear goals and priorities for yourself, and try to guide your Executive down this path if possible.
During face-to-face meetings, it helps to have a document that tracks goals and objectives. This will keep you on track, ensure that meetings are productive, and help you and your Executive stay aligned.
Understand the Context
Often, by the time you’re sitting down with your Executive to discuss tasks, projects, and strategies, they’ve already gone through various meetings, emails, and reports. Putting this information into context can be challenging, especially for poor communicators.
It helps if you come prepared with an understanding of what’s happening within your organization, as well as the key strategies and deliverables your Executive is focused on. Having this understanding will make it easier to ask questions, provide input, and help your Executive communicate effectively.
Be Honest About the Problem and Suggest a Solution
Most Executives don’t intentionally keep their Assistants out of the loop or have poor communication skills—they may just not be aware of their shortcomings.
If their poor communication is a recent change (perhaps due to remote work), a gentle reminder that you need consistent and clear communication could make a difference. If it’s an ongoing issue, you might need to have a more direct conversation about working together effectively. Consider suggesting that you both take a personality and preferences test to help improve communication.
Final Thoughts
Poor communication from Executives can be challenging to cope with—especially when working with them remotely. It’s essential to identify the aspects of their communication that need improvement, understand their behavior, and look for solutions to encourage better communication.
Keeping up-to-date on your Executive’s commitments is also vital for success, along with maintaining healthy boundaries and setting clear expectations. Finding effective ways to communicate with a poor communicator may take time and trial and error, but it’s possible.
To ensure you have everything you need to succeed as an Assistant, check out our Strategic Business Partner Online Course, which provides in-depth training on handling complex personalities and increasing productivity. Remember, building a successful partnership with your Executive benefits everyone involved. Put in the effort to make your relationship work for a smoother journey ahead!