4 Tips for Delivering Difficult Messages

4 Tips for Delivering Difficult Messages

Jan 21, 2013

Having spent the majority of my time in Senior Management working in either “Start-Up” or “Turn-Around” environments, I assure you I have delivered more than my fair share of negative news.

Whether it has been rejection from VC’s or other investors or coming to the realization that the company is going to have to make personnel cuts, this type of news is never easy to swallow. And if the receipt of the negative news isn’t gut wrenching enough, when you serve in a leadership role this means that you are likely going to be the one to have to deliver the bad news to everybody else.

While for me, the experience working with companies in particularly fragile states may have led me into more situations where I’ve had to deliver bad news. However, these situations evade no business; this is because businesses are fluid and no matter where they are at today, there is always room for improvement which likely includes some tough conversations.

No matter what the bad news is and why you have to deliver it. There are specific considerations that must be given in these situations.

Here are four keys to delivering a difficult message that will lead to making the best of a difficult situation.

Planning: I have always felt it is best to rip off the band-aid. It drives me crazy to know about material changes in a business that need to be made yet delaying to make them. HOWEVER – you must take the time, as little or as much as necessary to plan the information that you plan to deliver. This is what will allow you to do the next 3 things better.

Brevity: If you have ever heard someone deliver bad news it probably isn’t all that common that you have heard them ramble and start rationalizing like crazy. Perhaps you have done this yourself. However, this nervous habit of rambling and justifying the bad news basically makes the situation worse by adding “Bumbling Fool” to your resume. I’m not suggesting to lack compassion and humanity; what I am suggesting is that a brief message that quickly gets to the point is generally appreciated by everyone involved. Even in one on one situations, the awkward build up to the “Message” is painful for both people. So get to the point, and when in doubt say less than you feel is necessary.

Clarity: The line between brevity and insultingly short lies in clarity. What I mean by this is that you can deliver a tough message concisely, however if the message lacks clarity then you may leave more questions than you do answers. This can be really detrimental to an organizations people and their morale. During the planning phase make sure you think of the virtual FAQ that will help the receivers of your message understand clearly what you are trying to get across. When you successfully do that in a concise and direct communication you are mastering “bad news,” one of true hard parts of leadership.

Empathy: Business is human. This is a theme of my book, my blog and my leadership. Therefore your message must be human. And whether you are firing someone, demoting them or taking food off their table, people deserve to be the recipients of a compassionate message that shows empathy. Easier said that done thought. If you have ever had to let a person go and you see the tears in their eyes it truly tests your humanity. If it doesn’t phase you a little bit you have lost touch with the world. However, the decision you made was likely the right one and at the very least a rational one. So you have to keep yourself together but be considerate of others. The brief and clear message I mention above are actually a big part of this. But to take it one step further, you do need to make some time to listen and respond after your message has been given. While this shouldn’t change the course of your decision, listening can go a long way and shows that you care.

Being the bearer of bad news is never fun, but following these four tips can make it a little less difficult for both you and those that you are delivering it to.

In this short video we discuss the delivery of tough news and how we can all do it just a little bit better.


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