Recommended 1:1 Topics for Early Employees and Startup Executives

Across the startups I’ve been at I’ve seen early employees struggle to know what to talk about with C-suite executives in 1:1s (one-on-ones). Early stage startups are small enough that most employees have monthly or even weekly 1:1s with the CEO or other executives. These executives usually have their hands too full to provide the usual career planning or project review discussions of a normal manager-managee 1:1, so they need to be approached differently.

Here are 3 no-prep-required topics that can work repeatedly in 1:1s with early-stage startup executives:

• Ask them what’s top of mind, e.g., “In your mind, what are the two most important things this quarter, this month, and this week?”. You can use their answers to ground your work in the company’s highest priorities, understand what projects are coming up for your team next, or identify ways to contribute that the executive hasn’t thought of yet.
• Ask for feedback. This usually only works if the company is early, or you report directly to the executive, because otherwise they’re too far removed from your work to provide tangible guidance. However, often, executives will ask you for feedback about the company, and you shouldn’t be concerned about reciprocating the question. If they are struggling to provide concrete feedback for you (as expected!) broaden your question by asking how your team is performing.
• Ask them to reflect on an entry in an article like Joining a Startup for the First Time? 30 Actionable Tips From Folks Who’ve Been There (First Round Review). Spend time reflecting on the topic together and feel free to share experiences you’ve had related to it. The variety of topics in the article can open up new conversational threads and contribute to company culture building in low-stakes conversations. Many of the First Round Review listicles are well curated and have 20+ topics, so they can last you for a long time.