Aenslee Tanner - Leadership Coaching | Vertical Development

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How to give effective feedback and have courageous conversations

Do you ever shy away from giving feedback?  Sharing your perspective?  Asking for what you want?  

If so, you’re not alone.  

Feeling torn between having something to say and fearing what the repercussions might be if you say it is a common challenge raised by many of my clients in coaching sessions.  I get it - speaking up and sharing your perspective and needs can feel risky sometimes.  No one wants to come across as a jerk but you would like to find a way to influence the situation and create a different result or outcome going forward.

The good news is you don’t have to stay stuck in a pattern of keeping quiet, venting your frustrations to uninvolved parties, or waiting for anonymous 360 degree surveys to be administered.  Your options aren’t limited to either holding your tongue or giving the other person a tongue-lashing.  

With a little creativity, an open mind, and a dose of courage, you have the potential to generate many more possible pathways for moving forward.

Here are a few tips on how to give effective feedback or have a courageous conversation.


  • If you’re questioning whether you really need to bother giving feedback or having a courageous conversation at all, here’s a rule of thumb you may find helpful: If you find yourself talking to other people about person X, it’s likely a sign that there’s a conversation you need to be having directly with person X.  Remember, people need a fair chance to understand their impact if you hope for them to change their behavior.

  • Get clear on your desired outcome.  What would success look like from your perspective?  What change would you like to see?  How might this conversation serve to deepen your relationship?

  • Consider what mindset will serve you best in meeting your intention.  Often when it comes to standard workplace performance conversations where you’d like someone to change their behavior, it’s more helpful to approach the conversation with a lens of curiosity rather than criticism or defensiveness (e.g. “I’m curious to understand…” or “I wonder if…” rather than “You’re an idiot.” or “You’re wrong.”).

  • Take time to prepare for the conversation - don’t wing it.  If you care about positively influencing a situation and want to maximize your chances of success, it’s worth investing time to prepare your thoughts, words, and approach in advance.  This enables you to make sure your thinking is clear, your key points are ready and you’ve prepared for potential obstacles.  

  • If you’re engaging in a difficult conversation where there’s discord or conflict, know that it’s absolutely normal to feel discomfort in your body.  Understanding that can help you mitigate any urges you may have to fight, freeze or flee. In this video, Zen teacher and award-winning mediator Diane Musho Hamilton offers sage advice for managing the discomfort that can arise during challenging conversations.

  • Although people are ultimately unpredictable, it can be helpful to try to anticipate how the other person may react.  What’s the best case you can imagine?  The worst case?  The most likely case?  How do you ideally want to respond in each of those scenarios?  Preparing for different situations in advance can help reduce the likelihood of floundering in the heat of the moment by making your desired responses easier to access.


How people at different stages of vertical development respond to feedback

Given people at different stages of vertical development make sense of the world in vastly different ways, you may find it helpful to reflect on how people at different stages of vertical development typically respond to feedback:


  • It’s often helpful, and empowering for the other person, if you check in and seek permission before launching into giving them feedback.  Are they open to receiving it?  Is now a good time to have the conversation or would scheduling a later time be better for them? (e.g. “I'd like to have a conversation about [fill in the blank as relevant: my workload/our relationship/some ideas I have about improving our team dynamics/etc].  Do you have half an hour now or could we schedule a meeting sometime next week to come together?”)

  • A useful way to warm into the conversation (and help lessen any tension that may be present) is to start by sharing your appreciation.  Anything you’re genuinely grateful for in relation to the other person will do, for example, “Thank you very much for taking the time to discuss this with me”, or “I’m really appreciative that you’re open to discussing ideas that I have”, or “I’m grateful to be learning so much from our collaboration on this project.”

  • While many leaders falsely assume they need to always present a perfect, composed, and confident exterior, another powerful move to build trust and lower the other person’s defenses can be to show some vulnerability (e.g. “I notice I’m feeling nervous about having this conversation…” or “I know I made a mistake and want to start by apologizing…” or “I feel bad about how I…”).  Author Brené Brown is a great resource for more information on tapping into this underutilized leadership superpower.

  • Sharing your positive intention towards the beginning of the conversation can be a helpful frame to support the other person in making sense of the conversation in a productive way rather than feeling threatened.  Here are a couple of examples:

    • “My hope is that by having this conversation, though I’m aware it may feel uncomfortable in the short term, we’ll come to better understand each of our unique perspectives and build a stronger working relationship for the long term.” 

    • “I've been thinking about ways [fill in the blank as relevant: I could step up my contribution to the team/we could improve our communication/etc].  I have some ideas I’d like to share with you that I think would help us achieve that and I’d like to hear your ideas as well.”

  • To increase the chances your conversation partner will remain open to what you have to say, it’s important to share your perspective as your perspective and take ownership of how you feel.  You can share the impact something’s having on you without blaming others or making assumptions about their intent.  For example, “I’ve been noticing how stretched and tired I feel from trying to juggle all these different projects” shares the personal truth of your experience in a way that doesn’t accuse the listener of being at fault.

  • Striving to be both clear and kind, balancing candor and empathy, is another helpful aim for making sure your message is able to be heard and digested by the other person.

  • What’s your request of the other person?  Extend your invitation for them to make a change clearly so there’s no confusion about what you’re asking for (e.g. “I’d find it helpful going forward if you…” or “Would you be willing to try…?”).

  • To ensure you and your conversation partner are aligned in your understanding, it can be helpful to ask how what you’re sharing is landing for them (e.g. “Does that resonate with you?” or “Does that make sense?” or “Do you have any questions?”).

  • Before you wrap up, it can be helpful to inquire as to what you’re each taking away from the conversation and what your commitments are going forward.  Perhaps you’d find it useful to even get a follow-up meeting in the calendar as an opportunity to check in on and discuss progress?


I hope these tips have helped you start to see fresh options for how you can unleash even more of your personal power, deepen relationships, and amplify your influence as a leader.

You have a valuable, unique perspective to offer.  You don’t have to keep it to yourself - you can make a different choice.

You can choose to have a courageous conversation.  It just might be the conversation that changes everything.