To say that I hate Valentine’s Day would probably be both an overstatement and an understatement. It’s not that it feels like some contrived holiday created by a secret cabal of greeting card and confectioner company CEOs. Nor is it the idea of helping our kids “make” Valentines for each and every one of their classmates (nor how in my childhood, such equanimity was nonexistent and I went many V-Days with an empty shoe “mailbox”). No, it’s an understatement to say that I “hate” Valentine’s Day because it brings to mind the stinging memory of being unceremoniously dumped by my then girlfriend / future (i.e. now) wife immediately following Valentine’s Day dinner1. It’s only an overstatement because I don’t really give the “holiday” much consideration2.
While we laugh about this now (more than a decade later), in the moment it was a pretty low point for me. Here I was, CONVINCED that this was THE absolutely right person for me and here she was (potentially) making it clear that I was out to lunch. I’m not going to deep dive our discussion, but I’m sharing this story because of what I learned about feedback (given to me in this moment and my response to it in general).
We often say to our kids that doing something wrong doesn’t make them a “bad person.” We aren’t solely defined by our actions. Making a mistake, being told that you aren’t as smart/funny/responsible/etc. as you believed yourself to be, failing a (proverbial or actual) test, or just flat out feeling like “your best isn’t good enough” can all spark feelings of defensiveness, embarrassment, or shame. This is not limited to critical feedback — even constructive criticism can cut deeply into our finely tuned self image. This can result in many things (hurt feelings, meet “shame spiral”), frequently directly at odds with the intended goal(s).
Related, just “taking the feedback” isn’t ideal either. Sometimes there’s a mismatch in style — communication or otherwise. Sometimes expectations are (and always have been) misaligned. Sometimes there is an unknown (private or truly unknown) issue that is leading to dysfunction or dissatisfaction. Any of these (and more) can create the conditions for feedback that is built on a shaky or incomplete foundation or that is taken too literally (or not literally enough). By the way, this isn’t inherent to negative (ie “critical”) feedback — it doesn’t feel great to hear “great job” or “keep it up” when you felt like you underdelivered or have no idea what the “it” is that you should continue doing.
What was so impactful about Angela’s feedback wasn’t just the content, but that it made me reflect on how she was receiving me relative to my own expectations. Once that clicked, it caused me to revisit my initial reaction. I’d describe my experience as a feedback loop: positive intent, negative reception, reflection, and realization that the positive intent in context was important to internalize. I’m not sure “feedback loop” has a positive connotation, particularly in the context of modern filter bubbles.
But in this instance, I think I needed to complete the cycle to really find the optimal path forward.
Positive Intent: she told me that I seemed uncomfortable talking about my feelings, in particular when it came to sharing when I was upset and acutely with regard to things she was doing to upset me. In short, I seemed like a people pleaser who didn’t know how to (have a) fight. In her view, I needed time to develop these skills.
Negative Reception: What I heard was that I was emotionally immature, which — while probably accurate — in that particular moment (given my stunted feelings?) felt deeply unfair. I saw myself as someone who let most problems roll off of me and who cared deeply about making those I loved happy; sometimes that meant subordinating my feelings or sitting on my frustrations.
Reflection: Once we got past that moment (and the next day’s shopping spree), I spent the following few weeks thinking about a number of topics, including our individual relationship histories, our time together so far, why I thought we clicked, what other things she made clear were important to her, etc.
Positive Intent in Context: I realized that “people pleaser” signaled to her that I was actually unable to take care of myself and was going to need her to constantly put aside her own feelings and frustrations to take care of me. Woof!
She needed me to demonstrate that I could express how I was feeling (sad, angry, annoyed, disappointed, whatever) without worrying that it might elicit a similar (or wildly different!) feeling for her. In this instance, somewhat ironically, this meant telling her that I thought she was being willful and shortsighted for opting to walkaway from what seemed like something special (see above) because she wasn’t willing to fight for it. Taking her feedback directly — being more open and vulnerable or shouting, “you are making me angry!” when I was upset — was more likely to exacerbate than to correct the problem. The recognition that we can’t (constantly) each rely on the other to bear the burden of our own individual shit serves as the foundation for our partnership. It allows us to work as a team to create a (much more supportive) version of this dynamic with our kids and to “take care” of each other when actually needed most.
I believe this led to our getting back together, getting engaged, getting pregnant, and getting married (in that order!) all in the span of 19 months. Given we had only been dating for 3 months at the time, this dynamic drove a lot of “getting” in short period. More critically, this completely upended my approach to receiving and internalizing feedback personally and professionally going forward. While by no means am I perfect — particularly “in the moment” — I’ve found that when I can connect what I’m hearing to what I know about the specific circumstance (me, the stakeholder, our relationship, the events, etc.), I’ve been able to bounce pretty hard off of some very low moments.
As one small example, while in a new role and in the midst of managing an external partner during a very difficult and drawn out negotiation, I was told that I was coming up short because I was too prone to assuming people operated with the best intentions.
Positive Intent: The underlying message was really “just make sure you maintain your skepticism and operate accordingly” — insightful and impactful feedback.
Negative Reception: What I reflexively heard in my brain was “you are too easy going and people are taking advantage of you,” which raised my hackles. To my mind, I was leveraging my natural disposition to genuinely build report, hoping to work the deal to a fair and logical outcome in a perfectly friendly manner. I figured that the stakeholder “wouldn’t see me coming” if things went sideways and I needed to drive to a specific outcome. Plus, outside of any real timing constraints, if it yielded good results, I saw no issue “assuming good intentions” until it became apparent otherwise. Who were they to call me soft or imply naïveté?
Reflection: In truth, until I either shifted into “enforcement mode” or achieved my desired result, how were my key internal stakeholders supposed to know any of that?
Positive Intent in Context: Mine is certainly not a “typical” negotiating style and in our business it’s actually more common behavior of those about to get fleeced. They were naturally worried that I was going to whiff and were trying to communicate as much to me without saying, “hey, you are about to fuck this up.” That was on me, not them.
Though it may not be temperamentally obvious, I love negotiating. I find it to be some amalgamation of solving a logic puzzle, navigating small group social dynamics, distilling of complexity, teamwork, and copy editing. However good (or not) I am at each one of those things, I very much enjoy all of them. Over time, I’ve proven to be pretty effective at leveraging unique combinations of skills in those underlying areas to achieve differentiated deal results3.
The natural outcome from this type of feedback could easily be to conclude “well, maybe I’m not the right kind of person to be in the middle of negotiations” or conversely, to unnaturally try to be something that you are not. I’m certainly not lobbying against expanded self-awareness; not every person is right for every role. Nor would I suggest that you avoid extending outside of your comfort zone; you don’t build muscles without lifting increasingly heavier weights. Understanding yourself in context — the “why” behind the feedback — is a key ingredient to making change for the better. Taking someone’s feedback on its face (or simply emulating their behavior) might lead to change, but I don’t believe it leads to growth. It’s particularly unfortunate if that feedback keeps you from pursuing something about which you are passionate about or (worse) that you could be uniquely great at.
A second example — both a lower career ebb and more explicitly relevant to what I write about here — came when I was told that a peer’s performance was stronger than mine because they “will run through walls, clearing the way for everyone else” while I “will make sure we are running through the right walls.”
Positive Intent: The subtext of the feedback was that I was thoughtful and diligent, but also that I seemed to need a high degree of certainty before moving forward.
Negative Reception: What I heard (once the steam stopped pouring out of my ears) was that I was really strategic, but too risk averse to be an entrepreneurial leader in a growth environment. I think I may have responded with a snide comment referencing lemmings, Wile E. Coyote, and the need for at least one person to consider what and why we were doing something before actually doing it…not one of my finer moments.
Reflection: I felt like I’ve operated comfortably with limited information through most of my executive career. The goal has always been to have enough information to 1) increase the probability of success, 2) reduce the probability of doing something that unnecessarily reduces the probability of success, and 3) ensure that the risk (or probability) adjusted return was large and skewed to the upside. While I know more than many, I recognize that I know a tiny percentage of all there is to know. I’m also destined to be wrong (a lot), but am comfortable4 with it. Despite this, I was being received as a “strategy guy.”
Positive Intent in Context: There’s nothing wrong with being viewed as thoughtful and diligent — I think these traits are in relative short supply, despite being critical to building an optimal strategy. I also believe that strategy without execution is really just an academic exercise; otherwise, they are inextricably linked. Thus, delivering against any particular strategy requires the same type of rigor that’s needed to build it.
Ok, so what was the growth outcome here? What changes did I make or how did I internalize this in how I work and how did that help me advance in my career? There isn’t a clean answer. We’re talking about professional growth during a career — sometimes there is no one-to-one result in the current circumstance. You may not “see” the benefits of development until the next time you find yourself in a similar situation. Or you may “see” it in indirect ways, like how you take “critical” feedback in the future.
I view (albeit difficult) moments like these as essential to informing my worldview and pivotal in getting me to where I am today — both for the learnings and in the “butterfly flaps its wings” sense. Do Angela and I get (and stay) married if she doesn’t dump me? I don’t know, but I also don’t spend a lot of time thinking about alternative timelines because I’m busy trying to be a better person in this one.
To be clear, this feedback loop works for me. It might resonate with you in its entirety or partly (or not at all!). What I want to convey is that however you think about growth, it’s important to do two things:
Do not internalize what you are hearing in real-time, whether it’s positive or negative. Listen, ask questions, and engage — but don’t act.
Sit and reflect — not just on what you heard, but from whom you heard it, your relationship with them, the state and trajectory of your time in this role, the state and trajectory of your business/company, what you expected going into the conversation, how those expectations were exceeded/met/subverted, and anything else that can help you extract the most meaning out of the guidance you are getting.
The more you understand ‘why' you are receiving certain feedback, the more likely you are to know how to maximize its impact.
As if a sign of what was to come, the restaurant at which we dined closed the next day…permanently.
Other than to tell this story AND because February 14th is also my mother’s birthday. Happy birthday mom (and sorry that I’m here shitting on Valentine’s Day)!
Important to note, negotiating a “great deal” is a small part in getting to a great overall outcome for any project. Very (very) often, success is predicated on an effective external partnership, which while legislated by a negotiated deal, is going to be grounded in a real live operating relationship. In this case, I don’t want to imply that driving to a “great deal” can overcome a meh (or bad) partnership nor that a good (or great) partnership is immune from an overly aggressive negotiation. I am really just talking about success at this stage of a project lifecycle and my belief that the dynamics of addressed in this footnote need to be top of mind when conducting any such negotiation. How’s that for a feedback loop!?
However successful I become, I will continue to make mistakes in my work: my ideas will be wrong, my strategy will be ineffective, my work product will have errors, I’ll have the wrong read on someone, and/or I’ll say the wrong thing (and with way too many words). After some struggles earlier in my career, I’ve developed enough self awareness and have enough experience to be comfortable with this dynamic. While I like to be correct (I’m human!), I’m now just as motivated by learning something from the each of those times that I’m not.


