Image Credit: Justin Chen

One question intrudes while I’m presenting the case for improving personal coachability and being open for more feedback.

“How do I give feedback to the boss?”

While I try to steer that question back to first serving as a coachable role model, I’ve learned to provide a few cautions and tips.

“It’s still a tiger,” executive coach Dennis Adsit says, warning us that:  

“Offering feedback to a boss, especially early in one’s career, can be a nuanced and delicate endeavor. It involves balancing authenticity with diplomacy to foster positive change without jeopardizing your working relationship or career progression.”

In researching this topic, I contacted over two dozen successful senior leaders and executive coaches for examples of positive outcomes from giving upward feedback.  I was surprised by the scant number of positive experiences, and in fact, some were compelled to share bad outcomes, including damaged relationships and stalled promotional opportunities. One cited a reaction so adverse he soon quit the organization even though he was rated as a top performer. 

The Warnings

The group collectively provided cautions about giving feedback to a boss, along with strategies for mitigating these risks while being authentic and effectively using your voice.

  • Risk of Misinterpretation: Your feedback may be interpreted as criticism or an attack if not delivered carefully. This can damage your relationship with your boss and affect their perception of you.
  • Defensive Reaction:  We all can become defensive when faced with feedback, particularly if it touches on our weaknesses or mistakes. This defensiveness can derail the positive conversation you intended. Remember, not everyone has read my book, Coachability: The Leadership Superpower, or taken it to heart.
  • Impact on Your Reputation: Giving feedback to your boss can sometimes be viewed negatively by others, potentially impacting your reputation within the organization.  You might be unfairly labeled a self-centered complainer vs. a well-intended helper. Know your culture’s unwritten rules of upward feedback.
  • Career Progression: Even with the best intentions, things can go wrong.  In the worst-case scenario, if the feedback significantly upsets your boss, it could affect your career progression, including opportunities for advancement, recommendations, or important projects.

Strategies for Giving Feedback to the Boss

Tiffany O’Brien, President of Ultimate Technologies Group, shared how evening text messages from her boss made it difficult to live a healthy work/life balance.

“I was vulnerable and shared a personal story with her about how my lack of boundaries negatively impacted my family life. She responded with great understanding to that. I also knew that she came from a work environment that valued work/life balance, so I was able to acknowledge how difficult it was at the company we worked at to find that personal space. We already had an excellent working relationship built on mutual respect and trust, so I believe this also helped it be an effective conversation.”

Anton Vincent, President of Mars Wrigley North America, discussed giving his boss coaching to help him be more decisive and face hard conversations with senior team members to move the business forward. When reflecting on what made the feedback work, he said,

“I had a reputation as a truth-teller. I shared my truth in a way that he knew I was helping to push our agenda.   We were still early in our relationship, but I believe he appreciated the honesty.”

When asked what strategies they used to increase the odds of a successful boss-feedback effort, the group of leaders passed along these ideas:

  • Decide if it’s worth it: Three questions can help you decide if it’s worth the risk.  First, how strong and positive is your working relationships?  Second, will the boss want and appreciate the feedback?  Does their past reactions to feedback signal coachability or defensiveness?  Third, is this just your style preference or a more mission-critical observation?  Mission critical points to core values, organization policy, and human respect. Style preferences are your subjective disposition when other choices are equally acceptable.
  • Prepare and Be Specific: Avoid immediate reactions or off-the-cuff remarks. Preparation is key. Be specific about what behavior you are addressing and have examples ready. This helps prevent misinterpretation and keeps the conversation focused on facts rather than emotions.
  • Choose the Right Moment: Timing and location is crucial. Look for a calm, private setting and a time when your boss is more likely to be receptive, not during high-stress periods or in front of others.
  • Use “I” Statements: Frame your feedback from your perspective to reduce defensiveness. For example, “I feel that X impacts my ability to do Y,” rather than “You do X wrong.”
  • Coach the Positive: Clearly describe what behavior would be more effective and how you can support the boss.   Express your feedback to show you’re on the same team, aiming for a common goal. This shows you’re committed to constructive outcomes, not just pointing out problems.
  • Be Prepared for Any Outcome: Despite your best efforts, be prepared for a range of reactions. If the feedback isn’t well-received, remain professional and seek to understand your boss’s perspective.

Give the boss feedback?  Step back and recognize the risk, decide if it’s worth it, and show savvy in approaching the conversation.  Upward feedback is tricky to successfully navigate the complex task of giving feedback to a boss. It’s about balancing authenticity and respect for the hierarchical structure, always aiming for constructive and positive outcomes.   And above all else, serve as the coachable role model for others, including those above you.

Your Message Awaits – Will You Receive It?

Do you think someone right now has valuable feedback to share with you but is hesitating?  They might see something important that you might not be seeing.  How would you score with the “tell or don’t tell” checklist as the other person considers taking the risk?

 Are you seen as someone open to input and not misinterpret or react defensively? Have people experienced you as someone willing to listen and understand the message first?  Have you demonstrated your curiosity and coachability to hear different perspectives?  Do you show appreciation for those taking the risk to help you? 

And when was the last time someone gave you feedback?  If it’s been a while, perhaps you should seek it out.

Give the boss feedback?  Maybe, think it through.

Signal you are open for feedback?  Definitely, it’s the sign of a coachable leader.