🤸 3 questions to ask your team, ex-COO of Stripe, & cringe chats

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

I recently shared 3 questions on Twitter to help assess whether you’re a good manager👇

The post resonated with my community, so I decided to take it a step further by adding questions that allow you to gather feedback directly from your team. This will help you incorporate their perspective into your self-assessment.

I recommend asking these 3 questions either in your 1:1s but sharing them ahead of time or through a survey. If you go for the latter, make sure to discuss the key points and next steps to close the loop with them in your next 1:1. Once every quarter should be a good starting point.

Before asking for feedback, keep these 5 things in mind to find insights, gaps, and opportunities for improvement to create a more trusting environment:

• Be specific: Ask for specific examples to better understand their perspective and help you take actionable steps for improvement.

• Don't make it personal: Remember that this conversation is not about you, but about how you can better support them.

• Listen actively (especially to how they’re feeling) and take notes: Give your full attention and avoid interrupting. Take the time to understand their perspective, write down key points, and ask follow-up questions.

• Acknowledge their feedback and vulnerability: Show appreciation for their willingness to provide feedback.

• Take action and close the loop: After receiving feedback, identify what’s working well and where you can improve to meet your team’s needs. Follow up with them to let them know how you're addressing their feedback.

Here are the 3 questions

Ask this: What are some areas where you feel supported by me as a manager, and where could I improve?

• To understand if: they feel motivated and empowered to take ownership of their work, and whether they have the necessary resources, context, and clarity to do their best work.

Ask this: When we communicate, especially during 1:1s, how does my communication style make you feel?

• To understand if: they feel like you're actively listening to their concerns and feedback, and whether they feel seen, understood, and valued by you and the wider team.

Ask this: What’s stopping you from going faster?

• To understand if: if you're creating the best environment for your team to thrive and to understand what their biggest blockers are to help you guide and support them to achieve more together.

→ What questions would you include or adjust to assess if you’re cultivating a trusting environment for your team?

What we're learning this week

• 🎧 Lessons from scaling Stripe | Claire Hughes Johnson (ex-COO of Stripe) - In this conversation between Lenny and Claire, you’ll find a ton of tactical advice on how to tackle tough conversations, align teams, and make decisions 🤌.

• 📚 I also recommend Claire’s new book, “Scaling People: Tactics for Management and Company Building” - I'm only 1/3 of the way through, but I'm already loving it. This is for you if you're looking for a practical guide on how to build high-impact companies and be an effective leader in a high-growth environment.

• 📚 I’ve also just finished re-reading "Dare to Lead" by Brené Brown - If you haven't read it, it’s an actionable playbook that explores the characteristics of brave leaders, based on decades of research. P.S. It's fitting to mention Brené early on because we're both massive fans. 👀 Jenni may even win the trophy because they both share a deep love for pickleball. Is this a new trend? Am I missing out? 😅

What we’re laughing at this week

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

See you next Thursday! 🤸‍♀️