In my last post, I promised that I would be starting off today extolling the virtues of playing chess online. Raincheck.
This week, I received several requests for a “how to depart your job” guide. It's something I wish I had myself when getting ready to leave Silver Lake. So, while it's fresh on my mind, I want to share my checklist.
If you aren’t planning to leave your job soon, this particular newsletter might be a good one to skip or just tuck in your back pocket.
First, a little bit of context. I am in a 2 year program at Silver Lake. Only a handful of associates elect to stay for a 3rd year (less than 5 since the program was started over a decade ago). The idea is that we spend our mid-careers in the tech world, learn a lot, and then some of us might boomerang to become senior team members a decade or more down the road (of the Operating Partners/MDs during my time, ~40% were such boomerangs).
All of this is to say that leaving Silver Lake is a uniquely expected / comfortable thing to do. The firm has been extremely supportive at every step of the process.
But not all employers approach attrition the same way. So take everything below with a few hunks of sidewalk salt, especially if you’re leaving a radioactive environment.
Regardless, here are the main guiding principles for any exit process:
Relationships are the most important thing you take with you. Recency bias - for better or for worse - means that what you do in your final days will have a disproportionate impact on most of those relationships.
Keep your data. When you lose access to offices and IT systems, some things will stay behind. Make sure you have what you need before you leave.
Be careful with your finances. Especially if you are jumping into a start-up, optimizing your finances is laying wet asphalt on the end of your start-up’s runway. Money buys you time. So do it well.
Unfortunately, Substack doesn’t support checklist bullets. If you want the checklist-friendly version, here is a Google doc with the same content as below.
Relationships
Give notice thoughtfully.
HR. ~2 months before I departed, I set up time with HR to discuss all the logistics of leaving. I wasn’t giving notice, but I wanted to understand the offboarding process and any big items to think about. Silver Lake has a fantastic HR team, and so I didn’t fret the politics an iota. But, again, you may need to.
Your boss. Your boss, ideally, should be a mentor. And a mentor should be in-the-know as you contemplate your next career move, months before it actually happens. When you give formal notice, you should send a formal email to your boss with your date of departure, and cc HR. But if this email is truly “news,” that’s probably not ideal. A 1:1 should pre-date the formal resignation email.
Colleagues. Order and timing matters. If you are close to someone, you don’t want them to hear through the grapevine that you are leaving - it telegraphs a certain “distance” between you, which is fine if that sense of “distance” is mutual but otherwise will result in their feeling slighted. My approach was to schedule ~30 mins with the colleagues I had worked most closely with over the past 2 years. The invites were titled “Farewell chat” so that everyone learned at the same time the fact that I was departing without a dramatic farewell email weeks before the actual farewell.
Clients / portfolio companies / vendors / other external partners. Some of my closest relationships at Silver Lake were with consultants and other vendors I worked alongside. It's easy to become firm-istic in the hustle and bustle. That’s why I added this item on your checklist!
Do great work. No matter how “nice” you are at the farewell chats, the real way you show kindness / love to your team is by doing great work until the very end. I’ve been on the other end of a colleague catching a bad case of senior-itis in the last weeks of work and it totally changed my view of them and their good faith. Doing good work at the end involves:
Clear milestones. Whatever you need to do to “tie a bow” on your current projects, do it. The sense that you finished everything is powerful and appreciated. Most importantly, it builds in optionality for your boss / colleagues as they navigate disruption.
Thorough handoffs. That excel sheet with 37 tabs and 7 nested index matches... requires you to walk the new owner through it for an hour or two. Make the time. Ensure everyone understands who is “owning” the thing you are dropping. And drop it lightly! However you can hand-hold up to the day you leave, the better.
Well-wrought documentation. Everyone likes easter eggs and good documentation is like leaving easter eggs for your coworkers. Do not let once-loved colleagues rue the day you joined the firm because of the shoddy documentation you left behind.
Data
Keep personal files. Build a single folder with all the personal documents you want to take with you. Send the folder to HR or compliance and get their approval in writing. Don’t forget:
Email directory
Phone directory
Photos
Transition security tools.
Password manager. My life would collapse if I lost access to my Dashlane/Lastpass/1Pass type tool. Make sure you export your password manager data and fully convert to a new one before you leave, or change the underlying email required for access. My suggestion would be to do a “forgot my password” exercise to ensure the new email is working. Do this while you still have both email addresses!
Two factor authentication tool. Okta/AuthO/OneLogin are examples of places where your two factor authentication codes might live. I had my Facebook auth tied to the same tool I used for Silver Lake. Glad I moved it!
Update your resume. Special note on resumes. Redo your resume before you leave your role, even if you aren’t recruiting immediately. Your memory / ability to verify data will never be better.
Finances
Create a financial model. Many decisions you make in your last few weeks (expanded on below) will hinge on your expected income for the remaining calendar year. Build a strong understanding (preferably in Excel!) of your income and expenses as best you can. Build in uncertainty but put a stake in the ground!
Read the documents. 1-2 months before your departure date, sit down for 2 hours and read your entire benefits packet / insurance policy / employment agreement. Every plan is different and you want to know the significant “fine print” in your benefits. You may also find things that you didn’t know existed and are worth maxing out before you leave (for me, this was commuter benefits - whoops!). When you receive your offboarding packet from HR, you should do the same reading exercise. Like most things in life, there are probably 3-5 major pieces that comprise over 80% of the financial picture for you. So don’t get overwhelmed!
Start a calendar. Cutoffs, deadlines, etc. are often (1) different based on the benefit and (2) complicated because fiscal and calendar years are often not aligned. By way of example, Healthcare Reimbursement Accounts (HRAs) are frequently calendar-year aligned while underlying healthcare insurance is frequently fiscal-year aligned. Each benefit on the calendar should include 3 significant dates:
When the benefit renews / reups. (ex. When your HRA gets reloaded)
The last day you can accrue expenses for the benefit. (ex. Your dental insurance might allow you to accrue costs only up to the day you leave)
The last day you can submit receipts / requests for the benefit. (ex. You may only be allowed to submit reimbursement for office equipment within the 30 days it was purchased
Max out your benefits
End of year / performance bonus
Medical insurance. Complicated. Largely depends on how much deductible you have left and the details of your new plan. Sometimes you want to wait to have all those appointments so the expenses count against your new deductible.
Healthcare Reimbursement Account (HRA)
Healthcare Savings Account (HSA): Even though its your money, you might lose it if you don’t use it before you leave!
Office equipment reimbursement
Health / wellness reimbursement
Education / 529 reimbursement
Retirement benefits (ex. 401k). I allocated 50% of my last paycheck to my 401k plan. As someone who anticipates being “unemployed” for a significant period of time, the benefits to me were (a) the employer match, (b) the tax shelter, and (c) money in the market sooner. But, this is NOT the obvious decision. Why? Because if you over allocate early in the calendar year (“frontloading”), you may reduce the ability of your future employer to fully match your future contributions in that same calendar year (some policies limit the match as “up to XX% of any given paycheck”). Remember, you can only allocate $19-20k annually to these retirement plans. A better writer explores the tradeoffs of calendar-year frontloading here.
Download all tax-relevant information.
W-2s / pay stubs. You’ll often have access online after you leave, but tracking down passwords is a hassle. Just create a folder and download what you need in case you need to rent a new apartment!
Charitable giving receipts. From sites like Benevity
Stop using your corporate card. As early as you can, stop using your corporate card! You don’t want to be fighting reimbursement from outside the company walls.
Submit all expenses. ASAP.
Transfer or use your reward points. Even if you can use them later, you’ll forget.
Figure out your healthcare. This is a huge topic that I won’t explore in full here, mostly because I haven’t fully decided my own path. But let me just offer some incomplete and meandering observations
Go to the source. Healthcare is complicated, but government documents and company documents should be tractable. Whatever decision you make, you want to be able to point to real text that backs up your assumptions.
Plan documents.
COBRA documents. The US Dept. of Labor got you covered! Check out this snazzy FAQ page.
Healthcare.gov: for all the heat Obama got for this site, it now works really well and is clear / transparent
Don’t jump to decisions. You have 60 days to enroll in COBRA or Obamacare if you’re going one of those routes. But - and this is so important! - you lose the option for COBRA when you take Obamacare, and you lose the option of Obamacare if you take COBRA. So think it through.
Backdating. Let's say you don’t elect any coverage initially, and then have open-heart surgery 10 days after leaving your job. You’re ok! On day 11, you can enroll in COBRA and be covered for days 1-10 as well. Weird loophole, but that’s the law (“COBRA coverage is retroactive if elected and paid for by the qualified beneficiary” - CMS.gov).
Always consider provider coverage. I am choosing between an Oscar plan (Obamacare) and COBRA (Cigna Open Access Plus). The thing I really care about is getting a plan with in-network coverage that includes a major hospital. Note that - at least in some states - Obamacare plans are mostly HMOs not PPOs, this means that the network is small and local rather than national, without out-of-network benefits too.
Weigh the subsidy: If you’re going to have low income, weigh the subsidy. But understand that if your income exceeds your estimate, you'll pay that subsidy back at the end of the year, perhaps with a larger bill than if you had stayed on COBRA.
Am I missing anything? Let me know and I’ll update this list!