Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, identifies Julie Szudarek’s leadership approach as a corrective to one of the most common misreadings of what it means to be a people-first CEO: the belief that kindness and accountability are opposites. Szudarek has been a CEO twice — turning around a $2 billion international business at Groupon across 15 countries, then scaling ATIDA from a single-country European pharmacy into a seven-country operation through organic growth and multiple acquisitions. She now leads Self Financial, a fintech company on a mission to bring credit-building tools to more than 100 million Americans. Her view is direct: hard conversations are not the opposite of kindness — they are a more demanding form of it.
This episode is for CEOs who have realized that being well-liked has become a substitute for performance reviews — and who need a framework for reintroducing accountability without destroying the culture they built.
Key Takeaways
- CEOs who give specific, honest feedback give their teams what they actually want: a clear path to succeeding in the role. Avoiding that feedback to protect relationships withholds the one thing that makes improvement possible.
- CEOs who delay hard conversations to preserve a people-first culture are not protecting their teams — they are protecting themselves, and team performance pays the cost.
- Fast-moving decisions in regulated environments must be filtered through a one-way/two-way door test — two-way door decisions move fast, one-way door decisions with compliance or consumer risk move deliberately.
- AI adoption at Self Financial is structured as a company-wide capability, not a departmental tool: every employee has an enterprise ChatGPT license, each department has a named AI champion, and every implementation requires a measurable ROI — quantitative where possible, qualitative where not.
People-First Leadership Fails Teams When It Avoids Hard Conversations
Szudarek names the blind spot plainly: “I think it’s taking the people-first to mean that you can’t be hard on people or that nice or values-driven equates to outcomes — and it doesn’t, it just doesn’t always equate to that.”
The failure pattern is consistent. A CEO forms genuine relationships with their team. Those relationships make difficult topics feel risky. The CEO avoids bringing up inefficiencies or problems because the relationship feels good. The team member never gets the feedback they need to improve or course-correct.
Szudarek’s own development as a leader required breaking that pattern: “I’ve needed to teach myself to see through some of the relationships that I have with people to understand that my relationship isn’t blinding me to maybe inefficiencies that that person might have, or help that that person needs.”
Glenn Gow has seen this dynamic in his coaching work with CEOs who describe themselves as empathetic leaders. His observation: when “nice” is the dominant word in a 360 review, it almost always signals that accountability is missing — and that the team has learned they will not be held to commitments. The CEOs who act on that feedback and introduce clear accountability structures report that performance improves and that the culture they were trying to protect actually strengthens.
The reframe Szudarek lands on is straightforward: “Hard conversations in and of themselves can actually be a form of kindness. It’s just a more uncomfortable form of kindness that you need to get used to and develop the muscle around being comfortable with.”
Gow’s framing for how those conversations work: treat them as adult-to-adult. “You made a commitment and now I’m asking you whether or not you’re going to achieve that commitment. And if you haven’t, we need to talk about that.” That is not a cruel conversation. It is a clear one.
The underlying assumption Szudarek brings to feedback is that most people want to improve. “I generally assume good intent, and I think most human beings want to achieve and want to do better. I think that’s sort of innate in people. And so allowing people to do that through your feedback — that’s magical, if given correctly.” Feedback, given well, is what makes that improvement possible.
How CEOs Make Fast Decisions in Regulated Industries Without Creating Risk
Szudarek has scaled two businesses in heavily regulated spaces — a pharmacy business operating across seven European countries under divergent national regulations, and Self Financial, a fintech operating under multiple overlapping financial regulatory bodies. Her framework for moving fast without creating compliance risk starts with a single question: is this a one-way door or a two-way door?
Two-way door decisions are reversible. If the decision turns out to be wrong, you can come back through and adjust. These move fast. One-way door decisions — those with potential consumer harm, regulatory exposure, or decisions that are hard to undo — move deliberately.
At Groupon, Szudarek absorbed a move-fast-and-adjust culture that she found genuinely useful. But unfiltered, it creates risk in regulated environments. “In both ATIDA, which was a B2C pharmacy business in Europe fraught with regulation, and now in Self, which is a fintech, I use that fast moving for these two-way door opportunities and slower moving for the one-way door opportunities.”
On regulatory ambiguity specifically — and Szudarek is clear that regulatory ambiguity is the norm, not the exception — her practice is to document reasoning in real time. When two regulatory bodies say contradictory things about the same topic, her team works back to intent: what is each body actually trying to accomplish? The words may differ. The underlying goal usually does not. From there, she applies a reasonableness filter: given what we understand about the intent, what is the defensible interpretation for this specific business? That reasoning gets written down. “Writing is a very good way to make sure that you can articulate something and that it makes sense. So just writing it down to make sure that it makes sense and that you have a record of why you did that particular thing.”
How CEOs Structure AI Adoption Across an Entire Company
At Self Financial, AI is not a tool used by one team. All 400-plus employees have an enterprise ChatGPT license. There is a centralized AI operations function — an AI center of excellence — and each department has a named AI champion.
The process works bottom-up from department knowledge. Each champion identifies the top three AI opportunities for their function. The AI ops team then helps each champion figure out how to implement those opportunities, builds the workflow, and trains the broader team on how to use it, how to interpret results, and how to maintain it over time.
Szudarek gave two concrete examples of how this plays out by department. In marketing, the team identified automated push notification content and email subject line generation as a high-priority opportunity. The AI ops team worked with the marketing champion to build that workflow programmatically, then trained the rest of the marketing function on how to use it. In customer service, the team mapped which query types could be handled by automated AI responses versus human agents — and built a workflow that routes accordingly, with human escalation paths defined in advance.
ROI measurement is non-negotiable. “I’m a very numbers-focused CEO. And so any investment that we have, I want to make sure we have metrics around it — around usage of course, but more so around ROI.”
Some ROI is directly quantitative. Customer service automation is one area where the math is straightforward: Self Financial calculated the number of queries that could be handled by automated AI responses versus human agents, and determined how many outsourced FTEs that eliminated. Szudarek made the case for consistency as a quality argument, not just a cost argument: “You want the answer to be the same every single time. And if you have 50 agents that get one of these queries, you know, every 20th query that they answer, you’re probably not going to have the exact same answer.” Automation produces a more reliable output at lower cost.
Other ROI is qualitative but still tracked. A marketing analyst who used to produce three campaigns now produces ten, and reports that the work is better. The volume increase is observable even when individual minutes are not tracked. Szudarek accepts that as legitimate evidence of return.
Gow named what Szudarek is doing: AI from the inside out. Not piloting a tool in one corner of the business. Not waiting for a vendor to sell the company on a workflow. Building company-wide capability by giving everyone access, identifying the highest-value use cases by function, and building support infrastructure that makes adoption stick.
How CEOs Scale by Scaling Themselves: The Principles Behind Julie Szudarek’s Leadership
| Principle | What It Means in Practice | Named Evidence from This Interview |
| Hard conversations are a form of kindness | Avoiding uncomfortable feedback is not empathy — it withholds what people need to improve. CEOs must build the muscle to initiate those conversations directly. | Szudarek found that relationships formed across ATIDA’s seven-country expansion had begun to obscure performance gaps in direct reports. Introducing direct feedback loops produced faster identification of where leaders needed support or replacement and cleared accountability blockages that geography and familiarity had created. |
| Filter speed by reversibility | Move fast on two-way door decisions; move deliberately on one-way door decisions with consumer, regulatory, or operational risk. | At ATIDA, applying this filter across seven European regulatory regimes allowed Szudarek’s team to move quickly on reversible product and operational decisions while slowing down on consumer-facing pharmacy decisions — keeping the business agile without accumulating regulatory exposure. |
| Document ambiguous reasoning in real time | When regulations conflict or are unclear, work back to legislative intent, apply a reasonableness filter, and write down the reasoning before acting. | Szudarek’s documentation practice across both ATIDA’s European pharmacy regulations and Self Financial’s U.S. financial services compliance created a defensible record of intent-based reasoning — protecting both businesses when regulators later reviewed decisions made under ambiguous guidance. |
| Structure AI adoption as company-wide capability | Give every employee access to AI tools. Name a department champion for each function. Centralize implementation support. Require measurable ROI for every investment. | At Self Financial, this structure produced a marketing function that increased campaign output more than threefold per analyst and a customer service operation that eliminated a measurable number of outsourced FTEs through automated query routing — with qualitative and quantitative ROI tracked for both. |
Quotes from This Episode
- “I think it’s taking the people-first to mean that you can’t be hard on people or that nice or values-driven equates to outcomes — and it doesn’t, it just doesn’t always equate to that.” — Julie Szudarek, CEO, Self Financial
- “Hard conversations in and of themselves can actually be a form of kindness. It’s just a more uncomfortable form of kindness that you need to get used to and develop the muscle around being comfortable with.” — Julie Szudarek, CEO, Self Financial
- “In both ATIDA, which was a B2C pharmacy business in Europe fraught with regulation, and now in Self, which is a fintech, I use that fast moving for these two-way door opportunities and slower moving for the one-way door opportunities.” — Julie Szudarek, CEO, Self Financial
- “Writing is a very good way to make sure that you can articulate something and that it makes sense. So just writing it down to make sure that it makes sense and that you have a record of why you did that particular thing.” — Julie Szudarek, CEO, Self Financial
- “I’m a very numbers-focused CEO. And so any investment that we have, I want to make sure we have metrics around it — around usage of course, but more so around ROI.” — Julie Szudarek, CEO, Self Financial
Frequently Asked Questions
How should a CEO give hard feedback without damaging a people-first culture?
CEOs who avoid hard conversations to protect relationships are actually harming their teams by withholding the information people need to improve. Julie Szudarek, CEO of Self Financial, frames direct feedback as a more demanding form of kindness — one that requires developing a specific muscle over time. Her baseline assumption is that most people want to improve and that giving them honest, specific feedback is what makes improvement possible. The culture does not suffer from hard conversations. It suffers from their absence.
How do CEOs move fast in regulated industries without creating compliance risk?
Szudarek uses a one-way/two-way door test to determine pace. Two-way door decisions — those that can be reversed if wrong — move fast. One-way door decisions with potential consumer harm, regulatory exposure, or hard-to-undo consequences move deliberately. When regulations are ambiguous or contradictory across regulatory bodies, her practice is to work back to legislative intent, apply a reasonableness filter, and document the reasoning in writing before acting.
How should a CEO structure AI adoption across an entire company?
Szudarek’s approach at Self Financial is built on three components: universal access (all 400-plus employees have an enterprise ChatGPT license), departmental ownership (each function has a named AI champion who identifies the top three opportunities in their area), and centralized implementation support (an AI ops team that helps champions build workflows and train their teams). Every AI investment requires a measurable ROI — quantitative where the math is clean, qualitative where productivity gains are observable but harder to track to the minute.
CEOs Work with Glenn Gow to Scale Their Companies and Careers
Glenn Gow is The Scaling Executive Coach — he coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
