Uh-oh. Jack just learned that he did not win a contract that was supposedly all but certain. He was counting on this deal to make his quota and had been bragging to the vice-president of sales and his co-workers that it was in the bag. What’s more troubling is the fact that he’s been under the gun by upper management over the past few months to improve his production. Now what?

Jack has to deliver the bad news. The first thought running through his head is that he’s going to be fired on the spot. He’s deep in debt and has a wife and two small kids at home. What does he do? Unfortunately, Jack chooses to do what so often happens in situations like this. He fudges the truth. He tells his boss that he hasn’t yet “heard the final word” from the client. Jack holds onto a thread of hope that he might be able to salvage the deal.

It’s obvious that delivering bad news is never fun. It actually starts with an organization’s culture. What is the reaction to bad news by the leadership? Is there screaming, yelling and threats? How about chaos and recriminations? If so, this sets the tone for anyone on the wrong side of having to report unfavorable results. It’s human nature to try and avoid painful encounters of this sort. Thus, some people may have a tendency to stretch the truth, fudge the facts or outright lie about the situation, rather than endure the wrath of the boss.

In a healthy organization, delivering bad news is just another routine task to be performed. The enlightened leader will encourage team members to openly talk about what isn’t working including setbacks that have recently occurred or are anticipated. He or she will work with the team to understand what went wrong and how to avoid a similar result in the future. There’s no negative emotion or drama associated with this analysis. In so doing, team members feel safe in bringing news of any sort – good or bad.

A leader who operates in a fair and even-handed manner is entitled to expect full and total integrity from the team. The team member in a healthy organization who fudges the facts like Jack did should be dealt with in a severe manner. Here’s the calculus. I won’t blow up and make you feel lower than whale poop, and you owe me complete transparency. It’s as simple as that.

If you are part of an organization that struggles with bad news, first look inward and remember that it’s a two-way street. If the organization is unwilling to react in a calm and measured way, then it cannot expect team members to want to deliver bad tidings.

There’s another element to delivering bad news. It may be that the leader does not have an angry tantrum at all. This individual may always be very upbeat and optimistic. But members of his or her team may still not want to tell it like it is. Why? Because they don’t want to disappoint him. In many situations feeling like one has let down a co-worker or a leader is a powerful motive to duck or delay the inevitable. It’s circumstances like this where the leader must take care not to send any signals that he/she may be disappointed. In fact, this leader should go out of his way to encourage members of his team not to equate bad news with a disappointed boss.

One way to solve this dilemma is to embrace failure as simply a step in a process. A forward-thinking entrepreneur will model this attitude by sharing his or her failures with the team. Being vulnerable in this manner may encourage others to be more comfortable doing the same without fear of disappointing the leader.

Let’s replay Jack’s scenario with a different twist. Jack learns that he did not win the contract. He immediately goes to his boss and explains the facts of the situation. His boss says, “Jack, this reminds me of a situation a few years ago where I was positive I was going to win the brass ring only to be left holding the bag. But I scrambled together a radical new approach and took a long-shot by asking to see the client one last time. Believe it or not he changed his mind and I won the deal after all. You might try the same approach.” Maybe Jack went on to win the deal and maybe not. Regardless, there was no hesitation when it came time to deliver the bad news initially.

Delivering bad news can be done in a matter-of-fact fashion if an organization’s culture encourages it. If not, we can expect that people will take extreme measures to avoid this unpleasant task.

This blog is being written in tandem with my book, “An Entrepreneur’s Words to Live By,” available on Amazon.com in paperback and Kindle (My Book), as well as being available in all of the other major eBook formats.