Practical Advice For Changing Jobs
6 min read

Practical Advice For Changing Jobs

Tips for effectively managing a transition while working remotely.

Leaving a great job is never easy. I've been involved in many projects as a salaried employee, each with its own set of people, timelines, and deliverables. Some projects were long, some were short, but your transition is the last project you will be responsible for.

This essay describes how to design and execute an effective transition plan. I believe that your transition is the last thing your colleagues will remember about you, so it's important to get it right.

A few points to remember:

You are the CEO of your transition.

There is no one else who has the complete picture of your work like you do. This means it is your responsibility to structure your last few weeks. Each project will require a different time commitment during your transition period.

Allocate your time accordingly -- don't let a project where you are a minor contributor take up valuable cycles. Delegate your last few weeks because there won't be time for "just one more meeting" when you’re gone.

Be selective, then decisive.

You want to be very selective about who you share your news with at first. Early on, only a few people will know what your plans are. It’s critical to choose these people correctly to ensure a smooth transition. There is an order of operations that determines who you should communicate your departure with first.

Think about this like a set of concentric rings with you at the center. The people who you most interact with have a smaller orbit. This includes your direct project teams, your manager, and the executive you report up to. Prioritize your time with these people, as they will likely be the ones responsible for picking up your slack when you leave.

Try to avoid having people hear things "through the grapevine." As a rule, those within the same rings of your circle will tend to talk to each other. If there is a group of highly networked people that you work closely with, make an effort to meet with each of them within a short time frame — ideally within the same 24 hours. The word will get out eventually, but your goal should be to tell as many people as possible that you are leaving personally. This will be exhausting, but you will thank yourself for doing it.

If you are a people manager, you should contact HR and the person you directly report to. This will allow them to put together a plan for the best way to transition your team to another manager. It will feel strange not being able to share with your team, but you are optimizing to make sure they are well cared for. When an appropriate replacement has been found, you should gather everyone into a meeting with the new manager and be prepared to answer questions. There will be questions: you've just told your team that they will need to rebuild the trust you've developed together with a new person. You must support the new manager and take care not to undermine their credibility.

If you are an individual contributor, you should contact your manager and your HR representative or equivalent. Together, they will be able to work out the proper procedure for the transition process. Your direct teammates should be next. Explain to them that you will be devoting your full attention to wrapping up loose ends. It's natural to feel like you should apologize for leaving: try to avoid this. Transitions are difficult, but if your team is supportive they will understand your decision.

Once you have told your direct team, it is less clear about who you should tell next. It won't be possible to get to everyone, so try to prioritize those who you have worked closely with in the past or would like to maintain a non-working relationship with. Schedule as many 1:1 meetings as possible and tell them that you are leaving the company. Make it clear that they needed to hear the news from you. Tell them that you will be sharing your plans more broadly when you are ready. This is a discreet way to signal that you’re not quite ready for everyone to know.

Eventually, people will start reaching out to you. When this happens more than once or twice in a single day, it's time to open the floodgates. This means sharing a broader communication to a company email distribution list or Slack channel. Touch on the main points, including your last day and any specific points of contact. If you feel comfortable, this is also a good time to provide your personal contact information or links to your professional social media (this is not the time to share your personal Instagram with photos from the beach). Emphasize the positive - the few times that I've received a screed from a disgruntled employee it has not helped to enforce a positive opinion of them.

Documentation beats conversation.

When you tell people that you are leaving, there will be a tendency to suggest setting up a meeting. This is fine for saying goodbye, but it is a poor way to transfer knowledge.

Whenever possible, try to push back by saying the following:

"I would love to meet, but my schedule is pretty crazy over the next few weeks. Let me put my thoughts down on paper and send it to you. Then if you still have questions we can meet."

This works for two reasons:

  1. It is the truth. When you make your departure public, there will be far more requests for your time than you can give. Making this your default answer will make it fair.
  2. Documenting your work will provide your colleagues with information even after you have gone. Meetings tend to be ephemeral; they feel good in the moment, but no one can quite remember what was said afterward. By providing the documentation upfront, you can spend the meeting time discussing specific questions.

The content of this documentation will vary based on your role, but here are some general themes:

  • Email Summary: Provide a 1-3 paragraph summary of the project. This should be easy to drop into an email and send. The objective of this summary is to replace conversations where you give an overview of the project. Your audience is someone within the company who is interested but has zero context.
  • Responsibilities: List out all of the things you were responsible for, including deliverables, environments, and relationships. Explain what you did, how you did it, and be explicit in your instructions. This should be a recipe book for your job — pretend you’re writing a hiring description for yourself.
  • Commitments: Describe everything you’ve committed to and to whom. Include the scope of the commitment, including what is due and when it is expected. Provide a warm introduction between the person or customer you’ve committed something to and a member of your team who can act as the new point of contact.
  • Risks: Outline any potential risks that others may not be aware of. Flag gaps in coverage that will result from your departure. Provide options for mitigation of these risks, understanding that your work will now need to be completed by new people.
  • Priorities: If you weren’t leaving the company, what would you be working on for the next three, six, and twelve months? Describe these as priorities and explain your rationale.
  • Materials: Provide your team with the “keys to the kingdom” — a zipped folder containing all of your documentation related to the project. Explain your organization structure and folder hierarchy in an email. Make sure to flag specific documents that you were responsible for maintaining; don’t expect someone to dig through hundreds of files with no context.

This documentation has zero marginal cost to distribute. If you need to provide the same information to ten people, you can write the document once. If you do a thorough job, this will save you from repeating yourself and wasting other people’s time.

Help build relationships.

Often, projects succeed or fail because of informal relationships developed during an employee's time with a company. If you are involved in a project where you have been the key point of contact with someone else in the company, make an effort to introduce your teammates. Set up a meeting or send an introduction email. Your communication strategy isn't just a broadcast; it's also a way to patch the holes that will appear when you leave.

If relevant, this is a great time to recommend that a junior employee or colleague gets an opportunity to step up. A quick email or message can change someone else's career trajectory, especially to a manager who is now responsible for delegating your responsibilities and looking for a trusted resource.

Transfer social capital.

Most of the social capital that we've built inside a company stays locked up when we leave. Your ability to influence and make decisions will diminish, but your relationships don't have to. Take the time to exchange personal phone numbers or email addresses with people. Then, actually reach out to them with a thoughtful note.

Social media is a great tool for this. Adding someone on LinkedIn is the standard approach, but other measures feel more personal. Consider writing certain colleagues a recommendation or setting a reminder for yourself to reach out in the future.

If you maintain an active presence online, this is a good time to share it. I know many people who write newsletters -- these can be an effective tool for keeping in frequent communication. It tends to be mostly one-sided, but I've stayed in contact with former colleagues who reply when I write something that resonates with them.

There is never a perfect time to change jobs, but the steps above can help make the transition smoother for everyone involved. Treat the process as something that you're executing on rather than something you're passively observing. Remember, this is your last project — do you want it to be a success?

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