If I created a word cloud from my coaching conversations over the years, “success” and “failure” would be smack in the middle, overshadowing every other word. They are the two words I hear most often.

And here’s the truth: I find them to be quite useless words.

“Success” is usually very closely connected to expectations: expectations you may have held, or hold for yourself (e.g., “At age xx, I will be…”), expectations your family members, colleagues, friends or society in general hold for you. Or at the team/organizational level it might sound something like “by the end of Q2, we will have completed xx widgets.”

“Success” usually shows up as a checklist, with individuals, teams, organizations pushing, working, and exerting a tremendous amount of effort to methodically tick each item off that list every day. With each tick, the theory seems to go, the better we will be.

What I’ve learned is this: those with all or most of the boxes ticked aren’t necessarily any better, any happier. Those individuals often feel like something is still missing, and those teams and organizations are just as likely to have toxic or far-less-than-ideal workplace cultures.

“Failure” is also connected to expectations, usually when not enough of the “success” boxes have been ticked. Or if you’ve faced an unsettling or saddening event. At the individual level, this might be losing your job, a relationship ending, or a business venture losing money. At the organizational level, this might mean delayed projects, running over budget, or product launches that just don’t take with the market.

What I’ve learned is this: these “failures” often lead to transformational change and are often (dare I say: usually) the pivot point to something great.

So, talking about success and failure in traditional, binary terms doesn’t interest me. What I’m much more interested in is the insight gleaned from any and all of our experiences. Here are the 5 questions I’d like you to ask yourself instead of getting stuck in the success/failure binary:

  1. What is fulfilling me? (for teams and organizations: what tangible, positive impact are we having?)
  1. What is unfulfilling to me? (for teams and organizations: what’s not working well?)
  1. What am I learning about myself? (for teams and organizations: what are we learning about our culture/our clients?)
  1. What do I want more of in my life? Less of in my life? (for teams and organizations: what do we need to be doing more of? Less of?)
  1. What do I value most? (for teams and organizations: what do we value most?)

Asking yourself these questions, you’ll glean important insight that will support you in taking fulfilling, impactful action.

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