There are phrases you hear that just stick. They get burned into your brain and become part of your operating system.
For me, one of those phrases is, “You don’t know what you don’t know.”
I first heard it from one of my former bosses, Greg Warner, the founder of MarketSmart. Greg had a whole list of “Greg-isms” he shared with the team, but this is the one that’s stuck with me for over a decade. On my first day, he left a hand-drawn cartoon character of himself on my desk with a “Welcome to MarketSmart” note. I still have it. It was a small gesture, but it set the tone for a philosophy he wanted our team to live by.
Greg taught me this idea was bigger than business. It was about how you treat people. I can still hear him saying “You don’t know what you don’t know… you never really know what someone is going through or what challenges they are experiencing.”
I didn’t just learn that lesson; I lived it.
During my first year working for Greg, my mother had a severe schizophrenic episode. I was across the country, and for reasons I’ll never understand, I was the only person she would speak to. My then-husband didn’t get the urgency—he was mad I was going to miss his birthday party. Many of our friends in D.C. didn’t get it either. To be fair, you don’t really understand that kind of crisis until you’ve lived it.
When I told Greg I needed to fly home to Utah, I kept it vague, only alluding to some issues with my mom. He didn’t pry or ask for details. He just said something along the lines of, “Do not worry about a thing. You go take care of what you need to take care of. We’ve got everything handled here”
He didn’t need to know the specifics because, on some level, he already understood. Later, I learned why he had that capacity for empathy. He told me how he worked from his own mother’s hospital room during her final battle with cancer. He got it.
That trust was everything. I was a young professional, and let’s just say I face-planted more times than I care to admit. But his trust gave me the space to learn from my mistakes, recover, and grow. I’m proud of the work I did there—the client microsites and marketing campaigns that eventually evolved into the product suite MarketSmart provides to non-profit fundraisers today. It’s a journey that started with that hand-drawn cartoon on my desk and ended years later with a going-away plaque from the team that I still have.
The Wisdom of Knowing Nothing
The idea of “you don’t know what you don’t know” is often tied to the philosopher Socrates. His famous line, “The only true wisdom is in knowing you know nothing,” isn’t about being unintelligent. It’s about being smart enough to admit you don’t have all the answers.
It’s recognizing that we all have blind spots—the “unknown unknowns”—that keep us from even asking the right questions.
In our professional lives, this is a powerful check on the ego that can lead to bad decisions. Greg told a story to every new hire, which he also included in the first chapter of his book, Engagement Fundraising. He was at a conference watching a vendor pitch an email product to a room of fundraisers. The audience was hooked, letting out “oohs” and “ahhs” as the salesperson showed off the product’s high “open-rate percentage”.
Greg saw the problem immediately. He knew open rates are a classic “vanity metric”—often inaccurate and rarely a sign of actual success. The fundraisers, however, were ready to buy. They were confident, but they were confidently wrong. As Greg put it: “It wasn’t their fault; they didn’t know what they didn’t know”. Their blind spot was about to cost them, because they didn’t know to ask about better metrics like clicks, conversions, and real engagement.
Putting the Principle into Practice
That experience with my mom taught me this idea is a practical tool for leadership and life.
In Leadership & Empathy: Greg didn’t assume he knew my situation better than I did. He gave me his trust. That’s a vital lesson for anyone who manages people. When an employee is struggling, our first instinct is often to judge. But we don’t know what we don’t know. We don’t see the personal crisis, the health scare, or the financial stress happening after they log off. Even the person who seems to have it all together might be fighting a battle you know nothing about.
But this principle has another side. It’s a leader’s job to know that what you don’t see can be just as important. Some of the most dedicated team members are the least likely to ask for help because they don’t want to be a burden. You might think things are fine because no alarm bells are ringing. But “you don’t know what you don’t know” also means you don’t know if someone is struggling silently. A good leader asks thoughtful, open-ended questions—not to get the answers they want, but to create an environment where it’s okay to veer off course, okay to be stuck, and where asking for help is not just accepted, but encouraged.
In Strategy & Execution: The story from Greg’s book is a perfect MarTech example of this principle in action. We get so focused on a tactic or metric that we fail to ask if it’s the right one. We get so excited about launching a new platform that we don’t step back and ask if we have the right strategy. Remember, despite what enterprise vendors show you in slick demos, a tool isn’t a strategy—it’s just a tool. To fight this, we have to:
- Seek other perspectives: Talk to people outside your bubble. They’ll see things you can’t.
- Ask “meta-questions”: Don’t just ask, “How do we solve this?” Ask, “What assumptions are we making?” or “What are we missing?”.
- Embrace being wrong: The goal isn’t to be right; it’s to get it right.
This mindset is what separates good professionals from great ones. It keeps you curious, adaptable, and a lifelong learner—a theme I return to again and again.
The world is full of people certain they have all the answers. But the leaders and colleagues who make the biggest difference are the ones humble enough to admit they don’t. They operate with a quiet confidence that comes not from knowing everything, but from knowing they are asking the right questions, tackling the right problems, and using appropriate tools and processes to figure it out.
So, my question for you is: Where are your blind spots? And more importantly, what are you doing to find them?
This year has been a lot for many of us, but as I’ve shared before, there is always so much to be thankful for. I wish you and yours a wonderful Thanksgiving holiday filled with good food and great company.
See you next month, Seth
A Note on Process & Transparency:
This issue was fun to work on and brought back a lot of great memories. I’m incredibly grateful to my former boss and one of the important mentors in my early career, Gregory Warner, for modeling the kind of leadership that I still strive for today. Many of my colleagues from that time are still with the company over a decade later, which in this day and age, says more about his leadership than anything I can write. It also means I was lucky enough to work with some truly awesome people. So, a cross-coast “blast from the past” shoutout to some of the old MarketSmart crew: Cheryl Papsch, Shari Delaney, and Jeff Giannotto.
In the spirit of transparency, I partnered with Google’s Gemini 2.5 Pro as a thought partner to help structure my reflections and connect my personal story to the broader concepts. As I always say, AI isn’t going to take your job, but people who leverage AI to their advantage will. Be one of those people. (Seriously, leveraging AI has been a game-changer for my fractional consulting practice over the past year, and I wouldn’t be able to do what I do without it. Again, it is only a tool, and it has many limitations. You will only truly learn and understand what those are by testing it out yourself.)
