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A 5-point assessment to help you navigate a career crossroads

A senior executive with a great gig has another job opportunity. Maynard Webb offers a checklist to consider before you stay or go.

A 5-point assessment to help you navigate a career crossroads
[Photo: Yeshi Kangrang/Unsplash]

Editor’s Note: Each week Maynard Webb, former CEO of LiveOps and the former COO of eBay, will offer candid, practical, and sometimes surprising advice to entrepreneurs and founders. To submit a question, write to Webb at dearfounder@fastcompany.com.

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Q. I’ve been approached by a company with a great new opportunity. I’m at a great company already. What should I do? 

-Senior exec deciding whether to stay or go

Dear Senior Exec,

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As the pandemic starts to ease and things have changed with work and families, it appears that a lot of career movement is beginning to happen.

I’m an advocate for gaining as much knowledge as possible about all your options. This includes truly assessing where you are and finding out everything about where you might go.

  1. Know where you stand. If you are in a great company and have a good job you first should determine your prospects at this company. It’s possible you know this already. If not, find out through asking a series of questions. You can ask things like, Where do you see me in five years? What might be the potential role or roles? How can I have a long-distinguished career here? What do I need to work on? By asking questions like this, you are not making demands but learning where you stand and what is possible.  It is important to know this whether you are weighing an offer from another company or not. If you decide to take another job, you will soon find out how much your company likes you. Will they do everything to save you and offer more money and another role or will they thank you and wish you well? It’s always better to know where you are before you try to resign and find out. 
  2. Weigh the new opportunity. What are the prospects at the company you are considering? What will they hire you to do? Where will this job lead? How much can you personally contribute? Sometimes good executives at one company are recruited to be top executives at another company, but that company may not have the same long-term potential. What are the company’s strengths and weaknesses? Consider all the factors. What is the stature of the company? Many people are drawn to joining pre-IPO companies, but not every company on the IPO path has a successful offering or ends up being a transformational enduring company. You can still do very well in public companies. Also, assess the talent that is there. Who will you be working with? What is the culture—what does it feel like inside? How much do they emphasize innovation? How much fun will you have?
  3. Decide what you want going into any discussions about leaving. These situations create anxiety for you and the company. I have seen a lot of people who thought about leaving end up becoming retained. The company could fight for you and throw things out to try to get you to stay—it can money, or guilt, or love, so it’s important to think about what you want before someone tries to turn it around. If you have really decided to leave it’s best to make it clear that you are not looking for them to find a way to have you stay; don’t open the door for a counteroffer. Be gracious and thank them for being an important part of your career and journey and ask how to help make a smooth transition for everyone. 
  4. Live up to your commitments. Think long and hard before saying yes to an offer from another company but once you do, generally you should live up to that. If you committed and don’t go that leaves a bad taste with the company that made the offer. It also requires that you rebuild trust at the company where you decided to stay because they know you were looking to leave. (That said, things are very different than when I started my career and the idea of loyalty to a company has changed as talent is more in the driver’s seat than the employer. People no longer get fired for looking at other job opportunities and employers understand that individuals are the ones in control of their careers.)
  5. If you make a mistake, sometimes it can be corrected. In my industry we have people who leave and find the new opportunity isn’t all that they hoped and they return to the company they left, which is often happy to have them come back. We call them boomerangs. If it is all really about talent for companies—which it has to be—companies should fight hard not to let someone great go, and they should also be willing and delighted to have them return. 

Finally, every person needs to manage their career and choices wisely and thoroughly. It is in your hands to decide the path that is best. It is up to you to decide where you will be most fulfilled and likely to grow your potential.

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