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My teamleader and I struggle to communicate sometimes. One day a week I'm allowed to work from home so we communicate via Slack or Skype calls. We speak the same native language but there's a 30 year age gap.

When we talk in real life it doesn't always go well, but with a lot of pointing and showing examples she will understand what I mean.

Through slack however I found that conversations like this keep happening:

Her: I can't find X in invision?

Me: I'll have a look for you, one moment.

Her: We also need Y in a separate project.

Me: Y is already in it's own project, here is the link. URL - And I just uploaded X again and you can find it here: URL

This is followed by at least an hour of silence, to get this as a reply (mind you that our history is not cleared)

Her: Where is X in invision?

Me: You can find it through the link I just shared or in the A project.

Another hour of silence followed by:

Her: Did you put Y in a separate project yet?

I tried emailing as well but that only seems to cause more confusion as she will send out multiple separate emails about the same thing that I then all have to reply to.

How can I start the conversation with her about how badly our communication is going without sounding like I'm just nagging to her about things going wrong? Should I propose a solution or should I let us come to that together?

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I've been in similar situations in the past. When there's a communication problem, this tends to be very frustrating for both parties: you're not getting your thoughts across, and the other person is frustrated that it's taking them so long to get their information. It's easy to get lost in your own side of the argument, since to you, it seems like you're crystal clear in your communication, how could it be misunderstood?

The trick is, that whether or not you're right is irrelevant. Your goal is to work together with this person. This means that you need to communicate in such a way that they understand the message you're sending. So, start your conversation from that point of view, taking care to use a neutral tone without any hints of sarcasm:

Hey X, can I get some advice from you?

I'm having trouble finding a way to convey things to you in the right way. Last [day I was working from home] for instance, you wanted to know about two things. After I thought I had answered, you later asked the same question again, which leads me to think that I hadn't succeeded in properly conveying the information to you. Here in the history, you can see the format I used to try to answer. It seems apparent that I'm not wording this right; how can I word this in a way that makes sense to you?

If the case is truly as you describe, the answer will hopefully be some awkward shuffling on the part of the other person, followed by a concession to be more careful when reading your replies in the future.

However, there is a good chance that you will be surprised at the answer. If there is an actual improvement to be made, the other person should be able to suggest a way for you to send the information in such a way that they can easily understand it. As the sender of the information, you already know it, so it's easy for you to read your answer and get the information from it. This may not be equally simple for the other party.

Either way, you've taken a constructive approach to the issue and you're not blaming anyone. If the other person suggests a new way to communicate and it's still not working, follow the same routine: raise the issue in a neutral way and look for a solution together.

It may seem like an injustice when in a situation like this, you have to put in all this effort when you were being perfectly clear in the first place. While that is true to an extent, in life in general but especially in the professional world, it always pays to be the 'bigger person'. Your life will be much easier if you're using this sort of methods to solve your problems because you'll get a reputation of being easy to get along with and easy to work with. Especially in the corporate world, competence is not always the most important aspect that decides one's career path. I've seen relatively incompetent people get raises and promotions over others, simply because they're easier to work with.

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    Thanks, this is indeed exactly why I want to resolve this. I might be wrong, we both might be wrong, but it'll be better for both of us if we can resolve this. – Summer Jun 11 '18 at 12:36
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How can I start the conversation with her about how badly our communication is going without sounding like I'm just nagging to her about things going wrong?

First and foremost, if you do this, do it in person. There she can't misinfer your tone.

To avoid sounding nagging, make it about you and how you need to change. Also mean it. If you're thinking negative thoughts about her that will come out. You didn't sound like you were, but I thought it was worth mentioning.

"Recently we had a conversation online. I answered your question. You asked again. What am I doing wrong? What do I need to do differently so that I answer your question the first time."

Should I propose a solution or should I let us come to that together?

The second. Ask a question like above.

I tried emailing as well

When email or IM fails one time, you should switch to in person or phone. I believe some people don't do written as effectively as verbal. Additionally I find some people just don't listen to me. I find if they're older they're much more likely to not listen to me.

On that note I've found my relationship with people dictates how well they listen to me, even if they're older. So, out of genuine interest for her well-being, perhaps pursue a friendship? At least show your interest in her life. That should help her listening.

When we talk in real life it doesn't always go well, but with a lot of pointing and showing examples she will understand what I mean.

This might not apply: Sounds like when there's miscommunication you do a lot of talking to overcompensate and it works. Do you also do a lot of listening? Sometimes it's quicker for you to ask her questions, learn what she thinks and then adjust your explanation to her vocabulary, rather than just a long-winded explanation.

she will send out multiple separate emails about the same thing that I then all have to reply to.

Feel free to respond to those in person or all at once. If she's not on top of her IM and email she probably doesn't expect replies to be in separate threads.

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Are you getting the sense that she is growing frustrated that she feels (apparently wrongly) that you haven't answered her questions?

Or is she apparently quite neutral on this, and just seems to work better asking for things over and over?

If the latter, then I'd recommend you just try to go with it. Every time she asks, just calmly and pleasantly give the (same) best answer. It may be that she's overloaded, and balancing many priorities, and just isn't mustering the short-term recollection that she's asking for the same thing over and over. In the long run she will appreciate your co-operation, and your readiness with clear answers.

"I've already told you that" or "it's in the last exchange we had" are accusatory and not helpful.

If you're getting the sense that she doesn't think you're communicating well, then for sure sit down with her and talk about it.

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