Getting the most out of your exit

So, you’re ready to leave your company? 

Getting the most out of your exit requires careful management of your work, communication, and available options. 

Ideally Leave for a New Role

The ideal scenario is usually staying in your current role until you line up the next role, even if that means you are in a job you don’t enjoy.   We know that it can be scary to look for a role while you are in one.  That is why we built Whispered.

Once you are clear you are leaving, optimize your time to show immediate progress on near-term objectives, especially if you are feeling pressure from execs. This ensures you show you are still valuable to the organization and don’t risk getting pushed out before you have your next role. It also allows you more leverage when you put in notice. Finally, you avoid any questions about gaps in employment. 

How to get a package

If it’s not feasible to stay in your current role, you may be able to work your way to a package. This usually has to be prompted by the company, since resigning is always an option and saves the company the hassle of paying out a severance package or running a performance improvement plan (PIP).  

However, you don’t want to underperform your way to a package, since you will need references for future jobs, and you can’t control who a hiring manager will reach out to. So, how do you walk the tightrope of convincing the company to offer you a package, without destroying your references? 

“You can’t propose your own severance.”   C-Level Exec

Here’s one example that worked for a Director at a unicorn. 

1) Read the room

Are you in a good position with the right scope, team, and exec support? Or are you under attack, under-resourced, with constantly changing objectives? At a certain level, the strength of your internal network can be as important as the work you deliver. If you feel like you are fighting uphill, and you are willing to leave without a role, it may be time to take matters into your own hands. 

This Director was on a track to VP, but when key execs left, they were lumped in with the “old guard” and the narrative quickly shifted. They were moved under a new exec, who kept them at arms length while driving what to do. Over time, they noticed instead of being pulled into key meetings, they were informed later. 

2) Ask clarifying questions

Asking direct, tactful questions will always tell you one of two things if you are observant. If the person you are asking is forthright, you’ll gain important information. If not, you’ll learn important clues about why they are withholding information from their body language. Tactful questions remove the emotional valence from a conversation. They are also infrequent enough to gather info without being obtrusive or demanding. It’s important to show you are still acting in the company’s best interests and not purely your own. 

In the Director’s case, they were passed over for promotion, and wanted to confirm if that was temporary or permanent. They broached it this way: “Do you think you’ll need a VP for this department long-term?” That’s a non-confrontational but direct entry point into a conversation, and with a neutral and curious tone the Director learned that their new manager planned to hire a new VP from outside the company, effectively ending the Director’s career track in that department.

3) Observe and name the narrative

It’s easy to explain away a single event or phrase, but a pattern is harder to dispute. Keep track of observations that build a pattern as you read the room and ask clarifying questions. You can mention these observations casually (infrequently) so it’s clear you and your manager have the same information. At some point, a narrative may become clear to you, and you can validate it with your manager. If you are lucky, your manager has been forthright and will address it directly. If not, you may need to find a way to involve HR and share your observations. 

In the Director’s case, the observations were plans for a VP above, a shrinking team below, and an exec increasingly excluding them from key meetings related to their role. They shared the observations neutrally first, without making it about you or forming the narrative. “I noticed I wasn’t included in this meeting, that is key to my role. You also mentioned that you will hire a VP above me, and move on of my functions to another department.”

Then they used a powerful phrase, “the story I’m telling myself is…” This separates the objective observations from the subjective interpretation. In this case, the narrative was “… the company’s new strategy is moving in a direction where my role won’t be needed.  Is that true or is something else going on?”

4) Walk the tightrope

Once you share that your future looks uncertain, it may be difficult to recover. If you broach first that you want to leave, you may not receive a package and may need to resign instead. Or, you may get strong performance management before you are offered a package. But if you can walk the tightrope of demonstrating that you intend to perform well for the company AND have concerns about your observations, you may prompt the conversation to an exit option led by your manager (or potentially HR). 

In this case, the Director’s manager was initially reticent and explained away a couple of the observations. However, faced with a growing list of observations (and a tactful approach), they admitted that the role was moving in a direction that might not be appealing to the Director. The manager asked, “what are you thinking you’d like to do about this?” The Director’s response was “Well, what are my options?” This could be a stalemate - neither side wants to be the first to talk about leaving or a package.

Luckily the manager engaged, sharing that they would support the Director in the shifting role or find a soft exit. Bingo! Now that the soft exit card is on the table, you can negotiate your way through. Don’t overplay it or push it - give the manager or HR time to gather the details. They may be caught off guard and need several days or several conversations to admit the person is not set up for long-term success, or that a soft exit is a mutually beneficial path. The Director said they would like to hear more about both options, and asked for time to follow up. 

The Director and their manager connected a couple of days later, and the Director continued to prompt, asking for details on the “stay” and the “go” options. If a manager senses at this point that they don’t think it will work long-term with a direct report, and they are not sure which option they will choose, it’s in the manager’s best interest to make the “stay” option less appealing and the “go” option more appealing. You should be authentic but it’s perfectly reasonable not to share which way you are leaning until you have all the details you need.

Once the Director had the info they needed, they negotiated a couple of key points and indicated that they preferred the soft exit, assuming it works for the manager and company. At that point, if you’ve agreed on terms, all that’s left is to wait on paperwork. 

5) Document as you go

It’s helpful to document and share key facts with your manager for two key reasons. First, it ensures you understood the key points of the conversation similarly. Second, you have a written record to refer to later if there is any dispute. Take notes, and summarize key points neutrally in an email if appropriate. 

6) Know what matters to you and them

In the negotiation, you should know what matters most to you, and estimate what matters most to the company or your manager (those last two might be slightly different!). For instance, you might value a longer exit date for financial stability or preserving benefits. Your manager might want for you to leave quickly so they can move on. Or, vice versa - you want to leave ASAP but they want time to transition. 

“The company/manager are most likely desiring a smooth transition which allows you to name an extended transition.”   Another Whispered Member

Where your interests line up, you both win. Where you value aspects differently, you can negotiate for the best outcome. Some common aspects to consider:

• Exit date. Longer generally feels more stable but sometimes individuals or companies are ready to move on faster. This could be two weeks minimum or multiple months for an executive. You could even negotiate to stay in as a consultant or advisor. 

• Severance. Often companies have a standard severance package, typically 4 to 8 weeks. 

• Vesting: The default clause is most often 'need to exercise within 30 days of leaving.' But generally accepted tax law allows the company the ability to push that date to 10 years from vesting.  Most companies don't want to grant that 10 years, but something like 5 is usually interpreted as a reasonable ask. This buys the employee the 'free option' to see if the equity is appreciating (and hopefully have a liquidity event) before having to pay to exercise (and the associated tax bill).

• Non-compete or non-solicitation. The company may want you to agree not to work with certain competitors or even in a certain field for a time. Similarly, they may require you to not poach employees. 

• Non-disparagement or confidentiality. The company may be concerned with blowback and include language about not speaking negatively about the company, or about certain aspects at all.

7) Decide what’s best for you

Ultimately the manager’s and company’s job is to operate in the company’s best interest so you need to stay clear-eyed about what is best for you and how much the company and you are willing to budge. If you’re reading the room accurately, broach the conversation well, and walk the tightrope, you have a great shot at getting the package you want to leave with. Good luck!