Hey Nixon. In my experience, it's usually smarter to keep job hunting quiet until you have a solid offer in hand, especially in a small startup where things can shift quickly. Your boss might be supportive, but telling them early could lead to subtle changes like getting sidelined from key projects or even a premature push out the door. I've seen it happen where a friend mentioned exploring options and suddenly their workload lightened, which made them feel undervalued right away. That said, if your relationship is truly transparent, waiting until you can discuss it with leverage from an offer might open doors to a counteroffer or at least a graceful exit.
Timing is crucial, so line up interviews during off-hours or use personal days without raising flags, and hold off on LinkedIn updates until you're ready to announce. For references, ask colleagues quietly or use past bosses to avoid alerting your current one. A simple script could be starting with appreciation, like 'I've really valued my time here, but I've received an offer elsewhere that aligns better with my goals - can we talk about what that means for us?' I once left a team mid-project by giving ample notice and helping train my replacement, which prevented a total reshuffle and kept bridges intact. If I did it over, I'd document all my processes early to make handover smooth, saving everyone headaches during busy season.
