Should I stay or should I go?

Aug 9, 2022

Hey everyone,

Here’s a question that’s coming up a lot recently:

Should I stay or should I go?

The answer, of course, is different for everyone, but let me share a story.

Last week, a member, we’ll call her Sam, reached out to ask for help (yay!).

Sam’s boss had just asked her to step down from the VP of Product role and move into a special projects job. This came after a difficult LT (leadership team) meeting where Sam had attempted to present her product vision. 

The meeting did not go well leaving the LT to think Sam could not be a product visionary.

Sam was upset and felt like she was being punished unfairly (part of the challenge came from the fact that the LT is not customer-focused and negatively reacted to some of the customer-based product changes she was suggesting).

So she called me to ask my advice on whether she should just angle for a severance package, and then go find another job.

I told Sam I’d be happy to discuss that, but first I wanted to learn more.

I asked Sam more about what happened, about the feedback, and about whether there was any part of the feedback she agreed with – perhaps, even a small part that would nonetheless be helpful to her.

I raised this not to justify how the LT treated her (or their anti-customer instincts), but because even bad feedback sometimes has a sliver of truth. 

This is part of what I call Positive Politics – and, in particular, the Caring/Not Caring mindset I recommend. 

Sam had a choice.

She could see this situation as a ‘punishment’, take it personally, and be hurt. 

Or, she could see that it unlikely has little to do with her – and the little it does have to do with her, maybe she could learn something from.

She agreed to think about it.

We ended the call and I asked her to get back to me in the next few days.

I heard from her the next Monday:

After sleeping on it over the weekend, I’m going to *not* pursue severance.


It would not have ‘hurt’ the executive team for her to quit, but it could have hurt her especially in this topsy-turvy job market. 

Unemployment is at an all-time low and yet layoffs in the digital world are beginning to happen more broadly (or at least hiring freezes).

And then she added this tidbit: 

Finally, my boss wants to work with me on overcoming the executive level perception that I’m missing thought leadership.  It’s still perhaps a fools errand, but it’s showing some intention on the surface that he hasn’t “given up on me.”

Even better.

This is Caring and Not Caring at its best. 

She’s interested, she’s curious, and she’s less reactive. Perhaps, she’ll learn something – if not about herself, then about how to play Positive Politics better.

At the same time, Sam will also join a Job Search Council for ‘slow seekers’ — people currently in jobs who want to slowly evaluate new opportunities.

Being on that JSC will help her be more productive at the company – by giving her a sense of optionality.

Ironically, it’s possible that the optionality and Caring/Not Caring combined will mean that Sam stays at the company and makes a big impact. 

Either way, if you are asking yourself the same question – should you stay or should you go? – then reach out so we can help you make the best decision for *you*



P.S. We will be playing Positive Politics at the fall meetings in La Jolla – in particular, we’ll run a Caring and Not Caring exercise that should help all of us navigate the frustrations we all experience.

About the Author

Phyl Terry

Phyl Terry, Founder and CEO of Collaborative Gain, Inc., launched the company’s flagship leadership program – The Councils – in 2002 with a fellow group of Internet pioneers from Amazon, Google, and others. Thousands of leaders from the Internet world have come together in the last 15 years to learn the art of asking for help and to support each other to build better, more customer-centric products, services, and companies.

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