If two friendly executives meet for dinner, it’s likely they start by exchanging just how messed up things are at work.
Initiatives are behind, layoffs are happening everywhere, the team is in disarray.
Then they’ll laugh, and switch topics. Sometimes one of the executives can’t navigate the switch, and will keep ranting throughout their meal.
Having problems is part of being an executive, but when you’re that second executive who can’t turn off the frustration, it’s time to start thinking about leaving.

Departing an executive job is much messier than leaving an individual contributor role, and will significantly impact the team and company around you. It’s also potentially impactful to your resume; I frequently talk with executives who hate their job, but don’t want to leave because they’re worried it looks bad. “If I just make it to two years, it’ll look great.”

The optics are real, and I understand why people get caught up in them. I’ve certainly gotten caught up in my own optics at times. That said, the deeper I get into my own career, the more convinced I become that we should think about departing roles in the context of managing our own energy.

We’ll walk through:

  • Succession planning before a transition
  • Making the decision to leave
  • How to think about short executive stints
  • Whether to line up another role before leaving
  • Telling the CEO
  • Negotiating the exit package
  • Transitioning out and actually leaving

Finally, we’ll end with a discussion about handling the hardest aspect of all, indecision.
By the end, you’ll have a framework for making the decision to leave, and a structure to coordinate your departure.

Succession planning before a transition

In a literal sense, deciding to leave your job is the first step in departing. However, in a smooth departure, the first step happens years earlier: building the team to support your eventual transition out of the business. Even if you intend to remain at your current company forever, life comes at you fast. Certainly, I never imagined I would have a stroke in my mid-thirties, with an infant at home, but then I did. I was fortunate to lead a collaborative team who worked together well in my absence, but that wasn’t an accident, it was the byproduct of ongoing succession planning.

This planning doesn’t need to be anything heavy:

  • In performance reviews, think about what your direct reports are missing to thrive in your role, and give them at least one of those areas to focus on in each review

  • As they make those improvements, talk to the CEO about the growth you’re seeing in your team. For the one or two with the best chance of eventually succeeding into your role, facilitate them building a relationship with the CEO

  • Every quarter, run an audit of the recurring meetings you attend. For each, can you delegate it to someone on your team? If it’s not something you can delegate, partner with them to improve on whatever is missing before they could be effective in that forum.

    While it’s hard to displace yourself from executive-only or board meetings, almost everything else is possible. For example, I’ve seen a number of companies where the engineering leadership team alternates running their weekly team meeting rather than the engineering executive

  • Go on at least one long vacation each year (aim for two weeks, if you can), and explicitly delegate your roles across your team rather than slowing things down.
    Avoid chiming in on email and chat.
    Even if mistakes are made, they’ll be learning mistakes

Ultimately, who replaces you won’t be your decision, it’s the CEOs, but doing a small amount of ongoing prep work will make an internal transition possible.
Without this proactive work, it likely won’t be seriously considered, which is a shame:
so many companies would do well to consider the talent they already have.

Deciding to leave

There’s a certain romance to abruptly quitting a job. I’ve seen two people legitimately rage quit their jobs. They went into a meeting, got upset, and quit immediately. In one, where the individual reported to me, they threw a piece of paper at my face, where they’d signed their name beneath a brief message, “I quit, effectively immediately.” In both cases, I unironically appreciated their momentary clarity with the situation. They were done.

There’s a lot less romance in quitting an executive job. There’s the dream that originally convinced you to join, still recognizable but frayed. There’s dozens of little frustrations, miscommunications, and disagreements. There’s years of preparation ahead of time to facilitate a smooth transition. There’s also a huge reservoir of things that have gone well: people you love working with, teams that you’ve helped build, and company successes you were part of. For many, being an executive is an important pillar of their identity, and that’s hard to walk away from.

When talking to executives grappling with this intersection of identity and frustration, there are four questions I ask them to help with making the decision:

  • Has your rate of learning significantly decreased? Even frustrating situations can be extremely valuable to you long term, as long as you’re learning. It’s when the rate of learning starts to slow that you should get particularly concerned
  • Are you consistently de-energized by your work? It’s normal to have bad days. It’s normal to have bad weeks. You will even have bad months. However, if things are consistently bad, then it’s time to consider change. Don’t trust your gut here, instead keep a journal of your daily energy level for a quarter. If you can’t find a trend of good days, it’s worth considering moving on
  • Can you authentically close candidates to join your team? Every executive I’ve known can flip into selling mode. They’ll give a warm, balanced, but optimistic view of why you should join their company. Even if you’re upset with your role, you should still be able to turn the sell on. If it starts to feel dishonest to switch into selling mode, that’s a sign that you’re losing your ability to effectively perform your role
  • Would it be more damaging to leave in six months than today? Sometimes executives inadvertently create a values oasis, where their organization’s values differ significantly from the wider company’s values. That oasis will feel comfortable for their team, but their team will acclimatize to the oasis’ environment such that they can’t operate effectively if the executive leaves. Your goal is to create an organization that’s successful beyond your tenure with the company. If you believe your organization is drifting away from the company’s culture, and you’re unwilling to steer it back into alignment, then you should consider if you’re putting your team’s careers as risk by remaining with the company

One question that I don’t recommend anchoring on is how much money you believe you’ll lose by leaving. There are two reasons for that.
First, you may be able to negotiate an exit agreement that minimizes your downsides.
Second, people are extraordinarily bad at determining the value of their own compensation package. Many tech executives are sitting on equity packages potentially worth between zero and tens of millions of dollars, and the actual value is simply not knowable. You can’t make a good decision based on that.

Finally, I would caution against making ultimatums, taking a last stand on something, or whatever. Being an executive is an ongoing negotiation with the CEO and management team on how the company functions. If you’re not willing, or comfortable, to continue negotiating with the current group, it’s time to move on. Even if you leave, you’ve still been part of the organization and are partially responsible for the steps they’ve made, even the ones you disagree with. Being an executive is, ultimately, a compromising position, where you’re working inside to effect change, rather than a role where you can ever wipe your hands clean.

Am I changing too often?

I often talk to executives who have decided to leave except for “one little issue.” While I believe that these issues are often deliberate impediments raised to avoid making the decision, there’s one that comes up frequently enough to address explicitly: should executives stay in their role to avoid a short stint on their resume?

If something goes very wrong, very early, then it’s always fine to leave and omit it from your resume. You’ve uncovered gross financial fraud in the two months? Yeah, it’s fine to quit, just scrub it off your resume. Similarly, once you’ve hit three to four years, there’s no meaningful penalty. It’s the intermediate interval, roughly six months to two years, where folks often get tripped up about whether leaving will hinder their ability to find another role.

Because the people making hiring decisions about engineering executives generally are not engineers, the evaluation tends to rely a fair amount on optics, and your search will place meaningful value on your previous tenures. The intersection between my experience, peer experiences, and discussions with executive recruiters is roughly:

  1. If it’s less than three months, just delete it from your resume and move on
  2. If it’s more than two years, you’ll be able to find another role as long as some of your previous roles have been three-plus years
  3. As long as there’s a strong narrative, any duration is long. For example, if your company is acquired by a larger company, the narrative is that you weren’t excited being in the larger environment
  4. If a company reaches out to you, there’s no tenure penalty. Say, you’ve been in a role for six months, but then you get an email about another role. Because they reached out to you, the short tenure would be because you’re very excited about them, and not a reflection on you. (Admittedly, it’s a bad look to do this multiple time in a row.)

If you don’t fall into any of those scenarios, there probably will be a moderate penalty on your next search, with potential employers asking, “But will they stay if we hire them?”
I certainly agree that this is unfair in some cases, but success comes from navigating reality’s many warts. In such cases, you may need to prioritize finding a next role where you can succeed for four to five years, even if it’s more of a lateral move than an upward one.

Leave with or without your next role?

Tied into the question of tenure, the easiest way to remove tenure risk from your search is to get your next role before leaving your current role. You’ll always have more leverage negotiating from an existing role, and if your primary goal is advancing your career, then I would recommend finding your next role before departing your current role. Similarly, executive searches tend to run slowly. You need to be comfortable supporting yourself and family for six-plus months to consider leaving your role without another role lined up.

That said, I personally believe the greatest risk to your executive career is running out of energy, so taking a bit of rest might be more valuable than the short-term numbers suggest. What if a three month rest gives you the energy to continue this work for another ten years? Then the obvious decision gets a bit less obvious.

Finally, leaving without a role lined up makes it much easier to support your outgoing transition, which often opens up the topic of exit packages, which I’ll discuss further down.

Telling the CEO

After you’ve made a decision to depart, your next step is telling your CEO. It’s important to go into that conversation with a firm grip on your goals. Many CEOs will try to change your mind, but it’s important to hold to your plan. If you are open to changing your mind, then you should be having a career discussion with the CEO, not a departure discussion. There’s a natural momentum here: once you start the departure discussion, you’re going to leave.
Even if you and the CEO leave the conversation believing you’re going to stay, you will leave. It’ll just take a few months longer than expected.

Trust is the underpinning of your relationship with the CEO, and fraying that trust will make whatever else is happening just a bit worse, confirming whatever other factors contributed to your initial decision to move on. This is equally true if you try to leverage your departure as an ultimatum to push some change through. It might work in the short term, but long-term you’re definitely on the way out.

The most important points to land in this discussion are:

  • Departure timeline: what are your preferred and inflexible timelines for leaving?
  • What you intend to do next: taking on a new role, taking time to recuperate, or whatnot
  • Why you’re departing: assuming you’ve been clear about issues up to this point, there usually isn’t something new to say. You’ve already said your piece, and they’ve acted upon it to whatever extent they’re willing. As such, I’d think of this as preparing the messaging for the board, the wider management team, and so on
  • Recommended transition plan: how do you recommend the CEO handle this transition? Who, if anyone, internally should step into your role, and so on. Keep in mind that once you start this discussion, you are now making recommendations, rather than leading the function

Generally, the CEO isn’t going to make any decisions in this meeting, just hear you out, say they’re going to think this through, and schedule a followup to discuss details after they’ve been able to figure out how they want to handle your departure.

Negotiating the exit package

Depending on the discussion you’ve had with the CEO, you may have a lot of leverage for negotiating an exit package, or you may not have any leverage at all. If you’ve lined up a new role and are giving two to four weeks notice, then you’re very unlikely to negotiate an exit package beyond that you negotiated in your initial contract.

On the other hand, if you’re willing to time your exit to the company’s preference, and you have a good relationship with the CEO, then there’s a great deal of leeway in the negotiations. If you agree on a three month departure, then you might be able to stay on payroll for a month or two after your last day. Or you might be able to continue vesting and receiving medical coverage, but not salary, until your next relevant vesting cliff. They might be willing to approve a secondary stock transaction, even if they typically don’t approve such transactions.

None of this stuff is guaranteed, it depends entirely on how much you’re willing to facilitate the exit, how the company values your past contribution, whether they like you, and your CEO’s preferences. It’s worth discussing a bit, particularly if you go in with clarity about the one thing that really matters to you (e.g. approving a secondary stock transaction, staying on payroll, etc).

Transition out and actually leave

While there’s a great deal you can do before you decide to leave, once you’ve communicated your decision to leave, you won’t be able to change much. It can be tempting to believe you’ll finally get the chance to address a long-standing issue, but you’re a lame duck. Even if your idea is a good one, you’ve lost credibility to propose it because you won’t be around to deal with the consequences.

The most common mistake I see outgoing executives make is trying too hard to help. At this point, you’re a consultant, not an executive. The best you can do in a transition is get out of the way, and support your CEO, your team, and the company in the plan that they choose. Once you give notice, it’s no longer your engineering team, and you’ll have to navigate the abrupt shift from leader to follower. Sometimes this means implementing plans you don’t particularly agree with. Even if you disagree with the plans, saying you disagree will only destabilize the team’s transition. Do your best to support them, and then move on.

Sometimes you’ll see folks stay very involved after their departure. They might keep one-on-one meetings, serve as an explicit mentor to team members they managed,
or attend social work functions. I understand the intent, but I strongly recommend against these sorts of prolonged departures.
They are usually motivated by a sense of guilt rather than a clear plan to help, and undermine the person who replaces you.

Revisiting the decision

There are many micro-decisions within the broader choice to leave a job, and one place I see folks get stuck is revisiting the decision repeatedly, sometimes on a daily basis. They have a particularly bad meeting, and then recite, “Yup, I’m out of this place.” They tell a few external friends that they’re done. Two days later, earnings are up, and they get excited again. They’re too embarrassed to tell their friends they’ve changed their mind (likely for the Nth time), so they wave the question off when they meet up next, “Oh that, yeah. Just a bad day.”

Some people exist in that cycle indefinitely. Earlier in my career, we hired a new manager who I reported to, and that manager told me–in our very first one-on-one on our first day–that he’d made a mistake, hated the company, and should quit. Most of our one-on-ones focused on my manager telling me how stupid the company was, and how he thought he should quit or get the CTO fired.
It wasn’t a particularly inspiring situation for me.

Getting caught in the decision is the least helpful thing you can do. You’ll spend a tremendous amount of your energy debating, but generally without a clear answer. If the answer was clear, you wouldn’t be stuck going in a circle. If you, for whatever reason, can’t make a decision right now, then I highly recommend establishing a decision date in the future. This could be a literal date, “the end of next month,” or after a particular set of circumstances, “once we see the impact of our latest product features.”

Once you reach that moment, then see if you’re in a place where you can make a decision. If so, then make it! If not, pick another date, and wait until then to reconsider. It’s not that the decision gets any easier, but it helps you spend less time spinning on a decision that you are clearly not ready to make.

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