Endgame Strategy When Switching Jobs

two white old men playing chess Photo by Vlad Sargu on Unsplash

In chess and chess-like games, the endgame (or end game or ending) is the stage of the game when few pieces are left on the board. Unlike opening theory, which frequently changes, giving way to middlegame positions that fall in and out of popularity, endgame theory is less subject to change. The endgame is critical. Sometimes defeat seems imminent, but we manage to save a draw that has the taste of victory. Other times success seems within reach, but it ends up slipping through our fingers.

In chess, if we're serious, eventually, we need to study end game theory. Losing or getting a draw after you've done much of the hard work and have the edge doesn't make sense. Yet, I don't see many people talk about that phase when they're switching jobs.

After getting an offer, we have usually gone through many hoops, battled a monster or two, and finally managed to be approved. This is the end game. At this point, we have a critical decision to make.

When switching jobs, we don't want to go somewhere to "test it out." Having to change jobs in a few months usually slows our careers down. There are always switching costs between companies, even if they're very similar. We reset the domain we're working with, reset the relationships we have developed within the company, and require a lot of work to ramp back up to how effective we were. So we need to treat this decision like we're committing to stay there for a couple of years, even if we end up not doing so for one reason or another.

I haven't personally switched jobs many times, but I have mentored and hired over 50 people up to this day and found some tips that help de-risk the decision and get a better outcome from it. And just like chess endgame vs opening theory, these tips haven't changed as much as the hiring processes have in the past 10 years and probably won't ever.

Reverse Interview Your Manager and Team

The most important thing is figuring out if this is the place that best matches what you want for your career right now. Every company says their process is supposed to help you evaluate them as well. Still, in favor of keeping the interviews short and extracting as much information as possible, the candidates usually have 5 to 10 minutes to ask questions in each interview and only to their interviewers. This is not close to enough time, and your interviewers are not the best people to give you a sense of what it's like to work there.

Gergely Orosz has a great post on this topic, so I recommend you check it out for details, but the key conversations to have are:

  1. With your future manager: Ask questions about the team, what they expect of your role, the key goals, work-life balance, anything that gives you a better sense if you're going to enjoy working with your team.
  2. With a future peer: Ask to talk with the senior-most peer you'll have. Ask them about the main challenges, things that aren't working, what they wish they'd known when they entered.
  3. With a relevant stakeholder (PMs, a director, or cofounder, based on the company's size): Get a sense from them of how they work with your team and what you'd need to do to create a successful work relationship with them.

Besides giving you a lot more context into the company, these conversations already start building your network therein. These people will know you from day one and be invested in making you successful since they helped bring you in.

Understand how big the switch is

I usually advise people to maintain their level of responsibility when changing jobs. However, that doesn't always mean maintaining the same title. For example, I'm a Senior Soft. Engineer Manager in QuintoAndar, there are about 30 engineers in my organization, and I have to lead their managers. In smaller companies, this could be a Director of Engineering or Head of Engineering. But if suddenly I needed to oversee Product as well (more of a CTO role) and still manage this number of people, that would be a HUGE change to my role. When we switch companies, we're changing the domain drastically and resetting some of the relationships that helped us succeed in our companies. Adding more change can be too much and paralyze or set us back. So taking a title cut isn't always bad. It allows you to maintain responsibilities while growing on how much you understand the domain and perform in that company. Gergely also has an excellent write-up on why titles change so much, how to prepare for that and how to avoid a down-level.

If you choose to go to a higher responsibility role, knowing that in advance and preparing is critical. Don't fall into that by accident. Instead, take the time to understand what the level you've been offered means, what your primary responsibilities would be in that role and what it takes to be brilliant at that job. This will give you a better sense of how to succeed in your role and a clearer picture of how big the leap is.

Reach the End Game with a Material Advantage

In chess endgames, an extra pawn is a winning advantage. In general, the player with a material advantage tries to exchange other pieces and win the game*.

There's a natural mismatch of information with hiring offers–the company usually has way more information than you have. For example, during the process, they collect your current salary. Furthermore, they have a lot of information on compensation both inside and outside the company.

So we can level the playing field by gathering accurate information for ourselves:

  1. It usually helps to have talked with people you know that either work in the company or companies of the same size and type to get a sense of how fair your offer is with your level. Understand if the company has a policy for equity, signing bonuses, relocation, anything that might increase the offer. Websites like techpays.eulevels.fyi, or even Glassdoor can also help you understand that.
  2. Try to get as many offers as possible from other similar companies. These will help you understand how other companies are assessing your skills. Sometimes a hiring process from one company doesn't let us shine as much as another's. But we can point that out and, in an eventual mismatch in level, use that to get another interview or a bump.

Get the numbers to a point where you're happy to accept. But be happy only for what's fair. Don't use your current compensation for that. Use what you can get. If the company doesn't negotiate offers, the worse they'll say is no. It's really rare for a company to pull the offer, even more so when you bring in data.

In Conclusion

Don't let a poor endgame spoil your hard work when switching jobs. With just a little extra time, you can:

  1. Get a better offer
  2. De-risk your change
  3. Set yourself up for success

It's time well invested and usually pays off both in money and time.

*I know it's usually not wise to exchange pawns at the end game. Instead, we try to exchange other pieces, but it was a nicer analogy :p