Should I stay or should I go?

While we put quite a bit of thought into when and how to move on from a role, we should be giving equal consideration to whether it’s better to stay. Sometimes, staying in your role or company and finding ways to extend your experience from within, such as taking a sideways step, can be the best option. Here are my reflections on how to know when to move on and when to stay put.

That feeling of waking up on Monday morning and wondering what we’re doing with our lives.

We’ve all been there. That feeling of waking up on Monday morning and wondering what we’re doing with our lives. Bored of our job or frustrated with our manager. Worried we’ve gotten too comfortable and that our career is going nowhere. Unmotivated. A little bit discontented.

In my long career as an executive-level recruiter, I’ve had many, many calls from people feeling this way. Their first instinct is often to leave the company entirely in search of that next step up. That’s probably why data released by LinkedIn at the beginning of this year found that around a third (33%) of Australians are planning to search for a new job; and this rises to 42% for Gen Y-aged workers (who are peak age for moving towards executive roles).

However, one piece of advice I always give people is: have you thought about staying?

I’m a big believer in being brave and moving on when the time is right, but I also think anyone who is discontented in their job should weigh up the alternative of pushing for improvement where they are.

The hidden benefits of staying in a job

“You cannot climb the ladder of success dressed in the costume of failure.” Zig Ziglar, author and motivational speaker.

Climbing the ladder internally can be a tricky proposition. On one hand, you’ve already proved yourself and have a certain amount of reputation internally which you can use to your advantage. On the other, you can be pigeon-holed, stuck in a company where no promotion opportunities are available, or even become a victim of your own success – so good at an operational-level task that no-one wants to lose you by sending you onwards.

It’s easy to see why people often choose leaving over making an effort to move up internally.

One way to make staying in a job worthwhile it to ensure you’re ‘wearing the costume of success’ by determining what is standing in your way.

For example, if you have your sights set on a top role, then you might need to consider staying with a company but broadening out your experience through a sideways move. Analysis from Adam Kleinbaum from Tuck School of Business at Dartmouth College found CEOs who follow a more atypical career path by gaining cross-functional experience (than purely through say operations or finance) make more organisational connections and are better able to prevent silos and develop new ideas. So, think about moving across before moving up.

Or, how about discussing a temporary secondment to another department? Asking the company to fund a training course? Or, accessing voluntary and extra-curricular programs which will look good on your executive resume down the track?

Alternatively, there might be another issue holding you back: career management. It’s not enough to simply do your job well. In my work as an executive career coach, I see many people who think they need to leave an organisation to progress, but in fact they just need to build skills like confidence and presence. Changing jobs takes a lot of energy and effort that may be better directed towards self-improvement, such as engaging a career coach or honing presentation skills.

Meanwhile, if your reasons for moving are to do with your current boss or team, it’s worth trying to sort through these issues. Try talking to team-mates, to see if they’re feeling the same way.  Network with other departments. Ask for a frank and meaningful discussion with your manager, as they might not know that you’re feeling unmotivated, or they might not know why. As part of this process, also try to be receptive to feedback – your own behaviour and limitations might be part of the reason your team is treating you in a certain way. Self-awareness is a crucial skill for leaders.

After all, if you were planning to leave anyway, then there’s no harm in trying to sort out problems first. If it doesn’t work, then at least it may validate your decision to leave.

The ‘stay or go’ checklist

Having said all this, deciding whether to leave or not is still a difficult decision. So, here’s my list of ‘do I stay or do I go’ questions:

  • What skills do I need to gain before I can move to the next level in my career? Is there potential for me to gain them here?
  • Where would I go and would it be any better than working here?
  • How often do the types of roles I want come up at my company?
  • Do I believe in the company I work for? Do I respect their values? Do I want to be involved with them long term? Is it the sort of organisation I want to lead?
  • Did I like the job when I started? Is the discontent recent or temporary, or has this job always been a poor fit for me?

And remember, if you do decide to stay, at least for a while, then take advantage by implementing all the steps I outlined above to make your current role better. There’s no point in staying if you’re going to remain stuck in your rut. If you need some help, give Hunton Executive a call – our executive career coaching can ensure you make the most of your current role. Or, we can find you a new one.

Hunton Executive can help you to make the most out of your current position, or give you the confidence to take the next step.


Contact Hunton Executive for a confidential conversation about how you can make the most of your current company or how to build a plan to start moving on.


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