Genuine regret extends far beyond outward expressions of apology.  It manifests as the painful bite of conscience that keeps us up at night wondering, “How could I do that?” or “What was I thinking?” It challenges us to make atonement and commit ourselves to doing better. Indeed, penitence is the root of penitentiary, what we aspirationally (but too often inaccurately) call a correctional institution. 

Sadly, much of this perspective has been lost, and social media is largely to blame. Our ability to spout off with relative anonymity and little accountability has contributed to a profoundly dysfunctional culture that promotes the most horrific behavior, while—simultaneously, yet paradoxically—encouraging us to militate against transgressions that are frequently less offensive and would be better off left in the past. 

Needless to say, we must not tolerate racist, cruel, or uncivil speech or conduct, all the more so from the unrepentant. But if we don’t allow the truly penitent to apologize, make amends, and move forward, then we disincentivize genuine repentance and, by doing so, further encourage bad behavior. After all, if I won’t be allowed rehabilitation from my past mistakes, what motivation do I have to try to make amends and do better in the future? 

Some apologies are indeed insincere, nothing more than pro forma attempts to sweep bad behavior under the rug. Genuine, heartfelt expressions of contrition manifest as a desire to learn from past errors and do better moving ahead. Time generally reveals which are which. Even the best fakers eventually expose themselves by reverting to irresponsible behavior. 

It’s not difficult to promote a spirit of penitence. Leaders simply need to adopt a conciliatory style when bringing mistakes to light. This is done by following a few simple guidelines: 

• Have conversations in private that point out missteps

• Acknowledge past contributions first when giving a rebuke 

• Express confidence in the potential to improve 

• Offer guidance and support 

• Reiterate that an organization is a team and that every member makes a difference 

In an environment where employees fear disproportionate retribution for even the smallest errors, they will keep their heads down, avoid taking chances, and never, ever show initiative. But when leaders demonstrate trust in their people to own up to their mistakes, then those people will come to trust their leaders and accept accountability. The resulting culture will be one in which growth happens naturally and organically, one in which small failures are nothing more than rungs on the ladder of success.