The Art of Contextualization

May 01, 2023

I needed a simple cotter pin. You know, the pin that holds your bike rack or boat trailer securely to the hitch of your car. My wife and I were all set to head out on our local bike trail, but as I loaded the rack I realized the cotter pin was missing. The cotter pin might be small, but without it there was no guarantee that our bikes would follow us to the trail.

I knew I had extra cotter pins for just such an occasion, but my daughter was using one to transport kayaks to the river, and my son had the other one on his car.

With my usual reserves exhausted I decided to pop into a local, boutique bike shop on the way home from our regular Saturday morning visit to the Fayetteville Farmers Market. Unfortunately, the only option they had was a high-end, very expensive, lifetime warranty pin. While it certainly would have gotten the job done, it would have been the equivalent of buying a paint sprayer because I misplaced my brush. It was way more than I needed, so I swung by Auto Zone to try my luck there.

I walked in and the guy manning the counter offered his greeting. “Hey partner, what are you working on this morning?” Notice he didn’t say, “How can I help you?” or “What are you looking for?” or even “How do you think the Hogs are going to do this year?” He wasn’t too over the top in his enthusiasm, but I also didn’t have to check his pulse to make sure he was still with me.

He assumed that I likely came in on a Saturday because I was working on a project, and he was correct. I was working on solving my cotter pin problem. When he asked me that question I thought, Perfect contextualization.

  • He knew exactly who was walking in the door.
  • He knew what to say.
  • He knew what not to say.
  • He knew how to say it.
  • He knew where to go in the store to solve my problem.

The Art of Contextualization

Contextualization is the craft of particularizing an idea, a message, an offering, or a product. Like when Leslie Knope tried to introduce fluoride to the citizens of Pawnee. Often it can be accomplished by widening the lens to include the background. Other times it can happen by bringing a tighter lens to the situation.

Who needs to contextualize? Anyone who connects to another person for any consequential reason.

  • If you are in sales, it is crucial to nuance your pitch to the audience in front of you instead of just hitting repeat from the last pitch.
  • If you are a physician, I need you to hear about my problem and diagnose my particular symptoms, not simply assume my ailment is the same as your last patient’s ailment.
  • If you are a minister, you must realize that an audience in the Deep South is not the same as one on the west coast and certainly not the same as one in another country.
  • If you are a coach, each new season brings its own set of personalities and particulars. You must adjust accordingly.
  • If you are a teacher, you know that the most effective communication surely varies with learning style from student to student.

Many leaders seem to be born with a mature, well-honed contextualization muscle, while others have to work to develop it. If you want to explore an expert in the field, check out my friend Andy Crouch. He has been at this for some time, and is a master at the art of contextualization.

Contextualization in My Work

In my executive coaching practice I typically work with no more than 8-12 clients at any one time. Even within this small group, it is critical that I customize my coaching style to accommodate the learning style and wiring of each client as best I can.

  • Some guys like to be in a room with whiteboards and technology streaming all around.
  • Some guys are paper heavy and love the constant exchange of document iterations.
  • Some guys love to be outside taking walks or standing in a trout stream.
  • Some are verbal processors, while others only process when they are totally alone and away from the moment.
  • Some want the agenda ahead of time, while others couldn’t find the agenda no matter how many copies were given out and emails sent.
  • Some like to start with top-of-mind items, while others gravitate toward the details.
  • Some people are more comfortable than others sliding between personal and work issues.

The craft of contextualization increases connection and receptivity. It doesn’t mean automatic success, but it sure does improve the chances on almost every occasion. I still have to give the message, choose the offering, take the advice…or buy the cotter pin.

And by the way, the bike ride was fantastic.

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