Welcome to an Overthinker's Almanac! Today, we're going to play a game! It's the first in a potentially never-recurring segment
"Don't suck at management!"
It's the show where we give you a scenario and see if you decide not to suck as a leader.
For today's question, you are the CEO of a major national retailer. A frontline employee at one of your stores builds up the courage to send a thoughtful 400+ word email with their observations and recommendations on improving operations.
Do you:
A. Respond to the email, thanking the employee for their dedication to the organization, and ask if they would be interested in following up with the appropriate functional leader, which you could facilitate?
B. Respond to the email, thanking them for their interest in improving the company, and indicate you'll consider their recommendations.
C. Blow them off entirely, never responding.
D. Respond to the email condescendingly, highlighting how their recommendations would destroy billions in value, and the rest of their recommendations are already in progress. Then, ask if the employee researched the company's strategy at all before emailing you.
Now, as an experienced leader, which do you choose?
I'll give you a moment to think about it.
Let's break down these options and evaluate each individual's perspective. We’ll examine feedback more deeply in an upcoming series, looking at both giving and receiving. We'll use today as a primer for that lengthier deep dive.
Handling Feedback as a Leader
For anyone who has given well-intentioned, carefully thought-out feedback to their supervisor, you know that this takes some guts. The wider the power gap, the more intimidating such an interaction feels. In my corporate days, we had an acronym for this because everything in business needs a TLA (three-letter acronym). Giving (cough) “constructive” feedback to leadership was deemed a potential CLM, or Career-Limiting Move. There's a risk of giving upward feedback. If poorly received, such feedback could lead to issues in your future reviews, reducing potential for promotion, or even threaten your current employment. You're relying on the professional maturity of supervisors, which is a big assumption.
The adage is "feedback is a gift." If we genuinely believe that, particularly as C-suite leaders and even lower-level managers, we need to be mindful of how we receive and respond to feedback. We must acknowledge the courage required by junior employees to share their observations.
If an employee is willing to share constructive feedback from very different levels of the organization, this is the type of employee that I would want to keep. They not only took the risk to share feedback upwards, but they did so with interest and commitment to help improve the organization.
To me, there are only two kinds of feedback:
the kind you agree with and
the kind you don't.
Regardless of your agreement, the employee took the risk and demonstrated interest in your organization. Obviously, at the retail store level, there's a significant power and knowledge gap. Still, a savvy leader needs to consider the implications of our potential responses.
So let's break them down.
Analysis of the Response Options
For Option A, replying, acknowledging their ideas, and recommending follow-ups with appropriate high-level individuals may be a bit excessive.
But imagine the impact on the individual!
"Wow! They actually responded! I feel heard! They're interested in my ideas!"
What do you think happens to engagement? Undoubtedly, it would increase, likely dramatically. You would be establishing an environment that encourages candid feedback throughout the organization. If you disagree with the feedback, this could be tricky, but it may be worth it.
That’s because it’s not just about the engagement of that employee. Imagine what they'll do with the response email. They're likely to share with their manager, peers, and, really, anyone who would listen. We've already established they're willing to speak their mind with the most intimidating levels of your organization, so we can safely imagine they're vocal in more familiar circles. Engagement and culture are likely to spread from this single interaction, and even if others never offer feedback themselves, they now know that opinions at their level are valued. Few HR-driven activities provide such a meaningful ROI on employee engagement, and it doesn't get much more minimal than a single email response and one follow-up meeting.
Instead, you may opt for response B. Thank them for their time and that you'll consider their advice. Sure, you took two minutes to read their note and respond. While your time is valuable,1 just providing a response is meaningful regardless of how much mental energy you put into the recommendation.
"Wow! I actually got a response! I wonder if they'll do anything with my advice?"
It's not as good, but it's still net positive, encouraging future feedback. It’s less likely to be shared widely, but still moves culture in the right direction.
Or, you can go with option C, and blow the email off entirely. Maybe you read it, perhaps you didn't. At least it didn't waste your precious time getting feedback from a frontline employee. I can't say I'd agree with this from an engagement standpoint, but in corporate realities, a lengthy email isn't necessarily something you have time to deal with daily. And feedback from one store-level employee isn't moving the stock price. Probably.
Lastly, we have option D. You take the time to respond, putting the employee in their place.
Who are they to tell me how to run a multi-billion-dollar company from the store level? I know all I need about retail; I run the whole company!
What is the impact on the employee? Likely, they will crawl into their shell and hide, never giving feedback again. Sure, this may be a challenge to some people, but for most, building up the courage necessary to give feedback only to be swatted down will leave a lasting impression. As a leader, you shut down feedback from this employee.
Though maybe you did more than that.
It's more than just one employee
As managers, we must remember that employees talk to each other. You didn't just eliminate feedback from one individual. You promoted a culture where feedback isn’t welcome, and frontline retail employees do not have a place to provide input, as the enterprise-level dashboards provide all the details needed in the C-suite.
Worse than destroying candor in feedback, you likely lose their commitment and the loyalty of any of the others they choose to share your message with. Just like the potential positive ripple effect from options A and B, responding with option D risks negative repercussions, driving pervasive disengagement and a culture where feedback is punished.
Or worse, maybe that employee shares such an experience with a guy who writes on Substack, who also has the willingness to call out poor management.
Ripped from Reality
As you may have guessed, I'm describing an actual event that happened recently. While I want to be sensitive to the individual and their employment situation,2 there's a bit more to this story than just a retail cog emailing their CEO. The person who shared this interaction was a frontline retail employee, but their prior resume lines include Director and VP-level operations positions at Fortune 100 companies. They chose to leave corporate life, now just wanting to live on their terms.
While you can remove the leader from the position, true leaders will always shine through and can't turn off their ability to inspire and support others. While trying to fly under the radar, bringing executive skills, empathetic leadership, and a master's degree in operations from a Top 5 university, while also caring about the job, you'll eventually get found out when trying to work an overnight retail shift. I'll leave it at that, but obviously, this individual has the chops for a bit more professionally.
The Situation & Response
So, this individual has been doing a pseudo-undercover boss type role, taking a job well below their skill and experience level for personal reasons. Eventually, their store management caught on that they had a person with the potential to be all of their bosses, yet, the desire for entry-level work.
After a few months in the role and being “found out,” seeing the inefficiencies at the store level, they shared feedback with their immediate leadership. They aligned to send the email to the CEO to see what happened.
About 30 hours later, they received a message that read as follows:
Other that [sic] converting 75% of our store selling space to back-end fulfillment (which would destroy approximately $40 billion in annual revenue), we are well on the way to executing some of your recommendations. Case in point, [retailer name] is the only retailer in the world with co-development partnerships with Nivida [sic], Open AI [sic], Apple, Palantir & Google. Question, before sent [sic] this email did you do any research on some of the initiatives we are working on? Good luck to you.
Get Outlook for iOS
Based on the misspelling of Nvidia and OpenAI and various other grammatical errors, along with the Apple Outlook sign-off, we'll assume the CEO typed this out on their iPhone. I say that not to be mean, but as supporting evidence that a human actually wrote this, and in this case, one particular human.
How would you feel if you were an employee (at any level) and received this email after sending feedback to your CEO?
What would your emotions be?
What would this email do to your engagement?
Also, assume you're the type of person willing to send the CEO a feedback email in the first place. Are you sharing this? Chances are, yeah! This email is going to get shown around. Whether that's a good idea or not is a different discussion, but as a frontline employee, expectations for cultural/engagement implications aren't your concern, and since it's from the CEO themself, the CEO is setting the tone for the company.
Checking for Biases with AI
I will acknowledge my bias in this story, being close to the feedback giver. To get meta, seeking feedback on my feedback, I decided to use AI to see if I was being fair in my analysis of the situation. So, I fed the original feedback email into ChatGPT with the below prompt to analyze my interpretation:3
PROMPT: "You are the CEO of a major retailer in the United States. Below is an email received from a store-level employee. Briefly assess the tone and intention of the employee."
Here is ChatGPT's response:
The tone of the employee's email is:
✅ Professional – It's clear, polished, and respectful.
✅ Constructive – The writer is focused on solutions, not complaints.
✅ Ambitious – They are proposing a bold, transformative vision.
✅ Sincere – They state explicitly they aren't angling for a personal promotion but are motivated by genuine concern and ideas.
✅ Confident – They highlight impressive credentials without arrogance, framing their expertise as relevant context.
We’ll skip ahead a bit to the summary.
Overall, it's an unusually thoughtful and well-articulated message from a store-level employee—clearly written by someone with significant prior leadership experience who is now working in a frontline role. The tone is respectful and forward-thinking, and the intention is to drive positive, strategic change rather than self-promotion.
Okay, AI interprets the original feedback email similarly to me. Since ChatGPT is playing the role of CEO, how would it recommend responding to this employee? So I gave it the following request:
Prompt: "Briefly, as the CEO, how would you recommend handling this email?"
ChatGPT's response:
As CEO, here's how I'd recommend handling it—briefly and effectively:
✅ Acknowledge promptly and appreciatively.
Reply or have an executive assistant respond within a few days to thank the employee for their thoughtful initiative and clear investment in the company's future.
✅ Assign appropriate follow-up.
Forward the proposal to the Chief Strategy Officer or Head of Digital Transformation with a note asking them to review it and consider a brief exploratory conversation.
✅ Close the loop.
Ensure the employee gets a response after the review, even if the ideas aren't adopted, showing respect for the effort and encouraging continued engagement.
Example short reply:
"Thank you for taking the time to share such a thoughtful perspective and well-developed proposal. I appreciate your passion for <COMPANY>'s future and your willingness to think boldly. I'm sharing this with our strategy and operations teams so they can review it in detail and follow up. Thanks for being part of our team and contributing in this way."
This approach shows you value insight from every level, without overcommitting prematurely.
Flipping things around, I shared the CEO's response text with ChatGPT, redacting the company and employee's names. I didn't need to redact the CEO's name since it wasn't signed; it merely ended with the "Outlook for iOS" tag.
Prompt: "This was an actual feedback email sent from an employee to the CEO of a Fortune 100 retailer. Here is the response from the CEO to the employee, redacting only the company's name and the employee's first name. Provide an assessment of this email as an experienced executive coach advising this CEO after the fact."
Here’s the beginning of ChatGPT's response:
Tone:
🔴 Defensive – The first sentence immediately focuses on refuting one idea and implicitly suggesting the sender doesn't understand the business.
🔴 Dismissive – The rhetorical question implies the employee was careless or uninformed.
🔴 Curt – There is no acknowledgment of the thoughtfulness, experience, or goodwill behind the outreach.
🔴 Unnecessarily adversarial – Even if the proposal was imperfect, the tone here is more confrontational than constructive.
Strengths:
✅ It demonstrates the CEO's clarity about the scale and strategic realities of the business.
✅ It points to specific initiatives underway, showing confidence in current execution.
Weaknesses:
❌ Missed opportunity to model humility and openness.
Even when an employee's ideas are impractical, the most respected leaders use that as a moment to reinforce a culture where people feel safe to contribute.
❌ Tone likely discourages future engagement.
Frontline employees and mid-level leaders who see this will likely think twice before sharing ideas in the future.
❌ No recognition of the sender's experience or intentions.
The employee clearly stated they had significant executive experience and were motivated by a desire to help. Completely ignoring that context comes off as dismissive.
❌ The email could easily be perceived as condescending.
"Did you do any research?" reads as rhetorical scolding rather than curiosity.
Lessons from a Bad Response
So, what can we actually take away from this? A few principles stand out.
1. Words ripple.
As a leader, your words don't just vanish into Outlook for iOS. They echo. A quick, careless reply might feel like nothing to you, but imagine yourself on the receiving end. You are their leader. You define how safe and engaged they feel, and whether they'll ever share their observations with you again. It takes guts to hit send when feedback goes upwards. Engagement comes from consistency, and you need to model the behaviors you want to see at every level. Culture isn't just built on HR campaigns. It comes from every micro-interaction.
And remember, it's not just one employee, it's everyone they share it with.
2. Feedback has to flow both ways.
We spend endless time teaching leaders how to give feedback, but far less on how to receive it. An authentic feedback culture means people at every level know their voice matters and leaders know how to hear it. That doesn't mean you agree with everything. There are two kinds of feedback: the feedback you agree with and the feedback you don't, but you need to learn (and teach) how to handle both. How we respond to feedback determines if anyone is willing to share more with us.
3. AI can be your coach.
Now, as someone providing professional coaching, I'm not saying outsource our humanity to ChatGPT. But before firing off a defensive email on your phone, why not sanity-check it with a neutral, less biased, less emotional partner? AI can highlight tone, suggest more constructive framing, or even draft a response that keeps you from looking like, well, Option D.
Obvious AI applications hidden in plain sight
I wrote the rest of this article before my little AI experiment, and it was oddly satisfying that ChatGPT chose option A in our management gameshow. Apparently, basic human decency and strategic thinking are available for a fraction of the cost of an eight-figure compensation package.
This is a fascinating case study on what not to do, not just as a CEO but as any leader who wants to build trust, promote engagement, and actually hear what's happening below them on the organizational chart. And before you brush it off with a smug, "Well, I would obviously never choose Option D," remember: this really happened!
The lesson here goes beyond one clumsy email and even a single feedback interaction. It's about culture and the importance of consistency, whether you're creating an environment where upward feedback is welcomed or quietly (or loudly) punished. As important as it is to give feedback effectively, ensuring everyone in your organization is able to receive feedback is essential.
And as for AI? Ironically, this CEO, who dismissed a thoughtful frontline email, rattled off a list of elite AI partnerships yet completely missed the most obvious, least expensive, and potentially more impactful use case: helping humans not sound like jerks in emails.
So here's my questions for you:
Which option would you have chosen in real life?
If you were the employee, how would you have responded?
How is feedback really handled in your world?
I'd love your feedback on this story, and on how we can all suck a little less at giving (and receiving) feedback.
Thanks for reading.
As likely reflected in your ~500:1 compensation ratio of CEO to retail employee
Not to create a CLM
I redacted the names of the CEO, company, and individual from the original feedback email and the CEO's response.
