This Question Of “Should I Stay Or Should I Go” Comes Up Often

A question came in this week in the form of an email from a former colleague with whom I have stayed in touch: 

“I would like to get together with you again for advice on where to go next. I still have a responsible position but didn’t get the leadership position cemented that I would have liked. 

When I met with you a few years ago, I said that I really enjoyed being the decision-maker or at least the one pulling the options together and obtaining approval of the recommended approach. 

After all this time, my boss is still at many times unavailable and leaves me to run many things.

But I don’t get the recognition I desire.

One of our main programmers just told me last week, “You’re doing almost everything.”

It is lonely being in this position, yet I don’t get anywhere asking for a regular 1:1 with my boss. 

Nor do I get the kudos I need to keep going on at this company.  

It’s been crazy busy as we are implementing a new system this Nov or Dec, also, and I’m a key person in the configuration. 

I just need another professional opinion on where to go next.

I don’t necessarily want to abandon all this and I have 15 years at this position, 8-9 in this particular role.” 

I think the question is one we all struggle with from time to time: “Should I stay or should I go?”

Step One: Reflection

One of the exercises I recommend to anyone who is in transition (or, in this case, contemplating transition) is to make a Top Ten List (borrowed from Letterman, but not near as funny).

Actually, I recommend three top ten lists.

Top Ten things you would use to describe the perfect:

  • job
  • boss
  • company 

In the case of someone contemplating a move, they should try not to think about their current job.

The bias may come through and they could end up with the top ten things they would prefer to change at their current job. 

Then force rank each list 1 to 10 (no ties). 

Step Two: Evaluate

Once you have those ranked lists, then think about your current job, boss and company.

Check each one that describes where you are now. 

It sounds like you are dissatisfied with your current position.

Does this exercise support that feeling?

Make you feel better or worse?

Leaving someplace where you have invested so much of your time and effort is difficult. Earlier in my own career, I had 12 years at one employer and 15 years at another. 

Leaving was incredibly difficult.

But…I wanted more. 

I think you have to ask yourself “why”.

What…

  1. drives you?
  2. motivates you?
  3. gets you excited to get up every day and go to work?
  4. things do you want to accomplish in the next three years?
  5. things do you want to accomplish in the next five years?

Step Three: Compare

If, after this exercise, you are still feeling stuck, network.

Talk to people about their roles in their organizations.

Share your top ten list with them.

How would they rank their position on your list?

Go on a few interviews. (This has the added benefit of keeping your resume current and interviewing skills sharp).

How do those roles rank on your list? 

So…should you stay or should you go?

Only you can answer that question.

Your top ten lists are going to be different than mine – chances are they will be different for everyone.

You may find your current role ranks pretty well in comparison…or, you may find it ranks dismally low. 

Do you relate?

If you relate to the above conversation, I would love to hear from you.

What are your Top 10 Lists?

Where does your current role rank?

Do you have different advice for my colleague? 

Post a comment, send an email, or give me a call!

I want to hear your stories! 

3 replies
  1. Brad
    Brad says:

    Love it. When it comes to evaluating current positions vs. new opportunities, to me the most important aspect is leadership. I look for leadership before product, role, fit, anything. That provides the insight most of us are seeking. When we do it backwards we shove square pegs in round holes. Leadership is a reflection of everything you expect from an organization. Weed things out from there, then look for role, cause, job responsibilities, etc. I’d much rather insert myself into an unknown role with great leadership than a comfortable job with no guidance.

    Reply
    • Jeffrey Ton
      Jeffrey Ton says:

      Great point, Brad. Poor leadership is also why most people leave jobs. I will probably dig deeper to that in a future post!

      Reply
  2. Glenn Keller
    Glenn Keller says:

    Excellent. I think now is the perfect time for reflection as there may be a fundamental shift in how we go about many mundane things. This will present challenges for some and opportunities for others. I think top 10 trends might be another good list as it may spur ideas for something you’d love to do.

    Reply

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