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Turning Missteps into Playbooks
A real-time case study on momentum, timing, and leadership lessons (and other stuff, too)
Table of Contents
The beauty of being a solopreneur is you can pivot when you feel the need without going through levels of approvals. And as I’ve spent time really thinking about my business (thanks to the eCornell Women in Entrepreneurship course and the Nasdaq Milestone programs), I’m realizing more and more the need to both diversify how you are getting your message across and the importance of building my own email list (these are also takeaways those in talent acquisition and marketing have long realized). So to those ends, I’ll be changing things up a bit… While I’ll still write my LinkedIn newsletter, I’m decreasing to once per month, and I’m going back to writing this one twice a month. In all honestly, the LinkedIn algorithm has been beyond wonky and I’d rather spend time cultivating my own email list.
How can you help? Well, if you’re reading this then you (hopefully) find value in this mix of narrative and actionable support. So, I’m asking you to forward this newsletter to 3 people who you think might benefit. And, if there are specific topics or resources you’d want me to cover, just email me to share. A few topics I have on deck: leading while neurodiverse, building community, and creative staffing.
What I’m Up To
You can catch me a few different ways for the next two months.
When Feedback Doesn’t Stick- I’m hosting a free webinar on Wednesday October 1 at 12pm EST. Most managers know how to give initial feedback. But what do you do when it doesn’t land? That’s when frustration builds, trust erodes. During this time, I’ll share tools to repair in the moment, surface friction and turn conversations into action. Anyone signed up will get the recording.
I’ve also just launched a new 3 week intensive on Leading with Clarity: Effective Communication for People, Team and Project Leads. Prices are currently $575 but will increase to $750 after October 3rd. In addition, as email subscribers, I’ll share another $100 off until October 1 using this link. (And I am offering up to 3 subsidized scholarships for early stage founders or folks who are self paying or in transition- just email me directly)
Leadership onboarding and strategic sprints- if you’d like more focused time to tackle a new project, team or challenge, email me or find time to chat here.
I’ll be speaking at the Future or Strengths Virtual Forum. My session is on October 3rd at 7pm, and focuses on designing leadership pipelines by leveraging strengths. Registration is open!
Learning in Real Time: When Things Don’t Go as Planned
There’s nothing like having to take your own advice. Spoiler alert: It’s not always fun.
I launched my initial Maven course on communicating with clarity and humanity. There was clear interest, and the free webinars were strong. The course sign-ups? Not where I hoped.
That stung. But part of leadership is learning in real time—not just after the fact. And there’s power in building in public—sharing the case studies, the misses, and the learnings—so others can grow alongside you. Even if it’s hard. Whether you are a solopreneur or taking on something entrepreneurial within your organization, these musings may help you plan your own steps a bit more thoughtfully.
Bright Spots
The topic resonated—great turnout and engagement at webinars.
Leaders are hungry for practical support on feedback, clarity, and tough conversations.
Progress
Proof of concept: The content landed. People showed up, stayed engaged, and asked questions during the webinars I led.
Audience clarity: I now see more clearly who this hits with, which sharpens targeting.
Content assets: Webinars, scripts, and slides are now reusable for future programs and posts.
What I Learned
Overcommunicate. After four weeks of posting and emailing, I was tired of hearing myself talk. But new folks were still finding the course—reminding me that people need multiple touch points before deciding.
Timing matters. Yes I had a great amount of lead up time— but during a time where I could only communicate virtually AND folks were in and out on vacation. Lead-up time is useless if half of it falls in August. PLUS September is so busy while people catch up from the summer backlog.
Time is also a Resource- This is an ongoing hypothesis. But while money can be a limiting factor, I’m finding time commitment is even more so. 4 weeks at a busy time is a double whammy of friction.
Don’t ease off. Early sign-ups ≠ momentum. Consistency does.
Buying patterns differ. Leaders often wait until the last minute. I closed too soon and could have had a viable group- small but viable- which would have allowed me to test my content and get feedback.
Check my caution. Trying to avoid “failure” sometimes blocks opportunity.
The Bigger Lesson
This wasn’t failure (I keep telling myself, anyway). It was learning.
Leadership (and entrepreneurship) means spotting the bright spots, noting the progress, owning the misses—and adjusting in real time.
I’m already applying these lessons as I prepare to relaunch.
👉 Join the waitlist for the next course HERE.
👉 Or, if you want something bite-sized, check out my next webinar on What To Do When Feedback Doesn’t Stick.
1% Solutions
Feedback Audit- Hard conversations are often harder- and eval season even messier— when we don’t step back as leaders to think about what we’ve said and what we haven’t. A feedback audit is a structured review of how feedback is currently being given, received, and acted on across a team or organization. It surfaces patterns—like vague language, bias, or lack of follow-up—that can quietly undermine performance and trust. By making these gaps visible, leaders can strengthen clarity, consistency, and accountability in their culture. Feel free to use this one that I designed. I’d use it monthly with myself and- if you manage managers— my team.
Calendar Audit for Alignment-Once a month, review your calendar: does it reflect your priorities, or just your inbox? Shifting even 5% of your time toward strategic work signals what truly matters.
Gut-Check Questions- End every 1:1 by asking: Did I miss anything? That small pause creates space for honesty, surfaces hidden friction, and builds trust over time.
Things I’m Reading and Listening To

The Types of Questions Every Leader Should Ask- Leslie K. John and Alison Woods Brooks, two Harvard Business School professors, share insights on how we can be more successful by asking better questions. In this podcast, they share questions to ask when you need information and when you need buy-in. Super helpful- I’d. suggest sharing this with all of your managers and leadership team.
H1B Visas- I- like many of you- are trying to understand the implications of the H1 B visas. This Business Insider article outlines the issue (though more from a tech perspective), and the White House has now put out an FAQ here (after Friday’s chaos). The order does not seem to impact anyone who already had an application in (for now).
Communication Tips to Build Trust and Morale- A slightly shameless plug, but I’m quoted in this article (along with some very smart people) offering actionable advice on how to navigate - well- <gestures around wildly>. I’d love to know what you find helpful— and what would you add?
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