How to nail a job transition: advice from Sukhinder Singh Cassidy

Executive overview

Most people transition badly — they leave too abruptly, linger too long, or mentally check out before they've actually gone. The damage is disproportionate: how you leave shapes your reputation more than most of what you did while you were there.

Four practices change that: stay present until the end, set a tight timeline, leave opportunity for others, and take middle steps before making a big leap.

The goal is to exit with the same standard you'd want to inherit.

Don't leave before you leave

• Mentally checking out before you've announced — or even decided — erodes the impact of everything you built.
• People remember exits. A poor exit can undo years of strong performance.
• Stay present by staying busy: a full workload forces presence; idleness invites drift.
• Even if others know you're leaving, your daily actions still shape your legacy.

Set a defined transition timeline

• Too short: you leave a mess. Too long: your impact declines because people mentally uncouple from you.
• Once a departure is known, senior attention and mentorship drop off sharply — lingering wastes everyone's time.
• Target a timeline where you can deliver ~95% of a clean handover and stay genuinely busy to the end.
• Short notice can be forgiven if every remaining day shows visible effort to wrap things up.

Leave opportunity in your wake

• Transitions create a window to identify successors and high-potential people who could grow into your work.
• Don't just avoid leaving a mess — actively set up the next person to succeed.
• You may know better than anyone who the non-obvious but highest-potential candidate is.
• Influence outlasts your title: the people whose careers you accelerated carry your impact forward.
• Example: at Google, Sukhinder spent months identifying and positioning her number two, Daniel, for her role — giving him every region and discipline over time so he was the obvious choice when she left.
• Example: at Joyus, she promoted her head of product to CEO rather than holding the title, then mentored him through it; he later founded his own venture-backed company.

Tie up loose ends

• Leave the situation you'd want to inherit: minimal mess, no deferred difficult conversations.
• Leaders who exit without dealing with a non-performer or a festering problem hand that burden to their successor.
• Don't surface grievances on the way out that you could have raised while you were there — it signals a lack of courage, not honesty.
• Constructive feedback is more powerful when delivered during the job, not as a parting shot.

Take middle steps before big steps

• The myth of the single choice: treating one decision as make-or-break puts paralyzing pressure on it.
• Between you and any meaningful outcome are likely dozens of smaller choices, each generating learning or progress.
• Before a big transition, explore middle steps: brainstorm what could change if you stayed, research alternatives, test the next direction before committing.
• Sukhinder's Google exit involved roughly a year and a dozen choices — a stint in venture capital, board work, industry research — before landing on the next role.
• Success is cumulative choice-making, not a single leap. Frequency of small decisions matters as much as the size of any one.

What changed during COVID

• Pre-pandemic assumption: extensive travel and long commutes were non-negotiable for executive effectiveness.
• COVID revealed this was a self-imposed myth — flexibility is possible without sacrificing impact.
• Binary thinking about "what it takes" to do a job is a common trap; most constraints are softer than they appear.