The Power of Regret in Leadership: Lessons from Looking Back | Michelle Gibbings

We’ve all had moments at work we’d rather forget.

A tense meeting that spiralled.

A conversation where our words came out wrong.

A decision made in haste that triggered a chain reaction we couldn’t reverse.

Regret is an unavoidable part of leadership and life. However, how you respond to it makes all the difference in what happens next.

Do you ruminate or reflect? The former leads to avoidance and self-blame, trapping you in a cycle of negativity. The latter, however, brings perspective, allowing you to uncover opportunities for growth and to take purposeful, redemptive action.

Why Regret Holds So Much Power

Regret is a complex emotion.

It signals a gap between what we did and what we wish we had done. It can prompt us to course-correct or keep us stuck in the past.

As Professor of Psychiatry and Neurobehavioral Science at the University of Virginia, J. Kim Penberthy explains in this article for The Conversation, regret can be intensely consuming because it combines negative emotions, self-judgement, and an inability to change the past.

Our brains obsess over these ‘what ifs’ as a way to mentally undo events, but this rarely leads to resolution. You’ve no doubt experienced that before. Your brain keeps replaying the scenario over and over, hoping that the ending will change. Of course, it doesn’t and being stuck in the replay loop is not helpful.

Regret can manifest in various ways. For example:

  • Emotionally: Leading to shame, guilt, and anger.
  • Socially: Prompting withdrawal and defensiveness.
  • Cognitively: Fuelling obsessive thinking and indecision.
  • Physically: Causing tension and fatigue.

The Emotional Undercurrent

Often, regret doesn’t sit quietly. It can morph into resentment toward ourselves or others and may even lead to thoughts of revenge.

Social psychologist Nico Frijda(opens in new tab) explored emotions(opens in new tab), including the phenomenon of revenge. He observed that revenge often stems from a desire to equalise a perceived power imbalance. He proposed that vengeance can restore self-esteem, pride, and a sense of control, and that it is motivated by the need to escape the shame or mental pain caused by being wronged.

While few leaders will act on revenge in extreme ways, the impulse to hold a grudge against a colleague who embarrassed us, a boss who overlooked us, or even ourselves is real. Grudges can be self-protection mechanisms when we feel regret.

This is where the founder of non-violent communication, Marshall Rosenberg’s insight(opens in new tab) becomes critical: “We are never angry because of what others say or do. The cause of anger lies in our thinking—in thoughts of blame and judgment.”

The same holds true for regret. To move past it with clarity, you must shift from judgement to understanding, from blame to ownership and from rumination to reflection.

The difference between rumination and reflection is subtle yet profound.

Rumination is a circular process that amplifies negative emotions without making progress. It keeps us stewing, rehashing, and judging.

Reflection, by contrast, is forward-facing. It extracts meaning, helps us learn, and allows us to move forward.

As Dr. Todd Kashdan(opens in new tab) notes in his book The Power of Negative Emotion, we often make decisions in one emotional state and experience the consequences in another. This emotional mismatch can lead us to second-guess or punish ourselves disproportionately.

But dwelling in regret doesn’t undo the past. What it can do, if we choose to reflect, is shape our path forward rather than trying to bypass the past.

The Path Forward: Perception, Intention and Action

As Rumi beautifully wrote, “The wound is the place where the light enters.”

Regret can open a gateway, not just to pain, but to possibility. When we choose reflection over rumination, we create space for wisdom to emerge.

To harness that potential, we must engage in three deliberate steps: perception, intention, and action.

1. Perception – See Clearly
Begin by examining how you’re making sense of the situation. Ask yourself:

  • What assumptions are shaping my view of what happened?
  • What might I be overlooking?
  • What emotional state was I in when I made that decision, and how might that be colouring my judgement now?

2. Intention – Choose Your Direction
Regret often points to something that matters. Clarify what that is by asking:

  • What truly matters as I move forward?
  • Am I trying to protect, prove, or pursue something?
  • Where do I want to direct my energy next?

3. Action – Forgive, Learn, and Lead
Forgiveness is a powerful and often necessary step towards yourself and others. It doesn’t mean excusing harm or forgetting the past; rather, it means releasing its grip so you can act with agency in the present.

Studies(opens in new tab) show that forgiveness literally rewires the brain. It reduces stress, enhances emotional regulation, and increases empathy by strengthening specific neural pathways including those associated with emotional regulation.

According to researchers, an effective act of forgiveness involves three key elements:

  1. Acknowledging the hurt that you may have caused.
  2. Admitting your mistake and the impact.
  3. Making the situation right.

For more information, check out this article(opens in new tab) from the Greater Good Science Centre.

Regret is not a sign of failure. It’s a sign that you care about your work, your impact, and the person you’re becoming. Use it as a guide, not a cage. Let it shape your leadership, not shrink it.

So, when you are thinking about your next steps and how to move forward, consider:

  • What conversation needs to happen?
  • What do you need to own, apologise for, or reframe?
  • What are your learnings and insights from this event?
  • What deliberate action(s) will you take today to move forward?
  • How do these actions align with your leadership aspirations?

One Further Insight

While regret is often felt personally, as a concept, it is equally relevant at the organisational level. Decisions are made organisationally that can give rise to regret and the need to forgive.

Research by Professor Jeffrey Harrison(opens in new tab) and colleagues in the Academy of Management Perspectives explores(opens in new tab) how firms decide whether to forgive stakeholders after a breach of trust.

Their model outlines that forgiveness is not just a moral act but a strategic decision, influenced by factors such as the severity and visibility of the breach, the stakeholder’s intent and response, and the organisation’s underlying culture.

The most generous forgiveness emerges in cultures that value benevolence and long-term relationships. Conversely, in more self-interested cultures, forgiveness is rare, unless it aligns with economic self-interest.

The key takeaway for leaders?

Forgiveness is a powerful lever not only for personal recovery but also for repairing trust, fostering resilience, and sustaining high-value relationships; whether you’re the one who’s been wronged or the one who regrets.

So, some parting thoughts…

In her beautiful poem The Summer Day, Mary Oliver asks a striking question: “Tell me, what is it you plan to do with your one wild and precious life?”

I remember when I first heard her poem, and the final line has stayed with me because it’s a question that lingers. Regret can tether you to the past, keeping you stuck in the cycle of rumination. Or, it can become a teacher who wisely shapes you.

The choice lies in how you respond: by reflecting with perception, choosing with intention, and taking wise, deliberate action.

Getting you ready for tomorrow, today®

Award-winning author and global workplace expert, Dr Michelle Gibbings, helps leaders, teams and organisations unlock strategic influence to accelerate progress.



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