The Importance of Early Checkpoints in Leadership

Alisa Cohn: From Start-Up to Grown-Up Alisa Cohn has been named the Top Startup Coach in the World by the Thinkers50 Marshall Goldsmith Global Coaches Awards and has been coaching startup founders to grow into world-class CEOs for nearly 20 years. She was named the number one “Global Guru” of startups in 2021, and has worked with startup companies such as Venmo, Etsy, DraftKings, The Wirecutter, Mack Weldon, and Tory Burch. She has also coached CEOs and C-Suite executives at enterprise clients such as Dell, Hitachi, Sony, IBM, Google, and many more. Marshall Goldsmith selected Alisa as one of his Marshall Goldsmith 100 Coaches – a gathering of the top coaches in the world – and Inc. named Alisa one of the top 100 leadership speakers. Her articles have appeared in Harvard Business Review, Forbes, and Inc. and she has been featured as an expert on Bloomberg TV, the BBC World News and in The New York Times. She is the author of From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business*. In this conversation, Alisa and I discuss the difficult reality that most leaders need to face: saying goodbye to an employee. We detail the mindset you need in preparation for letting someone go. Alisa also helps us with specific language that will help you follow-though on a conversation and help everybody move on — and move forward. Key Points Our human tendency is often to side-step problems that we need to address. By the time you take action to fire somebody, you are likely months late. Just because someone was effective in the role previously (or in the last role) doesn’t mean their role is right for them today. It’s helpful to be prescriptive in conversations leading up to firing on exactly your expectations — and the actions the other party has agreed to. There’s no way to fire someone without it being awkward and painful. You’ll need to make peace with that before you take action. Resources Mentioned From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business* by Alisa Cohn Interview Notes Download my interview notes in PDF format (free membership required). Related Episodes How to Challenge Directly and Care Personally, with Kim Scott (episode 302) How to Build Psychological Safety, with Amy Edmondson (episode 404) How to Balance Care and Accountability When Leading Remotely, with Jonathan Raymond (episode 464) Discover More Activate your free membership for full access to the entire library of interviews since 2011, searchable by topic.