One subtle technique that is useful is to never share news, particularly important news (good or bad, but with a special emphasis on the bad) without having previously hinted at it.
Since your relationship with your boss or client is another relationship, just like dating, it might make it clearer to understand the power of hints by looking at how hints are, or aren’t, used in dating.
Here’s a simple dating example, in the negative case. Imagine your significant other says to you, out of the blue, “I’m leaving you.” Now compare that to, the same person in the same situation, six months earlier saying, “I’m really unhappy and we need to change our relationship.” Five months earlier, saying, “I can’t continue on this path unless we make a substantial change.” Then increasingly strong messages to this effect four, three, two, and one month earlier. Note the surprise—that is, the lack of hints and emotional preparation—makes the bad news much harder to handle.
Or even in a positive dating example, the same point is true, in verse: not hinting at and preparing the other side for good news limits their excitement. Compare your significant other saying, “Pack your bags, I’m gifting us a trip to the Bahamas, leaving tonight! You have work to do? Doesn’t matter, your clients will wait two weeks!” As compared to, the same partner, six weeks beforehand, saying, “I really think we should go on a last-minute trip somewhere. If magically that could happen, where would you like to go?” Then five weeks before, “I have some extra money saved up so we may be able to go somewhere.” Four weeks before, “If we were to go somewhere, how much notice would you need to give to your clients to tell them you won’t work during those days, and could you work extra beforehand and afterward to compensate for your time away?” And then similar questions three, two, and one week before until, voila, your vacation is there. (How come no one gifts me vacations like that? I would love it! Hint, hint, to the world.)
These examples, in a fun way, show the importance of hinting at big news well before they happen. But let’s take these fun examples and see what lessons we can extrapolate as to why it’s important, especially in a business or work context.
One reason is that bad news that you are prepared for is much, much, much less terrible than surprise bad news. Any bad news that you see coming, you can prepare for them in both practical terms and emotional terms. This is key: it’s always bad if a bomb is dropping, but you only die if you’re unaware and it drops on your head. If you can prepare for it, you can get to a bomb shelter and emotionally prepare yourself for the devastation that lies ahead, so it will be a lot less bad.
But even for good news, you need preparation for practical reasons. This is especially true in business. If someone writes a bonus, free article for you, that’s great! You’re excited! But even better is, if you know it’s coming, so you can plan its place in the editorial calendar and prepare for it.
Also dropping hints forces you to prepare for the future, it’s a way to keep yourself accountable. If the people you’re accountable for expect A, B, and C to happen—even if not in a formal way, but in the back of their minds—then it forces you psychologically to make sure you actually indeed deliver it.
A final reason why this is useful is that it makes your work more literary, giving you the appearance of a bit more mastery and mysticism than you may have. This strategy, of hinting at things before you do them, is really just an application of Chekhov’s Gun to life. Chekhov’s Gun is a classic literary device in which every little detail is placed in a work of literature by the author on purpose. Chekhov’s famous example is something like: the only reason to have a gun hanging on a wall in Act 1 is if that gun is then used in Act 3. Chekhov’s Gun, applied to your life, can be deeply powerful: if everything that happens in Act 3 in your work is foreshadowed in Act 1, the quality of the narrative behind the job you’re doing will mature from a simple children’s tale of the sort that I write to a masterpiece like Chekhov’s Three Sisters.
