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When to connect with hard-to-connect-with people

By July 4, 2022July 6th, 2022No Comments

Have you ever encountered difficulty in connecting with someone and found it so challenging you wanted to give up? It might be your boss, an employee, or even a supplier. Not being able to connect with someone can be frustrating, delay projects, and undermine relationships. 

I was coaching a client of mine with this issue and offered the following suggestions that I personally have used many times and shared with many. 
(PS: If you’re interested in leadership communication coaching, hop over here: )

KEY: Choose a time that’s convenient for the other person.

Timing affects how you communicate and how the other person receives your message. If they’re not ready to listen, they won’t. Picking a time strategically when you bring up a topic, especially a sticky one, can make all the difference in the response you get. 

Two times to avoid:

  • When someone has just arrived and hasn’t had a chance to settle in yet;
  • When someone is in a rush to leave.

If you rush up to your boss soon as he or she steps foot in the office or barely turns on the computer to begin the virtual office day, chances are the reception you receive will be less than warm. These people need a bit of time to get into the right mindset, get organized for the day, and take care of the top priorities they may have on their list before they can even think of whatever topic you want to discuss. Give your boss a moment or two to get organized, get the coat off, arrange the files, and ease into the day. Then, and only then, approach them with your issue.

Neither is the end of the day when someone is rushing out the door, the moment to begin a discussion that requires more time. It will only add stress to the listener and the outcome is likely to be less than you’d hoped. Their mind won’t be on your topic as they will be preoccupied with catching that bus, getting home to the family, or dashing to that next appointment. This timing doesn’t serve you well. 

The exception to avoiding these two times is if you’re only giving a quick heads-up that you’d like to speak to them later about your topic, or if they are specifically anxiously awaiting an update from you on a critical issue. This alerts them without imposing and disrupting their schedule.

Two times to use:

  • Early morning
  • End of day

Yup, those are the exact two times I suggested you avoid, right? Well, not exactly. The key is to approach someone when no one else is around AND when it’s good and convenient for that individual. This is a great time to have a heart-to-heart.

The requirement for this strategy to work is that you give the person time to settle in and be comfortable.

This way, she or he will be more comfortable, less stressed, and more likely to be in “receive” mode. A sense of informality exists before and after regular office hours, so use that to your advantage. Note the regular arrival and departure times of the people you want to speak to and connect with, and then approach them at the beginning or end of those times. If someone is an early riser, catch him or her before the busy day begins. If they tend to stay late and burn the night oil, pop by to see them at the quiet end of the business day when the office is near empty and things have slowed down.

Change your timing, change your results.

Just as I discovered while driving this morning, changing when you do something, whether it’s driving or communicating, can result in easier access, less stress, getting closer to where you want to be, and provide a chance to unwind and discuss in a relaxed environment. 

It’s all in the timing.

©2022 Marion Grobb Finkelstein (MarionSpeaks)

Marion Grobb Finkelstein
Keynote Speaker / Corporate Trainer / Author
Recipient of APEX “Award for Leadership in Service Innovation” 
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Leadership communication expert, Marion Grobb Finkelstein shows leaders at any level how to build resilient and respectful workplaces by changing how they communicate. Chat with her at or and sign up for her FREE “Marion’s Communication Tips” at

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Marion Grobb Finkelstein

Marion Grobb Finkelstein helps leaders use their natural communication strengths to build resilient teams that talk.

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