User Guide, Redux

A few years ago, I posted my User Guide. The concept of “User Guide” is pretty straightforward – what should people know about me so that they can engage with me most effectively in practice?

At the time, Modulate was still fairly young, and the User Guide format reflected that. I think I correctly described a lot of key facts about myself, but it was extremely abstract. “I’m this sort of person,” rather than concrete guidance about how you can get the most out of working with me.

In the years since, Modulate and I personally have matured, and I’ve gotten a much richer sense of the kinds of practical questions my colleagues are actually most likely to have when it comes to connecting with me. So I wanted to revisit the User Guide concept, but this time with a more concrete focus – answering something closer to what are the ‘recipes’ you should follow in various common but stressful situations so that we can reach the best outcomes together?

I really enjoyed writing this – I think, even more than the original User Guide, it emphasizes the ways in which I’m not just “generic manager A,” and really does provide some pretty actionable insights. It *also* probably comes across a shade arrogant – after all, there’s a bit of a sense here that you should be adapting to me, instead of vice versa. All I can say here is that I really do try to invest time and energy to align with your own preferred style (and would love to read your User Guide!), but that saying “don’t worry, I’ll figure out how to best interact with you” isn’t actually very actionable and assumes a level of perfection I’m not going to achieve. We’re both going to have to work to find the best ways to collaborate with each other; here’s the best guidance I can offer you, and I look forward to reading your guidance for me as well!


Mike’s User Guide 2.0

If you’re looking for my approval on an idea…

First and foremost, differentiate between whether you are asking for permission or seeking advice from a fellow practitioner.

If you are asking for permission, most of the time, don’t. You need my permission only in three scenarios:

  1. What you are about to do has a real chance of “crashing the car” in terms of Modulate’s public brand, trust with its employees, or financial stability.
  2. I’m your direct supervisor and have explicitly asked you to prioritize pursuing a goal (this is rare, I’ll more often suggest key directions and look to provide context so you can decide what best to work on), and you have reason to believe that goal is inadequate, foolish, or simply not as important as others you’d like to pursue, so you are intending to forgo working on the project I’d assigned.
  3. You are intending to take an action which violates the spirit or letter of one of Modulate’s formal policies (including staying aligned to our planned budget), and I am either your direct supervisor or the individual responsible for that section of our policy.

The above list also applies with respect to me giving “orders”. If you think I’m giving you an order outside the scope of those three bullet points, I’ve made a mistake and want you to call me on it. Most likely, this is a miscommunication, where I’m trying to offer advice but expressing it as an order instead. Occasionally, I slip further – I have strong opinions, and can occasionally find myself trapped in my own perspective. In these situations, I greatly appreciate being reminded that your project doesn’t meet any of the above criteria – and that therefore, while my advice is welcome, the ultimate right to decide the path forward is yours.

What if I think I genuinely know better than you? Well, I do my best to tag my advice in three forms – either an fyi (here’s something you may not have considered or known, do with it what you will), a suggestion (I thought about this for a few seconds and here’s my first idea, take it or leave it), or a recommendation (I’ve put serious thought into it and believe it’s the right path.) I’ll tell you if I’m offering a recommendation; to be blunt, I’ll do this most often when I expect that I’m, at that moment, more competent or knowledgeable in the specific area than you are yet. But even if I think I know best, if it’s your assignment, then you have the right to decide the path forward. Even if it turns out I’m right, you can’t learn and grow just from doing what I suggest unthinkingly, so the ultimate decision has to remain yours.

If you’re seeking advice from me as a fellow practitioner…

Start with the high-level goal – what was the original ambition or pain point you were trying to reach? Be specific and clear about the benefit for Modulate – saying “I want our sales process to shift to a new CRM”, “I want to change our website design”, or “I want to clean up the tech debt in this codebase” are all bad explanations, because they don’t truly answer why solving these problems will benefit us. In other words, they are tactical pursuits, not strategic goals. (Strategic goals might be “Our sales team is unable to reach more than 10 prospects per week and it’s crucial that we scale up to keep demand moving”, “We have data that 60% of our qualified leads are churning away on our website without contacting us”, or “This codebase keeps having bugs that lead to embarrassing and costly downtime for customers.” Notice that all of these are problem statements, not proposed solutions.)

Once I understand your goal, let me know if you’re interested in brainstorming or in workshopping an idea. Brainstorming is most useful when you’re still fairly early (though not too early – don’t let my ideas bias you into missing other approaches!) and haven’t yet committed to specific direction. If this is the approach you take, feel free to basically hand me the floor after you’ve explained your goal. I generally am pretty competent at breaking down how I think through frameworks and problems, so I should be able to pretty quickly explain the major ideas that come to my mind.

Workshopping an idea is more applicable when you have a general plan for how to move forward, and are looking for my perspective on the weakest links in the plan which might pose extra risk or require shoring up (and perhaps how to shore them up as well.) In this case, I confess I’ll require a bit more work from you. I hate statements like “this is generally good”, “this is how things are typically done”, or “I’ve seen this approach be successful elsewhere.” If you present to me a plan that sounds like it’s deriving from this kind of logic, I’m going to be picking at it all day. This isn’t necessarily because I don’t trust the logic – previous experience can be an extremely valuable teacher! But I personally trend extremely hard on the detail-oriented rather than intuitive side of the spectrum, and I cannot engage meaningfully with a plan unless I have a gears-level understanding of why, specifically, it’s expected to work and how it is going to achieve the goal you’re pursuing. Once I have that, though, I consider one of my greatest strengths to be my ability to pick out gears that are slightly misaligned, incorrect shapes, or otherwise not fully thought through.

If you think I’ve made a mistake or am doing something bad…

TELL ME!!!!!

I am probably one of the hardest people to offend you’ll ever meet. (Yes, I know lots of people claim this without meaning it. I can’t truly prove that I won’t get offended, but I do encourage you to ask others who’ve been working with me as they can validate this perspective!)

When you have feedback to share with me, I also personally prefer to receive it as quickly, frequently, and directly as possible. I personally tend to find praise and compliments quite frustrating – I appreciate the kind intent, but to me these tend to feel like a waste of time when I could be getting stuff done or learning how to do even better next time. So don’t be shy about cutting right to the chase even if that leads to rather blunt phrasing – “hey, that sucked, happy to chat more if you want more details” is greatly preferred over sugar-coating or stalling for time! Slack, email, or in-person are all fine, though I usually find Slack most efficient.

Once I’ve heard your feedback, I like to give it the attention it deserves – it’s important info that I want to incorporate, and that requires that I understand your perspective. Please don’t be surprised if I ask followup questions – I’m not trying to “weasel out of it” or hinting that I’m unhappy to receive the feedback, I just want to make sure that I have the clearest mental model of what you’re calling out so that I can take action on it! I may also be slow to respond to feedback in the middle of the day due to my desire to wait until I can give it my full attention; though I’ll do my best to shoot you a quick acknowledgement just flagging that I see it and am grateful for your support.

(One final note – just because you gave me feedback doesn’t necessarily mean I’ll be immediately successful in changing my behavior. Sometimes I’ll just be a bit slow in really digesting the lesson into my habits! In this case, please continue to call me on it – the repeated callouts are super valuable to help me get used to the change more quickly!)

If you haven’t achieve your assigned goals or know that you’re not going to…

Then own the mistake and learn from it. I don’t mind folks failing at their objectives sometimes – heck, if you’re never failing, then you’re not taking big enough risks and certainly aren’t learning and growing as fast as you should be! Failure is part of the process, not a condemnation of who you are as a person. But the flip side of that is that when you *do* fail, you need to acknowledge that without reservation.

In the end of the day, reality doesn’t grade on a curve – whether you succeed or fail at a given task, there are no bonus points for being clever, or dedicated, or patient, or anything else. If you failed at a task, I will not accept excuses of “I tried my best.” Nor “our assumptions were off,” nor even “if only you’d given me more support things could have gone differently.” The moment you accepted a responsibility, there are only two possible outcomes: you meet the objective, or you personally messed up somewhere.

You might have failed simply by not thinking the problem through correctly, or not applying the right lessons or skills. Your failure may stem from an unwillingness to ask for help, or from not communicating your need for help clearly enough. It might even be that the root of your failure was that you accepted the job in the first place, instead of having a more accurate understanding of your own limitations. Understanding the source of your failure is crucial in order to be able to grow – but before you can reap that reward, the first step you always have to take is in admitting that if you were better, you could have avoided that failure.

If you take this sort of responsibility, you’ll find me an extremely forgiving manager and leader. Again, all the best learning opportunities come from failures – taking risks that lead to occasional failures should and will be celebrated. But if you begin to handwave away your mistakes, change the goalposts halfway through to disguise that things aren’t going as planned, or insinuate that we should just be satisfied with subpar outcomes since you/we “tried our best”, you’ll find me substantially less understanding.

(By the way, you might be wondering how this meshes with “the buck stops here” kinds of thinking. The answer is that I believe my responsibility as a manager and as a leader is to set the right priorities, assign the right people to those responsibilities, and listen to those people and dutifully provide them the support they need to succeed. When Modulate isn’t meeting its goals, it’s always because I haven’t sufficiently followed through on that trio with the level of competence we need. But, if you’re not taking personal responsibility for accepting work you couldn’t complete or delivering inadequate results, know that I’ll be increasingly considering the possibility that I’ve assigned the wrong person to your job, and will need to find someone else.)

If you’re trying to gauge how I’m feeling about your performance or a specific project…

First of all, ask! I’m never shy about sharing my opinion. That said, it’s worth noting that I tend to skew very far on the side of constructive criticism, rather than praise or adulation. Where others truly enjoy hearing praise for their own work, I personally tend to find it somewhere between boring and frustrating – nothing is perfect, and I always tend to be more interested in new learnings rather than validation – and I have a habit of projecting that preference on others as well. Let me know if you’re feeling frustrated by my jumping straight to additional improvements or talking about the next work to do – I’ll do my best to adapt to your preferences here, and at minimum can certainly take some time to reiterate where you’ve been knocking it out of the park! Otherwise, if you have similar preferences to my own, trust that as long as my feedback is around next steps, then I’m feeling good about the work up till now; if I’m dissatisfied, I’ll let you know explicitly rather than just glossing past it.

If you’re seeking a promotion, compensation increase, or expansion in responsibilities…

One of the most common pieces of advice around these sorts of conversations is to open the chat by selling yourself – emphasizing everything great you’ve accomplished and how you clearly have earned the boon you’re seeking. I strongly suggest you defy this advice when chatting with me – I respond poorly to assertions about what’s deserved, even when it’s true. My reasoning here is twofold:

  • First, I find that most people’s assertions about what they deserve tend to relate more to their effort than to the actual outcomes they’ve achieved. (See “If you haven’t achieved your assigned goals…” above.)
  • Secondly and more importantly, deserving a boost is only half the equation. The other half is whether putting you in that broader position is actually beneficial to Modulate. You may “deserve” a pay boost, but at a time when Modulate need to keep the budget tight; or “deserve” to take on new responsibility by managing folks, but at a time before Modulate has any strategic need to build out the team you’d be managing.

The second most common piece of advice here is to treat it as a negotiation. The company is trying to get as much value out of you for as little as possible; you should be trying to get as much as possible from the company for the work you’re doing. Once again, I strongly recommend you take a different approach with me. Modulate makes explicit in a myriad of ways that we want to support our employees as people, not merely as work-generators, and part of that is that we – and I in particular – enter these conversations from a perspective of genuinely wanting to collaborate to find a good outcome for both of us, together. For that reason, when the other person enters the conversation while indicating that they assume we’re “out to get them”, acts in bad faith, or otherwise makes the discussion adversarial, I’ll be substantially less likely to agree to their asks – and it will hurt our relationship quite a bit to boot!

I want to be clear that this doesn’t mean you can’t have your own wants and desires. You certainly do want things, and I want you to be forthright about that. If you’re doing things right, then it will be in Modulate’s interest to pay you more (to retain you) and promote you further (to widen your sphere of impact.) But the trick is that this is a path to mutual success – both of us getting what we want in a win-win fashion.

Employees that fail to get the promotions or compensation boosts they are looking for often enter the conversation instead by making demands. Would you work for a company that demanded you do extra work without any consideration whatsoever for your circumstances? No? Then please don’t assert that I or Modulate must satisfy your demands without any consideration towards what we need, either. Telling me “I’m obviously great, look at all I’ve done, folks like me get paid twice my current salary at XYZ Corp, so I should obviously be paid more” is a great recipe for me to seriously consider letting you go, even if you are right about all the facts. Instead, come to me collaboratively – “Hey, I’m really excited about Modulate but am struggling to justify my compensation against my skill. I’ve gotten a sense that I could command a salary like ABC elsewhere, and, assuming you’re happy with my performance, it’s obviously in Modulate’s best interest to pay me enough to keep me from wanting to go elsewhere. Can we talk more about what I’m seeing on the market and the value you feel I’ve been delivering, to make sure we’re on the same page that Modulate is the right fit for my career?” Most of the time, we’ll be able to find a great outcome together – but even if Modulate can’t meet your needs, the collaborative approach ensures I’m excited to support your career even if you leave the company to do so; while the adversarial approach turns your work with Modulate into a transaction, and leaves me in the mindset to simply treat it as such.

So if you want to achieve these career objectives, here’s my actual recipe of what you should do:

  1. Tell me, as early as possible. “Mike, my goal is, by X time, to have Y compensation/role/responsibilities.” It’s that simple. A lot of people feel uncomfortable talking about this – especially when it comes to money – but it’s a heck of a lot more comfortable to discuss together how we can do what you want than to be blindsided by it later and have things turn into an adversarial discussion.
  2. Next, instead of trying to convince me you deserve it, ask me, point-blank, what someone would need to do/achieve/be capable of in order for me to be happy to grant them the boon we’re discussing. (Of course, I’m interested in hearing your perspective on this point as well, especially where you might have important on-the-ground understanding of what’s needed beyond what I’m aware of!)
  3. Together with me, write down the goalposts we’ve agreed on.
  4. Over time, those goalposts might evolve. That’s not because I’m trying to screw you over – it’s because Modulate is a complex, rapidly evolving organization, and its needs may legitimately change over time. I know this can be frustrating or disappointing, and while I can’t promise it won’t happen, I do consider it my responsibility to flag if this happens ASAP so that we have as much time as possible to work together to course-correct. That said, if you want to be certain you’re on the right track, I strongly recommend…
  5. Regularly (monthly 1:1s are great for this) checking in with me. Don’t jump right into asking how you’re doing against the goalposts. First ask the much more important question – Mike, do you still feel fantastic about giving someone who meets these goalposts the boon we discussed? As mentioned above, it is possible my answer will be no, so it’s crucial we get on the same page there first – and only after, dive into discussing how you’re doing.
  6. Finally, at some point you’ll hit the goalposts, and you’ll get the promotion. At this point it shouldn’t be remotely a surprise to either of us. If it is, it means at least one of us – and probably both! – messed up during an earlier step.

In general, when interacting with me, you should know…

  • I will be just as quick to share feedback with you as I hope you are to share it with me. I’m well aware that the CEO carries a bit of a force-field – “the CEO is telling me this wasn’t good” often gets interpreted as “oh god the CEO thinks I’m terrible I’m going to be fired!” I don’t have any great solution to this problem except to say that I’ll tell you what I really think; if your job is in trouble I’ll let you know; and hopefully as you get more feedback from me (and others at Modulate!) more quickly, you’ll come to internalize that it’s meant as part of your growth trajectory, not as a statement that you’re necessarily not meeting the bar.
  • I hate that I’m so busy, but I am. When we started Modulate, I had a vision of responding to every single email that was sent to me or our general contact page. I probably responded to thousands of random emails before Modulate truly began growing and I started realizing that, much as I wanted to be polite to these folks, I simply didn’t have the time. I’ve worked to internalize that lesson, and am still developing my time-management skills given how many competing pulls on my time there are. So please don’t take offense if I cut you off during a long description or jump in to reorient a meeting. I’d love to get all the details and hear your full perspective, but sometimes I need to prioritize making sure my time is going to the best available cause. (That said, if I do this in a way that takes the discussion down a different road than you’d intended, please call me on it! It’s possible I had a different impression about the point of the meeting, and am accidentally usurping something that’s important to others.)
  • I’m a big believer in in-person culture. Despite Modulate’s focus on the metaverse, it’s just not possible to get the same kind of empathy, connection, and especially learning-through-osmosis and general vibes, through virtual connections yet. Of course, I’ll always do my best to engage with remote folks fully and authentically – but folks in the office will likely find unstructured opportunities to pick my brain or simply socialize a lot more flexibly.
  • I love whiteboards. Can’t think properly without ‘em. Another reason I prefer in-person, especially for complicated discussions.
  • I live out of my calendar. If you want me at a meeting, get me a calendar invite (and make sure I accept – if I don’t accept the invite, I’m not going to be showing up.) Feel free to follow up with me to make sure I spot the invite (though I’m generally pretty good at this). Similarly, if you want to chat in an unstructured way, I’m happy to do so – but you’d better be flexible to have me grab you whenever I happen to get free, without much warning. Otherwise you’re best off scheduling time, which I’m always happy to do!
  • I suck at lots of things. I have a habit of multitasking during conversations and am not good enough at it, so occasionally lose track of what someone’s saying – please do yell at me if I do this, it’s super bad! I’m not especially skilled at jumping into already-ongoing conversations at conferences or networking events (though I think I’m a pretty strong conversationalist once I’ve been welcomed in.) I have a love of data-driven decision-making that sometimes causes me to grab for not-quite-relevant-but-sort-of-similar data, which can slow my decision making or bog me down in ways that might not be obvious without seeing the data for yourself. I’m okay at avoiding putting my foot in my mouth, but I overall lack much social intuition – once I’ve left a group, I’m actually quite good at analyzing retroactively the real intent behind their actions, what the balance of power was, etc; but in-the-moment, I tend not to be very good at noticing those cues and adapting on the fly. Whenever I’m asked to explain anything remotely nuanced, I end up generating pages and pages of written content regardless of any requests for brevity. (I’ve got plenty more too, but you get the idea.) I don’t expect to ever be perfect, so sometimes I may decide that improving on one of these weaknesses isn’t worth the energy cost – but I’ll never, ever begrudge you pointing it out or offering ideas on how to improve!
  • But I also have my strengths. For one, I’m an extremely precise thinker, which is a skill I’ve been able to leverage through mathematics, physics, and software development as well as more recent focuses like business strategy, finance, and even law. I also come from a family of teachers and consider myself quite strong at the skill – in general, if I understand something, I’m pretty darn confident I can help you understand it too, and tend to enjoy doing so. I’m also extremely passionate about understanding thinking itself and “how to be wise” (to the point of giving some culture talks on the subject) – if you’ve never ventured into fields like cognitive psych, behavioral economics, or probability theory, I can probably offer some pretty helpful perspective on how to think more efficiently. And finally, I have a burning passion for personal growth. I’m never content with my own skills and capabilities; and am generally game to learn pretty much anything that you might happen to be knowledgeable and passionate about.

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