How can you be telling me this now? I was counting on you! If you had only told me this when you first knew! I can't believe you waited this long!

It's never fun learning a secret that's been kept from you.

It's not fun holding onto a secret either that will leave others (coworkers, friends, loved ones) disappointed and, in all likelihood, angry.

When, if ever, is it a good idea to keep secrets? And when is the best time to reveal them?

Let's locate this discussion in a few specific scenarios.

Scenario #1: You intend to leave the company in six months and have begun preparations to move into another state and workplace. When is the right time to tell your boss you're leaving? Do you give your boss two-weeks notice, a month, or more?

To what degree does the relationship you have with your current employer matter? If it's an adversarial relationship, you might be tempted to wait until the last minute to reveal your secret, but that's bound to create even more bad blood (and impugn your reputation). But does that mean you should tell your current employer the minute you know for sure you're leaving? What if that resulted in your firing and several months without paychecks?

Even if you're in good standing with your current employer, does honesty serve both parties? Will it lead to an uncomfortable six months?

Scenario #2: You are the CEO and owner of a business, and you plan on retiring in three years. You've begun your 5-year strategic plan with your staff. When do you tell your senior team and then the whole company that you're leaving?

Scenario #3: You're going on maternity leave and you don't intend on returning to work afterward. When would be the right time to let your company know?

"When is the right time?" This question has bothered me for years! The scenarios above all revolve around leaving an organization. There are many more secrets people keep from their coworkers and employers naturally, but few have as much impact. The end of a relationship--even a professional one--dredges of emotions and issues of worth and appreciation.

A few factors to consider:

#1: There's a window in which secrets can be revealed without violating trust between individuals. It's a short period of time really. A week maybe.

#2: The longer the secret is kept, the more likely trust will be violated.

#3: The longer a secret is kept, the harder it is to know when to reveal it. You may feel like the window has passed.

#4: When a secret is revealed, the party that's been kept in the dark will want to know how long the secret has been held--so that they can better assess the level of duplicity/dishonesty and their interactions with you during that period.

#5: Mental fatigue comes from holding onto a secret--and from creating lies or untruths to preserve it.

#6: How much will you need to rely on others to maintain your secret? Are they capable of doing so? And is it fair to ask them to do so?

#7: If you tell one person, do you need to tell everyone?

#8: Do you tell people individually or collectively?

There's a reason why people keep secrets! Revealing a secret isn't simple. It involves a lot of calculations, which is why, I suspect, people get paralyzed and fail to make a decision. Then time passes and they feel it's too late to reveal the truth.

What do you think is the right thing to do? When has this happened to you?