Letter Writing: Confrontational Letter Writing – 12 Tips

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A confrontational letter is a letter that confronts a situation, a problem or dispute. It seeks a specific objective from the recipient that will not usually be granted without resistance.

The writer wants a certain objective and the recipient of the letter will not grant that objective unless convincingly persuaded that he should.

Here are some tips as to how to effectively structure a ‘confrontational letter:’

1. Appearance is very important. The letter must be a hard copy and appear impressive and professional. You must use good quality paper and have the letter printed using a good printer on a professional appearing letterhead.

Emails do not project the impressive image that is truly effective.

Emails are unimpressive and these days a hard copy is becoming more and more rare. For that reason the appearance of an impressive appearing hard copy letter signifies that the letter is a serious letter and written by a writer deserving serious consideration. An impressive hard copy letter stands out from the crowd.

Have you ever noticed how much more respect a man in a well-tailored suit receives? The same principle applies and the physical appearance of the letter is very important and must project the writer as a serious, refined, educated individual.

Behind that projected image is implied the fact that the writer has the ability and wherewithal to take the matter further – i.e. to superiors of the recipient and/or to authorities that oversees the conduct of the recipient and his organization.

The serious and impressive appearance of the letter projects the clear understanding that the writer is the type of individual who may subsequently refer the matter to a lawyer for further action if the request for relief is denied.

What must also be borne in mind is the mindset of the recipient of a confrontational letter. That is to say, the greatest fear of a recipient of a confrontational letter is that his decision not to grant your request may be overruled by his superiors.

Therefore, if the recipient has received an impressive looking letter that is persuasively written this basic fear of being overruled will weigh very heavily on his mind. He may grant the request out of fear that the letter looks like ‘trouble’ both in appearance and content. He may therefore decide to quickly grant the request and close the file. The recipient will save negative responses for letters who do not appear to be ‘trouble.’ I personally have experienced this situation many times and that is why I place particular emphasis upon the physical appearance of the letter.

A professionally appearing letterhead can be easily created by a word processor. I recommend a border around the page and that the paragraphs be justified on both sides to give the letter a distinctly professional appearance. If you have a degree or some sort of designation include it on your letterhead.

I am not suggesting that if you have a weak argument that an impressive looking letter will in itself be effective. However what I am suggesting is that an impressive letter, in every sense, shall likely ensure that the persuasive argument contained within that letter gets the serious attention and careful treatment it deserves. And that objective is more than half the battle!

2. The letter must be well-researched and well-organized. If there is background and supporting information that must be conveyed to the recipient then that information must be included, accurate and complete. In order to keep the letter itself to a minimum consideration should be given to putting supporting information in an attached appendix to the letter.

The package put in front of the recipient must be total so that the reader does not have to secure other records in order to confirm or understand the situation correctly. This too is the mark of a professional and will have a positive impact upon the recipient. The recipient will feel that he is dealing with a professional who has his act together and that feeling shall increase his concern.

3. The letter must be entirely professional in tone and content and must project a distinct tone of civility and respectfulness. To deviate from this standard gives the recipient an excuse to place the request into the category of an unreasonable request. After a request has been characterized as ‘unreasonable – whether justified or unjustified – it is very difficult to rehabilitate that request.

4. If there are facts that have to be stated make sure that they are stated clearly and in short paragraphs of one or two sentences at the beginning of the letter. Short sentences and paragraphs are easier to read and the information contained is easier to digest. You want to make your factual case very clear and consideration should be given to numbering these paragraphs so that the recipient may easily refer to them by number.

5. State the request as briefly as possible and give justification for why the recipient should grant the request. Make your argument as short and simple as possible. Your letter should be as brief as possible because if you digress and add more detail you may put something in that an unscrupulous recipient may seize upon to unfairly deny your request. The touchstone – make things as clear and simple as possible.

6. End the letter in an up-beat manner. Indicate that you hope that the reader recognizes the merits of your position and invite him to respond if anything is unclear. I find the following sentence particularly effective: ‘If you are unable to agree to my request or if I am in error on any of the facts or, on any other aspect of the case I have outlined, please specifically advise.’

If the recipient gives you a detailed explanation as to why he is refusing your request it shall be your road map to further attempts to persuade him that he should agree to your request. It may also put him on the spot in a close case when his response is inappropriate and may be reviewed by a superior.

If the recipient does not give you a detailed explanation as to why he is refusing your request then that fact can be seized upon to suggest in a subsequent letter that the recipient is not being reasonable in considering your request.

7. Never refer to your ‘request’ as a ‘demand’. It should be respectfully framed as a ‘request’.

8. Always end the letter with ‘Respectfully Yours’.

That ‘respectful’ ending further and emphatically confirms that the letter has been respectfully submitted which is crucial.

If the recipient responds in a disrespectful or less than respectful professional manner then the contrast between his approach and your approach stands in stark contrast. This fact will be to your advantage when the letter and the entire situation is reviewed by someone else… i.e. someone in authority to the first responder, a regulator, another interested third party, etc.

Many of these confrontational situations are won only narrowly and can easily go one way or the other. The fact that your letter(s) is reasonable and respectful may be the crucial difference. I have seldom seen a disrespectful, unreasonable letter secure its objective. It is much more difficult to deny a request in a polite, respectful well-written letter.

9. Do not end the letter with a ‘cc’ to the regulator or any other third party that may stand as an authority to the recipient. It is completely inappropriate, unprofessional and the mark of an amateur.

Reference to a third party may be appropriate at a later stage but the first letter should stand entirely on its own and the recipient should not be made to feel that he has a gun to his head.

The recipient well knows that you may appeal to a higher authority and does not have to be reminded. Most first responders are very sensitive to this issue and so why antagonize him by waving that threat in his face? Do you really want to antagonize the person whom you are trying to convince?

10. A demand in the letter that there be a response within a specific time frame is completely inappropriate and unnecessarily irritating to the recipient and should not be inserted within your first letter.

True professionals fully understood that a timely response should always be provided and some responders take the request for a quick response as an indication of desperation or impatience and a weakness to exploit. For that reason many first responders will purposely delay their response in order to exasperate the writer and perhaps provoke an intemperate letter which is usually always to the recipient’s advantage.

Forget about asking for a quick or timely response – you have no control over that fact so why mention it?

In fact a tardy response can be a plus in your favor at a subsequent stage. A slow response can look bad when reviewed later and will tend to indicate that perhaps the recipient to your letter is being unreasonable, unnecessarily dragging his feet and acting inappropriately.

11. Make sure that there is nothing in your letter that can be criticized. Do not allow your anger to show through. Remember at some point your this letter is very likely to be reviewed by others and it should be completely beyond reproach. An understandable temperate expression of exasperation may be in order to prove a point but not anything more.

12. If you have the luxury of time then sleep on the letter and come back to it when you are fresh.

It is amazing what a fresh set of eyes can see and it also amazing what other points may occur to you as you go about your regular schedule.

Review the letter critically and tweak it so that it is as concise as possible and flows smoothly. Remember the key to good writing is ‘re-writing’.

If possible get a friend who has good judgment and good writing skills to review it. A good second opinion together with constructive criticism can be invaluable.

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