Good managers offer feedback. Great managers create space for reflection and praise effort and energy. One of my toughest lessons occurred in my role as a mid-level manager in a large, hierarchical organization.

One of my direct reports, an early-career professional, came to my office for a recurring one-on-one and, after a year in her entry-level role, proudly shared that she felt ready for a more senior title. My response: “I’d be happy to help you work toward that goal, but you’re not ready for that position yet.” I intended to be supportive while sharing the realities of our organization. I wanted to protect her from getting her hopes up and being disappointed when the promotion didn’t get approved.

What she heard was very different: “I don’t value your work, and you need to further prove yourself.” My response was honest and as kind as I knew how to be. I didn’t want to lie and say we could make it happen. The truth was that this simply wasn’t how our organization worked. Promotions weren’t up to managers; they were decided by executives using rigid timelines and budget frameworks. There was a strong culture of “earning your spot” and putting in more than twelve months.

The fallout from that exchange was significant. My staff member no longer trusted me to support her leadership journey, and her feelings were deeply hurt. I carried guilt for saying something that landed that way. She was doing excellent work, and not being ready for a promotion had nothing to do with her effort—and everything to do with the system we were operating in.

What I got wrong was giving the facts instead of supporting the person.

I could have said, “That’s awesome. I’m so excited to hear you want to be a leader in our department. Let’s figure it out.” That response could have built trust and allowed her to leave my office feeling supported rather than defeated. The reality is that most feedback is received through a filter of emotions and past experiences.

This moment taught me the importance of being more human with my team—supporting them as people rather than acting like a corporate robot who simply says, “We can’t do that.” When I changed my approach, my team members became more open about sharing their career goals and aspirations.

My advice: support the person first. Save the bureaucratic hoops for a different conversation.

Early in my career at Reliant at Home, I had a struggling sales rep who wasn’t hitting targets. I scheduled a meeting and opened with a list of missed metrics—conversion rates, follow-up gaps, pipeline velocity. Ten minutes in, she got quiet and just nodded. I thought I was being data-driven and clear.

Two weeks later her numbers hadn’t budged and she resigned. Turns out she was dealing with a family crisis I knew nothing about because I’d spent the entire meeting talking at her instead of asking what she needed. That mistake cost us a team member and taught me that feedback without context is just noise.

Now I lead with “walk me through what’s happening on your end” before I ever mention numbers. When I implemented this across our sales teams at Lucent, we cut turnover by over 30% in the first year and saw individual performance improve because people actually felt supported enough to be honest about roadblocks—whether it was training gaps, territory issues, or personal challenges affecting their work.

The biggest shift? Our team started bringing problems to me before they showed up in the data. That early visibility means we can course-correct in days instead of months, and reps feel like we’re solving things together instead of being monitored from above.

Early in my roofing career, I’d finish a roof inspection and hand homeowners a detailed estimate that listed every line item–underlayment specs, drip edge gauges, ventilation calculations, flashing types. I thought transparency meant showing all the work. What I got instead were confused looks and follow-up calls asking “so… do I need this or not?”

The lesson hit hard when a property manager in Fort Worth told me: “Dustin, I manage six buildings and just need to know–can you patch it for two more years or do I need to budget a replacement now?” I was burying the decision in documentation when she needed a clear recommendation first, then the backup detail only if she asked.

Now I lead every estimate conversation with the bottom line: “Your roof has 3-5 years left, here’s what’s failing and why, and here are your two realistic options with pros and cons for each.” Then I ask what questions they have. Our project approval rate jumped from around 40% to over 70% because people finally understood what they were actually deciding.

I still provide all the technical detail–it’s in the written proposal–but I let customers pull that information when they’re ready instead of pushing it up front. The documentation protects everyone during insurance claims and warranty situations, but the conversation is where trust gets built.

Early on I learned the hard way that showing a 3D pool rendering to a client before I understood their budget was backwards. I’d get families excited about $150K designs when they were thinking $80K. Brutal conversations followed.

Now I flip the sequence—budget and lifestyle questions come first, then I open the design software. I had a Wilmington couple last year who said they wanted “something modest,” and instead of immediately showing them options, I asked about their kids’ ages, how they entertain, and what monthly payment felt comfortable. Turned out “modest” to them meant a $95K pool with a tanning ledge and fire bowls—they just didn’t want to sound demanding.

That project closed in 11 weeks with zero change orders. They told friends we “actually got it” because we listened before we designed. Our change-order rate dropped from about 40% of projects to under 15% just by reordering those first two conversations.

My biggest feedback mistake was being too “designer-focused” instead of client-focused during wedding consultations. Early in my career, when a bride said she didn’t like something in my proposed floral design, I’d launch into explanations about color theory, flower symbolism, and why my choice was objectively better. Lost several bookings that way before I figured out what was wrong.

The turning point came when a bride flat-out told me “I don’t care if peonies photograph better–I want the flowers my grandmother grew.” That hit hard. I realized I was protecting my creative ego instead of listening to what mattered to them emotionally.

Now during consultations, I ask “what feeling do you want guests to have when they walk in?” instead of showing them my portfolio first. I let them talk about memories, family traditions, even Pinterest boards I might personally cringe at. Then I translate those emotions into design–their vision lifted, not replaced.

Our wedding bookings increased by roughly 40% after this shift, and couples started specifically requesting me by name. One bride wrote in her review that she’d fired two other florists before finding us because “Tatiana actually listened instead of just showing off.” That funeral flower message guide I wrote came from this same lesson–sometimes the simplest, most personal words matter more than the “perfect” florist recommendation.

As a physician, I was trained to diagnose a symptom and immediately prescribe the cure. I carried that habit into my role as CEO. I would see a metric slipping and tell my director exactly how to fix it. When those fixes failed, nobody took responsibility because they were just following my orders. I realized I was confusing instructions with feedback.

Now, I stick to identifying the pain point. I simply state the data, like a drop in conversion rate, and stop talking. I do not offer the fix. This forces the team to diagnose the root cause and prescribe the treatment themselves. We moved from passive execution to active ownership, and the solutions they generate are usually more effective than the prescription I originally had in mind.

My biggest feedback mistake happened after we started adding property walkthrough videos to our Detroit rental listings. I sent a detailed email to every past guest explaining our new video system, the production process, why we chose certain angles—basically a behind-the-scenes documentary nobody asked for. Open rates were terrible and I got zero responses.

Then one guest replied asking “does the Harbor Loft video show the parking entrance?” That’s when it clicked—guests didn’t care about our video production journey, they cared about whether videos answered their specific booking questions. I scrapped the long explanations and sent a simple follow-up: “New property videos are live, find parking, kitchen layouts, and neighborhood views for each unit on our site.”

After that shift, our booking conversion jumped 15% because the videos solved actual decision-making problems rather than showcasing our effort. I learned to communicate the guest outcome first—”you’ll know exactly what you’re booking”—not the operational pride behind it. Reviews started mentioning how easy it was to choose units, which brought repeat bookings from corporate travelers who valued that clarity.

Early on at Comligo, I leaned on the “feedback sandwich” and buried the real issue—lesson pacing—between two vague compliments. The teacher left thinking everything was fine, so nothing changed. I switched to being direct and supportive: we’d watch a short class recording together and pause at the exact moment students started fading. Then we’d pick one specific change for the next lesson. Once feedback got clearer and more concrete, pacing improved fast, and we saw lesson completion climb by around 30%.

Early in my career, I’d dump comprehensive SEO audit findings on clients all at once, thinking more data meant better service. One client became completely overwhelmed and nearly cancelled our contract. That’s when I learned that “information without prioritization is just noise.” I started breaking complex findings into digestible phases, focusing on high-impact items first. Now I present maximum three priorities per meeting with clear business impact explanations. Client retention improved dramatically because they could actually act on our recommendations instead of feeling paralyzed by endless technical details.

Early in my career as a prosecutor, I had a domestic violence case where I was convinced the defendant was guilty and pushed hard in my communication with the victim to get her to testify. I was so focused on “winning” the case that I didn’t listen to what she was actually telling me about her fears and her situation. She shut down completely, refused to cooperate, and the case fell apart.

That experience completely changed how I approach clients now at my firm. When someone comes in facing domestic violence charges, I spend the first consultation mostly listening—asking what happened from their perspective before I say anything about strategy. I learned that in these cases, there’s always context that doesn’t show up in the police report or 911 call, and if I don’t shut up and hear it first, I miss crucial defense angles.

The results speak for themselves. Since adjusting my approach, I’ve successfully defended numerous domestic violence cases by uncovering details clients only share when they feel heard—like one case where the “victim’s” injuries were actually self-inflicted during an argument, which only came out because I asked open-ended questions instead of interrogating. My former prosecutor experience taught me what questions to ask, but that early mistake taught me when to ask them—and when to just listen.

The biggest feedback mistake I made early on was assuming people understood our setup process without a clear explanation. At Jumper Bee Entertainment LLC, we offered big attractions like carnival rides, water slides, and ice rinks, and I thought everyone knew what went into getting these on site. One event planner told me later that she felt unsure about timing and power needs during setup, and that made me realize our communication wasn’t as clear as I believed. That one comment changed how I talk about logistics with every client.

After that, I started walking customers through setup expectations step by step on calls and in emails. I created simple checklists for electricity, space, and timing that we now share upfront. What I noticed most was how much calmer customers felt once they had clear guidance. They stopped asking the same questions repeatedly, and that made our prep work smoother before the event.

On event day, our teams showed up more confident, too, because there were no surprises about when or where things would go. Clients thanked us for removing uncertainty. It turned what used to be guesswork into a predictable experience for everyone involved. Now our focus is always on making events stress-free from start to finish, and that wouldn’t have happened without fixing that early communication slip.

Early on, I made the mistake of giving feedback to my team in long emails filled with general comments, assuming they understood what to change. This caused confusion, and within two months, project revisions rose by 27.6%, and missed deadlines increased by 14.3%. I realized the approach wasn’t clear or actionable, so I switched to short, specific feedback in weekly one-on-one calls, highlighting exact changes and positive progress. Within three months, revisions dropped by 32.4%, and on-time delivery improved by 21.7%. Team members reported feeling more confident and aligned, and overall productivity grew. This experience showed that clear, concise, and direct feedback—not long, vague messages—creates better understanding and measurable results. Business leaders can see that how feedback is delivered is just as important as the content itself.

Early in my leadership role, I mistakenly believed that all team members preferred direct, unfiltered feedback. After giving blunt criticism to a talented technician during a quarterly review, I noticed immediate withdrawal. The lesson was clear: effectiveness is not about my preferred communication style, but about adapting to the needs of the recipient. This experience changed our feedback culture. Now, we start with a simple question: “How do you prefer receiving performance insights?”

Some team members respond well to straightforward feedback, while others need context and encouragement first. By adjusting our approach to each individual, we have seen positive results. Turnover has decreased, productivity has increased, and trust has deepened. Most importantly, team members now proactively seek feedback instead of avoiding it. This has created a true culture of continuous improvement, where constructive conversations flow naturally in both directions.

Early on I assumed that when no one pushed back on a plan it meant everyone agreed. Turns out silence often meant people didn’t want to seem difficult or slow things down. I learned this when a project hit a wall that two people already saw coming but never raised.

Now I ask, “What could derail this?” before I share my own view. It sounds small but it changed everything. People speak up earlier. Problems surface when they’re still fixable. The adjustment took maybe 30 seconds per meeting but saved us weeks of rework.

Early in my leadership journey, I assumed that feedback quantity equaled quality. I would overwhelm team members with numerous improvement points during reviews, thinking I was being thorough. This backfired when I noticed decreased morale and minimal actual improvement. The valuable lesson was that humans can effectively process and act on limited information at once.

I adjusted by implementing what we call the “Power of Three” approach. Now I focus on celebrating three strengths and discussing three growth areas during feedback sessions. We create simple action plans around these points with clear timelines. Team members come to discussions eager rather than anxious, retention has improved, and we see measurable progress on specific skills rather than general confusion.

Feedback is most effective when it is prescriptive and grounded in reality. At EVhype, after an 18% drop in traffic over 4 weeks, I told one of my writers that we needed to raise the quality bar, but I didn’t deal with the issue. There was no engagement, and it was a blind rewrite.

To deal with this, I started giving feedback on engagement metrics, resulting in something actionable. I explained how the introduction of the piece had “lost” readers and how the bounce rate had increased from 52% to 71%. I assigned the task of rewriting the first 150 words and simplifying the headline. I also started a new practice of asking what blocked the writer, rather than just assuming it was the writer’s effort. This resulted in a considerable decrease in the time taken to make edits, a 25% increase in 2 weeks, and an improvement in our average time on the page.

One mistake I made with feedback was presenting critiques too late in the process, after a project was nearly complete. At the time, I thought it made sense to provide feedback as late in the process as possible so the team wouldn’t have to make unnecessary changes. But what I didn’t understand about the process was that it caused frustration and wasted the potential of team members who had already invested an enormous amount of time in their project. They were disappointed because they had already put so much time and effort into their projects and therefore saw the feedback as a roadblock to further development instead of an opportunity for growth.

When I realized this, I began to shift how I gave feedback to include continuous feedback during project development. I asked to meet regularly with the team to review progress and discuss where we could improve the project. In doing so, I allowed the team to identify problems before they became part of the final product. The result was that team members felt included every step of the way and supported in developing the project. As a result, our projects became much more cohesive and better reflected the team’s overall goals. The early feedback provided motivation and confidence to team members, enabling them to make adjustments and ultimately produce higher-quality products, while fostering a collaborative work environment. This experience showed me how important it is to communicate effectively and on time to create a positive working environment.

Years ago, I had to address recurring mistakes with an executive assistant on my team, issues serious enough that we needed a formal conversation about correcting course or parting ways.

Our head of HR happened to be visiting from Paris that week and decided to join. So the meeting became three senior leaders on one side of the table, one EA on the other. I felt uncomfortable with the setup but didn’t speak up.

The next day, I followed up with her one-on-one and asked a question I’d heard about but never used: “What did you hear us say yesterday?”

“I’m not sure,” she said. “I was bamboozled.” She’d spent the entire meeting wondering if she was about to be fired. With that wall of executives facing her, she couldn’t absorb a word of the actual feedback.

That’s when I learned: the geometry of a room shapes whether anyone can hear you. If you want feedback to land, the setup has to feel balanced, not like a tribunal.

Providing feedback which was actually good but untimely was worse than the problem itself. The error was to provide corrective instruction on-the-fly, usually alongside delivery or immediately following an error, and think that speed was identical to clarity. The message was right, but what the receiver heard was judgment and not advice. Defensiveness ensued and the change in behavior was delayed.

The modification was the separation of observation and reflection. Feedback was shifted to a structured period, typically in 24 hours, and began with tangible assessment of effect as opposed to purpose. As opposed to the question of what was wrong, the question became what the result impacted, like a two-hour missed handoff affecting the downstream or confusing documentation at the cost of QA. The conversation was based on common objectives.

The increase was quantifiable. Follow-up questions rose as well as pushback lowered and changes were retained more readily. Repeat issues cycle time reduced significantly. Communication was no longer about being correct at a point of time but rather matching the behavior with results. Such change established confidence and decreased the affective toll that typically looms over feedback discussions.