Susan Hailey
CHRO at Enable
Enable
Episode 114
The uncomfortable truth about scaling: your leadership needs an upgrade.
Current chapter: Built by People podcast features insights from world's top HR leaders
Built By PeopleJuly 9, 2025 · 14:05
Thesis
“Effective leadership development and strategic team building, supported by data and a willingness to make difficult changes, are essential for driving business growth and organizational stability, particularly during significant scaling phases.”
Show notes
Susan Hailey started her career at IBM in marketing and sales — and about halfway through, realized she was far more interested in the people side of the business. That pivot led her into executive search, then HR, then the CHRO seat at a series of high-growth technology companies. The pattern she's seen most consistently: companies scaling aggressively toward a revenue doubling often arrive there with the wrong leadership team for the next chapter.
Going from $250M to $500M requires fundamentally different capabilities than the people who got you to $250M. The mistake most organizations make is trying to promote their way out of that gap. Susan is direct about this: internal promotion feels like the right, loyal choice — but it's often the more expensive one in the long run. She recounts a case where the right move was an external executive search, and the moment that person arrived, team friction that had built across departments essentially evaporated. An overnight change in organizational energy.
Her advice for HR leaders navigating these conversations: ground everything in facts. Revenue numbers. Employee sentiment data from surveys. Observable friction between teams. The conversation is still hard — these are often long-tenured leaders with close relationships to the CEO — but a fact-based approach removes the personal dimension that makes these conversations break down. Her parting principle: "Not being afraid of a hard conversation. Not worrying about whether you will find the right person." Both of those fears cost organizations more than the problem they're afraid to address.
- Why the leadership team that gets you to $250M often isn't equipped to get you to $500M
- How to ground difficult leadership change conversations in facts rather than intuition or politics
- The internal promotion mistake — and when external search is the harder but correct call
- What immediately changed when the right leader was put in place: team friction, cross-functional dynamics, and energy
- How to build trust quickly within a newly formed leadership team, especially when founders are making the transition from inventors to scale operators
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What you'll take away
- 1Systematically identify leadership gaps by assessing capabilities against future growth aspirations, especially when transitioning revenue stages.
- 2Ground delicate leadership change conversations in objective facts, such as growth rates, employee sentiment from surveys, and observable team friction.
- 3Be prepared to conduct thorough executive searches externally, even if more costly, when internal promotions might not meet the specific demands of a new growth phase.
- 4Actively engage in team building and foster trust within new leadership teams to quickly reduce departmental friction and improve collaboration.
- 5Maintain flexibility and a growth mindset regarding where specific functions reside within the organization to adapt to evolving business needs.
What most organizations get wrong
- •Promoting internally isn't always the 'right' or 'easier' choice; sometimes the harder, more expensive external search is necessary for the next level of growth, especially if the internal candidate isn't equipped for new sales motions or scale.
In Susan's words
“About halfway through my career, decided I was a lot more interested in the people side of business.”
Highlights her pivot from sales/marketing to HR, driven by a deep interest in people and business impact.
“If anyone grounds them in the facts, look at what's happening, look at the numbers... I think the other thing you can look at is the sentiment, the sentiment of the employees.”
Emphasizes a data-driven approach to evaluating leadership effectiveness and making difficult decisions.
“The mistake was promoting this person from the inside and not necessarily doing the harder thing, which would be to go— and more expensive, frankly, to go do a search.”
A specific example where a common internal promotion strategy failed and necessitated a more strategic external search.
“As soon as this person came in, the team settled down, the friction between other teams almost evaporated, and just the contribution of this particular individual was just extraordinary for what the company needed at that time.”
Illustrates the immediate, positive impact of making the right leadership change.
“Building and strengthening teams is some of the best work you can ever do. It can be challenging while you're going through it.”
A powerful statement on the value and inherent difficulty of her core work in HR.
“Using a fact-based approach to how each of the functions are performing and how that particular leader is performing is your best strategy. Not being afraid of a hard conversation, not worrying about whether you will find the right person.”
Provides a concise summary of her actionable advice for HR leaders facing tough decisions.
The problems this episode addresses
- •Companies struggling to achieve revenue doubling (e.g., $250M to $500M) because existing leadership teams lack the specific capabilities required for the next growth stage.
- •CEOs and boards facing delicate and difficult conversations about leadership changes, especially when personal relationships with long-tenured leaders are involved.
- •Internal promotions that fail to deliver desired results, leading to internal team friction and necessitating costly, time-consuming executive searches.
- •Organizations needing to quickly build trust and coherence within newly formed leadership teams to overcome departmental friction and accelerate decision-making.
- •Founders needing to transition from inventing ideas to scaling a large organization, requiring them to learn new leadership dynamics and trust new executive hires.
In this episode
Built by People podcast features insights from world's top HR leaders
Built by People
You've been in the technology industry for most of your career
MRK: My Career Journey
Susan, when we last talked, you mentioned upgrading the leadership team capabilities
The Need to Upgrade the Leadership Team
Susan, how did you approach delicate conversations with CEO and board about leadership changes
The Difficult Talk About Leadership Changes
One company had a leadership transition that didn't go as planned
Have We Made the Right Leadership Transition?
Susan described seeing an immediate transformation after getting the right leadership team in place
Susan, in your current role
Building and strengthening teams is some of the best work you can ever do
Susan Cox on Building and Strengthening Teams
Topics covered
Organizations and entities mentioned
Full transcript
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