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Sean Killeen
Sean Killeen

Posted on • Originally published at on

How to Leave a Company Well

I recently had lunch with the owner of a company I’d moved on from. Besides being a general catch up, it served as a sort of check-in/reflection point on constructive criticisms from our time together.

I had (I think) a great relationship with the owner prior to my departure (which was due to other circumstances), but one thing in particular he said during this lunch made me extremely happy:

“You left like a gentleman.”

This was 100% my goal – and I think it should be everyone’s goal when leaving a company (assuming the relationship is not in tatters somehow). This caused me to reflect on what I’d done when leaving the company, in the hopes that it will serve as a boilerplate for myself and others going forward.

Prior to Transitioning

  • Know whether there is a counter-offer that would cause you to stay. Would more money cause you to stay? A title bump? Even if you don’t demand these things, be prepared for them to be offered and understand whether they would sway your decision ahead of time. The rest of this article assumes you’ve decided to transition after the outcome of this conversation.
  • Create a transition area/document. More on this below, but if you can already show management that you’re dedicated to a smooth transition, it can build a lot of good will.
  • Give more than two weeks’ notice : Whenever possible, as a sign of respect, I like to offer longer than two weeks notice when leaving a company. Your new employer’s needs come first of course, but providing more time for the transition helps you leave on solid footing as a professional.

The Transition

The heart of the matter.

The Initial Conversation is IMPORTANT.

This can determine the entire tone of your leaving.

  • Keep it positive. Folks are often eager to let someone know why they’re leaving a company, but this comes cross entirely wrong. You’ll be prone to offering less constructive criticism, it creates a possibility for the conversation to devolve in an argument, and it can make you seem petty and/or vindictive.
  • If pressed for a reason for your departure, keep things general and positive. If someone appears to be genuinely interested, and there’s nothing that could change your mind on leaving, offer to set up a meeting after you’re gone to talk about it. This allows them to follow through if they’re serious about improvement and saves everyone time and frustration if they’re not.
  • Figure out when it’s okay to tell others, and who should be told. I suggest offering suggestions but letting the manager know you’ll respect whatever order/timing they choose.
  • Ensure they know you’re dedicated to a smooth transition. Go out of your way to make it clear that even if it requires extra effort, you won’t leave them hanging.

Create a Transition Area and Transition Document

Find a place that is reasonably accessible to anyone who would need it, and create a transition area. This could be a SharePoint site, a Google Docs folder, a shared folder on your hard drive, etc.

Transition Document Suggestions

Bonus: I’ve created a transition document template for you! You can find it in my office templates repository on Github.

My transition document generally contains:

  • Projects I’m involved with : My current role, current status, outstanding major issues, suggested new point of contact, and links to documentation.
  • Roadmap / “Someday” items : a list of things you wanted to achieve there or hoped the company would achieve while you were there. Sometimes these can spawn real change. Depending on how open your company is, this may be a great place to subtly and positively nudge them to resolve some of your issues.
  • Internal/External Liaison Connections : Are you the leader of any groups or point person on any committees? Were you the primary contact of any vendors? List these so the company can transition them smoothly.
  • Accounts held with the company e-mail : This is important, particularly if the company is paying money for you to hold an account somewhere (MSDN subscriptions come to mind).
  • Software Licenses : Similarly, these can be freed up when you leave.
  • Passwords / Security access you have : Note any privileged access or accounts that you know a password to, as these should all be changed or addressed in some way.
  • Software I made use of : This can be helpful, particularly if this software was responsible for any “magic” results you achieved.
  • Web Sites I made use of : Similarly, a list of helpful web-based tools can do a lot to ease a transition.
  • Recommended Books : If there are books that I find would be good for development groups or companies to read, I’ll likely include them here, particularly if I felt that they would have helped us better align to avoid me leaving.
  • Next Actions based on assessment. This is probably the most important part. Based on everything you wrote above, what are all the things you and others need to do to ensure a successful transition? I would go so far as to add these tasks to a Trello board and invite the appropriate stakeholders so that they can keep tabs on things as they progress.

Meeting with Stakeholders

Meet with as many stakeholders as you can, as soon as possible. You need to soak up all the next actions and get a sense of what everyone’s wish list is for you before you leave so that you can figure out where things fall in the queue based on overal priority.

After meeting with these people, take the transition plan back to your manager so they can confirm that the priorities are correct. This will help ensure you’re on the same page in case there are some things you can’t get to.

Connect with – and Praise – Colleagues

Once word is out, add colleagues on professional/social networks if you haven’t already and if you would like to stay in touch with them going forward.

I like to take the time to send a number of personal thank you e-mails with detailed examples of how people have helped you grow or assisted you when you needed it. I send these to as many people as I can think of. This sort of thing goes a long way, but only do it if you mean it (people will know).

Additionally, it is a nice gesture to add a recommendation for someone on LinkedIn if they’ve really made a difference in your time there, or if the connection is particularly important to you going forward.

Lastly, a Nice Exit Gesture

How do you want your colleagues to remember your departure? I like to show my gratitude and appreciation by doing something for the office. At a previous job, I brought in croissants from a fancy bakery in the city and left them in the break room with a thank you note. These were incredibly well-received. Most businesses would never expect this, and that’s why it ends up being a nice thing to do.

What Do You Think?

I’m happy to have maintained largely positive relationships with my former employers.

I’d love to hear any additional advice you have. Sound off in the comments, or check it out on HackerNews.

How to Leave a Company Well was originally published by Sean Killeen at on February 27, 2015.

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