This is a transcript of episode 278 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.

Are “Try-Hards” slowing down your team? On this week’s episode, Jeffrey describes a type of person that shows up in a lot of organisations - someone who isn’t competent, but sounds like they are! Listen to find out about how you can spot (or self-identify) a “Try-Hard” by discounting their visibility and focussing only on their expertise.

Show links:

Listen to the episode on SoundCloud or Apple Podcasts.

Read the next episode in this series here.


Listen to this section at 00:11

Squirrel: Welcome back to Troubleshooting Agile. Hi there, Jeffrey.

Jeffrey: Hi, Squirrel.

Squirrel: So today’s topic is try-hards with an “S” at the end, which I think refers to some people. I’m really interested by what you meant because that was the term you were using: let’s talk more about try-hards and what to do about them.

Jeffrey: Yeah. So try-hards is like a bit of an internal jargon that I have and it comes from the experience I’ve had at many different companies about a certain type of person I tend to find, and I’ll tell you this, this came to mind recently because I read a blog article on called The Four Hobbies and Apparent Expertise, and it was that “apparent expertise” part that caught my attention in the article.

Squirrel: Link will be in the show notes of course.

Jeffrey: Of course. I came across this on Hacker News, it’s a discussion about how for any given hobby, there are people who are into the hobby and people who are into the gear, and people who are into actually doing the thing and people who are about discussing the thing. You end up with this kind of strange thing where the people who are most into doing the hobby have the most expertise on doing it, but they also have the least visibility in the community. The people with the most visibility are people who are into discussing the gear online. This is true for different hobbies, I think cycling or photography are classic examples, but he also makes links to programming and practitioners. This tension between expertise and visibility is really what brought to me traumatic memories of this try-hard type persona. This is someone who has made themselves very visible to management, often founders or executives, because they’re “really hard workers” and they’re always volunteering to do the dirty work. If there’s some project they’re stepping forward and willing to put in whatever time and effort it takes. But the challenge is in my experience, this type of person is defined both by that characteristic and also being not very good at their job.

Squirrel: Not a good combination.

Not a Good Combination

Listen to this section at 02:29

Jeffrey: Not a good combination. There’s nothing wrong with people who are maybe not very good at their job who could get better. But the problem is there’s two misjudgments going on here, which is both the manager or leader believing the person is an expert, and the person themselves believing they’re an expert. So there’s this miscalibration between their imagined ability and their actual ability. That’s this tension between visibility and expertise, where the people who actually are really good are over at their desk busy working and getting stuff done rather than being as visible to executives and managers and leaders.

Squirrel: And the people who aren’t very good but know it are busy learning from the people who are very good, and thereforethey’re not as challenging. Whereas this person, the try-hard is doing a lot, being very visible, looking for all the world like they’re really competent. But a practitioner actually knows this person doesn’t actually have the skill. Have I got it right?

Jeffrey: Exactly right. A manager who maybe is not as good at the work but knows it, they’re able to understand their limitations and they can be very good at delegating, very effective at bringing their team in, at listening and gaining advice, getting input from others who have more expertise, that can be really valuable. But that’s the tragedy. Here is someone who is not aware of their relative lack of competence, and it can be just very painful for the organization and especially for the people who are stuck reporting to them. So I thought that was worth talking about. “This model of this thing can happen.” And in particular, if you’re a leader, an executive, a founder or whatever, how do you make sure you’re not making this mistake? How do you make sure you’re not miscalibrated yourself or in regards to the people you’re putting trust into? I have something that we’ve talked about in the past: for me, the approach is around predictions.

Squirrel: Wait a minute. Who predicts something? Is it somebody outside the team who sets a deadline, or what do you mean by a prediction?

Jeffrey: No, no, it’s the idea of soliciting from the people doing the work what their predictions are of how long things will take or what they expect to have happen next.

Squirrel: Ah, there’s a trick here because this is going to distinguish these different groups. So the people who already know they’re not competent and are trying to learn will give a not very confident prediction. The people who are really competent will give a confident prediction and deliver on it. And our try-hards will give a confident prediction and not deliver on it.

Jeffrey: Exactly. You can get those three different groups and the people who are who know they’re not very good, they’ll probably say something like, “Well, I’ll need to talk to the team and get back to you.” Whereas the person who is the try-hard will say like, “Oh no, we can definitely get that done in three days”. And then when it takes three weeks, you realize there’s a miscalibration.

Incompetence Isn’t Malice

Listen to this section at 05:36

Squirrel: There we go. I want to insert something here just to make sure people don’t misunderstand. There’s a different group here that I don’t think you’re talking about—Jeffrey, tell me if I’m wrong—which is people who are malicious: they know they’re not very good and they’re playing corporate politics and trying to mislead other people into believing that they’re good. The try-hard is a person who has every positive intent in the world, who’s trying hard and working hard and probably eating a lot of pizza in the office late at night in order to get something done which they think is really important. So they’re really committed. They care. That’s actually worse because the corporate politician is a little easier to catch. They’re trying to fool you. They at least know. Whereas this person has fooled themselves and is giving all the signals of being really competent and super, but detecting them is hard. You’ve described a kind of filter that they can’t avoid and it’ll become evident to them as well, which I think will be very helpful for addressing the problem once you discover it.

Jeffrey: Yeah, absolutely. To me, the value of these predictions to me is as a learning cycle that can work for everyone. So this is not limited to detecting try-hards, this is generally a valuable thing, in part because not all the predictions will go according to plan and that’s okay. But we get to learn then. “What happened, what came up, what allowed us to succeed, and what then prevented us from succeeding?” We can learn on both sides. So really, this is about making predictions and then following up with a retrospective asking, “Well, how did things go according to predictions?” And that’s, I think, a good practice and can drive a lot of learning. And it also has the benefit here of detecting these people who can otherwise be be difficult to detect.

Squirrel: And helping them to detect themselves, because one of the worst things is to discover that you are a try-hard and to have believed that you were doing something competently for a long time and suddenly you discover otherwise. This happened to me at graduate school, for example. I thought I was absolutely wonderful at mathematics and no one could touch me. And I met some people who left me in the dust. I could hardly add compared to them, and that was a bit rude awakening for me. It would have been more helpful to come to that realization through learning about my own incompetence in a way like you’re describing.

Jeffrey: That’s a great point that I hadn’t considered, you’re right: if they can learn their own proper calibration, then that is a great benefit to them as well. So now what’s interesting to me is I shared this idea with you, but then you said that you had a different approach that you would use, and you used a phrase.

Picking Up Next Time

Listen to this section at 08:12

Squirrel: Even more strongly I said, “I don’t think about this.” This isn’t something that’s ever come up for me. And the reason is that I have a different way of solving this problem, which is more radical, may or may not be comfortable for everyone to try, but that’s a process called “marking to market.” You have a way of measuring the value of the software very, very frequently. But I notice we’re running low on time. Maybe we should pick that up next time. What do you think, Jeffrey?

Jeffrey: Yeah, I would love to come back and hear your full explanation of marking to market and how you go about it.

Squirrel: Excellent. Let’s do that.

Squirrel: See you then, Jeffrey, thanks.

Jeffrey: Thanks, Squirrel.