I've posted before on the subject of hiding problems. The short summary is -- DON'T. Hiding problems is a quick route to the unemployment line. Hiding damages the trust and confidence others have in you as a manager. Hiding takes you out of the loop when it comes to managing how others perceive the situation. Hiding is a gamble that something will come along to save the situation, and eventually you'll lose that bet, usually with significant consequences.
But disgorging your problems in raw form is almost as bad.
When you walk into your boss'es office and throw a big, stinky problem on the floor, it usually looks like you're delegating it upward. That's akin to saying: "Here is this big ugly thing, and I have no idea what to do with it." You don't want that to be the perception of your competence (or lack thereof).
There are two techniques I have discovered that soften the revelation of problems. The first is what I call "the bad news sandwich." When discussing your problem, preface it and follow it with a bit of good news. That way, the impression of the encounter is not entirely negative.
As a recipient, I even appreciated this approach -- the two slices of "good" news helped me keep things in perspective, and reduced those feelings of despair that come when the "meat" of the sandwich is particularly awful.
For example, imagine this hypothetical bad news sandwich: "We got a call back today from Phil at Widget Distributions, and he's very interested in our new superwidget. On the downside, I don't think we can hit the cost targets on project X, but I have some ideas on how we can deal with that problem, which I'll get to in a minute. And I almost forgot to mention, Lois accepted that offer we made on the marketing job -- she starts next week."
That makes the cost problem seem a bit more palatable, even if it is a big deal.
There are a couple of subtleties in the example -- for the good news parts, I used the pronoun "we," rather than "I." When good things happen, it usually does you credit to share the glory with your team. With the problem, I used "I." When there's a problem, bosses like to know you're accepting ownership, and "I" signals that.
You may also have noticed I said: "...I have some ideas on how we can deal with that problem...." That is critical to accomplishing the second technique for bringing up a problem -- present your best attempt at a solution. Few bosses appreciate having to do all the heavy lifting themselves, and it is definitely more difficult to create the options than to edit. By offering your solutions, you counter several potential negative impressions in one fell swoop.
The best way to offer your solution is to get the basics out first, then, if the boss allows it, try to explain some of the options you discarded. In most cases I've seen or personally experienced, the boss will quickly become involved in editing your solution -- which is okay. Maybe the boss actually has some insight that improves where you're going. At the least, he/she also picks up a tiny little bit of ownership in the problem by participating.
Here is a continuation of the above example: "I know we all agreed if we couldn't hit those cost targets, Project X was dead in the water, but I've been thinking -- if we create two versions of the product, and strip out some features of the entry level one, then we can hit the cost target, and still have the new features available in the high end version. We've tested the idea with a couple people in sales, and it just might work. I considered just cheapening the components, or taking it on the chin when it comes to our profits, but I think this is the best approach."
From this point (assuming the boss lets you get this far), you're likely to get some "help" in the form of ideas or directives. But that's certainly a lot better than the boss thinking you're an idiot who is expecting him/her to solve the problem for you.
Employ these two techniques, and problems will go down easier when you feed them to your boss.
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If you enjoy the ideas presented in my blog posts, then check out my novels. Corporate Thrillers LEVERAGE, INCENTIVIZE, and DELIVERABLES are all based on extensions of my basic experiences in the world of business.