(Image courtesy of https://www.funderstanding.com/educators/classroom-assessment/)

A topic that comes up often in coaching and leadership development is what people and organizations are doing to look back and assess lessons learned on successful and unsuccessful ventures. Some of the most powerful and frequently asked coaching questions are “When have you tried something like this before?” “What worked well for you then?”  “What would you do differently knowing what you know now?” “What would your stakeholders say were the most and least successful things you did?” These are really simple questions. Yet I’m continually surprised by how helpful they seem to be, because neither the individual nor their organizations have a process in place where these kinds of questions are being asked on a regular basis.

Looking back productively requires us to put aside natural cognitive biases that will want to create a story of what happened that makes complete sense and mitigates our responsibility in the areas we failed. Our brains will fill in missing gaps and areas of confusion to help us all get to a story we can live with. We have to fight against these natural tendencies. We have to acknowledge where we got lost, didn’t react well, or focused on the wrong thing. For an organizational process in which we do a deep dive on our failures to work, the culture has to support it. There has to be a system in place that builds structure around experimentation so that failure is productive. Failure is a positive when we can learn from it what to do differently next time. We don’t want to keep failing in the same ways, we want to come up with new, exciting, productive ways to fail. We are in a period of immense innovation, creativity and possibility. There is a great deal of talk about building cultures where people feel safe to fail. Given that we are fighting our own natures and a society that doesn’t in fact recognize failure positively unless it ultimately becomes a success, creating such a culture is challenging. Many a book could and will be written about this as our need to “fail forward” grows. It seems though that the way in which we look back is a good and easy place to start. We must have clear and open processes in place in which people feel safe to admit to and acknowledge where things went wrong.

While our organizations continue to figure out ways to enable their people to repeat successes and fail forward regularly, we can certainly work on this at an individual level. I’ve been trying to think critically about my own evaluative process lately.  There’s an exercise I often have participants  do after a day of learning and exploration that I’m going to try using more myself.  It’s as simple as making a note of what to keep doing, what to start doing and what to stop doing.  If we each committed to doing something as easy as this after each big meeting, sales pitch or new endeavor, imagine how quickly patterns would emerge that we could learn from. What do we say we’ll stop doing that we keep doing? What do we know we need to start doing that we don’t seem to be able to initiate? What are our stakeholders teaching us every time we meet them that we forget by the next time we see them?


(Image courtesy of https://www.flickr.com/photos/gforsythe/17255568561)

As the world around us keeps changing, one thing we can certainly track is our own interactions with it. If we put a trusted process around how we recognize and learn from our failures, it’s very likely we can get more comfortable with failure itself. And we can’t learn from failure until we are comfortable looking at it in the face.

So, what does any of this have to do with the Dating Guidelines mentioned in the title, you may ask? Well, I’ll tell you. An area of life in which I did extensive informal analysis and in which I failed in both stupid repetitive ways and in smart failing forward ways, is dating. I met my husband when I was 38, so I racked up many years of experience. I learned SO MUCH in all those years. And while I was learning, I was establishing new ways of approaching the process of dating and I was creating guidelines to help me stay in the often tiring game.  All those lessons learned and approaches that helped me enjoy it more seemed wasted rattling around in my own head. I needed to put some kind of structure around what I had learned both to document the energy and effort for myself and so that I could share it with others.

For any of you still in the dating world you will find these guidelines here. If you know anyone currently dating, I’d invite you to share these with them. They are not of the ‘how to catch a mate” variety, but are ideas for how to stay true to yourself, maximize your sense of fun and agency, and identify behaviors that may help you sort through common dating challenges.

If you prefer to listen to a summary, I was recently interviewed about my dating guidelines on Therese Barbato’s wonderful podcast about love, That’s What She Said. You can follow the link here for a listen.