Turning Learning Opportunities into Productive Habits.

A few years ago, I was working with an intern who frustrated me NO END.

VolunteerManager would make a mistake, we would correct it, and I would expect him to realize that what was learned could apply to similar situations.   And then the next big event would happen, and he would make ten more mistakes.  We would discuss, and he would correct those technical issues, but VolunteerManager seemed to have both a significant lack of judgement and an inability to apply the lesson from one situation to other, similar ones.

So, once we had a huge event, about the fourth or fifth that he and I had planned and run together, but the largest by far. Knowing that VolunteerManager had struggled in the past with the stress on the day of an event, I planned to discuss every detail of the event with him beforehand.   In that discussion, I had two themes or principles which I would argue came up in a few ways (including that I stated them explicitly).  (1)  VolunteerManager should have zero tasks to complete on the day of the event.  His only role was “air traffic control” and answering questions when asked.  (2) No surprises on the day of the event; planning should include thinking through all that is needed and reviewing it with all involved staff or leaders.

But on the day of the event, he failed to implement both some of my specific instructions and these principles.   VolunteerManager was trying to get people to sign forms while he was telling others their tasks.  VolunteerManager had failed to pay attention to the fact that we were registering guests on paper (we had sold tickets electronically) and thought that we could have volunteers register online at the guest check in.   However, he failed to ask the two staff in charge of registration if this would work for them!

So, in our post-event discussions, I asked him directly, “Why didn’t you follow my instructions?” He said, “oh, I thought that was just a suggestion, in case I started to get overwhelmed!”  and, “Why did you think you could add that to the registration desk on the day of the event” and his reply was “I just assumed we were doing it that way and it would be easy to include volunteers.”

Well, there were two things happening here.

First, my failure to ensure that instructions were clearly differentiated from suggestions.  That is a communication issue, and while I hoped that over time I could make less effort as VolunteerManager learned my style, that never really took place. He always needed explicit directions, and often, follow up afterwards to ensure he understood them.

But the second issue was more interesting to me.

Why did it seem that each time VolunteerManager made a judgement call, he failed to implement the lessons that earlier errors and corrections could have taught?  

What he incapable of taking “this one example” and translating it to other problems or situations? And if so, how does a person develop this skill: to take instruction and use it to increase your understanding of how it relates to new and similar but different problems?

My brilliant sister and I have come up with some principles to begin to encourage people to improve our accountability mindsets and learn from what we experience.


The prime lesson is that every (correction / error / discussion) can help elucidate the broader principles, themes, and norms by which work should be accomplished. Nothing happens in a vacuum, every correction can tell you something about the expectations or what is required to succeed.  But first we must ensure that the team is a place which encourages this kind of learning.  Blame, shame, competition, and image-management are antithetical to open and honest learning.  People develop a need to save face when they are worried their imperfections will be used to abuse, punish or diminish them.  Is your team a safe place to  learn, or does a school yard bully fit in, ready and willing to ridicule for mistakes and punish for innocent errors?

If your team is stuck in the vindictive and image conscious, please consider reading Managing from the Heart.

Next I have four questions for a manger to ask in discussion with someone seeking to transition from learning each technical corrections to identifying themes and principles for tactical and strategic judgement:

  1. What makes this situation different? What context will repeat?

First, you have to be able to understand what clues you use to put each project, event, or problem into categories.  When many of us solve problems, we often indirectly ask ourselves, “What have I seen that was like this before?” See if you can as a manager identify the common elements between the prior situations you have learned from, or share a few and explore together the potential similarities.

  1. What future situations will share those distinguishing characteristics? What situations may require a similar solution, but may look very different at first?

If you have done question 1 well, the idea of prognosticating into the future will feel less scary.  You are not trying to identify or avoid every future possible problem, but merely to confirm your initial descriptions of themes and principles by applying them to future hypotheticals.

  1. What are the “assumptions” I make on a daily basis that are less universal than I may otherwise believe?

This is a great place to stop and take account of industry norms, racism, classism, sexism, or other inadvertent forms of exclusion, but it includes more than that.  As an event planner, do I include best practices learned in a long ago course?  What books or thought leaders have I learned from?

One way to begin to ask this question is to fly to another city, rent a car, and try to drive in rush hour traffic.  I moved from Chicago to Atlanta in 2015 and spent my first four months of driving in Georgia thinking I was going to die.  Speed limits are suggestions in Atlanta.  When you turn on your turning signal to merge into another lane in Chicago, the cars in that lane will ease off the gas to make room for you, but in Atlanta they will speed up to get out of your way.  Both result in the same impact – you can merge – but they are literally opposite reactions. After almost two years of Atlanta driving, a friend from the Midwest moved to Atlanta and we now carpool together.  She hates Atlanta traffic because “speed up and get out of your way” seems rude to her – why did they do that, rather than ease off and let me in?  She’s beginning to figure out the weird foibles that are Atlanta roads, but her struggle really reminded me that a behavior I had learned to categorize as helpful (I still get to merge) looks extremely rude for someone accustomed to something else.

What patterns have your team, your community, your industry developed which need to be introduced to people, rather than assumed?   *Note in the church we called this “hidden language” a term useful to google if you’re interested.

  1. When are my expectations as a manager unreasonable?

I.e. when am I wishing that my supervisee would just read my mind?   It is unreasonable for me to expect my supervisees to know that I always print two-sided, except thank you letters.  Company styles guides are created because only designers know that the font matters, but so does the size of the lettering, or the decision to center align vs. left aligning a logo.  Ask yourself, does this need to be spelled out? And is it something I would have resented from a manager when I was entry level?  What could managers have taught me to reveal their goals and motivations?

  1. How can I as the manager better describe this specific situation to elucidate the important patterns and themes that should guide the work?

Honestly, part of your job as a manager is to equip your team for success, and on a regular basis that is going to mean some form of translation.   In order to translate to your team the goals, or principles, or boundaries of their work, you must first know the language of your team members.  You must be fluent in their assumptions and hopes and skills and industry expectations.  No, you should not be a expert in all the things they are experts in, but you should know enough to understand when you tell them to merge into another lane and they are in Chicago for the first time, they should not be surprised when someone slows down to create a sufficient gap.  Or in the reverse – in Atlanta? Just turn on that signal a little early and give the fast guys a momen to get out of your way.

Why I refuse to judge

Each person who comes to Living Room is unique, but many share a hard to describe determination. Like the brilliant woman who spoke during Taste of Life, many are working while caring for young children or elderly parents. Others have been working two or even three jobs, and still others have learned that work will not happen until they have daily access to a shower and some ability to launder their clothes.

This is one of the most remarkable, and frustrating, things about working with the homeless population. Their needs are infinitely simple, tangible, and attainable. In fact, their greatest desires are things I take so much for granted. I have been known to leave the keys in the lock to the front door of my house. Because I’m so accustomed to the privacy and safety of doors that close, and locks that hold, I forgot to double check. Some case managers have reported that will people who move into an apartment or private room after many months or years on the streets manifest a form of PTSD in which they become utterly convinced that someone has entered their room, taken, broken or moved their things.
Because when you’re sleeping on the streets, that happens. It happens every night – someone steals your shoes from under your bed in the shelter. A group comes upon you and takes everything you have, no matter how worthless. You never fall fully asleep because you are afraid if you did, someone might take your last $5, the one you have been saving to buy breakfast. Or they might steal the last third of your sandwich.


No matter how severe the obstacles they face, people who come to Living Room do so because they bring a seed of hope inside of them.  A belief that they are not the “walking dead” just biding time until the  virus consumes their final t-cell and decimates their immune system.

They believe life can be better than that.    Their  minds betray them, as many of our minds are wont to do, but that hope? it actually DOES matter. It helps people eventually to believe that the lock stayed closed, their medicines will still be present when they wake up, and after a time, they can truely rest easy, in a chair, without counting the seconds before someone comes to usher them off.

Autonomy And Workers

what it takes to do my job well: we don’t have a policy on “refunds” after an event. but a VERY RELIABLE and LONG TIME donor was overcharged by $10. he didn’t ASK For a refund, just wanted me to know of the overcharge, so I refunded him, as a GOOD FAITH expression of his relationship to the organization. I didn’t think to ask until afterwards, but DID inform my supervisor.

…Having that kind of authority to make decisions is LITERALLY the difference between the ability to thinking strategically and not.

BY which i mean, if i’m worried or primarily engaged (emotionally OR rationally) in pleasing my superiors, than I’m NOT primarily engaged (mentally) in thinking “what will create the best results).

this may be why after a few years of very external facing roles, I fantasize about the simplicity of an internal operations / HR / leadership development role. Because I will not have to negotiate the necessary and yet often frustrations of pleasing both the hierarchies and the customers/clients.

Why I Don’t Write

Do it every day.  500 words.  or more.

Never stop.  Choose a prompt, relax.  Share what’s on your mind.

But words are power.  They are connection.

and I find that rather than letting them flow, I am so much safer when I bottle them up.  Or, for a tiny piece of relief I will speak out my thoughts, let them pass through a friend’s ears and disappear.  No accountability when it’s not written.

But, in truth, I have things to say. and I need to become strong enough to put them down.

So, I’m going to write, because it’s scary.  but it’s worse to think that in five, ten, fifteen years, I’ll have lost what is happening now simply because I was afraid I could not do it justice.