How To Quit Your Job

We give quite a bit of thought to first impressions as we start a job – and not nearly enough to last impressions when we’re leaving one.

Years ago, I reached out to a fairly prominent CEO to get a reference for an individual who was in the final stages of interviewing for a job with one of our companies.

I asked about the candidate and the CEO was very decorous and cheerful, and said some supportive things.

And then I came to the question I always come to at the end of reference calls like this, “any concerns? Any worries? Any red or yellow flags I should be aware of?”

After a long pause, he replied, “Well there was one thing. He really didn’t leave well.”

So what does it mean to leave well, or in this case, not to leave well? The candidate in question had abruptly left both their team and their company in the lurch – so much so that it left a lasting impression on the CEO. He was excited for his new role and so he didn’t do the important work of buttoning up his last one.

Now, of course, there’s nothing wrong with leaving – often, it’s the right thing to do to advance your career. But it is possible to leave well, and unproductive for you to not leave well.

Here are some Do’s and Don’ts.

1. Tell your Boss First

This might sound painfully obvious but you’d be surprised how often news of a resignation reaches a manager before they’ve been formally told. While it might be tempting to share the news with close colleagues or friends at work, disclosing your departure plans to your boss first demonstrates professionalism, respect, and transparency. By telling your boss first, you are enrolling them in your succession plans.

2. Do Give Ample Notice and Plan for a Smooth Transition

Leaving a job well starts with providing your employer with sufficient notice before your departure. Startups move quickly but two weeks notice is still required. If you hold equity that you’ll retain and still believe in the startup’s mission, it’s more important than ever to offer to “do the dishes” and get a jump start on the recruitment process by offering to draft a JD for the team given your unique experience in the role.

Documentation is also crucially important when leaving an early stage startup where one person can hold entire swaths of knowledge and information without adequate documentation. During your notice period, be proactive in documenting your tasks, responsibilities, and ongoing projects. Share this information with your colleagues and the person who will take over your role. This level of preparation demonstrates genuine commitment to the success of the company – even after you leave and cements your legacy with the documentation you leave behind.

3. Don’t Burn Bridges – Keep it Constructive

Regardless of your reasons for leaving, it’s better to maintain a positive and constructive attitude until your last day at the job. Your final weeks should be a time of reflection and gratitude for the opportunities you’ve had during your tenure. Cultivate a sense of appreciation for the experiences, skills, and relationships you’ve gained, as opposed to the insults, injuries, or grievances that threaten to overtake you. These are the vibes your co-workers will remember, which lead to potential opportunities for you in a future you want to keep in mind. Remember, the professional world is much smaller than you think – and the startup world especially so. Consider that in your new role, the company you’re leaving could become a partner or a customer.

4. Don’t Neglect Exit Formalities

A lot of folks see exit interviews as an HR formality. Perhaps at big corporations that’s true. Not so much at startups. You might have an instinct to not rock the boat and say anything too pungent, but I encourage you to speak plainly. Say what you see in terms of your team, the company, market performance, how the company treats its customers, partners, and employees. All of it. Avoid being grumpy, casting aspersions, or taking personal potshots.

Don’t just critique, craft. Prepare for your exit interview. Come with ideas. “I think XYZ is broken. If I were you, I would think about buttressing the engineering team with such-and-such expertise.” You should suggest things that could potentially solve the problems you see.

Maybe the CEO or whoever you’re doing your exit interview with will say, “yeah, that’s fine. You don’t have the whole picture.” But at least you’ll be appreciated for speaking plainly and working to improve the company all the way through to the end.

All of these actions ladder up to one important principle: never leave your CEO or your team in the lurch. To say nothing about how you’re perceived by your CEO, consider how you’re perceived by your teammates. Who is going to internally refer you for a role 10-years down the line when their last memory of you is cleaning up the mess you left behind?

The way you leave is the last waypoint with the company and a critical reflector of your overall performance. Nothing stays in the vault. CEOs call around.

Leaving badly means you’ll be perceived as churlish or impetuous or unsteady. Do not let your enthusiasm to jump into the next gig bite you in the ass when you’re looking for the next, next gig. Leave a strong final impression – if not for your team, for the sake of your future career prospects.

I didn’t hire the man who left poorly. After seeing him zig and zag and flounder since that time, it was the right call. And I’m grateful to his former CEO for keeping me off those rocks.