Donald Trump’s Guide to Delivering Negative Business Messages


Ever watch the Apprentice? I enjoy waiting for Trump to pull the trigger and give it to them. ‘You’re fired!’ It’s nice to watch this from the safety of our sofas. We’re involved but also separate from it. And we can switch off.

In the real world, it’s not so cosy. Sometimes you’re the one that has to give the bad news, sometimes you’re the one that has to give negative appraisals. Sometimes you’re the one that has to fire people. In many respects, this may fall under the umbrella of your Communications Plan strategy.

‘All of the women on The Apprentice flirted with me – consciously or unconsciously. That’s to be expected.’ Donald Trump

Negative v Positive Business Writing

This week we look at how to write negative messages. Not nasty messages, emails and such but material with a negative edge.

For example?

In some ‘negative messages’, you may have to address faults or issues with a team member. When writing these emails, reports or messages such, keep a professional tone, avoid attacking your colleague – but make your position on the issue clear.

Don’t fudge it. That creates other problems.

‘Do you mind if I sit back a little? Because your breath is very bad.’ Donald Trump

One school of writing encourages us to ‘express bad news in a positive angle’.

To do this, avoid such words as:

  • Cannot
  • Deny
  • Fail
  • Forbid
  • Impossible
  • Prohibit
  • Refuse
  • Restrict

Look at these examples. The first draft is phrased in cold and negative terms; the second is positive, cordial and generous:

Negative writing:

The incredible amount of information you requested in your report is too much ad means that I cannot help you without disrupting our work schedule. Revision: I see in your letter that you require specific project information, which I will help you locate. However, due to our work load, I can answer only a few of the questions right now….

Negative writing:

If you do not complete and return this contract by Jan 1, 2011, you will not receive your apartment. If we have not heard from you by this deadline, we will sell the apartment to another person.

Positive writing:

Please complete the enclosed contract and return it to us by Jan 1, 2011. After this date, we will have to put the apartment back on the website. I hope we hear from you before then.

Negative writing:

While I am willing to discuss changes in the Functional Requirements, I am not prepared to change the project deadlines.

Positive writing:

I am open to suggestions and comments about specific Functional Requirements, or your thoughts on additional areas that you think we should examine. However, I want to ensure that this does not impact the project deadline as you can understand.

‘If you want a guarantee, buy a toaster.’ Clint Eastwood

How to re-position negative communications?

Focus on the other persons:

  • Needs
  • Interests
  • Purposes

If you must talk about yourself (or role) in a business letter, make sure it relates to your concerns for the other person (and their role).

Develop a You First Attitude

This recipient-oriented ‘you-attitude’ writing style means the recipient is the focus of the letter, not you.

Negative writing:

We have changed our pricing policy to save our company time and money. In an operation like ours, it costs us a great amount of labor time to clean our equipment…

Positive writing:

We will update our pricing policy effective December 15th, 2015. This will enable us to serve your needs more often and without delay…

Like Donald Trump you will have to deliver bad news on occasion. The approach you use, and how you structure your arguments, will influence the outcome. Instead of creating conflict, you can help the Project Manager or Proposal Team Lead to see your side and try to accommodate your needs.

The trick is to acknowledge their needs first and then outline where you stand in relation to these. Don’t bulldoze them into submission. You may win the first battle, but you’ll lose the war.

What’s the worse piece of news you have to give someone in the office?

About the Author: Ivan Walsh provides Business Tips for Smart People on His also runs the popular Business Planning Blog at

PS – The Communication Plan Template is here