Mandy Musings


a knife sitting on top of a table next to a keyboard
Photo by Dmitry Shkaev on Unsplash

One of the hats that I wore at a former employer was being the “dean” of the internship program. I was responsible for recruiting efforts, offers, and mentor training for the 12–20 interns that joined us each summer during my tenure. In doing so, I gained a lot of appreciation for how difficult it can be to avoid the Curse of Knowledge 1.

A huge part of ensuring a great experience for interns is setting clear expectations—especially when it comes to performance related questions like, “What do I need to do in order to get a full-time offer at the end of the summer?”

This led to an directive that I repeated often enough that I’m sure all of the mentors got sick of hearing it:

No intern should be surprised by whether you recommend them for a full-time offer at the end of the summer.

This might seem like an easy, obvious goal, but that’s where The Curse comes in: while a mentor may clearly understand their expectations for their intern, how can they know whether they’ve conveyed that understanding clearly?

It’s tricky.

Trouble brews

One summer day, I passed the Director of Engineering in the hallway, and he stopped me to say, “Hey, I just had coffee with Stephanie2. She’s motivated, and she wants a full-time offer, but she said she has no idea whether she’s on track for that. I thought you’d want to know.”

This is particularly bad: it means that even a positive result would—in some sense—be a surprise. Expectations were clearly not being communicated effectively; but how to fix it?

It occurred to me that if a single intern was willing to speak up about the lack of clarity, there might be others that were confused but not confident enough to say so. At the next mentor training session, I explained the situation, and I proposed an exercise for everyone in the group:

“At your next 1:1 with your mentee, I want you to have a discussion that starts with you asking the question, ‘What do you need to do in order to get a “hire” recommendation from me at the end of the summer?’ If you’ve been effectively communicating your expectations, then they should be able to answer without any hesitation.

“…And to make sure that we have the opportunity to learn from each other, post a message to our mentor channel after you’ve had this discussion. Let us know how your intern answered, and tell us whether you were surprised by anything in the conversation.”

Stephanie’s mentor Pete3 was the very first to check in: “I just had this discussion, and we’re both on the same page. No surprises.”

A happy ending?

Now, I don’t want to say that I didn’t trust Pete’s judgment…but I didn’t.

So the next time I stopped by Stephanie’s desk to chat4, I brought up the topic: “Hey, I heard that you’ve had some concerns about whether you’re on track to get a recommendation from Pete. How are you feeling about that now? Do you feel like you have more clarity than you did a week ago?”

Stephanie shifted in her seat uncomfortably: “No…not really.”

I looked around and saw Pete across the room, so I beckoned to him, “Can you join us for a couple minutes?”

When Pete joined our huddle, I turned to Stephanie and repeated the original question: “What do you need to get a ‘hire’ recommendation from Pete at the end of the summer?”

“I…uh…um…yeah…I’ve got nothing.”

I turned back to Pete: “How would you answer?”

“Well…she needs to work more independently!”

At this point, I was starting to get a clue as to what’s going on.

“Working independently” is a phrase that can sound completely different, depending on one’s background. To a senior engineer, it conveys a mélange of subtle skills: investigating the behavior of an unfamiliar module, effectively perusing and internalizing documentation, and even asking good questions asynchronously are activities that fit within this box.

But to an intern, it probably sounds like the lazy teacher in High School who would dedicate half of the class period every day for working silently on homework. Clear memories, perhaps, but probably not anything that would help one improve as an engineer.

In this case, the Curse of Knowledge cuts both ways: the senior engineer believes that they’re communicating clearly, and the intern thinks they understand what’s being said, so they don’t push deeper. But critically, the intern’s understanding isn’t attached to any specific skills to practice, so any memory of the conversation quickly vanishes. Poof.

I dug in further: “Working independently. Good! What are some specific behaviors that would demonstrate that Stephanie is working independently?”

“Well…I don’t know.”

“OK, that’s fine. What are some current behaviors that demonstrate that Stephanie is not working independently?”

“Oh! Sometimes, she’ll come and ask for help locating a piece of code, and I think she should have been able to find it on her own.”

We were finally getting somewhere: “So you’d like Stephanie to get better at Code Spelunking5?”

Pete: “Yeah!”

Stephanie: “Yeah!”

“Awesome! So right now, when Stephanie asks you one of these questions, how do you typically respond?”

“Well, I show her where the code is.”

“Okay…so…then you’re actively sabotaging her opportunities to develop this skill?”

Pete took a beat to think about it, and then: “Yes. Yes, I am.”

From this point, we were able to have a discussion about how to get out of this cycle. Stephanie left excited because she finally knew what she needed to do.

The final twist

But Pete wasn’t the only one who got tripped up by the Curse…

Because I had also failed to effectively convey my expectations.

I’ll be open: it felt good to swoop in and play the hero in that situation. And given the constraints at that point—particularly the length of the internship and how far into the summer we already were—I still think it was the right call.

But it shouldn’t have been necessary.

If I had interrogated Pete’s understanding of my instructions in the same way that I interrogated Stephanie’s understanding of Pete’s instructions, it’s quite possible that no further intervention would have been needed: Pete could have been empowered to discover the deficiency on his own—and done so in a way that improved the trust between him and Stephanie.

As it was, my solution to the problem was riddled with tradeoffs: Stephanie may have gotten what she needed at the moment, but it came with an implicit message that Pete couldn’t be trusted to provide useful feedback. Additionally, Pete remained baffled by the experience, and he still didn’t understand why his previous discussion had failed to land, which means that I still hadn’t conveyed the message that I was trying to get across.

Communication is just hard, sometimes.

Wow, you read to the end!

I guess this is the part where I’m supposed to sell you something, but I don’t have anything to sell. 🤷🏼‍♀️

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