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On Noticing That Your Project Is Draining Your Soul

I was talking with a fellow consultant about what to do if you have a gig getting you down. Especially when you realize that the client isn't being helpful, and there's a bunch of learning curves that are exhausting you, and you still have several weeks to go.

In my master's in tech management coursework, I learned the lens that thriving is a function of a person times their environment. I think those of us who are used to trying harder, overcoming obstacles, etc. can be -- kind of out of self-protective instinct -- bad at noticing "this environment is so crappy it makes it systematically hard for me to achieve and thrive". Especially with short-term projects. At first, things like "I feel tired" or "ugh, new thing, I don't want to learn this and be bad at it (at first)" and "I'm worried that person doesn't like me" or "they missed the email/meeting/call and now it's harder to execute the plan" are identical to problems that we are reasonably sure we can overcome. Maybe we notice patterns about what's not working but think: I can take initiative to solve this, myself, or with my few allies.

Several papercraft pieces I made out of gold-colored wrapping paper, some alike and some differentThe data points accumulate and we chat with other people and, in the process, learn more data points and shape our data points into narratives and thus discover: this is a bad environment, structurally. But by the time we really figure out the effect a short-term project is having on us, it's supposedly the home stretch.

I'm looking back at gigs that I found draining, where, eventually, I had this realization, although I have never quite framed it this way before now. On some level I realized that I could not succeed by my own standard in these projects/workplaces, because there was so much arrayed against me (e.g., turf war, a generally low level of skill in modern engineering practices, lack of mission coherence, low urgency among stakeholders) that I could not do the things that it is kind of a basic expression of my professional self/competence to do.*

So I had to change what it was I aimed to achieve. For example, I've had a gig where I was running my head into the wall constantly trying to bring better practices to a project. I finally talked with an old hand at the organization and learned the institutional reasons this was practically impossible, why I would not be able to overcome the tectonic forces at play and get the deeper conflicts to resolve any faster. So we changed what I was trying to do. Running a daily standup meeting, by itself, is a thing I can do to bring value. I changed my expectations, and made mental notes about the pain points and the patterns, because I could not fix them right away, but I can use those experiences to give better advice to other people later.

An editor recently told me that, in growing as an editor, he'd needed to cultivate his sense of boredom. He needed to listen to that voice inside him that said this is boring me -- and isn't that funny? Parents and teachers tell us not to complain about being bored -- "only boring people are bored", or -- attributed to Sydney Wood -- An educated man is one who can entertain a new idea, another person, or himself. But pain is a signal, boredom is a signal, aversion and exhaustion are signals. Thriving is a function of a person times their environment.

Also, the other day I read "Living Fiction, Storybook Lives" (which has spoilers for Nicola Griffith's excellent novel Slow River).

How come I spent many years living a rather squalid existence... yet managed to find my way out, to the quite staid and respectable life I have now, when others in the same situation never escaped? In the course of writing the book, I found that the answer to my question was that the question itself was not valid: people are never in the same situation.

It takes substantial introspection and comparison to figure out: what kind of situation am I in, both externally and internally? Is it one where I will be able to move the needle? It gets easier over time, I think, and easier if I take vacations so I can have a fresh perspective when I come back, share my stories with others and listen to their stories, and practice mindfulness meditation so I am better at noticing things (including my own reactions). Maybe "wisdom" is what feels like the ability to X-ray a messy blobby thing and see the structures inside, see the joints that can bend and the bones that can't. In some ways, my own motivation and mindfulness are like that for me -- I need to recognize the full truth of the situation I'm in, internally and externally, to see what needs changing, to see how I might act.

The thing that gets me down most, on exhausting projects, is the meta-fear that nothing will improve, that I am stuck. When I realize that, I try to attend to that feeling of stuckness. Sometimes the answer is in the problem.

* As Alexandra Erin discusses, regarding her political commentary via Twitter threads: "I do the work I do on here because I feel called to it. For the non-religious, I mean: I have a knack for it and I find meaning in it."

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1 day ago
Melbourne, Australia
1 day ago
Mountain View, California
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Manager handoffs

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Y’all know how crucial I think one-on-one’s are for managers to get to know their direct reports: what they need from their manager, how they like feedback, what makes them grumpy, and so much more! But what happens when a person switches managers?

There are so many potential pitfalls when getting a new manager. Your new manager might not be familiar with all that you’ve done already, which could slow your career momentum. You can hope that your former manager and new manager did a handoff in which they shared lots of information like your goals, previous achievements, feedback you’ve received, and anything else that it’s helpful for a manager to know. But if they did have this handoff, it probably happened behind closed doors - you likely have no idea what was discussed, if everything was captured, and (the scariest bit) - whether or not the way your former manager represented things matches how you perceive the same things.

An Engineering Director at Etsy showed me a new way to do manager handoffs that combats these pitfalls: a 1:1:1 (“one to one to one”). A 1:1 is between you and your manager; a 1:1:1 includes both your former manager, AND your new manager, and is an opportunity to ensure your career momentum doesn’t experience that hiccup.

What’s the goal of a 1:1:1 manager handoff?

You, your previous manager, and your new manager meet in the same room or video call. Most of the talking happens between the managers, but there should be clear opportunities for you (the direct report) to jump in as you feel like it.

The goals are:

  • share relevant information from the previous manager to the new manager about the direct report,
  • do this transparently such that the direct report can get a good sense of whether there’s things unsaid or things that differ from their own perception, with an opportunity to disagree or clarify, and
  • reduce the natural career friction, pausing, or hiccups that happen when a person gets a new manager.

This is an opportunity to turn an otherwise lossy process into a much more thorough, supportive process for a direct report.

The agenda

Before this meeting happens, either manager should send out an invite stating expectations for the meeting, what each person should prepare for it, and what the goal is. Here’s an example:

Hey Other Manager and Direct Report! I’m booking an hour for us to do a ‘manager handoff’, with Direct Report sitting at the table, too!

Former Manager will cover:

  • Most recent review cycle feedback
  • More recent feedback, projects, and other info since the last review cycle
  • Direct Report’s goals, growth areas, things for New Manager to know

Direct Report, this will also be an opportunity for you to agree/disagree with how these things are described/characterized, and also an opportunity for you to have a complete picture of the info shared between Former Manager and New Manager. The goal is to make sure we’re transparent in the handoff of your career, how you want to grow, and the best ways New Manager can support you.

This stuff can naturally be very awkward for all involved :) This is okay (and normal!) - it’s awkwardness in service of clarity and fully supporting Direct Report’s career path, which can otherwise be muddled in manager changes.

I brought Etsy’s internal Charter of Mindful Communication over to Kickstarter Engineering when I joined. I usually reference that in the agenda, too, including reminders that each person in the meeting is responsible to do the following:

  • Consider power dynamics. They are pervasive and exist even if – and where – we wish they didn’t.
  • Meet transparency with responsibility.
  • Prepare to be surprised.

The 1:1:1

One of the managers should start by restating the goals (transparent handoff of career and manager info, an opportunity for the direct report to clarify and even disagree with what’s said, and reduced changes to the direct report’s career momentum).

After the restating of goals, the former manager should share their context directly to the new manager. Again, this is awkward, as the direct report is sitting right there, listening! But as much as possible, be transparent and honest (while mindful) as you share your context, history, feedback, goals, etc.

The new manager should feel free to ask questions as it happens naturally. Get clarification, aim for that shared understanding of history, goals, etc.

If the direct report is quiet, the new manager should be routinely asking them - how do you feel so far about what’s been said? Does this descrption match your experience? Are we missing something on that topic? Anything we should clarify? Anything you disagree with?

I’ve seen this be a super boring meeting where everything is clear and agreed with. I’ve seen this get sticky and uncomfortable when a direct report has an opposing viewpoint or different recollection. As necessary, acknowledge out loud that it’s okay if this is awkward. If it gets to a point where the dialog isn’t productive anymore, the new manager should talk with the direct report separately and privately about their experience. It’s totally natural that the former manager and direct report have different perceptions of the same events or feedback - we’re humans, which means this stuff is messy. Where it helps, restate those original meeting goals.

More often than not, even when things get uncomfortable, it’s still a really productive use of everyone’s time, and starts the new reporting relationship off on a much healthier foot. It’ll be quicker for the new manager and direct report to form a trusting relationship. And thanks to the shared understanding of events that the new manager had no prior firsthand experience with, hopefully nothing is changed about the timeline for the direct report’s future promotion process, trajectory towards goals, etc.

The follow-up

If the former manager was surprised that at the direct report’s perception of the same events, this is a great reminder to be continually checking in with one’s reports, gathering their feedback, and reducing surprise wherever possible.

If the direct report was surprised at how things were described by their former manager, this is also a nice reminder to routinely check in on how your manager is thinking and feeling about things, especially feedback they have for you. While ideally managers are giving routine feedback, your career path is truly your own responsibility; do the work to make sure you have a shared understanding with your manager about your path forward.

And lastly, where possible, make sure documentation of all this context (like previous reviews, lists of goals, etc.) are shared between folks and easily surfaced. I have an Evernote file with each person’s answers to those first 1:1 questions, which makes it super easy to share in the future with a new manager.

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5 days ago
Melbourne, Australia
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here’s a massive discount on the Ask a Manager job-searching bible

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how to get a jobLooking for a job?

For the next few days, I’m offering a discount on
my e-book, How to Get a Job: Secrets of a Hiring Manager. Use this discount code today for a massive 40% discount off the regular $24.95 price: newjob

If you’ve ever wished that you could look into the brain of a hiring manager to find out what you need to do to get hired, this is for you. Written from my perspective as a long-time hiring manager, this e-book gives you step-by-step guidance through every stage of your job search … explaining at each step what a hiring manager is thinking and what they want to see from you … from getting noticed initially, to nailing the interview, to navigating the tricky post-interview period, all the way through your offer.

You’ll learn things like:

  • what hiring managers are looking for when they ask common interview questions
  • how to talk about sensitive issues when you interview — firings, bad bosses, and more
  • how to avoid companies that aren’t a good fit
  • 6 ways you might be sabotaging your job search
  • 2 ways you can turn rejection to your advantage

Here are some things readers have said after purchasing it:

“Thanks to following Alison’s advice in this book, I’m about to start a new job in a stretch position. The director of HR kept complimenting my professionalism through the entire process, and really loved the questions I asked during my interviews. My new manager is so excited he was vibrating when I signed the offer last week. And partly due to selling myself well, and partly due to changing from clerical work to network administration, I have a 50% salary increase and room to grow.”

“Thanks to the tips, tricks, and advice in this book, I landed an incredible new job in a new-to-me industry doing something I love. I was also able to negotiate a great hiring package including a big jump in salary and benefits. I’m sure I would have found a decent job without this book, but I absolutely feel that I was able to find something incredible with it.”

“This morning my husband had an interview. I bugged him for over a week about reading your guide and he ignored me. Yesterday, I twisted his arm and finally got him to read it. He liked the advice so much he read it a second time. He really took it seriously and followed all of the advice you gave … He just called me to tell me the interview was done and that it had been the best interview he had ever had.”

“I used to have 50/50 luck getting past phone interviews and into the actual in-person interview. Once I read your book, I went 100% in getting past the phone interview, and I was ALWAYS in the top running for every position since then. I absolutely know it was because of your advice in the book. I could just feel the quality of my interviews go up exponentially after I read it.”

Get your copy with this 40% off discount code (newjob) now!

here’s a massive discount on the Ask a Manager job-searching bible was originally published by Alison Green on Ask a Manager.

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7 days ago
Melbourne, Australia
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“Dear Dana: After you break up with someone, how do you move on?”

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My friend Dana Norris writes a good companion piece to our plethora of “or you could break up?” posts here: “Dear Dana: After you break up with someone, how do you move on?

“Staying with the wrong person won’t make you happy, but leaving the wrong person also won’t make you happy. Leaving the wrong person doesn’t create happiness—it only creates space. And that space can be filled with any possible thing. At first it will be sadness and loneliness, then restlessness, and then, maybe, eventually, hopefully, a form of happiness. But at first, you take your slight daily misery of being with the wrong person and you ratchet it up so it becomes an acute daily misery of mourning a relationship that has ended.

In order to completely change your life, to leave the person you love and set out anew, you have to basically take a portion of your life and set it on fire. You have to metaphorically burn it down to prevent yourself from going back. Some people may be well-versed in the art of breaking up with a long-term partner and still staying friends, but I think only 10% of the population can pull that shit off. The rest of us light a match, throw it, and run.

Burning down your life sucks because you’re surrounded by ash and rubble and you’re also on fire. Because, you see, in burning down your old relationship, your old life, you’re really burning down yourself. You’re the one who’s on fire. Lots of profiles on dating sites and apps state strongly that they aren’t looking to date anyone who’s fresh out of a relationship. Why not? Because people fresh out of a relationship, especially fresh out of a long-term relationship, are kind of awful. They’re metaphorically aflame and can’t be any good to anyone until enough time passes that they can put the fire out. But, in the meantime, they walk around, burning, singeing everyone they try to kiss. They can’t be of any use to anyone until they calm down, accept their new single state, put out the fire, and allow for something new to grow.”

Read the whole piece for how to do the next steps, which Dana calls “1) Wallow 2) Fuck Around 3) Do The Damn Thing.”


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7 days ago
Melbourne, Australia
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#1019″ “I’m scared of spending money and everybody in my life pressures me not to.”

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Dear Captain Awkward,

I have a stable job, am financially independent, and have savings for a rainy day. Yet I have trouble when it comes spending money on myself, and I’m having increasingly emotional reactions to people who comment on how I spend money.

I feel guilty when I spend on necessities – if it’s stuff like health, or personal well-being, I can ignore the guilt. I’m fine when I buy presents for friends. However, the more these items fall into the “personal wants” category, the more agitated I get. But I want to! I want to pamper myself occasionally, or buy new jeans to replace my old ratty ones, etc. It’s my money, and I’m spending well within my means, logically that should be enough. Sometimes I go ahead and spend it… but then I start rethinking my decision and agonizing instead of just enjoying it. Other times, my mind just doesn’t stop overthinking whether I should be spending that money in the first place, and I just don’t spend it.

It doesn’t help that my parents are extremely thrifty. Their reactions to my purchases have always been along the lines of, “Oh, you got 3 shirts for $X? I could have gotten 5 for that same amount”; or, “How does this contribute to your personal development?” Some of my friends do this too. And though they are also financially secure, they might sometimes opt to buy movie tickets in person so they can save on internet booking fees, or choose to skip lunch to save the money. I have no issues with this, until I get roped into it – like if we end up missing the movie because they didn’t want to book seats early (and it’s insanely hard to reschedule due to our conflicting schedules), or if they naturally assume I’m skipping lunch with them – and when I speak up about it, they say something like, “Well I’d rather not spend that money, but we can do that if you want to”, which makes me feel like I’m making them spend that money just to assuage me. Or I’d be telling them about buying something for myself and they’d comment, “Wow, that’s expensive. Someone’s rich!”

I don’t know which came first – my problem with not-spending, or my unhappiness at such comments – but they keep bouncing off each other and it’s making me feel extremely confused and upset. They’re entitled to their opinions, yet I can’t fight how upset I get, which makes me feel unhappy about overreacting. I’ve started feeling like a horrible person for wanting the things I want, and feeling like I don’t deserve to spend on myself if I react poorly to such comments.

Am I silly for wanting them to lay off these comments? Is there any way I can stop having such extreme reactions? I’d greatly appreciate any advice you could give me. Thank you so much.

Best regards,
Scared of Spending

Dear Scared of Spending:

You’re not silly!

A thrifty and organized person like you probably already has a monthly and yearly budget, but if you don’t, it’s time to make one, and if you do, it’s time to add or beef up some categories in it, stuff like:

  • Clothing: For replacing old things and investing in new things. Also, alterations, mending, sewing on new buttons, fixing hems, dry-cleaning winter coats, etc. Make replacing your ratty jeans or getting something seasonal and snappy into planned expenses.
  • Fun: Include the cost of the occasional movie ticket AND the $1.50 convenience fee as you figure out the cost of 2 movies/month or whatever. Mentally adjust the ticket price up so that it’s the real total price of buying the ticket online in a way that is convenient for you.
  • Upkeep: Regular haircuts, personal grooming, etc.
  • Lunches: Whether you bring lunch from home most days and eat lunch out with friends sometimes, this assumption that you’ll somehow skip a meal (??!!!!??) is super not working for you. Put a set amount for lunches in the budget.
  • Giving/Charity: You probably already do this, too, but if you don’t, put a small amount toward giving money to a cause you believe in. You are fortunate right now, and this will feel really good to do. It will help you feel in control of your money.
  • Rainy Day Fund: You’re already building this. Keep going!
  • Short-Term and Long-Term Savings Goals: Retirement & emergencies, yes, but what else are you saving up for? A great trip? An educational opportunity? A house? Daydream a little bit.

Your budget doesn’t have to look like anyone else’s budget and you never have to show it or justify it to another living soul. Make a new one, and/or edit your existing one to add in some things that are important in your life. Track your actual expenses against your budget categories using whatever method works for you (paper notebook, keeping receipts, various apps). Schedule a few times a year where you tweak and adjust your budget based on changing goals and actual spending information.

Got your budget? Great. Here is your script for your friends and for yourself, now and forever:

“It’s in my budget.”

Scenario 1: 

Your friends: “We’re skipping lunch today, aren’t you? Who wants to spend all that money? or “We just assumed you’d be skipping lunch, too.”

You: “Why would you assume that? You do what you want! I’m hungry, and it’s in my budget.”

Then eat lunch if you want to eat lunch! Starving yourself to conform to friends’ ideas about thrift is not reasonable.

Scenario 2: 

Your friends, commenting (rudely) on a new purchase: “Whoa, someone’s rich!”

You: “What a weird thing to say. Anyway, it’s in my budget.”

(Or “Wow, someone’s rude!” or “Wow, it’s so weird to comment on another person’s spending like that, what’s that about?” or a gentle “Why would you say that to me?”)

Scenario 3: 

Your friends: “We’ll just get our ticket at the theater, we hate paying the $1.50 fee.”

You: “I’m going to get my ticket in advance. The fee is in my budget.”

Them: “Why would you pay such a useless fee?”

You: “I don’t love it, but I budget for it because it’s worth $1.50 to me to not have to spend the next three months planning another time we can all be together. Hopefully I’ll see you at the theater.”

It’s okay if they don’t want to pay the fee. It’s okay if you do. Express your own needs without judging theirs and hope they’ll do the same.

Scenario 4: 

You: :internally freaking out and feeling weird about a purchase:

Also you:Wait a second. I planned for this. It’s in my budget.

If it’s not in your budget, and you still want it, put it in your budget. Is it worth saving $5.00/week to have it someday? Is it worth trading off for something else you want? Only you can decide that.

Changing how you respond to these pressures may lead to an interesting conversation with some of your friends. “Don’t you think the way we talk about money is messed up? Where do you think that comes from?” Try some baby steps first and see who is responsive.

Now, let’s talk about your parents. You are a self-supporting adult and unless you are asking them to be reimbursed for some favor you did them, you never ever have to tell them what you paid for anything ever again.

Your current pattern: 

Parents: “New shirt? How much did you pay for that?”

Current You: “I got it on sale for only $10.00.”

Parents: “$10!!!! That much? I could have found it on sale for $3.00!”

Current You: Feels annoyed and ashamed even though you haven’t done anything wrong.

New pattern:

Parents: “New shirt? How much was it?”

Future You: “You like it? Thank you.” + [subject change]

See if you can get away without discussing price at all.

If they keep pushing, like, “No, seriously, how much was it?” you can say “It was on sale, but I don’t remember exactly how much.”

Yes, I am advising you to lie and say you don’t remember how much it was. You are trying to break a weird pattern of shame and blame and “kids these days!” and how much the shirt was is not actually important information to anyone, or anyone’s business but yours, ever. Don’t tell them the prices of things anymore.

You can also say “What a strange question, why do you want to know so badly?” or a very gentle “Ma, what are you really asking?” and put the awkwardness back on them. See what happens when you absolutely avoid giving them a number. One possible thing is that they will accuse you of paying too much/not being thrifty, like so:

Parents: “You probably paid too much!” (+ generalized grumbling because they sense a pattern is being broken)

AGREE WITH THEM. Don’t give them an argument. “I probably did pay too much, anyway, this soup is great is it Grandma’s recipe?” or “Maybe so! But you’ve taught me to never pay full price and to stick to my budget, so I feel good about it.” + subject change of your choosing.

Okay, let’s talk big picture for a second:

Competitive and performative thrift like this is a habit that’s often born in real deprivation and fight for survival. It’s cultural, it’s tied to class, it’s generational (meaning the attitude can be handed down in families even if the current generation is much more prosperous), it doesn’t happen overnight and it doesn’t go away overnight. It can be a way to turn a source of deprivation into a virtue in a culture that hates and shames and devalues poor people, like, I may be poor but look at how ingenious and wily I am to find these bargains! It can quickly get toxic when people yuck other people’s yum (the way your friends are doing, or the way every wedding planning community has the totes superior person who fed their guests only moonbeams and wove their dress themselves out of autumn leaves & recycled garbage bags) but it’s not coming out of nowhere.

It also speaks to what people value. Some people value getting the best deal above all else, where others are focused on the opportunity cost and the time involved. You value time with your friends and the ease of making plans with them more than you value that $1.50 for the movie ticket, and that’s an okay thing to value. Many times I’ve been in a grocery store with Mr. Awkward and he’s pointed out that potatoes are slightly cheaper at another grocery store and he’s 100% right about that but also we are not in that other grocery store and for the money & time it would take to go there we might as well buy these bourgeois potatoes? He’s trying to conserve money and I am trying to conserve spoons and both of these conservation attempts are rooted in us having lived very, very, very close to the bone where that extra $.30/lb or that extra hour on public transit to get to the cheapest potatoes adds up to misery and deprivation. Being poor is exhausting, mental illness is exhausting, and it’s hard to shake those stressed-out habits of mind even when circumstances get better and we can just buy the damn potatoes.

I say this to remind you to have compassion for your friends and your parents and also for yourself as you try to change the dynamic. Go slow. Be gentle, especially with yourself. You can’t control how your friends or your parents will talk or think about money, and you might keep getting rude or nosy or judgmental questions for long time while people adjust. Some people in your life might really resist your change in thinking and behavior around money, but others might find it liberating to not have the pressure of having to find the absolute cheapest (shirts/potatoes/movie tickets) hanging over them all the time. Finding a way to sustainably live in a way that’s true to your values, where you can have pleasure and financial freedom is a good and worthy project, and I wish you the best with it.

Thanks to Hannah & Matt of Hannah & Matt Know It All who chewed on this question with me on their podcast this week.

Moderation Note: Money talk brings up a lot of weird feelings, right? Probably people guessed this, but it bears saying that this is not the thread for sharing handy money-saving tips or extreme thrift brags or cheap life-hacks. This is one of those things like diets and food where a) do what works for you! b) don’t judge other people’s habits, and, d) there are entire websites that aren’t this one devoted to people sharing the intricate details of their personal programmes – if that appeals to you, go find one and have fun!




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12 days ago
He’s trying to conserve money and I am trying to conserve spoons and both of these conservation attempts are rooted in us having lived very, very, very close to the bone where that extra $.30/lb or that extra hour on public transit to get to the cheapest potatoes adds up to misery and deprivation.
Melbourne, Australia
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How do managers* get stuck?

*May also apply to senior ICs

Earlier this year, I wrote a piece called “How do Individual Contributors Get Stuck?” This was an attempt to help ICs provide constructive feedback to their peers, by identifying common challenges that I have seen developers struggle to overcome. 

This piece is a little bit different. I want to answer the question that I often hear from first-line managers, that is, managers who manage only individual contributors: “How do I get promoted to the next level of management? How do I prove I’m ready to manage managers?” 

Managers often believe that if they are handling the demands of managing their team, they should naturally be promoted to manage more people, bigger teams, teams of teams, as quickly as such an opportunity comes about. And yet, just as often as those opportunities come about, someone else is chosen, a person is hired from outside the company, and the eager manager is passed over. You’re stuck. When you find yourself “stuck” in terms of management career progression, what might really be happening?

Usually, getting stuck as a manager falls into one or more of the key areas of management: Failing to manage down, failing to manage sideways, and failing to manage up.

Scenario One: You aren’t actually scaling yourself effectively, aka, failing to manage down

You may think that you’re handling your team well, but when you look at your schedule, you’re working nights and weekends and then some to juggle all of the new tasks that managing a team entails. Sure, there are some companies which expect that from everyone, but it’s rarely a sign that you’re using your time effectively. Look at your team. Is it a well-oiled machine? Do you feel like the team is able to operate independently, get things done, without you micromanaging every detail? If not, you’re probably stuck on the basic needs of your current job. Some examples of this include:
  1. Can’t delegate. Look at all hands-on tasks you own, and ask yourself whether you are the only person who could be completing these tasks, or whether you could assign them to another senior engineer. If you are spending a lot of your time doing hands-on work that someone else could be doing, you probably aren’t delegating effectively.
  2. Not training your team. If there are too many tasks that only you can complete, you have made yourself a key dependency for your team. Who are your potential successors, and have you spent time training them on the things only you can do?
  3. Not enough attention to the process. Is your team drowning in alerts with no end in sight? Why haven’t you spent the time to allocate people to fix that? Have you spent time paying attention to the way work is assigned in your team? Do you actively participate in the planning process? When was the last time you tried changing it to see how it could improve? Process is part of your life now, and you need to tend to it.
  4. Won’t say no. If your team is completely overwhelmed with work, well, it’s partially your fault. You are the manager, and you are the person who is responsible for pushing back on the work commitments for the team. 

Scenario Two: You haven’t shown that you can expand beyond your team, aka, failing to manage up

Maybe your team is running well enough, but that’s all you’re doing. Opportunities for advancement are usually given to people who show up for those opportunities. You can easily get stuck by just getting comfortable in the place that you’re sitting. Someone who is failing to manage up often exhibits one of the following problems:
  1. Doesn’t attend to the details. Everything from clearly communicating the things that your team has accomplished, and sharing challenges or setbacks, to keeping your manager in the loop about major design decisions or roadmap changes, these details all matter. The best managers push information up without being asked and are quick to provide more details as necessary. Your manager wants to know that you are paying attention to what is going on.
  2. Complains a lot about things that are not working well, but never volunteers to fix them. If you are free with your criticism about the way things work, but don’t feel the need to do anything more than complain, you are holding yourself back. Instead of complaining, volunteer to lead the initiative to fix that team-wide problem. Bring problems and solutions.
  3. Drags her feet when given a clear task that is outside of her comfort zone. I have seen so many managers fail at the simple act of taking a clear assignment and seeing it through to completion. When your manager asks you to do something, either do it, or say you can’t/don’t really want to. But don’t just drag your feet and fail to do it.
  4. Doesn’t show a professional face to more senior managers. Do you openly look bored, distracted, or impatient in meetings? Do you write emails that communicate clearly? Do you think your manager would be comfortable having you present to her peers, alone? Your verbal, written, and body language communication is more and more important the more senior you become, and if you are lazy here it can hold you back.

Scenario Three: Fails to show peer leadership, aka, failing to manage sideways

Some people have well-running teams, they jump on fresh assignments, and yet they still get stuck. This is often due to the fact that your manager knows that she cannot put you as the manager to any of your existing peers. You are stuck because you haven’t shown enough peer/relationship management. This can sometimes look like:
  1. Doesn’t build strong peer relationships. If you spend most of your time focused downward or upward, you’re missing a step. When was the last time you helped out one of your peers? How often do you spend time with your peers, 1–1? Do you seek out feedback from your peers on your ideas, or ask them for help with your challenges? Having peers who trust and respect you, and more to the point, who might want to work for you if they had to, is needed for successful growth.
  2. Doesn’t look for additional tasks. You should be looking for opportunities to lead projects or initiatives outside of your team. How can you help your peers? You may be the best person to lead your area, but if you rarely push yourself outside of that area to talk to others and see places you could volunteer to improve, you’re missing a critical element of leadership.
  3. Doesn’t create a compelling vision or strategy that others want to buy into. You might have a clear roadmap for your team, but how much have you thought beyond your team? Have you ever shared any ideas you have for the larger group with your peers, and gotten their buy-in? Many people think that strategic thinking starts and stops with forming the strategy itself, but getting people around you excited by your ideas is critical to achieving them. 
  4. Doesn’t seem like someone a manager would want to report to. Ultimately, if you want to manage managers, a manager should want to work for you. That means that you are going to help train them, help them grow their career. You’re not going to be spending all of your time telling them exactly what to do, when to do it, no questions asked. If one of your peer line managers wouldn’t want to work for you, you might be stuck on giving the impression that you’re looking to progress solely so that you can acquire more power and influence.

What about senior ICs?

As you may have noticed, this advice applies to more than first-line managers. Many senior individual contributors start to trip on these issues. They can crank out code for days, but communicating, getting buy in, and going outside of their comfort zone stops their progression. Few senior ICs get promoted beyond a point on the strength of their ideas and code alone. 

Getting Unstuck

How do you get out of your rut? It starts by noticing where you are stuck. I noticed something that I’m not doing well just writing this list! Be honest, which of these are you really doing well at, and which are you failing? If you brought this list to your manager, what would they say? There’s only one real way to find out, so think about it, ask for feedback, and start to formulate your plan of attack for the things that are holding you back.
For more ideas, check out my book, The Manager’s Path, which addresses many of these stuck points!
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12 days ago
Melbourne, Australia
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