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Should I Stay, or Should I Go?

Should I Stay, or Should I Go?

The world-of-work is changing fast with unemployment at a record low and the talent war in full swing. The worker’s market has given everyone the opportunity to reconsider their values and assess whether their current workplace is a best fit.

As a career and leadership coach, I hear on a regular basis from clients asking – “Should I stay, or should I go?” as they contemplate where they can do their best work.

[Related: Stuck in Career Transition? Your Type of Imposter Syndrome May Be Holding You Back.]

This is not the boss I ordered.

The adage still rings clear that people don’t quit organizations, they quit bad bosses. It’s true that not every leader is well suited for leadership-level responsibility and grooming and developing others. But we must also acknowledge that finding the unicorn best boss is unrealistic and may never happen.

If you are seeking new opportunities, you must interview your prospective boss before you accept a new role. My LinkedIn article on that topic will help you know what to ask.

But what to do if you like your work mission and your organization, but your boss sucks? Mary Abbajay’s book, Managing Up, offers insight about how you can become a boss detective and piece to together the puzzle that is your boss.

Boss assessment 101.

According to Abbajay, you must learn how your boss ticks by listening and noticing who works well with her and why. Look for patterns of behavior and learn to communicate in a way that resonates with her style.

Ask yourself the following questions:

  • What is your boss’s work style personality? How does she interact with others?
  • How does your boss like to receive information? How does your boss communicate?
  • What are your boss’s priorities? What are her goals? What are her concerns, challenges, and pressures?
  • What is her boss like, and what does the organization expect from her?
  • What does your boss expect from you?
  • What are her pet peeves and what truly matters to her?

The list could be endless and from my coaching vantage point, many people experience conflict with colleagues and bosses at work because they have not taken the time to understand each other and establish the two-way rules of engagement. 

Is the grass really greener elsewhere?

Let me be clear – if you are experiencing egregious behavior from your boss like harassment, misconduct, or unethical practices, by all means, get out fast. But if you are on the fence about staying or moving on, here are more questions from Mary Abbajay for you to reflect upon as you decide.

  • Do you love the work tasks and the mission of the organization? Are you playing to your strengths?
  • Do you need the job financially – or the benefits like healthcare and a 401K?
  • Is this role/organization enhancing your future career development and upward mobility?
  • Where are you on the scale of happiness and stress?
  • Where is your boss on the scale of difficulty?
  • What are the politics and organizational culture of your company?
  • Do you want to thrive, solidify, or survive?

[Related: Are You a Multiplier or a Diminisher?]

Clarity on workplace values.

Deloitte conducted research on the top workplace values prioritized by Gen Z and Millennial talent in 2022:

  • Good work/life balance.
  • Learning and development opportunities.
  • High salary or other financial benefits.
  • Positive workplace culture.
  • Opportunities for career advancement.
  • Sense of meaning at work.
  • Flexible work model.

Frankly, this list appeals to me as a Gen X professional and I’m grateful to the younger generations who have helped employers understand that work/life integration is non- negotiable, and flexibility is not just a pandemic whim.

Sunday night blues.

How do you really know if you are ready to move on, or if you should buck up and stick it out? My mantra has always been “The suckiness is real, but the suffering is optional,” as I explained in my TEDXWomen talk. You must get quiet with yourself and reflect about how your work is impacting your life and career to make an informed decision.

If you are experiencing the Sunday night blues – that anxious feeling about the next work week that sets in about 5pm on a Sunday – then you should consider the following to help you assess your work situation.

Kathy Caprino, a coach, author, and career expert whom I admire, wrote a great piece in Forbes about the undeniable signs it’s time to leave your job:

  1. Are you unhappy most of every day doing this work?
  2. Is the work environment tainted with extreme toxicity, including your boss and your colleagues?
  3. Are the skills that you’ve been hired to use for this job not a fit for what you’re good at or enjoy?
  4. Do you believe deep down that you’re meant for better, bigger, and more thrilling things?
  5. Do the outcomes that you’re working toward feel meaningless or negative to you?

My gratitude to Kathy Caprino for her no-nonsense clarity that will help you consider your next move, or not. I have always believed that even if you are blissfully happy in a role, you should always be considering an exit and a growth strategy simultaneously so you can design your career destiny and not let it happen by default.

Changes like mergers, acquisitions, down-sizing, and lay-offs happen beyond our control, and it is incumbent upon all of us to be ready for what’s next by nurturing your network and being seen and heard for your good work beyond your organization, so you are a recruitable player.

You deserve a place where you can do your best work.

The hot job market favors talented professionals, but it’s never wise to run away quickly from a bad role or a bad boss unless the situation is harmful or egregious. Take the time to run toward something you are truly excited about that allows you to play to your strengths and continue to develop.

A wise mentor told me many years ago to always ask myself, “Is this a place and a role where you can do your best work?” That has been my north star in career decision-making and I hope it helps you moving forward.

[Related: Creating Space for Connection]

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Caroline Dowd-Higgins authored the book "This Is Not the Career I Ordered" and maintains the career reinvention blog of the same name. She is Vice President of Career Coaching and Employer Connections for the Ivy Tech Community College system and contributes to Thrive Global, Ellevate Network, Medium, and The Chronicle newspaper in Indiana. Her online video series about career and life empowerment for women is on YouTube. She hosts the three-time award winning podcast, Your Working Life, on iTunes, Spotify, and SoundCloud. Follow her on Facebook, LinkedIn, Google+, and Twitter. Her TEDxWOMEN talk about reframing failure and defining success on your own terms is available on YouTube.


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