"Employability Credit in the Bank" – Trust, the Inner Circle, and Embracing Tough Conversations

When I think about employability credit, I think about the trust we build over time—the way long-standing relationships accumulate like credit in a bank. I’ve worked with the same teams and individuals across multiple companies, and I know the power of that inner circle—what Simon Sinek calls the circle of safety. It’s the foundation that allows leaders to trust their teams and make decisions faster because they know they’re all aligned.

But here’s where it gets complicated: As your company grows, the skills and mindsets that helped you launch the business aren’t necessarily the ones that will help you scale it. Founders often find themselves at a crossroads when they realize that new leadership is needed. The inner circle can start to feel uncomfortable when new leaders enter, especially if those leaders bring tough conversations to the table.

Sinek’s inner circle is about creating an environment where people feel safe enough to challenge each other, to have the conversations that lead to better outcomes. Yet, in my experience, bringing in new leadership to a trusted team often means inviting discomfort. These new leaders are not there to be "yes men"; they’re there to push boundaries, ask hard questions, and help the business grow up.

💼 The Inner Circle vs. New Leadership: A Necessary Tension

In the early stages of a company, your inner circle is likely made up of those who were with you from day one. They’ve earned their place, they’ve put in the work, and they’ve built up what I call employability credit. But as your company scales, you need to expand that circle. You need leaders who bring fresh perspectives, challenge the status quo, and sometimes push back. That can be hard for founders who are used to total alignment with their core team.

Simon Sinek talks about the importance of building a team that can trust each other enough to disagree. In a startup, it’s easy for everyone to get on board with the same vision, but when you move into scale-up mode, the stakes get higher, and the need for diverse perspectives becomes essential. You don’t want a team of "yes men"; you want a team that’s not afraid to have those grown-up conversations.

🔄 Balancing Trust and New Leadership

One of the challenges I’ve seen as a CFO is the struggle to balance trust in the inner circle with the need for new voices at the table. Founders often feel that their trusted team knows the business inside out, and there’s a strong inclination to lean on them. But as Ben Horowitz points out in The Hard Thing About Hard Things, the team that launches the business isn’t always the team that scales it. The new leaders you bring in—whether they’re in finance, operations, or strategy—are there to help the business grow, even if it means rocking the boat a little.

So, what makes a great team? Is it a group of talented individuals, or is it the trust and collaboration they share that truly drives success? Patrick Lencioni argues that trust is the foundation of every high-performing team, but that trust needs to extend beyond just the inner circle. You need to trust the new leaders you bring in to challenge your assumptions and push for better solutions.

🚀 Avoiding the Pigeonhole: Growing with the Business

Another challenge founders face is the risk of being pigeonholed. It’s easy to think of the inner circle as only capable of what they’ve done in the past, just as new leadership can sometimes be dismissed as "disruptors." But if you’re going to scale, you need to see both groups for what they are: key contributors who bring different strengths to the table.

As a CFO, I’ve seen companies struggle with this balance. Founders may want to hold onto the inner circle because they trust them, but the business outgrows certain processes. At the same time, new leaders come in with fresh ideas, but they’re sometimes dismissed because they’re not "part of the team" yet. That’s where Simon Sinek’s idea of the circle of safety becomes crucial: It’s about creating an environment where new ideas are welcome, where trust is extended, and where everyone feels safe enough to have the hard conversations.

🔥 So, What Makes a Great Team?

It’s not about choosing between a trusted inner circle or fresh leadership. It’s about building a team where both can thrive. The key is to create an environment where trust and accountability are present, but where there’s also room for disagreement and debate. This isn’t always easy—especially for founders who have relied on their trusted team for years—but it’s essential for growth.

As Sinek puts it, leaders eat last—they create an environment where their teams feel safe to speak up, challenge ideas, and ultimately push the business forward. If you can build a team where trust, collaboration, and open dialogue exist alongside the willingness to have the tough conversations, you’ll be well-positioned to scale successfully.

💡 Navigating Trust, Tough Conversations, and Growth

So, how do you balance the tension between trust in your inner circle and the need for new leadership? Here’s what I’ve learned:

1. Expand Your Circle of Trust: Your inner circle is valuable, but it can’t stay static. You need to bring in new leaders who will push you—and the business—to the next level.

2. Embrace the Tough Conversations: New leaders aren’t there to say yes—they’re there to have the grown-up conversations that lead to real change. As uncomfortable as it may be, it’s necessary for growth.

3. Focus on Team Dynamics: Great teams are built on trust, but also on the ability to challenge each other. The best teams combine the trust and loyalty of long-standing relationships with the fresh perspectives of new leadership.

My view

I hear a lot about bringing in the world's best talent for each position in the company. Anyone who follows sport will know that is not necessarily the answer. Business is different to a certain extent.

One of the features of a "trusted individual" is that quite often you will be willing to trust them to do something new as well. One of my worst recruitment mistakes was choosing someone who looks ideal on paper but the interview gave me a nagging doubt. Bringing someone in to do exactly the same job for a similar company is often the clients brief to a recruiter but what does the candidate gain on that cold Monday morning once joined?

Trusted individuals who you may have worked with a number of times may be actually more willing to express their unfiltered views as the boundaries between work and personal can be minimal. They have been to each other's homes and know each other's families.

Simon Sinek's example of the Navy Seals and the importance of Trust over Performance rings true in my own experience. Low Trust and High Performance can be toxic or dysfunctional and would prefer to work with low Performing and High Trust, although High Performing and High Trust is the obvious aim.

Getting the mix of trust and new is often the right way forward to get the diversity of ideas you need. Not everyone has the motivations and ambitions but share in the values and visions of the company. New individuals can bring new energy but respect those who have brought you this far.

Its particularly difficult for founders to know when to let go and may have false starts that reduce the trust in doing so.

Its a small world. Long term relationships within and outside your company are critical.

Love to hear your experiences ...I am sure they are all different.

#CFO #Leadership #SimonSinek #StartupVsScaleUp #TrustInTeams #BenHorowitz #PatrickLencioni #EmployabilityCredit

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