Lesson 5: When to Hold On, When to Let Go
TEN Years, 10 Lessons: What We Wish We Knew When We Started
In October 2025, Eleven Eleven Talent will turn 10. To celebrate, we’re sharing 10 lessons, one each month about what we’ve learned in a decade of building a business. From community-building to resilience, from hiring to firing, these are the insights we wish we knew when we started.
Whether you’re an entrepreneur, a recruiter, or navigating your own career path, we hope these lessons support you in building something meaningful and lasting.
Lesson 5: When to Hold On, When to Let Go
The honest truth about hiring and firing, and how the right people can shape your business and the wrong ones can cost you everything.
If you’re building something, whether it’s a business, a team, or even a vision for your life, you’ll quickly realize:
People will shape it.
Some will walk in, pour themselves into your work, leave it stronger and more beautiful than when they arrived.
And some… will drain it.
They’ll take more than they give. They’ll lead with entitlement, not gratitude. They’ll see your generosity as weakness.
We’ve experienced both.
We’ve had team members who brought energy, ideas, and loyalty (thank you C) and who made our business better than we imagined. And we’ve had others who left us questioning ourselves, our leadership, our willingness to keep our hearts open.
I (Tess) still carry a lesson from before Eleven Eleven Talent, back when I was Director of HR at Earls Restaurants. I was in a meeting with the executive team, and we were discussing how to handle an employee who wasn’t working out. The President of the company (Mo Jessa) paused and said something that’s stayed with me:
When in doubt, be generous. With your time. Your words. Your grace. And when you think you’ve given enough, give a little more. That’s where everything starts to change.
I found that to be a profound lesson in leadership and one that shaped how we lead our company today.
However, there have been times, (more than a few), when we’ve questioned whether our generosity was being taken advantage of. After being burned, it’s natural to wonder: Are we being too generous?
Where’s the line between kindness and firmness? Between grace and boundaries?
As women, as leaders, as business owners, we’ve had to figure that out. It’s a sweet spot, a balance of heart and head, that we’re committed to exploring as each situation presents itself.
Here’s What We’ve Learned (So You Don’t Have To)
Hire for values, not just skills.
You can train for tasks. You can’t train for integrity, curiosity, or resilience.Pay attention early. Small warning signs don’t usually disappear. If someone shows you their work ethic, or lack of it, believe them.
Be generous, but clear. Clarity is kindness. If something’s not working, say it. Be specific. Be respectful. But don’t let things fester. (And document).
Letting someone go doesn’t make you a bad leader. It means you’re protecting the vision, the team, and the energy of what you’re building.
Celebrate those who leave well. There are people who’ll contribute beautifully and then move on. Honor them. They’re part of your story. Companies are not doing enough of this.
This lesson wasn’t easy to learn. It challenged our identities as leaders, as women who believe in giving people opportunities and who intend to do good. We’ve had to let go of how we are perceived at times in order to make the right decisions for our business, our people and, ourselves.
Letting go of being seen as ‘nice’ is one of the main reasons we’re still here, stronger, clearer, and more determined to build a company where generosity is paired with unwavering accountability.
If you’re in a leadership role and wrestling with this balance, we see you.
You’re not alone. You’re not failing. You’re deciding - to lead and let go.
Tess & Alisha
Next up: Lesson 6: Don’t Put All Your Eggs in One Basket: Why diversifying your clients, revenue streams, and strategies can be the difference between stress and stability.
