This 1-on-1 Cheat Sheet offers things to keep in mind as you go through your first 1-on-1 with a new team member:

1. Foundation

Start by stating you’re establishing the foundation for the relationship between the two of you. Talk through some principles and intentions. You will start by explaining your perspective and then asking them theirs. I learned later that in coaching, this is referred to as a designed alliance.
See also: Where to Begin the Journey? and New Hires

2. Solving for them

Make it clear to them that you believe they will be the most valuable to the team if they love what they’re doing with a passion. Hence, as their leader, you aim to solve to that end. They should know that if they don’t believe this, it will get in the way of everything that follows.

  • Nose-to-Nose vs Shoulder-to-Shoulder. Explain how with a foundation of trust of mutually solving for the same outcome. You can collaborate at getting there even if you have different opinions on how to best get there. This is built upon the notion of API – Assume Positive Intent.
    See also: Everything a Gift and The Edge of Chaos Where Startups Thrive
  • Communication and Management Techniques. Explain that the root cause for effective communication and management lies with a genuine intent to solve for them. With that intent, all the tools are easier to execute genuinely. Such as active listening, empathic listening, powerful questions, making eye contact, not interrupting, paying attention, withholding judgement, echoing back, radical candor, …

3. Two-way Radical Candor

With a trusted relationship that you’re solving for them in a partnership. You may deliver feedback on what they could/should’ve done better, but with the intent to help them be a stronger, more effective and successful team member. In return, you expect them to feel comfortable being radically candid with you.
See Also: Radical Candor

4. 10x Impact

Help them appreciate that you’re all about impact. Much as an engineer may strive to have a 10x impact, a manager that can help inspire and support a team of 10 to become 10xers, the manager could now be viewed to having a 100x impact… As a leader, you excel if your team excels.
See Also: The Root Cause of a 10x Engineer

5. Where the Magic Happens

You may at times push them out of their comfort zone, because that’s where the magic happens.
See also: The Room Where it Happens

6. Vectors of Influence

Explain how there are many things that impact how and interaction transpires that may be completely unrelated to the topic and people involved.
See Also Vectors or Influence

7. Powerful Questions

You will at times ask open-ended questions to start a conversation or to dive deeper.
See also: Powerful Questions and Active Listening

  • “What do you want?“ This is one example – you want to know what they want out of life, as that can set the context for what they want out of their job. Hence the current project and working relationship.
  • “What do you want from me?“ This could be in general or on that day or in the context of a specific issue. The answer could be to inform: just listen.
  • Who are you? – two other questions can help set the shared context and foundation:
    • Tell me about an event or experience in your life that fundamentally changed who you are.
    • Tell me about one thing that you’re really passionate about.

Offer something in return. You’ve asked them to open up and be vulnerable so you can get to know them. Don’t forget to offer the same in return. However, it’s important that you do so in service of them – so that they get to know you better in ways that will help them know how to approach you and how to better hear what you’re saying or asking.

Who are you, what changed you, what are you passionate about?

See Also

Internal References from the Document

External References