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Less Regret. Giving More Critical Feedback.

Have you ever left a conversation with regret when you dared to disagree? I have. Under pressure, I can be impulsive, leaving me wondering if I was helpful. It could be that you internalize your thoughts and cannot find the right words to say. Let's face it. Upward dissent and critical feedback are the vegetables of communication. We know deep down these difficult conversations are good for results and relationships, but most of us would prefer to avoid them. Issues too bad to ignore often are too big to fix quickly, and pushing ahead without a proven plan can leave others feeling resentful instead of encouraged. Just like any good leadership habit, mastering difficult conversations requires skill and deliberateness. With a little effort, you can give more critical feedback —with less regret later—keeping these three keys in mind.

Why you should dare to critique or disagree

When leaders avoid difficult feedback or do not handle conversations well, it can lead to relationship strife, failure, and missed growth opportunities. Mastering critical feedback creates the best possible outcomes for the leader, the leader-follower relationship, the team, and the company.

Critical feedback can lead to exploring diverse, innovative ideas that drive organizational growth. As businesses invest time pursuing innovation, it is easy to become increasingly less willing to question an idea. But, it is essential to receive critical feedback that challenges innovation assumptions. Organizations that dare to question assumptions are able to keep the focus on the best ideas.

One of the greatest gifts any leader can receive is the rare gift of being told what they need to hear but others are unwilling to say. If everyone in the room is always agreeing, you may not have the right people in the room.

Isolation is a frequent challenge for executive CEOs and executives. The power distance created by their position limits the critical feedback they receive. Increasingly, leaders are looking to executive coaching relationships outside of the company to find the thought partnership needed to improve ideas.

In the following Ted Talk, Margaret Heffernan provides a powerful story of why most people do not dare to disagree and why great teams, relationships, and businesses do.

Key #1: Focusing on What Matters Most

Masters of critical feedback create a gap between action and response to choose what conversation matters most. Like a ship approaching an iceberg, what alerts a leader of a potential problem is often what is seen, but what lies below the surface presents the greatest opportunity to be addressed.

"Don't let the truth run faster than love." Erwin McManus

In addition to choosing the right issue, selecting the right level of conversation is essential. There are three basic levels:

  • Level 1: The first level is a conversation about a specific issue, such as showing up late for a meeting and exploring the cause. A simple conversation in passing may be appropriate.

  • Level 2: The second level is a conversation about a pattern of topics, such as showing up late for several meetings. Meeting in private is best to discuss the reasons for this conversation.

  • Level 3: The third and most serious level is the health of the leader-follower relationship. These difficult conversations result from a lack of trust, concerns about competence, or loss of respect for the other person.

Key #2: Being Vulnerable

Regardless of leadership level or amount of experience, all leaders struggle with the tension of being vulnerable or not. When receiving critical feedback, followers want to know their leader cares about them. But, concerns about managing perceptions can keep leaders from showing vulnerability. And when leaders are guarded, it promotes distrust.

Although leaders are expected to convey an image of competence, confidence, and power, followers already know you are not perfect. Being vulnerable in challenging conversations requires courage. Leaders must learn to be comfortable without being right or having all of the information wanted or needed. Leadership vulnerability involves the willingness to be open and take risks that might create the best of what might be in the organization.

There is no single checklist of potential actions that leaders can use to show vulnerability in every difficult conversation. However, the following list of proven good leadership habits that promote vulnerability:

  • Being transparent

  • Putting others first doesn't mean thinking less of yourself

  • Asking for feedback and willing to learn

  • Being selfless

  • Taking action

To identify your tendency—to be vulnerable in difficult conversations —take the following free five-question quiz and learn your vulnerability leadership score.

Key #3: Checking Your MVP

Fail to plan and plan to fail. To avoid regret, your communication plan should include checking personal motivation, vision, and perspective (MVP) before giving critical feedback.

  • Motivation. Is your motivation about caring for others first? Or is your motivation to be right? Reasons for a conversation matter. It is less likely that the conversation will lead to positive changes without a positive reason.

  • Vision. How do you see the result of the conversation going? Is it the best of what might? Or is what you see a list of all the things that could go wrong? When you anticipate a positive step in the journey, it provides a sense of purpose and direction to inspire your best and achieve success.

  • Perspective. When the lens through which you perceive the difficult conversation is off, your results will turn out poorly. Is your paradigm for the difficult conversation that real transparent conversation will provide the best foundation for a healthy culture and your relationship? Or is your perspective that it is best to avoid difficult conversations because you need to manage your image?

Conclusion: Less regret. More critical feedback.

After you decide to give critical feedback, you will want to consider more than choosing when and where to have the conversation to bring out the best in others.

Focusing on what matters most will ensure the greatest opportunity is addressed rather than simply reacting. Being vulnerable in the conversation will communicate that you care about them and establish trust and safety. Also, taking the time to clarify a positive motivation, vision, and perspective will keep you focused on being helpful.

Giving critical feedback, in turn, encourages others to take risks with you. Leading to improved communication, productivity, and relationships. Others want to see that you care for them and are also open to learning.

What critical feedback do you need to give? What is the real challenge for you?


Bartell, R. (2011). Before the call: The communication playbook. Hudson House.

Berkun, S. (2010). The myths of innovation (1st ed.). O'Reilly Media, Inc.

Brown, B. (2022). The Power of vulnerability: Teachings of authenticity, connection, and courage.

Drucker, P. (2006). Innovation and Entreprenuership. Harper Business.

Grenny, J., Patterson, K., McMillan, R., Switzler, A., & Gregory, E. (2021). Crucial conversations. McGraw-Hill Education.

Hayes, J. (2008). Workplace conflict and how businesses can harness it to thrive. CPP Global Human Capital Report.

Patterson, K., (2005). Crucial confrontations: Tools for resolving broken promises, violated expectations, and bad behavior. McGraw-Hill.


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About Dr. Jeff Doolittle

He is the founder of Organizational Talent Consulting in Grand Rapids, MI, and Program Director of online graduate and continuing business education at Olivet Nazarene University in Bourbonnais, IL. Executive leaders who work with Jeff describe him as thoughtful, decisive, intelligent, and collaborative. Jeff is a business executive with over twenty years of talent development and organizational strategy experience working with C-suite leaders in Fortune 100, Forbes top 25 private, for-profit, non-profit, and global companies in many industries.

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