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Should I Stay or Should I Go?

Category: Work

Date: March 23, 2021

Sarah Stamboulie, an executive, transition and leadership coach, joined us for a Work conversation about how to professionally start over while remaining in your current occupation or place of employment. She offered advice about how to navigate career development and proactively create opportunities within your organization, while being aware of and sensitive to workplace culture. She shared tips about how to determine your standing in the company, identify various risk factors to employment, and negotiate a higher salary and/or position.

How To Know Your Standing At Your Current Job

Performance Reviews
If your current organization has performance reviews, you can rely on these to some degree to provide a sense of how you are doing within the company; however, be sure to take any “areas for improvement” very seriously, even if they seem like an afterthought. Dissatisfied managers frequently fail to communicate the degree of their dissatisfaction in employee reviews, so you should pay attention to any signs that your manager is not happy with you and your work.

Organizational Awareness
If your manager does not conduct performance reviews or provide other regular feedback, you’ll have to work harder to ascertain how you are doing. If appropriate, do try to initiate a conversation with your boss about your job performance. You can ask, “What would excelling in this position look like?” or “If you had to pick something I could change or do better, what would it be?”

If that’s not possible, try to build relationships with reliable coworkers who can offer tips about approaching managers and who are savvy about the happenings within the company and how to navigate them. It’s invaluable to have colleagues who will tell you if you have made a workplace blunder, for instance.

And don’t forget that if you share your strengths generously (i.e. Excel, reporting, crafting emails, etc.), people will be eager to help you in return.

Different Kinds of At-Risk

Economic Factors: current events impact job security based on the economic repercussions. For example, in the past year, the travel industry, hotel chains, airlines and event companies have been at risk due to the pandemic. Additionally, low stock price and poor product or divisional performance puts your job at risk.

Situational Factors: For example, a new boss may want to bring in people from their previous employer.

Organizational Factors: Consider if what you do is peripheral to the organization and can be outsourced. Additionally, a cyclical position with busy and idle periods is more at risk than positions with steady work flows.

Individual Factors: Keep in mind, if you appear miserable at your job, very often your boss is unhappy with your performance as well.


If you are concerned that your job is at risk, and you need to increase immediate job security, start working on some important projects; ideally, ones that are cross-departmental.

If you suspect that your job will be outsourced to a firm, you may be able to negotiate a different job. Consider positions that offer opportunities for growth. Or, another option is to offer to manage the outsourcing; ask the vendor to hire your employees and arrange to manage the vendor relationships for your company, adding to your experience and making you a more valuable employee.

When negotiating for higher compensation, if you have a competing offer and are salary-driven, you can go to your boss and make the case that you are underpaid. You can also share some of your personal responsibilities that necessitate a higher salary. It is important to highlight your institutional knowledge and what a loss it would be for the company if you left. Underscore your value in an assured manner, but also clearly communicate that you are torn about the decision to leave.

Working with a Coach

Company-Sponsored Executive Coaches
Your employer is their client, so you should ask your coach what they agreed to in terms of communication and confidentiality with your company. Their level of candor depends on what they were hired to do, so they may not be able to say if you should leave but can often work with you to better your work situation.

Self-Paid Executive Coaches
You are their client, not the company. A self-paid coach can always put your interests first.

Tips & Takeaways

  • If the timing of promotions is unclear, you can ask HR, or even casually bring it up at a department meeting. Don’t be afraid to be a squeaky wheel. You’re more likely to be considered when people are aware of your ambitions.
  • Quitting without a job lined up is a difficult and personal decision, highly dependent on the particulars of the situation. If you have a desirable degree without breaks in your resume, you have more freedom to do so. If you think your job search will be challenging, it’s better to have a job.
  • The second you think your job is at risk, you should see a coach. They can help you fix the issues within your current position or assist you in crafting a proposal to your employer. They can help you find a manageable way to leave, such as working for a vendor or client, so you can leave in everyone’s good graces and preserve the relationship.

Sarah can be reached at [email protected] and 212-206-9929.

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