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Should I Stay or Should I Go?

If you’re considering leaving your job, you should first try doing everything you can to stay.

(originally published by Booz & Company)

We’ve all faced the same question during the course of our careers, sometimes more than once: Should I stay or should I go? But after asking ourselves this question, too many of us end up making nonsensical decisions. Last week, I had a conversation with an executive who was seriously considering a lateral move to a small, family-owned company. When I asked him why, his only justification was that he’s fed up with his company’s toxic environment. 

But running away is not a strategy that builds careers. When making job decisions, the best approach to leaving is actually doing everything you can to stay. Don’t throw away years of hard work and goodwill before you invest time clarifying your goals, getting out of your own way, and discovering your worth.

Running away is not a strategy that builds careers.

Clarify your goals. Identify where you ideally want to be in five years or so by identifying your values and goals, and mapping out how to get from where you are to where you want to be. Make an educated guess—one that makes you smile and your heart skip a beat—and use it as a touchstone for deciding your next move. Pondering the future makes many good brains shut down. Intimidated by the task of mapping the future, many executives end up articulating some generic pabulum about what they want: “A senior leadership position responsible for driving change in a collaborative, innovative environment,” or some such thing. Don’t settle and don’t get stuck. Instead, have a glass of wine and do a bit of dreaming, or talk to someone who knows what makes you tick and how to get you to think.

Get out of your own way. Determine how you are acting as co-conspirator in your own frustrations by considering the major reasons why people quit their jobs:

Disliking their boss and feeling disempowered: Chances are, if you don’t like your boss, he doesn’t like you either. Accept that you are half of the problem and start treating him like a difficult, but important, customer, linking everything you say and do to his goals, bonus, concerns, and fears. If you lack empowerment, you are probably sweating the small stuff, and asking for permission rather than forgiveness. Everyone hates being micromanaged but, as long as it doesn’t impact your overall effectiveness, let it go. Resist the natural temptation to avoid your boss—instead, keep in close communication, focusing on the “what,” listening to your boss’s “how,” and then delivering the “what” using whatever “how” you think is best. Deliver results. Give your boss the credit. Rinse and repeat. 

Resenting the politics: People use the word “politics” when they are on the losing side of the influence game. But as much as it may feel that navigating your organization is akin to being in the “Hunger Games,” you can improve your positioning with a few simple measures: identifying your key stakeholders; treating them like difficult, but important, customers by understanding what makes them tick; making sure they see their reflection in your plans; and giving before you expect to receive.

Feeling unappreciated: Research indicates that people who love what they do pick great colleagues and shape their jobs into ones they want to keep. Given that there are an infinite variety of leadership challenges surrounding you, look around your company and figure out who you want to work for and how you can help them.

Discover your worth. Now that you have done all you can do—by defining your goals, being a model employee, and identifying meaningful opportunities within your company—it’s time to discover your worth by engaging your boss (or sponsor) in a career conversation that goes something like this:

You: “In five years, I would like to have the skills and experience to do [insert your “best guess” five-year career goal]. In order to attain this goal, I am thinking that I need to learn how to do [insert necessary skills] and develop a track record of [insert necessary experience]. What do you think?”

[At this point, boss hopefully responds with interest and wisdom.]

You: “As I look at our company, I think my next move, in six to 12 months, would be to become [insert jobs you want in the company]. What do you think?”

This is the critical point where you discover your worth to the company. If your boss responds by affirming your ideas or offering up his own, you will know you are valued. Move to close the “deal” by asking for specifics in terms of next steps and time frames. If he gives you a blank face or equivocates, thank him for sharing his insights and mumble something about continuing the conversation at a later date. You now know that the only person thinking about your future is you. You have tried everything possible to stay, and now you know it’s time to leave.

With 46 percent of new hires failing within 18 months, it’s a good idea to leave your company by first trying to stay. Relationships, reputation, and cultural fit don’t transfer. If you are successful in negotiating a new opportunity with your old company, you will advance your career at lower risk. And if not, then you can leave with confidence, knowing that you are running to a brighter future rather than simply running away from a frustrating past.

Susan Cramm

Susan Cramm, leadership coach, author, and former CFO and CIO, is committed to the principle that the best leaders take care of business by taking care of the people entrusted to their care.


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