Getting to know a team

These are some questions I've put together while chatting to folks about their experiences in leadership (particularly engineering leadership).

I found them to be useful starting points for learning about how a team functions. The list is too long to try get through it all, but that's not the idea - the important thing is to ask a question about a topic you're interested in and then get inquisitive about what they say to keep diving deeper. e.g.

• When did you adopt that approach?"
• What made you adopt that approach?
• How did the team react when you told them about that approach?
• What successes have you had since adopting that approach?
• Any lessons learned you'd give as advice to others who might do the same?

The questions

The general stuff

• What size is your team?
• How do you structure your teams? By project? Feature? System? Skills?
• Do you have any team ceremonies?

Engineering process

• What does your development process look like? Can you describe how a feature goes from idea / request to live in prod?
• What is your CI/CD approach?
• What is your approach for different environments (develop, staging, preview, etc)?
• What's your QA process, especially when working on new projects?
• Do you have an official process for discussing / deciding larger architectural pieces? Do you have specific roles for this?
• What is your infrastructure change control process?
• Do you have a good culture of documentation? How do your processes drive this?
• Do your product / design and engineering teams work closely together? How do they collab on new features, projects, products, etc?
• Do you encourage pair programming?
• What is the working relationship between development and devops / infra?
• Do you use a Design System? When was it first introduced? Is it something that generally has a high level of buy-in from engineers?

Agile

• Do you subscribe to any of the Agile values?
• What practices from the toolbelt do you implement?
• What ceremonies do you perform?
• Do you have any processes / practices that you'd consider non-standard or uncommon?
• Do you use sprint goals? What approach do you use to make it not just describe the work included?

Operations

• How do you make progress on work that touches various projects available to non-devs?
• Do you actively try to minimise handoffs? If so, how?
• Do you set team or individual OKRs? Do you find them effective?
• How committed to writing and maintaining specs are you? Who owns them?

Leadership

• What does success in your role look like? What are your core responsibilities?
• What have you found to be the biggest factors to engineering retention in your organisation?
• How often do you have 1:1s with your team?

Startups / Growth

• Are there roles that you think are overlooked in smaller, growing teams? Skills that you think generally should be brought on board sooner than they are?
• What are the most common pitfalls you've seen in established teams that you've joined?
• Any common blindspots that you've seen in teams migrating from being scrappy startup to more established process-bound organisations?