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Coaching Yourself: Career Coaching Personas for Everyday Engineers, Part Two - The Overoptimizer

Summary

This episode continues the series on self-coaching personas for engineers, focusing on the ‘overoptimizer’—a thought experiment where you imagine optimizing ruthlessly for a single goal, like a promotion. By temporarily setting aside other values and incentives, you can uncover hidden gaps or conflicts that might otherwise go unnoticed. For example, if you’d need to lie about performance metrics to get promoted, that reveals a gap between your current performance and expectations, which you can then address constructively.

The host emphasizes that this is not about abandoning your values, but about using extreme simplification to identify what truly matters. Once you spot the gap (e.g., needing better metrics), you can switch to the ‘available manager’ persona from the previous episode to figure out what support or changes you need from your manager to close that gap. This interplay between personas helps you move from vague frustration to actionable asks.

The overoptimizer persona also helps in understanding others’ behaviors. By asking ‘What might this person be optimizing for?’ you can build empathy and better collaboration. For instance, if a teammate is disengaging, considering whether they’re optimizing to avoid burnout or signaling frustration can guide how you approach them. However, the host cautions against relying solely on this analysis—direct conversation combined with this perspective yields the clearest picture.

Ultimately, the overoptimizer is a tool to simplify complex situations into workable models, helping you uncover blind spots in your own career and better align with colleagues’ motivations. It’s part of a broader toolkit for gaining clarity and purpose in your professional journey.

Recommendations

Community

  • Developer Tea Discord — A free Discord community where listeners can share experiences using coaching personas and discuss career development topics. Invited listeners to join at developertea.com/discord.

Tools

  • Wix Studio — A developer-first website builder that allows full-stack JavaScript integration, VS Code-based IDE or local development with GitHub, and AI-assisted coding. Mentioned as the episode’s sponsor.

Topic Timeline

  • 00:00:00 — Introduction to self-coaching personas — The host clarifies that these coaching personas are not meant to replace external feedback but to provide an additional perspective. They recap the ‘available manager’ persona from the previous episode, which involves preparing for manager conversations by identifying what your manager can realistically do for you. This sets the stage for today’s persona: the overoptimizer.
  • 00:04:07 — Introducing the overoptimizer persona — The host introduces the overoptimizer persona, explaining it’s a thought experiment, not a negative trait. You adopt this persona by asking: ‘If I was optimizing only for X, what would I do?’ This extreme simplification helps uncover hidden incentives and gaps. The example given is optimizing solely for a promotion—which might lead to considering lying about performance metrics.
  • 00:08:54 — Example: Optimizing for a promotion — The host walks through a concrete example: if you were optimizing only for a promotion, you might consider lying about performance metrics. This thought experiment isn’t about endorsing lying, but about revealing that those metrics matter for promotion. If you’d need to lie, it indicates a gap between your current performance and what’s expected. This insight lets you switch to the ‘available manager’ persona to address that gap.
  • 00:13:41 — Using the persona to understand others — The overoptimizer persona can also help understand other people’s behaviors. By observing someone’s actions and asking ‘What might they be optimizing for?’, you can build empathy and better collaboration. For example, if a teammate is disengaging, they might be optimizing to avoid burnout or signaling frustration. The host cautions that this is just one tool and should be combined with direct conversation.
  • 00:19:14 — Why understanding incentives matters — Understanding other people’s incentives is crucial for collaboration and management. It helps you align goals, prevent burnout, and create mutually beneficial situations. The overoptimizer persona simplifies complex human behavior into rough models, giving you a starting point to approximate reality. The host encourages listeners to try this technique and share experiences in the Developer Tea Discord community.

Episode Info

  • Podcast: Developer Tea
  • Author: Jonathan Cutrell
  • Category: Technology Business Careers Society & Culture
  • Published: 2024-11-12T08:00:00Z
  • Duration: 00:21:47

References

Podcast Info

Transcript

[00:00:00] In today’s episode, we’re continuing our discussion on self coaching.

[00:00:17] I want to be very clear.

[00:00:19] Uh, I do not believe that you can totally replace, uh, or that the advice that I’m

[00:00:28] giving in these episodes should lead you to think that you can totally

[00:00:33] replace the voice of an external coach.

[00:00:39] Now, an external coach doesn’t necessarily have to be someone who

[00:00:44] calls themselves a coach.

[00:00:46] So maybe the better way to think about this is, uh, that this, this episode

[00:00:51] is not proposing that you can guide yourself, uh, for your entire career

[00:00:59] without any external observation, any external feedback, I don’t think that

[00:01:04] that is a likely path to success.

[00:01:08] Okay.

[00:01:08] Uh, this, this is not intending to be, you know, your way of

[00:01:13] canceling your coaching membership.

[00:01:15] Um, that is not what we’re talking about doing here.

[00:01:19] Instead, you should think about this as another voice, an additional perspective.

[00:01:26] You’re providing yourself the opportunity to learn how to shift your own

[00:01:31] perspective into a different mindset.

[00:01:37] And so that’s what these coaching, uh, personas are in the last episode, we

[00:01:42] talked about the available manager.

[00:01:45] And the idea here was instead of going into your next one-on-one and trying to

[00:01:49] work out what you think your manager can help you with, or having them try to

[00:01:55] work it out, going in with an ambiguous goal and, uh, you know, talking through

[00:02:00] that problem and hopefully eventually getting to, okay, here’s my ask of you.

[00:02:06] Try to do that work ahead of time.

[00:02:08] Try to do that for yourself.

[00:02:10] Imagine that you are your manager and you want to know, how can I help this

[00:02:16] person within my boundaries of access and agency, what can I do for them?

[00:02:23] You know, if you do the pre-work here and you identify what your manager can do

[00:02:28] for you, what are their boundaries?

[00:02:29] What are their levels of agency?

[00:02:31] Where can they operate on your behalf?

[00:02:34] If you do that in advance, then you can have a much more productive

[00:02:38] conversation with your manager.

[00:02:41] Instead of spending, you know, 20, 25 minutes, uh, just working out your

[00:02:46] thoughts and feelings about the subject, which may be useful, uh, the, the

[00:02:51] perhaps more useful or more tactically useful approach might be to come with a

[00:02:57] more direct ask and providing the ask upfront, and then diving into the details

[00:03:03] with your manager, if it’s appropriate to do so, uh, why is this useful?

[00:03:07] Why is this persona useful for you?

[00:03:10] Because there’s very likely more conversations, more constructive

[00:03:14] conversations that you could have with your manager.

[00:03:17] Uh, and if you take the time to eliminate, uh, the back and forth, if

[00:03:23] you take the time to kind of pre-process some of this stuff, uh, then your manager

[00:03:28] will have the opportunity to move into potentially more valuable discussions.

[00:03:33] This is the first step, by the way, if you’ve ever wondered how do I ever get

[00:03:37] to the managing up part of my job, this is the first step towards that.

[00:03:43] Okay.

[00:03:44] Because managing up takes space, it takes time.

[00:03:48] And if you have this one-on-one time with your manager and you spend most of it

[00:03:52] talking about your own issues, then you don’t have the opportunity to discuss

[00:03:57] your manager’s issues and ways that they might be interacting with your other

[00:04:01] teammates or in skip levels with your own reports, for example.

[00:04:05] So in today’s episode, we’re going to talk about another one of these

[00:04:07] personas, the over-optimizer.

[00:04:12] And this might sound like a negative thing, but remember there is no

[00:04:15] negative, uh, when it comes to these personas, right?

[00:04:19] Uh, this isn’t real.

[00:04:20] It is a thought experiment.

[00:04:22] This coaching persona that you’re adopting is not actually you.

[00:04:26] It’s you playing a role.

[00:04:29] We talked about Domona’s hats in the last episode.

[00:04:31] If you missed that, I encourage you to go back and listen to it.

[00:04:34] That is kind of the, at least the application model that we’re

[00:04:37] using for these personas.

[00:04:38] You’re not actually going to act this way.

[00:04:41] You’re going to play this role in order to explore a subject, right?

[00:04:45] So the prompts you might give yourself when you’re sitting down to journal, or

[00:04:50] if you’re going to think through this on a walk, uh, the prompt you would give

[00:04:54] yourself is if I was X, what would I do?

[00:04:59] Right?

[00:04:59] So if I was my own manager and I had all the time in the world, what would

[00:05:05] I do that was covered in the last episode?

[00:05:07] In this episode, we’re covering the over-optimizer.

[00:05:10] The question you’re going to ask is if I was optimizing only for X, what would I do?

[00:05:19] As it turns out, this is a very valuable question to be able to explore both for

[00:05:24] yourself and in understanding the motivations of other people.

[00:05:29] We’ll talk about that right after we talk about today’s sponsor.

[00:05:41] Today’s episode is sponsored by Wix Studio.

[00:05:45] When I say website builder, if you’re like me, if you’ve been building, uh,

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[00:07:16] That’s W-I-X studio.com.

[00:07:20] Thanks again to Wix for sponsoring today’s episode of Developer Team.

[00:07:34] What would I do if I was optimizing only, only for X?

[00:07:43] This is the key question for the persona that we’re talking about today.

[00:07:49] What would I do if I was optimizing only for X?

[00:07:52] Now I want you to think about this.

[00:07:54] How do we understand our behaviors?

[00:07:58] How do we understand even our own behaviors?

[00:08:01] In most cases, behaviors are essentially described, uh, and this is, this is

[00:08:08] just basic behavior science, right?

[00:08:11] They are essentially described as incentives and disincentives, or they’re

[00:08:16] described by the incentives and the disincentives.

[00:08:18] In other words, we need a reason.

[00:08:20] We need a reason for doing what we do.

[00:08:23] Now there are multiple incentives and disincentives, uh, in any given situation.

[00:08:29] And, and those, uh, incentives, they tend to interact.

[00:08:33] And so our decision in a given moment is a balance across many different things.

[00:08:39] Usually we’re not just thinking, uh, in a single, uh, kind of singular

[00:08:44] way, uh, about a single incentive.

[00:08:47] Uh, this, this, uh, persona, however, will allow you to think in that single incentive.

[00:08:54] So for example, let’s imagine that your primary incentive is, uh, you want a promotion.

[00:09:01] That is the only thing you’re optimizing for.

[00:09:03] It’s your whole goal.

[00:09:04] It’s your whole purpose in life.

[00:09:07] Okay.

[00:09:07] So you would do anything that it takes to get that promotion.

[00:09:11] Perhaps you would even lie to get the promotion, right?

[00:09:15] Now this again, uh, understand that this is a thought experiment.

[00:09:19] We’re not suggesting that you go out and lie in order to get a promotion, but

[00:09:23] understand that the incentive, uh, to be truthful is not present in this thought

[00:09:29] experiment, right?

[00:09:30] The incentive, uh, to be honest is not here.

[00:09:35] And so if you wanted to get the promotion, you would lie in order to get the

[00:09:40] promotion because you don’t have an incentive to tell the truth.

[00:09:43] And you might be thinking, okay, well, I’m not going to do that.

[00:09:46] I’m not going to, you know, uh, set aside all of my values.

[00:09:49] For example, I have an incentive, uh, to maintain my values because it gives me a

[00:09:54] sense of identity and it gives me a sense of purpose in life.

[00:09:56] Uh, remember the goal of this podcast is to help you find clarity, perspective,

[00:10:00] and purpose in your career.

[00:10:02] So certainly I’m not telling you to set those things aside at all.

[00:10:06] Instead, try to imagine why, uh, the incentive that you’re optimizing for,

[00:10:12] why would you be led to lie?

[00:10:16] Or perhaps more tactically, what would you lie about?

[00:10:19] Perhaps there are certain numbers that you are trying to prove.

[00:10:23] You can reach, right?

[00:10:25] You want to have certain performance numbers or, you know, some kind of, uh,

[00:10:29] metric that you care about that, you know, your boss cares about.

[00:10:33] It may be the very first time that you’ve ever realized that those metrics

[00:10:39] being at a certain place would give you an upper hand in trying to seek a promotion.

[00:10:46] Think about this for a second.

[00:10:48] If you’re optimizing for the promotion, you might lie in order to get the promotion.

[00:10:53] What are you going to lie about?

[00:10:55] Well, you’re going to lie about your performance metrics.

[00:10:57] Why do you need to lie?

[00:10:59] Now, this is the interesting part.

[00:11:02] Okay.

[00:11:03] As you begin to understand, uh, this, this kind of perspective of how you can

[00:11:08] optimize for something, you can start to uncover gaps that may have

[00:11:12] otherwise gone unnoticed.

[00:11:16] You may need to lie about your performance information because you’re not performing

[00:11:21] up to the degree that your boss would require in order for you to get a promotion.

[00:11:26] So now you can revert back to the previous persona that we’ve talked about,

[00:11:31] the manager who has plenty of time to talk about that gap.

[00:11:36] Okay.

[00:11:36] What is it that’s causing that gap?

[00:11:39] Maybe you’re in too many meetings.

[00:11:41] Maybe you feel like the work that’s getting assigned to you, uh, you don’t really

[00:11:46] have the skillset that you need in order to complete that work.

[00:11:50] And so your real ask for your boss might be, can we consolidate some of the meetings

[00:11:56] so that I have the time to meet the performance expectations that you want me to meet?

[00:12:02] Or your ask might be, I really need to level up in these particular areas, or

[00:12:08] perhaps shift my focus to tasks that are in a different area that I do have expertise in.

[00:12:14] Which one of those do you think would be better?

[00:12:17] Now, if you notice, this is a conclusion that you’ve come to by way of two

[00:12:23] different personas interacting.

[00:12:25] Okay.

[00:12:25] The first persona is what are you optimizing for and ruthlessly optimizing

[00:12:31] for that going against your personal values even, and then backing out of that

[00:12:36] and wondering, okay, you know, if, if I needed to do that in order to get that

[00:12:41] thing, then what is the version of that, that retains my personal values that I’m

[00:12:48] willing to actually take a step towards in this case, we said you’re going to lie

[00:12:53] about some performance metrics.

[00:12:55] Well, instead of lying about those, why not try to improve those performance

[00:12:58] metrics, then you don’t have to lie, but you’re also meeting the gap that you

[00:13:03] need to, to both optimize for that outcome and retain your integrity.

[00:13:09] Once you’ve identified the gap, then you can revert back to, okay, now what do

[00:13:15] you need for me in order to make this happen?

[00:13:17] Your manager may have the agency, for example, to get you the training that

[00:13:22] you need or to talk to the relevant stakeholders to shift the meeting

[00:13:26] schedule around.

[00:13:27] They may have more sway than you do on that particular topic, but that may be

[00:13:32] the thing that’s holding you back from achieving the thing that you care about.

[00:13:37] Now, we mentioned that this could be an insightful persona to adopt, to

[00:13:41] understand other people, and it’s for basically the same reasons.

[00:13:46] Essentially, when you observe a behavior in a person, you may ask, why is that

[00:13:51] person doing that?

[00:13:52] Let’s say, for example, that you yourself are a manager and you’re trying to

[00:13:55] understand, why is this engineer that’s on my team who previously was engaged,

[00:14:02] why are they disengaging?

[00:14:03] What’s happening?

[00:14:04] So you’re going to participate in a variant of this optimizing the over

[00:14:10] optimizer or the ruthless optimizer.

[00:14:13] In this case, you’re putting on the hat of the person that you’re trying to

[00:14:17] understand their behavior and you’re using their behavior as the basis for

[00:14:25] this optimization.

[00:14:26] So I’m engaging in this behavior, this specific behavior in order to optimize

[00:14:31] for X.

[00:14:33] Now, notice this is very similar to what we remember, you know, balancing

[00:14:38] equations in algebra, right?

[00:14:41] Previously, we were looking at, okay, I want to optimize for X, therefore I

[00:14:45] need to do what, right?

[00:14:47] So I want to optimize for some outcome, like a promotion.

[00:14:51] So I need to do X.

[00:14:54] In this case, we’re looking at, I’m doing X, right?

[00:14:58] In this specific example, we’re saying that you’re withdrawing or you’re not

[00:15:02] participating as often in order to optimize for something optimized for, you

[00:15:08] know, insert variable here.

[00:15:10] Now I would caution you to remember what we said about the, the idea that

[00:15:14] incentives can mix, you get a multiple incentives in any given situation, just

[00:15:19] because you have one idea for why this person might be optimizing or, or what

[00:15:23] this person might be optimizing for doesn’t mean they don’t have multiple

[00:15:26] things going into that discussion.

[00:15:28] Uh, you know, multiple like, uh, inputs, incentives, inputs, but in the vast

[00:15:34] majority of cases, if you were able to come up with, let’s say three or four

[00:15:38] different reasons why this person may be behaving this way, uh, a lot of the

[00:15:44] time we have a primary motivation in our behavior.

[00:15:49] In other words, even though we may have some competing incentives, usually

[00:15:53] there is one that is overriding the rest.

[00:15:56] So let’s say, for example, in this case, you come to the conclusion that perhaps

[00:16:01] this person who is withdrawing, uh, and not engaging with the team as often,

[00:16:07] maybe they are trying to express a frustration, uh, but they’re also

[00:16:13] afraid of expressing it explicitly.

[00:16:16] So maybe they are withdrawing from, uh, participating with the team out of

[00:16:20] frustration or disgust or, or some other emotion, and they want to respond,

[00:16:26] um, because they disagree with the direction of the team they’re withdrawing

[00:16:30] in order to send them, uh, send some kind of signal, right?

[00:16:33] A social signal that they disapprove of what’s going on.

[00:16:37] So this might be a possible hypothesis that you use to understand

[00:16:41] another person’s behavior.

[00:16:42] But you may also, uh, have a hypothesis that this person is just burnt out.

[00:16:49] They’re tired.

[00:16:50] They have nothing particularly, uh, disagreement with what’s

[00:16:54] going on with the team.

[00:16:55] They’re burnt out because they’ve been working too many nights and weekends.

[00:16:58] So the important thing to understand here is try to understand the context,

[00:17:04] uh, that this, that you’re evaluating this stuff under the truth is most of

[00:17:08] the time, uh, there’s going to be too many options for you to nail down

[00:17:13] unequivocally why somebody might be acting this way.

[00:17:16] This is one tool, one tool that you can use, uh, to, to build your own

[00:17:23] empathy and trying to understand the reasoning, trying to understand where

[00:17:27] this person is coming from, you know, doing this without judgment, right?

[00:17:31] It don’t come into this with, um, you know, a priest, a presupposition of

[00:17:35] what you think this person is doing this thing for, you know, what, what

[00:17:39] their incentive is trying to prove that your incentive is right.

[00:17:42] Instead, try to view this, uh, through the lens of an objective observer, right?

[00:17:47] You’re, you’re trying to understand their behavior and the incentive that

[00:17:51] is leading them to that behavior or the disincentive that’s leading them to that

[00:17:54] behavior.

[00:17:55] Of course, this particular kind of, uh, you know, persona that you’re adopting,

[00:18:01] uh, this is mostly for your own coaching.

[00:18:04] Remember, we’re not talking about you trying to figure out the political

[00:18:08] landscape at your company necessarily.

[00:18:10] Instead, we’re talking about you trying to coach yourself so you know how to

[00:18:14] approach these conversations, uh, with your coworkers in the future.

[00:18:18] In almost every case though, uh, if you’re, if you’re sitting back and doing

[00:18:22] this silently over in the corner, you are much more likely to get better

[00:18:26] information by just talking to the people that you’re trying to evaluate,

[00:18:30] right?

[00:18:30] Trying to, trying to psychoanalyze somebody.

[00:18:33] Uh, nobody is going to be particularly great at that.

[00:18:37] Um, if you try to understand what people’s behaviors are and you talk to

[00:18:41] them, you’re likely to get a much better picture of reality.

[00:18:46] If you only talk to them and you take everything they say at face value, that

[00:18:49] is one kind of, uh, distorted reality.

[00:18:52] And if you only trust your intuition or you only trust your, you know, uh, kind

[00:18:57] of armchair psychoanalysis that we’re talking about doing here, um, then that’s

[00:19:02] another kind of distortion of reality, right?

[00:19:04] The more angles you can get on the situation, the more accuracy you can

[00:19:09] build, uh, in understanding that person’s motivations, understanding their incentives.

[00:19:14] Now you’re probably asking like, why, why do I need to know what other

[00:19:17] people’s incentives are?

[00:19:18] Why do I care about that?

[00:19:19] This seems a little bit invasive.

[00:19:22] And truth is understanding other people is a fundamental building block of a

[00:19:28] good career, whether you are managing that person and trying to get out ahead of,

[00:19:33] for example, burnout, maybe they don’t even realize, uh, that they are burnt out

[00:19:38] and you have to recognize the signs of burnout yourself, or if you’re just

[00:19:42] trying to collaborate with another person better and you want to understand,

[00:19:45] okay, what is this person trying to get out of this situation, right?

[00:19:48] What, how can I collaborate best with them so that it can make it a, a, a

[00:19:53] mutually beneficial situation?

[00:19:55] These are the reasons why you would want to understand other people’s incentives

[00:19:59] so you can figure out how you can align with them in meaningful ways that are

[00:20:04] productive for both of you.

[00:20:06] Ultimately, this persona, the overoptimizer persona allows you to

[00:20:11] simplify things into very gross models that have a lot of assumptions, uh, you

[00:20:18] know, kind of rough edge, rough edges to start to approximate a picture of reality.

[00:20:24] That is the goal of adopting this hat.

[00:20:27] I’m very interested to hear about your experience as you start using these

[00:20:31] different techniques and adopting these coaching personas, uh, in your personal

[00:20:36] reflection, if you want to share your stories, please consider joining the

[00:20:40] developer T discord community.

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[00:20:46] That’s developer t.com slash discord.

[00:20:49] Thanks again to today’s sponsor Wix your old bad memories of website builders.

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[00:20:56] Wix studios, developer first ecosystem allows you to spend less time on tedious

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[00:21:28] That’s w I X w I X studio.com wix studio.com.

[00:21:34] Thanks again to Wix for sponsoring today’s episode of developer team.

[00:21:38] Thanks so much for listening and until next time, enjoy your tea.

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