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All of my bosses just quit. Am I on a sinking ship?

Cue "Move On Up" by Curtis Mayfield: In the latest edition of advice column The Lossless Leader, find engineering manager Leemay Nassery's advice on how to figure out if you should stay or go.

Is it time to ditch the ship you're on in favor of smoother waters? (Photo by Pok Rie from Pexels)

This is The Lossless Leader, an advice column written by engineering manager Leemay Nassery.

Why call it The Lossless Leader? An engineering leader is someone who inspires their team, communicates well, grows their people to become leaders themselves, removes blockers or painful aspects of their team’s day-to-day, delivers on product requests and so much more. In tech, lossless compression is a technique that does not lose any data in the compression process; it reduces the size of files without losing any information in the file so quality is maintained.

Combining the two: Leaders aren’t perfect. Sometimes they manage to not lose any data while leading their org, and other times it may seem like they’re losing it altogether. This column is called The Lossless Leader because we all admire those leaders who strive to stay true to who they are and the people they serve (their team). They admit fault when necessary, learn from their mistakes, sometimes flourish in difficult situations — all while not losing themself along the way.

Submit your question to The Lossless Leader

The question: 

“My entire reporting chain up to the top has left in the last four months. Is this a sinking ship? Should I be looking?”

The answer:

Let’s not overthink this one and simply state the problem at hand: Have you stepped onto the Titanic, and if so, will you be Rose or Jack?

Jokes aside, I’m going to attempt to answer this as succinctly as possible and then share a story from my past that you may relate to. This isn’t just an advice column, or at least I don’t think of it that way. It’s also about stories. Stories connect each other. Sometimes, we find more solace in stories and experiences than the actual advice.

Here’s the best thing you can do: Don’t let it eat at you, that these leaders have left. Instead, use it to your advantage. Can you step into an area that is currently lacking because a leader has left? Or can you use it as a means for pivoting an architecture or project the way you want to do it, that may have failed to get buy-in as a result of the previous leaders? Sometimes real change can happen in situations like this (as you’ll see with my personal story).

If you can’t use it to your advantage, important questions to consider:

  • Do you have equity in the company such as RSUs or stock options? Has the share price, for instance, steadily declined for the past few months? If so, it will impact your total compensation if you continue to stay.
  • Let’s say the company is a sinking ship. Is there still real estate for you to work on novel things in your current team that would be enough reason to stay?
  • Even if the company as a whole isn’t “thriving” from a product or business point of view, are there some areas of the company that are thriving? Is there a team that’s building software you’re interested in or has a team culture that you would want to be a part of?
  • What are you missing out on by staying at this company? More competitive pay? More interesting work?

If the answers to these questions are bleak, then use the next few months to clean up your resume, and seek out work in your current job that could set yourself up for success at your next interview or with your next employer. Then jump on the bandwagon and start looking around. Your bank account will be thankful you did (as I mentioned in a prior column).

If you had a connection or admired the leadership of the folks who left, you could follow them. Apply to the company they’re at, then send them a LinkedIn message asking for a referral to push your resume further along the pipeline. Make your message something actionable — not just one of those “Hi, how are you?” notes.

The fact that your entire reporting chain up to the top has left the company is certainly a signal of something. The market is hot, even for executives. I can imagine they are being offered hefty equity packages, especially if they’re good at their jobs. Finding good leaders is so, so hard. Companies are desperate for them. I once worked in an organization that took over 10 months to find a product area lead. That’s a long time for an organization to lack an overarching product owner; imagine the approaches recruiters will take to seek good leaders to fill a role like that. Recruiters are approaching leaders who aren’t even putting their resume out there — which could have been the case for one of the leads who left your company.

Ok, it’s story time. Many years ago I worked at a company in which I had a similar-ish experience. My favorite leaders left. I also thought, am I on the Titanic? At some companies, especially this one from my past, the door between senior director and VP was constantly revolving – they came, they saw, they left.

Leemay Nassery. (Courtesy photo)

I admired the heck out of the handful of leaders that eventually left. The sad part of this story is that I truly missed their presence in meetings, team discussions, overall strategy, etc. The good part is that I learned so much from them; their drive to do good on the product, to care about the customers, and most important, to be good to their engineers.

Shortly after these leaders left the company, I stepped into a leadership role that was open because of their absence. I led both product and engineering of an under-used aspect of the product. During this time we pushed a big change to our customers while also building a wonderful team that I still think fondly of to this day. If those leaders had not left, I suspect I wouldn’t have had this opportunity to have such a big impact so early in my career. In the chaos that was these great leaders leaving the company, I saw my chance and took it. (“Chaos is a ladder,” after all.) I made an impact. Then I found greener pastures at another company.

This is all to say, consider taking advantage of this situation you’re in. It’s not a great feeling when everyone in your leadership chain leaves, as it makes you wonder why you’re still there. Try not to think about that as much, and instead think about the novel experiences you could create or ways you could improve the product for your users as a result of the change in leadership. If this isn’t possible, and your pay or general experience at work is less than ideal, then pivot.

As for the song that best suits this question, maybe this is an opportunity to move on up or maybe it’s time to follow in the footsteps of the leaders who left. Regardless of which route you choose, please enjoy this song by Curtis Mayfield: “Move On Up.” This is one of those songs that you’ll find yourself snapping your fingers to — and hey, maybe it’ll provide some inspiration, too.

Submit your question to The Lossless Leader
Series: The Lossless Leader

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