Practical Tips for Giving Your Boss Constructive Feedback

Practical Tips for Giving Your Boss Constructive Feedback
By: The Humphrey Group

Picture this. You’re an employee in a mid-sized marketing firm, and every week you have a scheduled one-on-one meeting with your boss to discuss progress, address concerns, and get feedback on your work. The problem is your boss keeps canceling – and one time he just didn’t show up.

At first you brushed it off, but now you’re starting to assume he’ll cancel, and when you’re right, you feel undervalued and neglected. The cancellations also mean you don’t get the chance to seek guidance or bring up important issues that are on your mind. So, what do you do? Is it ever okay to give your boss feedback?

The idea of giving feedback to your boss is probably daunting, but giving constructive feedback is a key leadership skill. No matter what level you work in, or what your role is, giving constructive feedback is about giving people the opportunity to adjust behaviors that aren't working, which is ultimately rooted in respect.

At The Humphrey Group, we believe leadership is about the ability to inspire and that doesn’t only mean the people who work for you, it can be anyone, including your boss. A core principle we teach in our Leader’s Mindset is that speaking as a leader takes courage, and it takes courage to speak up to your boss.


Psychologically safe workplaces

It’s important to first address the issue of power dynamics in the workplace. In a healthy work environment, everyone should feel psychologically safe to voice their opinions, share concerns, and offer feedback without fear of repercussion.

This is often referred to as psychological health and safety, and signs that your workplace fosters it include open communication channels, a culture of respect and trust, and leaders who actively encourage feedback and dissenting opinions. 

However, even in psychologically safe workplaces, the idea of giving feedback to your boss will likely still feel intimidating. That’s okay. Take your nerves as a sign that whatever you need to say is important to you and that honing the skill of giving constructive feedback is critical.


How to give your boss feedback

Even if there are challenging emotions underlying your feedback, it should always assume the best of the recipient. Give them the chance to understand where you are coming from and provide them with an opportunity to act or make a change. 

High-quality feedback is surprisingly rare. The good news is that both giving and receiving it is a skill. At The Humphrey Group, we have created a breakdown of the fundamentals of providing feedback that works regardless of context. In the following section we take those steps and apply them to the context of providing feedback to your boss:

  1. Prime the recipient. No matter who you’re delivering critical feedback to, make sure they’re in the right headspace to have that kind of conversation. When it comes to your boss, consider timing and context. Choose a moment when they’re not under significant stress or pressure and try to avoid catching them off guard.

    Additionally, consider the context. Would this be best done in a private setting, or would a more informal approach be appropriate? By thoughtfully considering these factors, you can increase the likelihood of a productive and well-received feedback conversation.

  2. Frame the conversation. To do this effectively, use a specific example that illustrates the behavior or issue you want to address. When you provide feedback to your boss, it’s best to choose a specific incident or action that you’ve observed rather than to make broad generalizations. Focus on the impact of their behavior, rather than blame.

  3. Demonstrate impact. This is the time to explain the consequences that occurred because of their behavior. This could be things like affecting team morale, productivity, or even the quality of your own work. By being clear and objective, you help your boss understand why this matters to you.

  4. Create dialogue. At this point, you've had the chance to share your insight and it's crucial they have a chance to speak as well. In the case of providing feedback to your boss, it's essential to approach the conversation with humility and openness.

    Give them space to share their perspective and listen actively to the feedback they may have in return. Remember, the goal was never to assign blame but rather to identify areas for improvement and promote a positive working relationship.

  5. Commit to change, together. By mutually agreeing on actionable steps and outlining a clear plan, both parties commit to driving positive change and progress. Especially when it’s your boss, it’s essential to approach the commitment phase with tact and diplomacy. Express a willingness to collaborate to find solutions and emphasize the shared goal of improvement. 


Let’s go back to the scenario from the beginning. Armed with this knowledge, you decide to go to your boss and talk directly. You schedule a private meeting and calmly express your concerns, framing the conversation around specific instances where the cancellations affected your ability to complete a project to the quality you wanted. 

To demonstrate impact, you also explain that the cancellations made you feel undervalued. Then you invite your boss to share their perspective and actively listen as they respond. It turns out they have been busier than usual and had no idea the meetings were so important and impactful to you. You mutually decide to schedule meetings every two weeks instead of weekly to accommodate their work volume, but they also promise to make them a priority.

By approaching the situation with tact and diplomacy, you not only address the issue at hand but also strengthen your relationship with your boss and foster a culture of open communication and mutual respect in the workplace.


Empowering change through feedback

Giving feedback to your boss can be a powerful tool for growth and development, both for yourself and for your organization. At The Humphrey Group, we've seen how structured feedback can transform relationships and enhance communication within teams. By following these steps, you can navigate the process with confidence and help foster a culture of open communication and continuous improvement.



If you want to learn more about giving and receiving constructive feedback, check out out learning experience Inspiring Feedback