🤸 5 rules on letting people go gracefully, Stripe’s culture of excellence, & meeting IRL

Hey — it’s Cristina & Jenni.

Each week, we share leadership reflections, resources, and laughs to help you excel in your role (+ have fun along the way).

As two tech leaders, we’re here to “lead in public” by sharing what we’re learning in our day-to-day roles, encouraging others to do the same, and learning and growing as leaders together.

Enjoy!

What we’re reflecting on this week

Do you know one of the most costly mistakes I've made in my leadership journey?

Firing too slowly.

It may sound a bit harsh but whether you're a founder, a CEO, or a manager - it’s important to recognize that the success of your startup is intrinsically linked to the people who work there.

So when we identify someone who isn’t a fit culturally or is underperforming, the cost of our slow response or inaction can be more detrimental than we often realize.

Not only does it prevent them from finding the right context where they could thrive, but it also creates a cycle where changing their behavior becomes increasingly difficult.

And while there’s no painless approach to letting people go, there is a method to navigate this process that preserves relationships, minimizes legal risks, and ideally, negates the necessity to fire anyone at all.

Through trial and error, my leadership team and I have learned to manage this better and we’ve taken these experiences as opportunities to scrutinize our recruitment, training, and management practices by constantly asking ourselves:

“What can I do to make sure this doesn’t happen again?”

Mistakes and emotionally-driven decisions are part of the journey, but it’s through reflection that we truly grow.

When we introspect, we're not just making amends; we're fostering a culture of safety in our company. Mastering this approach also gives us the advantage of letting people go earlier, once we understand they aren't a good fit.

This prevents undue trauma for the individual, the company, and ourselves.

Drawing from our experiences we've devised a set of “rules” for letting people go gracefully. These guidelines will help you assemble and maintain a team most capable of steering your startup to success.

Rule #1 - Let your values dictate your hiring and firing decisions.

• Your values are the lifeblood of your startup. They should shape your culture and steer your decisions.

• Hiring people who embody these values is critical, but so is the readiness to part ways with those who don't. By doing so, you uphold high standards which fuels a culture of striving for better.

Rule #2 - Set the bar high and prize resourcefulness and initiative.

• Startup gurus like Paul Graham and Patty McCord advocate hiring the "relentlessly resourceful" employee who exhibits high performance and adapts to the company's shifting needs. It’s not enough to work hard - you want someone that can think on their feet, solve problems creatively, and drive themselves to keep moving forward no matter what.

• Articulate your expectations and performance benchmarks clearly. If an employee's performance is merely "adequate" and not stellar, give regular feedback and be prepared to have a serious conversation.

Rule #3 - Communicate with clarity and compassion.

• When you have to let an employee go, understand that it's typically due to a mismatch between their strengths and the company's needs, not their incompetence.

• Invest genuine effort into helping the person secure their next job promptly. Offer a fair severance package, preferably providing them with a minimum of 4 weeks to find a new job.

Rule # 4 - Reflect and take accountability.

• Ask yourself: "How can I prevent this from recurring?" This self-reflection will help you enhance your recruitment, training, and management practices.

• By taking ownership of your actions, you cultivate a culture of security. This approach helps you to take calculated risks in hiring high-potential talent, knowing you have a thoughtful process in place to end the relationship if required.

Rule #5 - Hire deliberately, fire swiftly.

• Keeping a problematic or underperforming employee can harm the team more than parting ways with them. As Paul Graham suggests, weigh the opportunity cost; if the employee isn't a good fit or underperforming, it's often better to sever ties sooner rather than later.

• This rule holds particularly true in early-stage companies, where bypassing a formal Performance Improvement Plan (PIP) and letting the person go is often the best choice.

We hope that these rules guide you to take a proactive and thoughtful approach towards team members who may not be the right fit for your company. Instead of sidestepping the issue, you’ll be equipped to tackle it directly.

By acting decisively and managing the situation with tact and grace, you not only mitigate long-term impacts but also pave the way for them to discover more fitting opportunities. And we believe that this will set your company on a trajectory towards greater success.

→ Reflecting on your own experience of letting people go, how can you apply these rules or craft your own?

What we’re learning this week

• 🎙️ A great podcast episode with a tech industry giant, Stripe’s CTO - David shares the secrets behind their culture of excellence, top-tier hiring practices, and unique approach to planning at scale.

• ✍️ Check out the tweet from Leadership coach, Dave Klein, that inspired this post - Dave has over 20 years of experience leading high-performing divisions at Bridgewater & Moody's. Follow him on Twitter for weekly wisdom-packed tweets and threads.

• 📚 Looking for a new book? - Join us in exploring Edward de Bono’s timeless classic, “The five-day course in thinking”. De Bono was an MD PhD (Psychology) who wrote more than 60 books and pioneered ‘thinking about thinking’.

What we’re enjoying this week

Hi from us 👋 

Fun fact: After connecting in a digital writing course in January - we finally had the opportunity to meet in person last week! Cristina lives in London and Jenni in Edinburgh. 🇬🇧

That’s it for this week — thanks for reading.

See you next Thursday! 🤸‍♀️