Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, sat down with Shannon Swift, founder and CEO of Swift HR Solutions, to uncover the people-side patterns that determine whether a fast-scaling company holds together or falls apart. Swift has advised scaling companies for over 21 years and spent more than 13 years as a leader in the Entrepreneurs’ Organization (EO), including as Seattle Chapter President. Her view is direct: most scaling problems are hiring problems in disguise.
Who This Episode Is For
This episode is for CEOs scaling past their first few dozen employees who want to stop losing good people and start building a culture that attracts more of them.
Key Takeaways
- CEOs who define culture before they hire protect their company from the compounding cost of the wrong person in the wrong seat.
- “People are hired for what they know and fired for who they are” — the implication is that your screening process must weight character and values above credentials.
- Settling on a hire because a role is open is the fastest way to degrade a culture that took years to build.
- If a value is not something you would hire or fire on, it is not actually a value.
- When AI absorbs administrative onboarding tasks — the I-9 processing, paperwork collection — the first hour of a new hire’s day shifts from compliance to culture, which is where belonging is built.
Why CEOs Must Define Culture Before They Make Their First Hire
Shannon Swift has spent over 21 years advising scaling companies. She will tell you the same thing every time: the companies that get into trouble almost always skipped the same step.
“I think really what I have seen over the years is how important it is to focus on culture right from the beginning. So who are we as an organization? Who are the people that we want to bring onto our team? Who are the investors that we want and the cultural aspects of that relationship?”
That is not a soft observation. It is a structural one. If you do not define who you are as a company before you start hiring, you will hire people who reflect the absence of that definition. And when things go sideways, you will not be able to point to a clear standard you violated. You will just have a team that does not quite work together and a culture that drifts.
Swift is specific about co-founders in particular. Alignment conversations between co-founders must happen before the company reaches scale. Before you develop, as she puts it, “cracks in the foundation because we haven’t really sussed those conversations out.”
Glenn Gow reinforces this from his coaching practice. He works with a CEO he calls a “black belt in culture.” That CEO operates by two principles: culture lives in language, and culture sticks through stories.
The language piece matters more than most CEOs realize. A word like “integrity” means something different to every person who reads it. Swift defines it precisely for her own firm: “integrity is the I in Swift. And what that means to us is that we’re predictable, our words match our actions.” That specificity is what makes a value real. Without it, a values statement is decoration.
The story piece is what makes a value stick. You can tell an employee that customer comes first. They will not believe it until they hear about the time someone stayed until midnight to fix a problem for a client. Stories are how values get transferred from the founding team to every new person who walks in the door.
Swift’s recommended starting point: write down your three to five values. Then write a single sentence for each one that defines what that value means in practice at your company specifically. Then collect one story for each value. These are your onboarding materials.
How CEOs Lose Good People Before They Even Know It
Turnover does not show up on a profit and loss statement. That is exactly why most CEOs underestimate it.
Glenn Gow lays out the real cost: you exit the person, you absorb the lost work during the gap, you carry the opportunity cost of what they would have produced, you load the burden onto the remaining team, and then you start the full cycle of recruiting, hiring, and onboarding all over again. Every one of those costs is real. None of them show up as a clean line item.
Swift’s response to that is to go upstream. Stop trying to fix turnover after it happens. Fix the hiring process that causes it.
“People are hired for what they know and fired for who they are. And so really focusing on who the person is that we’re bringing in and having that culture screen being very intentional about making sure that everybody that comes on board is going to fit the norms, the culture, the values of the organization.”
She makes an important observation about what actually stays constant during a company’s growth: “Our priorities will change. Sometimes our entire business model will change. But the people that we need to accomplish this together is pretty consistent, and that’s in that value set.”
That is worth pausing on. Your product will change. Your go-to-market will change. Your team structure will change. But the type of person who belongs at your company — the person who operates with the values you have defined — stays constant. Hire to that standard every time, not to the version of the company you are running today.
Swift also points to a cost most CEOs overlook entirely: “turnover is costly. And in addition to some of the things that you mentioned, I think also just bad PR, right? I mean, people are on social media all the time and the message that people have around their company experience gets out and that kind of builds your employment brand.”
Every person who leaves your company with a bad experience becomes a signal in the market. It makes your next hire harder. It raises your recruiting cost. It narrows your candidate pool. The damage compounds quietly.
Swift’s recommended approach: add a structured culture screen to every interview process. Write three to five behavioral questions that surface whether a candidate operates by your stated values. Score candidates on culture fit separately from skill fit. Do not move someone forward who fails the culture screen regardless of their technical credentials.
CEOs Who Settle on Hires Pay for It in Culture Decay
Swift names the first behavior a CEO must stop when scaling fast:
“I think settling, right? It’s like, okay, we’ve got this position open and this person, we know they’re not a fit, but we’ve got to fill this role. So I think settling is the first step toward really degrading and debilitating the culture and leading to more and more, like if we’re gonna settle on this topic or this value, we can settle on others.”
This is how cultures go from intentional to accidental. One compromise in a role that felt urgent. Then another. Then you have a team where some people operate by the values and others do not, and you have signaled to everyone watching that the values are negotiable. They will draw their own conclusions about what else is negotiable.
Swift offers a test that makes this concrete. When you are reviewing your values, ask yourself: “If we wouldn’t hire or fire on this particular attribute, it’s not really a value. It’s not really critical.”
Apply that test to every value on your list. If you would not actually pass on a great-on-paper candidate because they failed the culture screen for that value, it is not a value. It is a slogan. Remove it or commit to enforcing it.
When a CEO Recognizes It Is Time to Step Aside
Shannon Swift, who has sat in board rooms with founders at pivotal growth transitions across her 21-year advisory career, identifies communication failure — not competence failure — as the reason most CEO exits go badly. That pattern holds even when a CEO knows their time in the seat is limited.
Roughly 60 percent of venture-backed CEOs get replaced within five years of a funding event. Glenn Gow observed this directly during his time in venture capital and traced it to a predictable pattern. The company that earned the investment had the right CEO for that stage. But the company changed. It scaled. And the board eventually concluded the CEO had not grown at the same rate.
Swift witnessed this failure mode from inside the room. She was present when a board voted to remove a CEO who had no idea it was coming. What she saw confirmed her view.
“I knew that the CEO had a definite plan on when he was going to exit out, but hadn’t communicated that with the board. And so there were a lot of assumptions made, but no conversations that were had.”
Her advice to CEOs who want to stay in the seat: be honest with the board about where you are and what you need. Tell them you have not grown a company past this point before. Tell them you want to get there. Ask them for candid feedback. That conversation is uncomfortable. The alternative — a surprise removal — is worse.
Her advice to CEOs who recognize they are not the right person for the next stage: lean into that clarity. Know where your contribution is strongest and build a structure around that. Bring in a COO to operationalize. Bring in a president. Protect the work that gives you energy and that the company actually needs from you.
“I have definitely had colleagues that have gotten, grown their businesses to a point where they’re like, okay, I’m not having fun anymore. Like I did this business because I love what I do. And now it’s like, I don’t want to deal with all this people stuff and, you know, all of these other things. And so I think, you know, it’s like, hey, maybe it’s time for me to bring in a CEO or bring in a president, maybe that can, or a COO that will operationalize.”
That is not failure. That is self-awareness. It is one of the harder decisions a founder makes, and the ones who make it well tend to protect both the company and their own satisfaction in the work.
How AI Gives CEOs Back the Time to Lead Like Humans
Swift started her HR career at Zillow doing things that no longer require a human. Every Monday morning, the first hour with new hires was spent watching them fill out paperwork. Collecting a photocopy of a driver’s license. Processing I-9 forms by hand.
That time is gone now. AI and automation have absorbed it.
“Now we have people show up and that’s all done, it’s already in the system. And so we get to really focus on what’s important. We get to focus on, you know, who are we as a business, seeing a demo of the product, you know, having them really fit into, you know, what is my role?”
That is the actual opportunity AI creates in HR and in every function of a scaling company. It does not replace the human work. It surfaces the human work by removing the administrative layer that used to bury it.
Glenn Gow points to one capability AI will not replace: empathy. A CEO who is no longer grinding through low-value administrative work has time to understand what their people are going through. That empathy builds loyalty. Loyalty reduces turnover. The whole chain of value flows from having capacity for human connection.
Swift’s recommended audit: identify the HR and people-related tasks on your team’s plate that are administrative and time-consuming but not generative. Automate or eliminate those first. Redirect that time toward the conversations and decisions that require human judgment.
What Shannon Swift’s Framework Produces in Practice
| Principle | What it means in practice | Named evidence from this interview |
| Define culture before you hire | Write specific definitions for each value, not just labels. Collect one story per value. | Swift has advised scaling companies for 21 years. This is the single lesson she says would have saved the most pain from day one. |
| Hire for who, not just what | Build a culture screen into every interview. Score it separately from skills. | “People are hired for what they know and fired for who they are.” Candidates who fail the culture screen do not move forward. |
| Never settle on a culture fit | A value you will not hire or fire on is not a value. Treat every compromise as a precedent. | Swift identifies settling as the first behavior that degrades culture during fast scaling. |
| Communicate with your board | Have the candid conversation about your growth plan and your limits before the board has it without you. | Swift witnessed a CEO removed without warning because he had not shared his exit plan with the board. |
| Use AI to free up human time | Automate administrative hiring and HR tasks. Redirect that time to empathy, culture, and judgment. | Swift’s early-stage work at Zillow required an hour of paperwork per new hire. That hour now belongs to culture onboarding. |
Quotes from This Episode
- “People are hired for what they know and fired for who they are.” — Shannon Swift, Founder and CEO, Swift HR Solutions
- “If we wouldn’t hire or fire on this particular attribute, it’s not really a value. It’s not really critical.” — Shannon Swift, Founder and CEO, Swift HR Solutions
- “Our priorities will change. Sometimes our entire business model will change. But the people that we need to accomplish this together is pretty consistent, and that’s in that value set.” — Shannon Swift, Founder and CEO, Swift HR Solutions
- “I think settling is the first step toward really degrading and debilitating the culture and leading to more and more, like if we’re gonna settle on this topic or this value, we can settle on others.” — Shannon Swift, Founder and CEO, Swift HR Solutions
- “I knew that the CEO had a definite plan on when he was going to exit out, but hadn’t communicated that with the board. And so there were a lot of assumptions made, but no conversations that were had.” — Shannon Swift, Founder and CEO, Swift HR Solutions
Frequently Asked Questions
How do you build a culture screen into the hiring process for a fast-scaling startup?
Start by defining each value in a single concrete sentence that describes observable behavior, not aspirations. Swift HR Solutions defines integrity as “we’re predictable, our words match our actions.” From that definition, write two to three behavioral interview questions that reveal whether the candidate operates that way. Score the culture screen separately from technical skills. Do not advance a candidate who fails the culture screen regardless of their credentials. The cost of a bad culture fit compounds through team friction, manager time, and eventual turnover, making the screening investment straightforward to justify.
At what point should a CEO bring in outside leadership rather than try to grow into the role?
The decision point is when the job has changed more than the CEO has. Glenn Gow observed that roughly 60 percent of venture-backed CEOs are replaced within five years of a funding event, typically because the company’s stage outpaced the CEO’s development. Shannon Swift advises CEOs to ask this question early: where do they see their role transitioning, and what does that look like? The productive path is either committing to personal development and asking the board for direct feedback, or bringing in a COO or president to operationalize so the founder can focus on the contribution where they add the most value.
How should CEOs use AI in HR without losing the human element that drives retention?
Use AI to eliminate the administrative and compliance-driven tasks that consume HR time without generating insight or connection. Shannon Swift describes spending the first hour of every new hire’s first day at Zillow watching them fill out paperwork. That hour now belongs to culture onboarding, product demos, and role context conversations. AI handles the I-9 process. Humans handle the work that determines whether a new employee feels like they belong. The freed-up time is the opportunity to lead with empathy, which builds the loyalty that reduces turnover.
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.
