Believe or not folks tend to let you know what the scoop in communicating with them is in a variety of ways especially with in a profession or a given level of management group think. Listen and observe. Folks don't always hit you over the head with it so you will find it more subtle. The bottom line is you must go after it. Can you tell when a friend has the blues and doesn't tell you neither that they have blues nor exactly what it is that is causing it but you sense that something is wrong? Do you proceed to inquire if they are troubled and if so what is causing it and how can you help? It's in the same vein as that but it's usually lingo. So pick up on the lingo and approach them on their terms. After all that 'is" what they understand.
Take the word productive, you can say that something is productive, non-productive or counter productive. With many top dogs the key way to phrase it is that something is not being productive. The reason is they don't like failure especially since it tends to reflect on them so they view things in two ways they are either being productive or they are not. If they are not even although that is bad it's not being painted in a negative light it's simply not being productive.
Productive is something they understand and you are not being negative by saying that it is not being productive. There for what ever it actually is, it is not a failure or worse counter productive it's simply not being productive and productive is the desired outcome. When something is not being productive the desired outcome is to find a solution that turns it around and makes the outcome productive. That can be taking actions that stop a project that is not being productive and in doing so those actions are productive.
When you approach them on their terms and speak their language they will know that you are observant, adaptive, intelligent and humble enough to do so while still being aggressive. That is something the big dogs like although it may very well scare the heck out of your supervisor and torment your peers. It's often referred to as being a TEAM player and a GO TO person.
On the communications front at times it is prudent to follow the philosophy when in Rome do as the Romans. That gets you noticed and from there you do many good deeds which builds their confidence in you and with that you slowly build a personal relationship to which you can give a (more colorful) confidential point of view in a one on one situation and some cases to the small group that holds the most influence or real power. It certainly has an element of politics in it but you are "not" selling anybody out and that is the key.
If you do those things they will know that they are not dealing with the stereotypical IT person.
You can use this approach when dealing with most folks if not everyone, not just the big dogs. If you deal with everyone in this manner you will find the outcome to be very productive.
Take note that some folks don't bring much to the dinner table and to that it is what it is. Your attempt is likely not to be productive since they are what they are but the fact that you attempted to do so, that is likely to be noticed and it will be viewed as being productive.
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