Choosing Your Next Boss – Save Yourself Part 2

Once upon a time, a professional in the middle of her career had two opportunities. One was working for a company where the job seemed well-defined, a step up in her career, and her peers would be people she loved working with. The other was for a company where the role was really ambiguous and a bit uncertain, but the boss was someone she liked, respected, and was certain would challenge her growth.

She chose the safe route. She was 2015 me.

I chose what made more sense on paper. I chose safety instead of following what my intuition was saying. It was the most miserable year of my career. My gut was saying “choose Ben” but I didn’t, and it is one of my few career regrets.

Simply stated, the jobs I’ve loved the most in my career, were the ones where I said yes based more on who I was going to work for and what I would get to learn, rather than my title or comp package.

In a recent study of the teams of 1000 managers, the data shows that 57% of people have quit their jobs because of their bosses. As leadership coach Michael Sever states,

A good boss in a mediocre company will protect you and support you

A bad boss in a good company will frustrate and demoralize you

A good boss in a good company will unlock your potential

So…what does this have to do with Saving Yourself?

In order to Save Yourself from repeating bad mistakes, you MUST decide what your criteria are for finding your next boss. And you MUST then follow those criteria even when an opportunity sounds “too good to pass up” or the money seems impossible to ignore. Take it from me…miserable and well paid is still miserable.

When I took my current job, I met with my bosses (I work for co-founders) individually, then together over a dinner, and finally talked to one on the phone a couple more times. It was a process and though I probably made it more difficult for them because of the time it took, it was so important for me to ensure we were going to be a good fit for one another.

I was looking for the following…

  • Energy – I wanted to work for someone who wasn’t embarrassed to show excitement about what the company is doing and their role in that. Show me someone who is energetic about what comes next, and I’ll show you somewhere that I’ll feel safe to bring my high energy levels to the mix
  • Communication – I needed someone who could keep up with the pace of my thinking and communication. A boss who isn’t annoyed by my directness and who is able to banter and spar a bit even in the interview process is important
  • Integrity – When I ask about the difficult side of their work or company, I need to hear an answer I can believe. If it’s all sunshine and unicorns, it’s also bullshit. If something sounds too perfect, it probably is
  • Humility – If they are hiring me, there is likely a gap somewhere. A boss who can admit that there is a need in the team that they cannot fill, is usually a boss that will make space for you and give you ownership
  • Humanity – If the person in front of you does not come across as anything other than a boss…meaning they don’t also seem human…then it’s a hard pass. I’m a human with feelings, ambitions, joys and sorrows and I want to work for a human willing to show the same. Robots and Ice Machines need not apply for the role of “Leah’s Boss” ever again

On that note, I chose my current job based on a few criteria (not a fintech, a product I’d actually use, based in Berlin, small but winning, interesting challenges that needed what I have to offer, etc.) but without a doubt the most convincing reason was the two humans who sat across from me at a dinner as each side wrestled with a big choice. Some of the questions I asked included:

  • Are you still friends as well as co-founders?
  • Who do you feel accountable to and why?
  • What sort of culture do you have? What sort of culture do you want? Who do you need on the team to get from one to the other?
  • What will it look like when we disagree or when I say “no” to you? (because BOTH will happen)
  • How desperate are you to hire this position? (Meaning…will you settle or are you patient enough to find the right person.)
  • What keeps you up at night?
  • What do you do for fun?
  • Where are you from and what was that like?

To Save Yourself from your current job and not just jump into a familiar replica, you must know what you value for yourself and what you value in a boss. If you are a leader many of these values will also be what you challenge yourself to be for your team and you want to work for someone who will champion this about you not try to stifle it.

Save Yourself by choosing your next boss…not your next company, or next title, or next rung on the ladder. If you don’t know enough to say yes to an offer, ask to talk to him/her again. If they say no, consider that data and keep moving.

I still pat myself on the back for choosing Safwan (I bravely emailed him and asked him to consider me if he was hiring and he did!) and Russ (he changed the course of my life as a leader because of his demonstrative and heartfelt energy at a whiteboard during an interview) even longer ago. I’ve had to forgive myself for not choosing Ben and for playing it safe (not something I do often). Each decision had a consequence and, honestly, each decision led me to the opportunity I had to save myself and end up where I am today.

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