Time to Say Goodbye

A subject that many executives feel incredibly uncomfortable addressing is their ultimate departure. Nothing lasts forever. The average tenure of non-founding executives seems to revolve around three years. Yours might be a bit longer or shorter, but refusing to accept the fact that it will come to an end might just make things worse when you finally decide to part ways.

The End is Near

How can you tell that you should move on? That’s naturally a highly individual decision that involves a lot of factors. Nevertheless, I always advise my clients the keep in mind that life is short. If you’re not having fun, haven’t been having fun, and don’t envision things becoming better-you probably should’ve quit earlier. Often, executives push themselves too far, to the point where they left after being burned out for months, and therefore both they and the company suffer needlessly.

Why does this happen? In the startup industry, where the average tenure seems to be two years and dropping, how come the star players tend to overstretch their stay? Because they’re good people. Having worked with dozens of companies and talking with hundreds of executives worldwide, “golden handcuffs” seldom were brought up. These people stay because they care about the company and their teams. They’re afraid of harming the startup that they genuinely care about.

You’re Not That Important

I haven’t worked with many executives as they quit, but being brought in to help a newly hired executive is pretty common for me. That has allowed me to witness a lot of companies right after an executive has been replaced. Guess what? None of them shuttered their doors a month after the VP of Engineering decided to go off and start a new company.

Yes, you’re very adept at your role. Clearly, you have a lot of valuable knowledge and a great impact. Obviously, you’re beloved by your team. Don’t let these blind you to the reality around you: everything will be alright. I hate to use clichés, but Apple is thriving post-Steve Jobs. Certainly, your organization will be able to march on.

How Long?

The period between deciding that you’re going to leave till your actual departure can be tough. I’ve seen leaders that felt it was unethical to continue hiring people and start initiatives when they knew they were on the way out. My two cents are that you have to do the thinking and weigh whether you still believe in the company-regardless of your stay there. If you still do, then there’s no unethical issue with hiring more people (at least, as long as the sale isn’t that they’re going to work closely with you).

If you no longer believe in the company, I recommend finding a way to jettison yourself ASAP. I’ve seen a handful of these scenarios, and they never work out. Those are the cases where ripping the bandaid fast tends to work best.

Similarly, considering how long of a notice you should provide, I believe that something around 2–3 months is adequate for most startups. Any more than that, and your organization might lose momentum as it will be led by someone that no longer thinks longer-term (I don’t care how good your intentions are). Putting aside the rare projects that are genuinely make-or-break, there’s usually no reason to stay longer.

Whenever possible, don’t make your departure widely known across your entire organization too long ahead of time (e.g., make it known until about 4–3 weeks before you leave, or when your replacement is hired and starts meeting with people). I know that it can make life harder, but if possible, it just keeps morale higher in my experience. Without it, initiatives tend to get stuck, long-term changes grind to a halt, your feedback-even if genuine-might be disregarded. Kind of like a government official that everyone knows is leaving in a few months.

How to Leave

Lastly, we should address how you should spend your remaining time. Rather than going into a frenzy, I’ve seen a few areas that tend to have the biggest impact on setting your successor to succeed.

First, coach your direct reports with even more focus and attention. Helping them become better and more able in their positions will be helpful while your replacement learns the ropes. Often, they will be carrying the torch of your thinking (unless one of them is to be promoted to replace you).

Second, map out areas where you have exclusive ownership of knowledge. In most healthy organizations, these are rare but should be actively sought for nevertheless. Is there a stupid Slack bot that you set up personally when you were the only employee and still restart once a quarter? Any systems that still rely on your personal email address?

Lastly, go over the long-term strategy and roadmap. Map out areas where you see screaming pitfalls, obvious wrong paths, and insightful options. The intuition you’ve gained over the years is one of the most valuable assets you have. Being able to share that is likely the best thing you can do for your successor.

Onwards to new adventures!

© Aviv Ben-Yosef 2021 — Originally published on the best newsletter for tech executives