So You’re Thinking Of Leaving Your Job…

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Shorter Version

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Leaving your job, whatever the circumstances, are waters that need to be carefully and thoughtfully navigated. Take some time to do it with as much style and grace as possible. Use the transition as best you can to keep, and even re-enforce, the bridges and relationships you’ve built. 

Leaving your job is a tough decision

Deciding to leave a job can be difficult. As you consider this please refer to the article Time for A (New) Job. Once you’ve completed the process it’s important that you leave your job on a high note. There are important steps to follow. Keep your plans to yourself until it’s time to share. This ensures you are in control of the messaging and timing.

Letting things leak out before it’s “official” can be very painful and should be avoided.

Invest in doing the transition right

There are many reasons you may be changing jobs. It might be your choice to leave and try something new. It may be your employer’s choice for a multitude of reasons. Regardless, many times on your way out the door you may feel like you want to vent about the shortcomings of your company, your boss, or your co-workers. You may even want to brag a little bit on what your new gig is going to be. Keep in mind, last impressions are lasting impressions. With so many ways to find connections and research people (LinkedIn, Facebook, trade shows, industry organizations) you always want to take the high road when leaving your job. It’s a small world. You never know the who, what, when, where, or how your transition may impact you further down the road.

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Longer Version

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Let’s work through this

Ok…so you know you’re leaving your job – maybe it is your choice or not. Regardless, you’re going to need to take some time to do the transition correctly as most of the time leaving is going to be awkward. This may be because you have some good friends at the company, your boss is counting on you, or maybe you’re in the middle of a big project. Maybe you just found out yesterday that you’ve been terminated.

My goal with this posting is just to set the stage and provide a general framework to get you started. There will be more postings in the near future to share additional perspectives and guidance.

Framework for success

Before diving into leaving your job, I’d like to share a few points to help you into the right mindset. Take some time to think about these three things:

  • Confirm what you are losing
  • Plan the steps
  • Take the step to make it happen

Confirm what you are losing by leaving your job

Clearly understand what you are losing and/or forfeiting when you leave.

These items should have been covered as you made your decision. Even so, it’s worth double-checking.

Think about the more tangible stuff first. It’s really important to understand things like the items below so you can be compensated correctly as you leave:

  • Pay for unused PTO.
  • The timing of when your employer matches hit your savings/retirement accounts.
  • Where you are in the “bonus cycle” and if/when you would get paid if you leave. Be careful here as there could be significant $$ involved.
  • If you have any contractual obligations that need to be met and/or broken including employment contracts or non-compete agreement (I recommend using a good attorney for this).

Now you have to consider the relationship side…

The softer yet more important side.

  • Where do things stand related to key business functions or projects? As best you can, work to find the right transition timing. Leaving your now “previous employer” in the lurch can leave a bad taste.
  • Who are the people you have a great relationship with? Who do you want to say thank you to? What can be done to ensure that you keep an on-going relationship with them?
  • Who are the people you might want to mend fences with? Yes, humbling, but in many ways can be super impactful.

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Plan the steps

Now it’s time to plan the steps to leave with the guiding principle of taking the high road and preserving, or maybe even re-enforcing, relationships you have.

Craft your “why I am leaving” explanation. Just a few sentences are all you need as most people are not looking for, or are interested in, the gory details. Keep the wording positive. Even if you were not at all happy with your job or your manager, a simple explanation of “it’s time for a change to explore new opportunities” will suffice. Grinding axes and negative comments can sabotage your exit and your relationships with your current peers. Some companies may ask for an official resignation letter. Follow the same principles for this as well – short and sweet is best.

Assess and determine the best date for your last day. Hopefully, you’ve considered this as part of your decision to leave and accept the new job.

As best you can, work hard to find the best (or least painful) date for your last day.

Determine your plan to communicate your decision to leave. Who will it be with? On what date and time will it be? Personally, I think face to face is best….an email is never acceptable. You may have to settle for a conference call due to the virtual world we work in. Remember, your manager has been through this many times. Most of the time it will be harder for you than it will be for them.

Determine once you’ve announced, who you want to spend additional time with to ensure you are preserving your relationships. Think about how and when you will do this.

While not always applicable, give some thought to what your response would be if your current employer asked “We’d love to keep you. What would it take for you to stay?” Think this through carefully. Why have you decided to leave? Would “the answer” truly address these reasons? What are the appealing aspects of the new job you’ve accepted? Why would you change your mind now?

Take the steps!

By now, you should have a high degree of confidence that you’ve made the right choice and have a good plan. If not, it’s critical to re-group and resolve any loose ends and angst. Once you announce, things are going to be totally different and most of the time very difficult or not impossible to undo.

  • Get to the right mindset. Be confident and positive yet dignified and humble. Remember, you want to leave with as much style, grace, and goodwill as possible. Leave your frustrations at home.
  • Follow the steps and plan that you developed.
  • Look for unexpected reactions and fall out. Move to address these consistent with the other parts of the plan you have developed. This applies particularly to things like exit interviews and surveys. If you do want to provide feedback, do so in a positive, constructive way using wording such as “my manager could be more effective if…”. Keep the suggestions for the improvement list to one or two things, as going on a rant and sharing a laundry list is going to be counterproductive.


By following these steps you’ve done your very best to take the right steps. You should be set to leave on as good of terms as you could. This will give you a clear mind and path to start your next great opportunity!

Actionable Steps


Take some time to confirm why you are leaving

Get in the right mindset. Confirm what you are losing. Think about things like benefits, contracts, obligations…as well as your network, relationships, and clients.


Plan it correctly

Take the high road and re-inforce relationships. Craft a farewell email, determine the best last day, think about the relationships you want to keep, and make sure you have a response if your employer asks you to stay.


Move forward

Be confident and positive yet dignified and humble. Leave any frustrations at home. Follow the steps you planned and start on your next adventure!

About the Author

Tim Rolfes

Tim Rolfes

Senior Program Manager

Tim is a Senior Program Manager at the Christ Hospital Health Network, where he recently led their team to open a Joint & Spine Center. From start-ups to mature businesses, local to global, Cincinnati to Hong Kong, he’s seen it all. As a business driver, community leader, and personal coach, he specializes in helping people and organizations find and maximize their talents and opportunities.
Full Bio | Connect With Tim | LinkedIn

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