Two failures, one week
+ learning more from lowlights than highlights
Who needs coffee in the morning when you can start your morning reading a message that opens with the above sentence?
This past week I had not 1, but 2 failures lessons learned. And I’m sharing these here because 1) selfishly, these essays are for me at the end of the day to reflect on what I see and observe and 2) to reiterate that marketing and growth in general isn’t always pretty - no one bats 1000, and that the learnings come just as much, if not more, from what didn’t work.
Sponsor: HockeyStack
You just closed a $150k deal. The prospect had their badge scanned at an event, saw 94 ads, got 5 calls/emails from a BDR, and read 3 blog posts. Now the CEO asks: “Who gets credit for this deal?”
But what if I told you that isn’t the question we should be asking?
For years, this was the question I was trying to answer because for years I operated with the “additive” mindset. What happens if we hire 3 more BDRs? What happens if we add $15k more ad spend? And then I would simply map out the anticipated ROI of that effort through our funnel and add it to our current expected outcomes. Hence “additive.”
And then the lightbulb went off. We weren’t successful because of one of those specific channels. We were successful because of how we leveraged the interplay between them.
I’ve had multiple chats with Emir Atli at HockeyStack over the past year about this subject, and this is exactly what they’re helping marketers and GTM leaders solve for.
Feedback loops + ego checks
Whenever I see results or get feedback that something didn’t go to plan, my immediate reaction is to want to hide from it, to pretend it didn’t happen, and move on.
Unfortunately, whether it be marketing or any growth-oriented endeavor, very few things are ever one-and-done activities. They’re most always things that are done consistently over time.
Multiple ad campaigns over the course of a year
A multi-step email nurture sequence
An ongoing educational webinar series
Or in the case we opened this newsletter with, local micro-events.
Knowing that we’re just starting to get these micro-events off the ground + that they’re going to be a big part of our marketing plan for the upcoming year, my head went to these two quotes, which sum up my options for how to move forward better than I could have said myself:
“Insanity is doing the same thing over and over again and expecting different results.”
”Learning is applying a new behavior under the same condition.”
This is where we need to let the feedback loop serve its purpose - letting us know that something’s not right, that if we do the same thing again, that we’re going to get the same (poor) outcome.
And this is the ego check part. This is where we need to be ok saying, “I don’t have it all figured out, but I know this isn’t it.” Then we come up with the next variation for how we want to approach it. Or to the above quote’s point - applying a new behavior and seeing how that affects the outcome.
Lesson 1 - local micro-events
“I want to be completely transparent, last night’s event in my opinion was a complete disaster.”
Local micro-events are going to be a big part of our 2026 plan. Early December is the recruiters’ slow season as they’re learning, networking, + preparing for the new year - AKA the perfect time to host an event where they can do exactly that.
We had one this past week. And that opening quote was the start of the feedback I got the next morning.
When I received it, I had two options:
Let my ego defend what happened, or
Take it as a learning mechanism and make sure it never happens again.
Option 1 is easy. Option 2 is hard. But that’s growth. So I braced myself, knowing the feedback was necessary.
What actually happened
I was optimistic about this event. Looking back, I was too optimistic/confident. I’d stepped back from planning when I should have leaned in.
We booked a venue downtown with the expectation of a private, exclusive space for networking. Here’s what attendees actually found when they arrived:
We had 3 tables in a busy bar. There was zero privacy as the tables were surrounded by other parties.
Other groups had ice buckets, full setups, and proper branding. We had nothing until a member of our team specifically asked for it.
And by 8pm, it had turned into a nightclub bar.
We’d invited 1-2 people per company - a decision that would end up haunting me. When the first attendees walked in, one asked: “Are we the only ones here?”
Yes. Because people don’t show up to these things alone, especially after a long day. That’s not on them. That’s on us for not thinking through the psychology of attendance. They’re much more likely to come if they have colleagues to share the experience with vs. going solo to a bar event.
When we debriefed with the venue, the story became clear. They told us our booking was “too small for a private section” because of the number of people we’d originally confirmed. And there lay the disconnect. Somewhere between our internal expectation, what we communicated to the venue, and what they understood, things got lost.
But here’s what gave me the most anxiety after getting this feedback - if the invitees from our strategic account list (prospect or customer) had shown up, this would have been a disaster. Not just logistically. Strategically.
We position ourselves as a premium brand. And we just hosted an event in the middle of a bar with no signage or privacy.
The lessons learned
Here’s what I didn’t do that I should have (and will in the future):
Expectation alignment with the venue: I assumed we had the same definition of “exclusive, high-end event space.” I thought “private/walled-off room.” They heard “communal bar area.” I should have gotten into the weeds and been explicit.
Invite strategy: I didn’t think deeply enough through who we invite or why. We scattered invites across companies assuming senior leaders would show up solo to a bar after work. They didn’t. Next time: invite groups from our top target companies. Make it feel exclusive and coordinated.
Execution perception: Every detail from the space, the setup, the signage, the drinks, and more sends a signal about who we are. This was a tough one for me to swallow as reflecting back on it, the signal for this event was significantly under our bar of acceptance. But the market doesn’t know that.
Ownership: The buck stops with me. I didn’t involve myself enough in planning and execution. And if we’re serious about running high-end events that reflect our brand, the resourcing + execution for these need to be leveled up ASAP.
And on that note - these events aren’t exclusive to marketing performance solely. Customers are involved. Prospects are involved. That means Sales and Customer Success are impacted by this.
The same morning I received the feedback about the event, I sent the exact initial feedback I received to our senior leadership group on Slack + an accompanying message. I don’t want them to be surprised and hear this from others before me. And I want them to know what we’re doing about it from here:
“Following up on the event yesterday with this group. The tldr from internal feedback on the event was that it was a flop. below is [redacted]’s feedback that lays it all out for this group to see in full transparency.
I’m gathering all feedback from the event this am + will follow up next week with a proper post mortem on all of this so we can course correct for 2026 ASAP. I own this miss entirely and will make sure this never happens again by inserting myself significantly more into the planning + execution of these until they’re operating at our Loxo expectation bar.”
These are tough + uncomfortable questions to ask and answer, but they’re important if we want to LEARN from the experience so we can improve the next time around.
Lesson 2 - communicating with execs
Marketers love words. They’re part of why most of us reading this love (or hate) our vocation. The creativity we’re given to express who we are, what we do, the feelings we want to evoke, the connotations we want implied by the words we choose, etc.
But with this love of words comes another very important responsibility - defining those words and making sure that all involved in the conversation understand the explicit meaning of each of them.
…and I had a fun reminder of this exact lesson this past week with our CEO.
This is a lesson I’ve learned before - and not just once either. It seems to be one of those recurring lessons that emphasizes the importance of proactively getting ahead of communications with any receivers, but especially execs.
Case in point: some recent messaging + positioning work
As AI has entered just about every market + industry this year, we wanted to come up with a better/stronger POV around it vs. just saying we’re yet another “AI-Powered [category] software”.
Months were spent working through different options, angles, enemies, frames, positions, and more and we landed on one we really liked that could truly stand on its own not just now with the AI craze, but as time goes on as well as an evergreen position.
The first 95% of the meeting was incredible. The team was speaking brilliantly to the insight uncovered, how we saw things playing out, how it compared to the market, what it meant for our marketing, etc.
Then the words “company positioning” came up. That this would be something that would cascade beyond marketing + to all internal team members so everyone was speaking the same language. But when our CEO heard “company positioning,” he had a different definition that operates by (rightfully so).
I made the critical mistake of not taking the time to better define the above and the conversation immediately shifted to not wanting to alter things product/market fit, etc.
We absolutely had no intent of shifting anything at that level, but the mistake had been made. I had accidentally allowed worry and concern in his mind to enter the conversation due to not being explicit in what we meant. And the last 5% of the meeting had a very different tone and feeling as a result.
This led to a few hours of clean up after the meeting ended to explain to him what we were (and weren’t) doing to put him at ease. And then a separate call with the other team members who were a part of the presentation to debrief on what went well, why things shifted during that last 5% of the meeting, and where things were at after talking to our CEO. A lot of time, energy, and enthusiasm went into this + it was critical not to let that momentum slip because of a lesson that I already knew but didn’t act upon appropriately.
Lesson learned (again).
Takeaway
Both of these failures had the same root cause: I assumed clarity in communication existed when it clearly didn’t.
With the event, I assumed I communicated expectations properly to our team + that the venue understood our standards as part of this. With the conversation with our CEO, I assumed we were using the same definition of “company positioning” relative to the meeting agenda.
Assumptions are expensive when trying to amend after the fact, but cost just a few minutes of prep/groundwork when done ahead of time. It’s much better to spend those few minutes up front to get everyone on the same page, even if I think everyone is operating under the same set of expectations/definitions. Our future self will thank us.
Book quote of the week
“Essentialism is not about how to get more things done; it’s about how to get the right things done…It is about making the wisest possible investment of your time and energy in order to operate at our highest point of contribution by doing only what is essential.”
- Essentialism, by Greg McKeown
See you next Saturday,
Sam