Reclaiming Progress at a Dead End

At work, unexpected things will happen. You’ll be cruising along just fine when, all of a sudden, your plan hits a dead end. You have to go back to the drawing board and reassess your efforts. Some teammates may have to start over completely. And that deadline you all expected to hit… yeah, it’s just not going to happen.

So what do you do?

In moments like these, when things don’t go how we want them to, we get to tell ourselves one of two stories:

The first story focuses on the potential downside. This is called the threat story. It happens when you encounter a situation and tell yourself, this is really bad. Threat stories assume that unexpected deviations from the plan are generally negative and should be minimized. When you tell yourself a lot of threat stories, you develop a threat mindset.

The second story is the opportunity story, which focuses on the potential upside. Opportunity stories do not assume that unexpected deviations from the plan are necessarily bad. Instead, they recognize that detours are bound to occur and might actually end up being beneficial. When you tell yourself an opportunity story, it might sound like this: Well, that’s not what I hoped would happen, but maybe that’s okay. The initial plan wasn’t necessarily the best plan, it was just the first plan. And now I need a new one if I still want to get to the goal. Maybe if I try hard enough, I can turn this thing that seems like a setback into a good thing. When you tell yourself a lot of opportunity stories, you develop an opportunity mindset.

Lessonly board member Scott Dorsey has a way of keeping everyone around him opportunity-focused, no matter the height of the hurdle or the size of the setback.

Whenever one of Lessonly’s plans hits a dead end, Scott responds the exact same way: He rubs his hands together, signaling excitement, and asks, “Okay, what are our alternatives?” Then, he picks up a whiteboard marker and starts leading an exercise:

Step 1: We decide if the original goal is still the right goal. Once we’ve agreed on the goal, we formulate a list of alternative plans.

Step 2: We whittle the list down to our three best alternative plans and debate the pros and cons of each.

Step 3: We pick the best alternative plan and that becomes the new plan for hitting our goal.

Every time Scott takes us through this exercise, I feel my energy rebuilding. In the moment, he doesn’t waste time faulting us for our errors. He doesn’t shake his head like a disappointed dad or let us sulk in our sorrow. Instead, he focuses all of the room’s energy around reclaiming progress.

Days or weeks later, Scott might pull me or Conner (Lessonly’s COO) aside to suggest ways we could have avoided the dead end in the first place, but he is excellent about waiting until we’ve picked a new course of action to give this type of advice. Scott knows that I don’t want or need a lecture right after I make a mistake. Instead, I want and need someone who can help me regain momentum. When I’m back in a position of energy and excitement, I can better handle and benefit from Scott’s more critical feedback—so that’s when he gives it to me.

In my younger years, I speculated that people with an opportunity mindset were irrational and possibly even phony. I know better now. An opportunity mindset acknowledges reality, but does so in a way that replaces self-pity and fear with possibility and forward motion.

Here’s to more opportunity in our lives,


This is Max’s note—a weekly message from Lessonly’s CEO about learning, leadership, and doing Better Work. Sign up below to subscribe via email. No spam, we promise!

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