3 Hacks for Courageously Letting Your Boss Know You’re Leaving

By: Teri DePuy, PHR

The time has arrived for you to make the move to your next great opportunity, and you are dreading the inevitable tough conversation advising your boss of your departure.  Recognizing you want to keep the relationship in tact with your manager in addition to the entire company, you might ask yourself, “What do I say? When should I plan to leave?  What if I’m asked to stay longer?” Let me share with you three hacks that with a little bit of thought and preparation can help you achieve the best of all outcomes.

1. What do I say?

In this situation, less is more.  Your goal is to be concise, get to the point quickly and do so with confidence. Envision if you will, a 3×5 index card and assume this is your maximum allocated space to write the salient bullet points of your message.  No more than 3 thoughts:

• Begin by acknowledging something positive you’ve gained from your work or time spent with the organization. Careful word choice is essential if your boss is the reason for your decision.
• Make the definitive statement that you are resigning as of a specific date. Two weeks is customary, or three weeks is appropriate for certain circumstances or roles. But beware, long drawn out farewells are not beneficial even with the best of intentions.
• Lastly, end with a brief, rational reason why you’re giving notice. If you don’t do this while also staying on script when telling others, someone else will make up the narrative for you.

2. Is there one time vs. another that is better to depart?

Yes!  Timing can work out a to your advantage when you plan wisely. Consider orchestrating your departure to occur early in the month, as companies often pay insurance premiums as the beginning of a new month approaches. Therefore, you may be eligible for healthcare benefits until the last day of the month. Similarly, be mindful of key dates such as equity vesting schedules, bonus eligibility periods and payout requirements, and start/end of pay periods.  Either of these can have an impact on your final payout.

3. My boss wants me to stay longer. What do I do?

Stay firm with the date you’ve chosen as your last day, with a slight twist.  Having a conversation about current business needs and providing optional departure strategies may go a long way in helping your organization. This is also an opportunity to earn good will with clients, coworkers or management.  So, consider posing some choices that will honor your last physical date but include some flexibility that may look something like this:

• Work a specific number of hours for a defined timeframe at an agreed to hourly rate.
• Be available on an infrequent basis, but with mutual agreement on the schedule, to answer questions, attend meetings, or review documents at an agreed to hourly rate.
• Negotiate a retainer for a range of hours within a defined timeframe.

Any one of these may ease the pain of your vacancy, or not.  But with these recommendations, you’ve signaled your cooperation and willingness to offer alternatives to address their business needs while courageously remaining steadfast with your decision to leave.

What other tips do you have to share?  I’d love to hear your ideas on how to make the best of a resignation.