4 Steps to Delivering Tough Feedback (Even if You are a People-Pleaser!)

Giving constructive feedback is one of the most important (and challenging) parts of being a manager. While it’s easy to celebrate wins, it takes preparation, clarity, and empathy to deliver tough messages in a way that helps people grow. This post will walk you through how to approach hard conversations with intention, so your feedback strengthens trust rather than eroding it.

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Last week, we explored how to write employee reviews that matter—using Microsoft’s “Model, Coach, Care” framework to create the kind of conversations that can shape careers (and yes, even relationships).

But what about when the feedback includes hard truths?

Here’s the thing: most people aren’t afraid of feedback itself. What they are afraid of is being misunderstood, mischaracterized—or blindsided in a meeting without so much as a heads-up.

I’ve been fortunate to receive thoughtful, constructive feedback throughout my career—insight that helped me grow and improve. But I’ve also had moments when feedback landed harshly, leaving me stunned and suddenly unsure where I stood. One conversation in particular stands out: the input was unexpected, off-base, and delivered in a way that left me feeling more confused than supported.

Instead of surfacing a blind spot to help me grow, it left me questioning the trust in the relationship.

And yet—experiences like that are part of the leadership learning curve. That moment didn’t break me (although it did sting). It actually made me double down on wanting to become the kind of manager who leads with clarity, empathy, and a real desire to help others grow.

If, as an employee, you ever encounter such a scenario, there are things you can do to ensure your performance is accurately represented. More on that in the future, so stay tuned! For now, here’s a breakdown of how to deliver hard feedback with care.

#1. Start With Clear Preparation and a Centered Mindset

Before you sit down with your employee, take time to ground yourself. What do you want the person to walk away knowing, feeling and doing? This question frames the conversation with purpose.

From there, gather your notes. Examine project outcomes, behavioral patterns, goals achieved, challenges encountered, and ideal end goals. Bring context along with data. If you have been having check-ins along the way, what has shaped a person’s performance should not be a surprise to you or them, including shifting team dynamics, personal milestones and setbacks, and resource constraints.

Then, consider what you want to convey, and keep in mind Harvard Business Review’s insight that high-performing teams need psychological safety through trust-building. A performance review resonates when it provides space for reflection, versus feeling like a verdict. If you want the person in front of you to grow, you must meet them with honesty and humanity, and that includes being as ready to listen as you are to speak.

💡 Tip: Use a bullet‑pointed “Highlights & Growth Areas” list. This helps you stay grounded in facts and brings focus to the upcoming conversation.

“If you care about the people you work with, then you want them to succeed—and that means giving feedback that helps them grow.” — Kim Scott

#2. Deliver the Feedback with Precision, Not Performance

When it comes to giving tough feedback, you don’t need a script, but you do need specifics. Telling someone they need to “improve communication” isn’t helpful. Use a specific moment instead, such as missing a vital client update that delayed a team timeline. Clear examples help someone understand the impact of their actions and reflect on what to do differently next time.

It’s equally important to name what’s working. Leave out the performative “compliment sandwich,” though. People may either miss the feedback or feel confused or manipulated if you wedge a critique between two compliments. Instead, build on positive observations by saying something such as “You’re great at staying calm and focused when things get hectic, which helps the team stay on track. If you can pair that strength with more frequent communication, specifically looping in other teams earlier, it’ll help them feel aligned and less rushed on their end too.”

Dani Donovan Compliment Sandwich - useful for giving more constructive feedback
Art credit: Dani Donovan

Feedback should never feel like a character judgment. You’re reflecting on patterns of behavior and outcomes, not giving opinions about who they are. Here’s an article from Forbes with key things to keep in mind in order to provide effective employee feedback.

💡 Tip: Kick off with a tone that’s supportive, not judgmental. Try a simple opener like: “I appreciate your hard work and want to partner with you on how to take your performance to the next level.”

#3. Navigate Hard Conversations with Compassion and Clarity

This article by the Muse suggests difficult feedback deserves direct language and a steady tone. Avoid sugarcoating, vague euphemisms, or roundabout framing, as what you’re trying to communicate can get lost in translation. Here is a helpful video on how to give constructive feedback without hurting anyone’s feelings

People can handle honesty when it’s paired with presence, and if they can’t, it’s crucial to know sooner rather than later. Pause after hard feedback and make space for the employee’s reaction. Not everyone will process on the spot, so plan how to be adaptable. The Radical Candor book — Kim Scott’s #1 bestseller on how to give constructive feedbackYou can offer: “I know that’s a lot to take in. Do you want to talk through next steps now, or take some time and reconnect tomorrow?”

💡 Tip: Leverage the key points in Radical Candor by Kim Scott, one of the most widely referenced books on giving effective feedback. 

  • Start by soliciting feedback: If you’re open to receiving it, others will be more open to your feedback too.
  • Deliver it immediately: Feedback is most helpful when it’s timely.
  • Do it in person (or live): Especially for critical feedback – tone matters.
  • Be humble: Assume you might be wrong, and be curious.
  • Be specific and clear: Vague feedback confuses more than it helps.
  • Praise in public, criticize in private: Protect psychological safety.
  • Gauge their reaction: Pay attention to body language and follow up.

#4. Reinforce Growth, Not Just Metrics

A review should be over when a person leaves with a clear sense of direction, not just when you’ve delivered your points. The most effective development plans and delegations are co-created, so performance reviews should feel like a collaborative effort, where both parties know their next plan of action to assist one another.

Here are a few key points to keep in mind along the way:

  • Make sure both of you agree on what success looks like going forward.
  • Tie development goals to the employee’s strengths, not just areas they “need to fix.”
  • Ask what kind of support or resources would help them follow through.
  • Schedule a check-in to revisit progress and stay connected.

Growth doesn’t always have to mean high-stakes assignments or consequences. It can be as simple as naming an area of focus and helping your employee feel supported in reaching the goal you co-created together. Any other suggestions you would add to the list?  Feel free to share in the comments below. 

Thanks for reading and sharing! xx

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Danielle Cullivan

Career Insight Studio

Danielle Cullivan is a seasoned leader in tech with over 20 years of experience in Fortune 500 companies. She is also the creator of Career Insight Studio, a career and lifestyle blog dedicated to providing insights and new perspectives for working women. Danielle lives in the Pacific Northwest with her husband and high-school-aged son, and visits her college-age daughter as often as possible! 

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