Resigning can be an uncomfortable and occasionally unpleasant conversation with your employer, but as it's a necessary part of career progression, it's important to know how to resign from a senior position.
If you are unhappy at work, should you threaten to quit? I think you can do it once. ONCE. Jason Lemkin (see terrific post on this)
Be clear about why you are leaving
Before you resign, be clear in your mind why you are leaving. You won’t need to discuss details with the company, but if you are on the fence or have doubts, it can create frustration for all sides.
Think through what (if anything) could change your mind. If there are things that could get you to stay, bring these up with your boss earlier, rather than threatening to quit to see if you can address them.
“I have come to believe that you should try asking for what you want before you start looking.” Phyl Terry - Never Search Alone
Prepare to Resign
Here are a few things to think about BEFORE you officially resign:
Think about how your responsibilities will be covered: Ideally, you have built a strong team and have people who can step in to cover so nothing will drop. Starting a transition plan is a great way to get this on paper and document what will need coverage. Additionally, be prepared to recommend where your teams’s reporting lines should go in the interim.
Understand your relationship with your boss: If you have a deep personal relationship with your boss you can start these conversations earlier so they aren’t surprised BUT you need to protect yourself so if there is any question, wait until you have a signed offer (see below). You don’t want to put at risk bonus payouts or vesting.
Make sure you have a signed offer for your new role: Companies can change decisions up until your offer is signed.
Check your current employment contract: Read your contract from your current employer to understand your obligations to them when you resign, such as notice periods, and if there are any restrictions such as a non-compete clause or a duty of confidentiality clause. These may impact what you can and cannot do, and for what duration, after leaving your current employer. You may even have a garden leave clause in your contract, by which your employer keeps you on the payroll at a reduced rate, and you cannot begin with a new employer until a set period of time in order to protect proprietary information.
Clean up your computer: Don't hand back your computer without doing this first
Don’t go to a competitor: We strongly advise against this. It will generally break your relationships with your company and colleagues (as you are now competing against them).
Leave the right way
“The more senior you are the more notice you give”
How you leave will have an impact on your relationships with your company, boss, and team. Here are some tips on how to resign professionally:
Tell your boss first: This might be obvious but you don’t want your boss finding out from anyone else. Make sure you do this in-person and not via an email/message. Ideally you aren’t rushed (see next point below) and if they aren’t in the office can tell them in your next sync.
Don’t sprint out the door: Your new company will inevitably want you to start ASAP. But, take the time to resign correctly with a reasonable transition. If you get push-back from your new company, explain to them that if you were leaving them you’d want to do right by them so you hope they understand you need to allow you to do right by your current employer. Rather than offer the traditional 2 weeks, consider offering 3-4 weeks “if needed” but once companies realize you are leaving, your responsibilities should wind down fast.
Try to leverage an existing 1:1 vs setting up an emergency meeting with your boss: It will allow you to have the conversation in a more casual setting and share the news in the way you choose vs. them showing up expecting a resignation.
Focus on where you are going, not why you are leaving: Do not focus on what your current position lacks, but what the prospective role offers in terms of career progression and personal growth. Be transparent about where you are going - everyone will see it soon enough.
Think about your team: You (hopefully) have built a great team and care deeply about them. Provide a suggested coverage plan for your team (who they roll up to) but recognize that since you are leaving, the final decision will be up to your manager. Making sure your team has ample notice and isn’t surprised is another reason you want to provide a long notice period.
Document with an email: To document your resignation, send an email documenting your resignation and departure date. This email should be short and sweet, no need to go into detail via writing, but should copy HR so they can start the offboarding process.
Let your boss guide how you inform the company: While you will want to “tell people yourself”, resist this urge. Defer to your boss on how to tell your team. If they respect you and you have handled yourself professionally they will often let you tell people yourself. Consider that your boss will want a few days to process and think about how the organization changes before they are ready to tell the team. This is another reason why the traditional 2-week notice is often too short for executive resignations.
Follow-up with a transition plan: Shortly after your resignation, create a detailed transition plan document for your boss which includes projects in flight, who is the right person to cover, and other considerations.
Be ready for them to try to get you to stay
Companies aren’t prepared for senior executives to leave. They will often try to get you to stay so you should be prepared for this.
Most of the reasons people leave likely aren’t ones that your company can address. If you are leaving because of:
Culture: You may get promises this will change but that requires a recognition at the CEO level of the issues and a clear willingness to change, which is unlikely.
Money: While they may match to keep you short-term, be aware that future increases will be limited and there will always be resentment both ways.
Career Trajectory: If you aren’t growing at your company it likely is because either there are other people in your way (hard to fix) or your company feels you are limited in some way. Forcing a promo with a threat of quitting will put you at a higher level and probably mean few future advancement opportunities.
“Most people who accept a counter-offer generally leave within a year, as the circumstances that caused the desire to leave have not changed. When you accept a counter-offer, you run the risk of marking your card internally, and your position can become isolated and eventually untenable.” Rutherford Search
During your transition, keep quiet
Once you and your employer have agreed on your end date, resist the urge to share more than you have to:
Don’t gossip about why you are leaving: While it is tempting and many will ask, staying quiet on this will serve you well. You don’t want to be the hot topic at the water cooler in your last weeks at your place of employment, and you certainly don’t want your boss to hear a story about why you are leaving that they were not already aware of.
Don’t be fully candid in the exit interview: This is not the time to vent or air all your grievances, and anonymity, although promised, cannot be guaranteed. Your opinions are not going to change anything at this late stage and could undo any good work you have done in the past. Keep it neutral, and constructive, and leave your emotions at the door!
When you are gone, stay in touch
Relationships you have built at work are valuable and forged through collaboration. Once you have left, make a list of people who you want to stay in touch with and check-in with them periodically - not to find out how things are going at the company but to see how they are doing and how you can help their journey.
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