Artisanal Concatenations of Sentient Emanations

I said I was going to write about previously this because I think it is important. I also think that this is one of those things you really need to learn how to do well and how to talk about it properly. I am very sure that one time, about five years ago, I cost myself a chance at a director job when I was in a room with three potential direct reports talking about how to teach people to fire other people. I may have sounded a little too enthusiastic to people who I may have been about to inherit as a team. Unfortunately, that’s usually how I talk about most things.

To start with, let’s talk about what this is not. This is not a substitute for the checklists your HR manager gives you. This is not a primer on labor law in your state of residence or employment. Finally, this is not something that is trivial or should be done lightly.

When I am interviewing a manager, or giving someone a battlefield promotion, I generally ask the question “Have you ever had to fire anyone before?” It is not surprising that not many people have, and for the people that have, most of them remember the first person they fired. Usually because it is something that happened swiftly and brutally, and often it is a moment that people feel they could have handled better. Some of them have shared horrible stories about it. Sometimes it is at a small enough company that there are improper HR practices in place and lawyers get involved.

If they have not had to fire anyone, then I want to make sure they understand how important it is and why it is important to do it right. I do point out explicitly that they will have a high likelihood of having to do this in their chosen profession, and it is worth getting to the point that it can be done compassionately, cleanly, and professionally. I have had to fire good people before and I have had to fire people who are great personal friends. I have been blessed that they still remain that way and sometimes I have brought them successfully into new roles elsewhere. I have given great professional references for people I have had to fire and also been happy to see when they have career successes. It is worth talking about that with folks and make sure they realize it is not personal.

Now that the stage has been set, hopefully you have a few years between this conversation and the next one when there is a person who is not meeting expectations.

It is a good idea to let your managers do most of the hands-on work themselves but at the same time you should offer to be present or offer to help as much as they want you to. From the meeting where they sit down and explain where the issues are, to the written statement of what needs to improve and the window that they have to make that improvement, this is something that a manager needs to do. Maybe they want you in the room to listen, or maybe they want you to ghost-write the written warning. Be available but not overbearing. This is a human conflict situation which some people do not like, and it is nice to have support.

Do not push a first-time manager to fire someone. You should explain to them why a role adjustment may be good in some cases and may not be good in other cases. They should realize that they have to fire the individual in question and be okay with it. If they disagree, it is worth resolving that between the two of you. The last thing you want to do is just remember that this needs to happen while you are running between meetings and you fire off an email saying “you need to fire that person ASAP”. That is a pretty poor way to push something so delicate to completion.

Now that there is consensus, you should give them some coaching on how to go through “the script”, when to hand it off to HR (if you have HR), and when to bring the meeting to a close. I have sat in on some of the final termination meetings with people (at the request of the manager) and it is better to say as little as possible, but I would advise adding a hand gesture or phrase to indicate that it is time to wrap up the meeting. I have observed that while you want to be compassionate for the employee in question, it is important that this does not turn into a negotiation. If it has gotten to the point where this meeting needs to happen, it should be pretty final, generally they have had warnings and time (up to a month) to make any adjustments needed, or have done something so egregious that it necessitates a rapid removal from the building.

I also advise people not to do this on a friday. I am now at the point where I prefer not to give people strong negative feedback on fridays. It sucks to go into the weekend with a heavy negative emotional load from your job. If there is no need for urgency (material danger, or risk of something happening on live operations), it is always better if you can move this conversation from a Friday to a Monday. You do not know the battles people are fighting, and I have started to land on the side of compassion and decency where possible.

There is probably a lot more to say here but we would be moving into the realm of “work with your HR partners”. This is their specialty and you should work with them on the particulars.

That being said, when you are giving a battlefield promotion to that hard-working, bright-eyed, ambitious, first-time manager, please sit them down and explain that this is among their responsibilities. Tell them some of the lessons you have learned from doing this during your career. Give them some guidance on how to do it cleanly, professionally and, most importantly, with some compassion.

If you have any tips on how to help people come to grips with this most delicate part of management, please share them!

At some point or another you are going to hit a professional wall. Either a wall of ability or a wall of compensation.

Maybe you developed an itch for pricey scotch or want to golf more often. Maybe you want to get a yacht, or have kids, or become a homeowner.

Maybe you are sitting at work with big ideas and you look down at your fingers and wish “gosh if only I had ten times as many of these!” as you do your job. Maybe someone in your firm got a pay raise, a fancier desk, and a new title of “Senior Director of Not Working Here Anymore”.

Maybe none of this happened but you just want to know what it is like to manage people.

This is a tough subject because when I get asked questions, the odd time I go and talk to people about career choices, people ask me “Do you prefer to manage or do you prefer to get your hands dirty?” and honestly, I fail this question so hard. I even start off my response to people by saying “This is a great question, and I fail at it so hard”.

I don’t have a preference between rank and file individual contributor work and managing. That causes eyebrows to be raised. Sometimes people nod quietly. Sometimes they are mentally deconstructing what kind of monster I am. Sometimes they are trying to figure out how to get me out of the building as fast as possible because some latent insecurity told them that is my way of saying “I AM COMING FOR YOUR JOB NEXT.”

I don’t know. This isn’t about me. Maybe it is, in some strange way. But I want to somehow make this about you.

At some point in your career, whether by magic eight ball or by need to get paid or by random circumstance, you are going to get an opportunity to manage people.

Regardless of whether you want to or not I think you should try a management role. You should do it once, and you should do one very important thing that most people do not do. You should make sure there is an escape plan. The worst thing that can happen to a company is you get promoted into a managerial role and then you leave because you did not like it.

When adjusting their compensation to the new role, I tend to have it built in as something they get to keep, and I make sure that we set a clear expectation to everyone that this is a new role and may not be permanent.

You want to make sure that everyone is supportive and that the person trying out this new role understands they can go back if it does not work out.

That is nearly impossible to accomplish by the way but it is totally worth it if you can. You want to have people understand that this is a risk,that there are rewards for taking risks, and that there is mutual trust here.

I have put people into management roles and had them ask to sunset their managerial responsibilities.

I have inherited people in management roles who needed to return to individual contributor work and had to slowly work with them to make the necessary adjustments to get there.

Regretfully, sometimes, I have done so without being so gentle.

Regardless, there is a lot to learn in becoming a manager and you should invest some time in what you need to know and what you need to do.

You need to understand that one of your primary roles is to make sure other people get their work done. You have to avoid being the heroic firefighter manager who jumps in at the eleventh hour because you know you can do it. Nothing will destroy your team and your individual contributors faster than being a better performer. Even if it is true, you are showing that you are not suitable for being a manager if you cannot enable people to do their jobs better.

Another thing you need to understand is how to communicate with people. I have done a number of things where they went super badly because I framed them poorly. Thankfully it is not a large number. Positive communication is vital to keeping people moving forward and being proactive. If you don’t know what a shit sandwich is, now is a good time to learn. Google has your back.

Finally you need to be able to understand that you have to take the beating for other people’s failures and reward them for their successes.

I have seen too many managers whom I refer to as cannibals. They take credit for their team’s work. They devour their teams. It is horrible to be in that situation soI look for managers who are cannibals and try to stay away from them as much as possible.

A good way to test yourself for management potential is to get involved as a youth sports coach. Soccer, basketball, baseball, softball, etc.. There are lots of great sports out there. You will learn more about managing people from a group of 10-year-olds than your average online MBA program and you probably get a free gift card to Starbucks at the end of the season if your team parents don’t completely hate you by the end of the season (hint: You should try to win *ONE* game).

I am pretty far into this article and I have not said half of the stuff I want to yet. Not even a third, actually. I am not going to be able to tell you everything you need to know or everything you need to do in your first-time management job in the space of one online article.

I sure would like to though. I did assemble a playbook of things I do for a first-time manager and I will do my best to share these in future articles and give them each a thorough treatment. From communication, to trusting your team, to how to make team adjustments with compassion.

And when I say adjustments I mean firing people. That is probably what I will talk about next actually. I find it odd that most people do not get some sort of formal training on how to fire people. It is a hard thing to do and it takes work and effort to do it with grace and class. More on that later.

I would love to hear some of your stories about things you did as a first time manager, good or bad!

One of the first things I realized I needed to learn in my career was how to deal with meetings. How to avoid the unimportant ones, how to survive the mandatory ones, and how to not blow up the important ones. Let’s face it, meetings are both really valuable and really horrible. I have had times when I have been sitting in meetings waiting to make a valuable contribution to the enrichment of everyone, and times when I have been furiously doodling in the corner hoping that the fire alarm goes off. Probably the worst meetings I have ever been at have been on projects that have multiple businesses involved and I am aware that there is at least one person at that meeting whose purpose is to destroy the meeting, or even the project, because they have some money or equity sitting in a vendor company that they would love to bring in to replace the company you work for. Let me tell you, spending forty-five to sixty minutes staring at that person is not a great use of time, mentally or emotionally, but I have been there. Sadly, you may be there someday too.

So what the hell are meetings all about? Let’s see if we can break it down without filling a buzzword bingo card.

A meeting is a group of two or more people to either distribute information to increase shared understanding or to establish a plan of action. I think there are subtle nuances in there (achieving consensus on an action plan, daily metrics review, etc) but fundamentally you are attending a meeting to convey your knowledge to one or more other people, create a set of actions by a group of two or more people, or to learn something.

I use this filter for myself frequently. I really don’t like attending meetings because not enough people understand the point of the meeting they are in or don’t understand meetings in general.

So how do you know what you are supposed to do in a meeting? No one I know has a degree in meeting-ology. I don’t even think there was a 101 class in my university that talked about professional meetings. There are almost zero pages in the employee handbook for the first time employee on what to do in a meeting. And everyone has that moment when someone comes into their office/cubicle/shared-work-table-quadrant and says “Hey we are having a meeting and you should come with us” for the very first time.

Truthfully, at that moment you should squeeze your eyes shut, cover your ears, and yell “NOOOOOOOOOOO!” as loud as you can. It is good practice for the road ahead. You probably should not go to this meeting, but you will, and it will help to reinforce one of the first bad habits of professionals—just attending meetings for the sake of attending them. The sooner you cure yourself of this affliction the better off you will be.

When you are invited to a meeting you should try to understand a few things:

1. What is this meeting about?
2. Who is at this meeting?
3. Why am I at this meeting?
4. What is the intended takeaway from the meeting?

If you do not have good answers to these, you should decline the invitation. This serves two purposes: First, it will protect your sanity. Trust me on this. It will. Second, if someone thinks you should be at this meeting, then they will invite you again and then the onus is on them to come up with the answers above.

These are loose guiding principles and there should be some caveats. I hope I don’t get an angry email someday from someone saying “I have a deadline and I missed going to an all-hands meeting where everyone got a leather jacket as some sort of perk for a milestone because YOU said I should avoid all meetings!”

First of all, sorry about the jacket in advance. If that was what you took away from this article, you are doing it wrong. That is okay—many people are. All-hands meetings and staff meetings are very important, and maybe not directly for your day to day tasks, but they serve the organization in disseminating information and increasing employee engagement. Sorry for the buzzwords. Those random social gatherings and quarterly status meetings from the CEO serve a purpose and it may not be readily apparent to you early in your career. If the organization in question uses these tools effectively, they are awesome. They should be used deliberately and judiciously in order to benefit the organization and its people.

As an individual contributor early in my career I was very oblivious to meetings and their purpose. I would sit in a room irritated that I am not coding. I honestly completely missed the point. I transitioned into a role in a sales organization and it wasn’t until I was told by my boss at the time “Hey you need to stop looking so bored in our meetings” that I really began to think about it. We would be out meeting pre-sales companies and I was gathering data on what we should be doing to close the deal. Apparently I looked horribly disinterested and if the prospect meeting we were at was someone who had some degree of insecurity, then the presence of the disdainful techie was counterproductive to getting their business. I think that is the first time I realized that I had to start modifying my behavior in meetings.

Okay so what do we get out of all of this? Meetings are important. Meetings are also horribly broken. No one teaches you how to behave in a meeting and it is hard to figure out what meetings you should be going to. I got involved in student government in university and also participated in youth athletics as a parent coach. Both of these are valuable tools if you can take advantage of them in learning how to behave in a group and what types of structures are good (or bad) for a group of people.

Part of the reason I am writing these articles is to atone for professional sins of the past but also to hopefully help people develop tools for their own future.

I think that being able to participate effectively in a meeting is important. Unfortunately nobody really teaches it as a valuable skill.

I would love to hear your thoughts on the best things and the worst things about meetings!

Joining a new organization as a leader is hard. I have done this repeatedly throughout my career and I take great care in getting settled in and making sure I fully understand things before starting to make changes. One of the reasons I write these articles is so people can get a chance to see things from a different perspective to help them grow professionally. Today I want to talk from a different perspective about joining an organization as a leader. I want to talk about what to do when you have to hire your own boss.

I know that sounds a bit strange at first, but it is not. It is pretty common that teams need to develop new leadership and sometimes the existing people in the team do not have the skillset, the experience, or the mindset to fill a leadership role internally.

Some companies try to give battlefield promotions to fill the gaps which tends to work out in the long term but generally has a pretty bumpy short term period where a new leader makes some unfortunate mistakes. I know this because I have gone through a few battlefield promotions and have made some of those mistakes.

For a variety of reasons, other companies are not comfortable with that approach and choose to look outside to recruit new managers, directors, and executives. Today we are going to talk about what that means if this is happening at your company, and the manager, director, or executive in question is going to be directly above you.

The first time this happened to me was very unpleasant. I found out in a company meeting that the person I was interviewing to be my peer was going to be my manager. I can assure you this is the worst possible way to discover you have a new boss. I was gone within a year, and if this happens to you, I would wager you would find your trust in your employer so sufficiently violated that you would likely want to leave too.

Companies today are hopefully much more transparent than twenty years ago. It stands to reason that if you are hiring a new manager into your organization, you are going to have some of the people who will be reporting to that person participate in the hiring process as interviewers. It is generally a sign of some sort of organizational problem if that is not true. It might be the case that you are being interviewed to solve some of those problems.

For the sake of the rest of this conversation, let’s assume you are participating in the hiring process. So what should you be thinking about?

Why am I getting a new boss from outside the company?

This is a perfectly valid question. If it is your goal to move into engineering management, it is easy to get upset or frustrated to hear you are hiring a new manager from outside the company. You do deserve an explanation about what the reasoning is, and what gaps you may possess that prevented you from being considered for the role.

In times that I have been interviewed by potential direct reports, I have felt their ire at being passed over for an outsider even in the interview process. I totally understand it and accept it.  At that point the challenge for me is to help someone accept that this could be a good thing and could present a learning opportunity to make a transition into a new career smoother and also more efficient.

It is worth noting that if this decision has already been made, you are likely not going to be in a position to reverse it. I have seen some people try to fight by vetoing every candidate that comes in.

That is a bad idea. What will eventually happen is that it will be noticed, and you run the risk of being removed from the interview process.

I would add that if you are getting a new boss and you are removing yourself from the process, either you will wind up with a manager with whom you have had no say in selecting, or you might find yourself in the crosshairs as a problem to be solved by a new manager when it is revealed that you objected so strongly to all of the candidates. Whether or not that is fair, you might find yourself in the spotlight for a while from your new manager while they try to figure out why you objected so strongly and how much time they want to spend in helping you through that process.

What should I be looking for in a new boss?

Now that we have established that just saying “no” over and over is likely a bad idea, you should try to figure out what it is you want from a new boss. There are going to be some easy and obvious questions you can ask which will likely result in basic platitudes and reassurances. When hiring anyone, I always recommend asking best case scenario / worst case scenario questions from candidates. My goal is to learn default behaviors and what I can reasonably expect.

Here are some good questions you can ask a potential future boss:

• Describe how you helped a previous employee get a promotion.
• How long did the best performing engineer work for you?
• Tell me about the best employee you ever had and where are they now?
• What do you do when an employee is struggling in their current role?
• How do you define success as a (manager or director or vice president)?
• What is your greatest leadership accomplishment?

If you can get them to talk about past successes with their teams, or past failures on their teams, it is a good way to learn about how you might be working together. It is important to learn about positives and negatives here. I remember having an uncomfortable conversation with a senior engineer when interviewing for a vice president of engineering role. They had asked me the question “how do I decide when I have to fire someone.” I described my thought process about trying to help people find their best role and how many opportunities make sense for someone who is struggling before putting them on formal notice that there is an issue there. I could tell at the end of that explanation that they were horrified by my answer. If asked, I think I would still answer the question in the same way because it is a serious responsibility to make team adjustments and you should have a plan to do your best for both the individual and the company to try to make things work.

I am pretty certain that individual vetoed my candidacy for a number of reasons, including multiple days of “this person looked at you on LinkedIn” which ended when I got the “we decided on a different direction” email. I am pretty sure each of us felt like we dodged a bullet of some kind.

Why is this person interested in this job?

This is always a tricky one to unpack. People have the strangest motivations for wanting a job. I always like to understand what they are. You should always ask your potential boss why he wants that job. I also recommend asking what they plan to be doing in five years time.

I would be here for hours if I was to list every motivation that people have for wanting a new job or wanting a particular job. Suffice it to say you should ask yourself if you like their answer.

I have taken a good number of jobs via referral because I am lucky to have many smart friends that I have greatly enjoyed working with over many years of my career. I am always happy to help them solve their problems.

If you can establish someone’s career plans and trajectory, that can help you determine whether or not you could have a great working relationship with them. “I need time-in-role as a Director of Engineering” suggests they are focused on getting promoted which has its good and bad parts. “I need experience leading larger teams so I can run a company division some day” is a different way to say the same thing, but it is a better answer. The latter candidate is fixated on team growth, and the prior candidate might be willing to do more upwards management to get a promotion.

How can I help the candidate that I like get hired?

After speaking to a few candidates, you might find yourself in the position of liking what you hear from one candidate over another. Please make that known to the decision makers who are driving the recruiting process! They may ask why, and your feedback might help steer them towards supporting that, especially if multiple people are saying the same thing.

If you find you have a genuine connection with a potential boss during an interview, you should definitely try to paint a clear picture of what life is like at your company, and that you are interested in supporting their candidacy.

I would also recommend reaching out to them to establish a more direct connection after the fact. After all, if your company does not hire this person, some other company probably will. It might be the case that there will be a potential future overlap.

It might even be shortly after they hire someone you don’t like as your boss. In which case it might be worth reaching out to them to see if they are hiring, considering you are probably about to start having a less pleasant time at work.

What can I expect from a new boss?

Now that we have explored a framework for hiring a boss, and all of that is finished, I should let you know that for the first while, you shouldn’t expect much from a new boss. It takes some time to get settled into a leadership role and to understand what is important and what is not important. Every organization has its own wrinkles and curiosities.

While I generally set up a weekly 1:1 with all members of a new team, it would be a good idea to ask your new boss if there is anything you can do to help them. Offer them a weekly AMA to help them get settled in and learn “the little things”. Figure out a list of people they should be getting to know and ask if they want you to facilitate some introductions.

The ultimate thing I do as someone’s boss is to figure out the best way to make them more successful. I have found that the sooner I have gotten successful in a leadership role with the help of my team, the sooner I can get down to the business of helping them become more successful.

Thank you again for reading. Something something social. See you again next week!

Oh, the omnipresent deadline. I know people love them and the huge whooshing noise they make when they fly past.

Software development is tricky work and it is tricky because it is not linear. In a linear process, when you are building something that takes 10 people, you can get it done twice as fast if you add 10 more people.

In software development it is not so easy. I believe that software development is geometric in complexity and sometimes adding people or adding tasks more than doubles the risk or the effort needed to complete a project.

That being said, everyone wants to know the ETA. It is important that people realize it is an “E” and not always an “A”. There are genuine reasons to ask for an ETA and genuine reasons why it is always wrong. That does not mean it is a bad question. In fact it is a very important question.

The number one response that everyone gives to an ETA is generally an acceptance that it is imperfect. I giggle inside when someone says”I am working on it right now.” That completely does not answer the question, and since it imparts almost zero valuable information, generally sets off a cascade of events. I am guilty of this. You are guilty of this. We all need to acknowledge that this is a perfectly acceptable initial reaction to being challenged with a deadline and move past it to really answer the question.

I have developed my own personal method for dealing with this question. I understand you will read it here and throw it in my face when you hear it, but I use it anyway and it will poison my little science experiment. When people ask me for an ETA, I often just respond “Whatever I tell you will be wrong. Do you want me to just make something up or get my work done?” and then go back to doing whatever I was doing.

This is an oddly useful answer. If you asked me for an ETA because you really want me to be done RIGHT NOW, you are probably going to leave me alone. That also tells me I should really hurry up.

If you reopen the conversation with a “we need to update the management” or “but someone wants to update <insert project management device>”, that means you really want me to give you a guess and hopefully will follow up with another question.

Having an ETA is really only useful to me as a manager if it is wrong. If it is right, then I did my job so good I should be on a beach right now sipping margaritas and fist bumping all my team when I get back. They are doing an amazing job and hopefully will be in the 0.1% someday because of how awesome they are. We all know the people who are always on time with their projects also walk on rainbows, and their sneezes contain glitter and smell like cotton candy and freshly baked pie. That is to say, that the person or project that is always on time, especially in the world of startups, is a rare fiction.

When an ETA is wrong, it is really useful because it leads to a secondary conversation. “Why did it change?” Project management, software management, and team management are all about this particular question. Why was there a change? All of these things are a form of change management and that is what really makes this stuff so tricky. It is like playing hockey with a self-aware puck that has (a) a jet pack and (b) low pain tolerance. Stuff is moving and not in a way you want it to. Having an ETA and understanding when that ETA moves is only mildly helpful on your current project. It will get you to check the boxes that need to be checked before the end of the day arrives. If that is all you are getting out of your ETA, then you are missing the real value of it.

The most important part of understanding why the ETA changed, is to incorporate those inputs into your next preflight mental checklist. Every failure, every misstep, and everything that goes wrong has to make it into the playbook in some capacity.

If you can do this perfectly every time, eventually you will have that glitter-sneezing team that ships everything on time.

If you do, I want to meet them and give them a handshake or fist bump. If I duck out of the way when they sneeze, it is probably because my wife doesn’t want glitter in the house.

Thanks again for reading! Looking forward to catching up with you all again next week!

Half of the time that I start writing I worry that the end result will be too long. The other half of the time that I start writing I fear it will be too short. This week is the latter.

The longer you spend in an engineering leadership role, the more abstract and difficult the problems become. The challenge is that you are so successful in building software that solves concrete problems that you might not be aware of the gradual shift into the more abstract world of suddenly much-less-solvable problems. I know that I missed it for a couple years.

It is an unusual experience to go from closing Jira tickets and regularly submitting repo commits to sitting around in meetings having lengthy conversations about comments added to proposals for processes. The tools that make you successful at the former do not always help you solve the latter. It is easy to come in armed with a preconceived notion and a pre-existing framework for success. It is also easy to get frustrated when that framework suddenly fails to be effective.

I remember the first time I ran into this. It was over fifteen years ago and it made me very frustrated. In due fairness to the worst boss that I ever had, I think he was trying to help me understand this. Unfortunately, he was terrible at his actual job and was such a poor leader that I zeroed out anything that he told me. I doubled down on thinking about problems on my own terms. I will leave off any additional rationalizations and justifications about my conduct at that time. I have come to peace with what happened and even apologized to a number of people who were in the blast radius of the months of that unfortunate failure to communicate.

I find myself on the other side of that conversation more often than not these days. Companies grow, marketplaces change, and people who do amazingly well at one thing suddenly get asked to do something new. I have already written about being mad at the wrong thing. Today we are going to speak a little more on that subject.

I go through a variety of emotions when I find someone who is in the middle of transcending from one role to another. I feel sorrow when I see they were ill prepared for it. I feel awe for people who are self aware of it. I feel excitement when I can see people making breakthroughs in their thinking and starting to realize their world is changing. The response varies pretty widely.

I have said previously that part of this writing exercise is therapeutic for me. I have also said previously that I want to help people make different career mistakes than I have. Today I am going to give a few pieces of advice on how to help make this process go more smoothlier.

Listen

If you have gone through any amount of career transformation so far, this will come as no surprise to you. Listening to feedback is important. I have seen people who have been given direct verbal and written feedback completely ignore it in as little time as five minutes later. In some cases they sought to minimize the lack of willingness to listen by making a joke about it immediately thereafter.

Being able to listen to people around you when you are growing is really important. Whether it is superiors, peers, or subordinates, everyone is going to try to tell you something that will help you. Acknowledge their feedback when you get it. Internalize what they are trying to tell you. Follow up with people who have given you feedback to offer examples of how you have taken their feedback and ask if there is anything else you should be doing differently.

Reflect

Set aside time to reflect on what you are doing and what you should be doing. This can be in the form of a personal “do not book” window on your calendar, or a mentoring session, or an additional 1:1 meeting with someone in leadership. When you are changing roles you should have meta-conversations with yourself and others on a weekly basis, if not more frequently. In addition to taking feedback from others, take a look at your actions over a window of time and ask yourself some questions about how you are spending your day:

“What is important to success in my current role?”

“What is important for me to learn before I am ready for my next role?”

“What could I have done differently?”

“Have I set myself up for success or failure?”

“What behaviors are setting me up for failure?”

“Is there a difference in my own definition of my success and leadership’s definition of my success?”

You would be surprised how many people are thrown into new roles without good guidelines or expectations and set themselves up for failure. It happens quite a bit when you are experiencing drastic career changes and professional growth. Being able to see that and figure out how to course correct for it is really essential to grow professionally.

Just Breathe

The last piece of advice probably sounds the dumbest. It is the most important.

Just Breathe.

This is some pretty universal advice honestly. Professional athletes and military personnel actually do some level of formal training around the importance of breathing.

This is relevant to software development and leadership.

I find a lot of the frustrations for first-time leaders are exacerbated by a need for clarity and closure as fast as possible. It is really easy to get lost in that immediate need and lose the bigger picture.

I think that some of the best advice I have given people who are taking on new roles or working to build new teams is to simply slow down and breathe.

This can literally be taking ten minutes to calm down in the middle of a tense online argument, or waiting a night before hitting send on a controversial email.

The number of times you need to urgently handle something is much less than you think, and even if it is moderately urgent, you can always respond by saying “I need some time to think about this.” If you are wrong then someone will correct you. If you are right, then the added time you have just acquired to reflect and listen will serve you in getting to a more thoughtful outcome.

Even if you are urgently needing to reply to something, taking a few deep measured breaths will help. It does not have to be some kind of Wim Hof thing, or multiple minutes breathing in accordance with beeps on some kind of watch or smartphone. 

Just breathe.

In summary, if you are finding yourself in a difficult situation in a new role, ask yourself some questions.

Did I listen to everything that I should be listening to?

Am I reflecting properly on what success is?

Should I take a moment and just breathe?

You would be surprised how many people will go zero for three. You might even be surprised how many people will go one for three.

If you can get proficient with these tools, it will help you grow faster professionally .

Thank you again for reading! 

It has been a while since I have explicitly asked you to tweetsnap, bikbook, or linklank my posts, so I am going to send you off with a mental picture of me piteously begging you to help me expand the reach of my rantings and ramblings.

Please promote these articles to people who could benefit from them if you find them interesting. If you do not know anyone interesting who would benefit from these articles then please just tattoo my blog url to your forehead and scream loudly at strangers to get their attention on the off-chance that these random terrified strangers will have an ounce of curiosity after you get escorted away from them by security or law enforcement.

In either case thank you for helping me and I will write some more next week!

Sometimes I meet someone who looks at all the available evidence that is visible to them and visible to everyone else, and then makes an obvious choice. It is like going to a bank teller and saying “may I please have one hundred dollars”. Most of the time they are going to look at you and say “not exactly”. You will need to show them proof of id. If it is a big bank, you may be required to sign a piece of paper or even enter your bank PIN. Almost nobody in the profession of Bank Teller is just going to give you $100, regardless of how you dress, what you need it for, or what time of day or year it is. And yet, in some professions, that kind of decision making is a requirement. You do not have the convenience of waiting for validation by PIN, or fingerprint, or passport photo, or signature. Sometimes you have to realize that you have to make a decision based on imperfect inputs and just do something even if it goes catastrophically bad.

I love it when I meet people who make decisions on imperfect inputs. I think they are the most amazing people in the world. I also seldom meet them. Most of the time, I run into checklist-managing bank tellers who have the worst job in the world. Their job is “Not Getting Fired”.

This has become one of the most important pieces of career advice I have given people over the years, and the people who have taken it to heart have become some of the most awesome people I have ever worked with.

It is very easy to wait as long as possible to make a decision and to do something that is inherently obvious and safe and can pass agreement by committee. When I was running my own game studio, I would often be working with early publishers and there were few things I hated more than coming into a meeting to talk about upcoming projects and hearing that “we just instituted a new green-light process.” The first person who gets that job usually comes there from a larger and more comfortable company and is going to spend the next six to nine months making safe bets—probably while figuring out the machinery and sorting out how their processes work. If that doesn’t happen? That guy Gets Fired. And he was not hired to Get Fired—at least not right away. The problem is that sometimes they get stuck into that pattern and then they get really good at Not Getting Fired.

I think this is a problem. I have done a few projects with a few companies that do not make financially successful products. The people involved will say something like “I am grateful that we had the opportunity to try something different, even if the market is not interested in a game that deviates from the current crop of hidden picture games.” Sure we did not make money (I thankfully broke even on it) but that statement alone made the whole endeavor totally worth it for us because we took a risk and we tested some assumptions. We tried something different, and we learned something.

Software engineering and startups are inherently risky. Most investors like to see the entire proposition massively de-risked before they write checks. That is perfectly fair. They are playing with Other People’s Money, and quantities that Carl Sagan would appreciate. For the average entrepreneur, you are taking pretty crazy risks and persuading people to bet their livelihoods on ideas before you are putting that kind of money in the bank.

I think that there is probably a time and a place to play it safe. Software development, especially consumer-facing software development, is generally a hard place for that. I think that the bigger the risks that people take, the higher the rewards. I have been blessed to have pretty decent passive income in the past by taking some crazy risks, and I will probably do so again despite having kids to feed.

Every once in a while I run into someone and get asked “what does that guy do at that company?” I sometimes respond immediately with the statement “His job is ‘Not Getting Fired’.” I generally have to follow that up with a pretty lengthy explanation, but I think that imparting that understanding is key.

If enough people realize how sad and boring and predictable and uninteresting that job is, maybe people will catch themselves looking in the mirror as they think “If I Do What I Want To Do, I Am Going To Get Fired.” And they will do it anyway because it is likely that it could be the right thing to do in that position.

And if they don’t, they may discover that ten years have blown by them giving people $100 bills in exchange for proof of ID, entering a pin number, and going home at the end of the day. And all things being equal, on those terms, I would not want to live my life Not Getting Fired. And I seldom do.

I hope you never become the person whose job is to Not Get Fired.

One of the reasons I write these articles every week is to help people avoid mistakes in their careers. If it is not possible to avoid them, then at least they can make well informed mistakes.

Today I am going to talk about the transition between individual contributor and manager, and how terribly that is often handled.

I have often had to explain to people that when they start taking on leadership roles, they are not providing an incremental increase in value to their employer. In fact, they are providing an order of magnitude more value. The table stakes are no longer just your own salary, but the salary of your entire team. It is hard to understand this initially because your salary does not jump up to that value, and generally that is one of the more obvious yard sticks people use to measure their value to the company.

The problem is that when you first make this transition into leadership, you are going into professional freefall and it is not always clear what you are supposed to be doing.

The first time a software developer transitions into a leadership role, they are generally not given much coaching or mentoring and are not sure how to solve problems at the next level. The first time that there is a crisis in their new role they will probably reflexively resort to their default behaviors. This is the wrong thing to do, and yet, it is okay. Sometimes the only way to learn things is by making a mistake. 

If you are a really good individual contributor and you start to code your way out of all your problems, then you will not make the transition successfully into a leadership role. This is where the problem becomes sinister. The first-time-leader here will want to prove they can do the job, and when there is a crisis, they will also jump in directly and solve it individually, usually when nobody is looking. They will spend seventy-five percent of their time doing their assigned role of a leader, and seventy-five percent of their time working directly on the codebase to make sure the work gets done.

Do you see the problem here?

It takes some time to start developing leadership habits and new default behaviors. It takes longer if you are falling back onto existing default behaviors that need to be unlearned. Furthermore, if you are jumping in to directly help your teams without a direct conversation about it, then you also risk alienating or frustrating your teams. If you are cannibalizing their work and doing it yourself, they could fall into a trap of learned helplessness. After all, why should you try anything if your boss is just going to jump in and take it over the finish line for you? At the very least you will go to them before doing anything significant so they can sign off on it, rather than investing some of your own time learning.

This is a difficult place to be. Unfortunately, it is also a common phase of everyone’s careers, especially at small companies. At a larger, more mature company, you might find more support for giving new leaders some room to grow, and more structure for identifying and preventing individual contributor default behaviors.

It is definitely worse in startups. The lack of institutional support and need to have stuff built before the company runs out of money is a pretty severe issue. Finding the right balance between starting to develop leadership and management skills vs building code will require burning some dry powder reserves. What makes that worse is that most startups are run by serial entrepreneurs who have seen this pattern before and think that it is normal and acceptable.

What is fascinating is when you are in conversation for a Vice President of Engineering role at a company and the recruiter or hiring manager asks “Do you still code”? Generally that is a sign that the business is very early, the title is fictitious, or the hiring manager does not know exactly what they need in this role. Sometimes all three could be true. I have had to bite back the urge in leadership recruiting conversations to ask “How much time does the Vice President of Safeway Foods spend stocking shelves?” It is a legitimate urge I experience, and also not very constructive. For clarity, by the way, I have to reply “Yes. I. Still. Code.”

Now we get to the really interesting part of the engineering leadership dilemma. It is not wrong to ask your engineering leadership about their technical experience. In fact it is vital that your engineering leadership has a good grasp of engineering problems and engineering practices. I have seldom met an effective engineering leader who has not been a software developer themselves in the past. Just about all of them have been through that seventy-five-plus-seventy-five transition period. Given the emphasis these days on work/life balance, why is this still so prevalent?

There are a few reasons.

The first reason is the expectation outside of engineering. Right or wrong, there is something ritualistic about startups. It is some sort of crucible that people throw themselves into, to see what gets forged in the fires of possibility. The upside of a successful startup is life changing even if it is very unlikely. This translates into significant material wealth for early staff at a company, and it is also very true for leadership. I have heard more than one serial startup executive state that they do not want to pay market rate for talent because taking a pay cut is a sign of commitment. That burns my soul. Generally there is not much cash on hand in early-stage companies, so maybe this is some sort of rationalization. I do think that the average person does not negotiate enough for more stock in exchange for this trade off. I also think that most of them forget that only a fraction of a percentage of startups make that gamble worthwhile.

The second reason is the expectation inside of engineering. Let’s face it—engineers are smart people. Smart people like to work for other smart people. They want to believe that their leadership has good, well-informed plans, and that they are making well-educated decisions. The instant that they work for someone who is not making well-educated decisions or does not have well-informed plans, they immediately lose trust and confidence in their leadership and perhaps even their company.

I have experienced this. I had a boss who had a poor understanding of technology. I offered to help them be successful in their role after they made a few obvious mistakes. They rejected my offer, reasonably politely, and pointed to their title as to the reason why they did not need my help.

It did not go well after that.

So what can we do here?

For starters, we can do what I am doing now. We can talk about it.

If you are in this position, you should examine your current role, your long term expectations, and what you are getting out of it in terms of rewards.

Most of the time someone is in a transition role between being a leader and an individual contributor, there is a short window of time on it. If it is more than a year and there is no sign that this will change, then you have a problem in your hands. If you are stuck in this role, you could potentially burn out, or even more likely, your self-preservation instincts will kick in and you will find a new role elsewhere that relieves the symptoms of your pain. Everyone loves to hire someone who is stuck in this position. First of all, it gives them an opportunity to be grateful to you for rescuing you, which is an added incentive to be successful in their new role. Secondly, you just got a new leader trained up on someone else’s dime.

Before you bail out or burn out, you should have a clear conversation with leadership on where you are, where you are going, and what needs to change for you when you are stuck in this place. In that event, if you do leave, they at least understand what happened and maybe understand that they were part of the problem. If they are unable to make a substantive change due to business reasons, they should at least bump your equity as consideration for your struggles.

Alternatively, you should reach out to people who have been through this before. I am presently mentoring a couple of people who are in this position. It does help to have someone inside or outside of your organization to discuss these struggles and to come up with things to do that help make things better, or at least help you develop new habits and break through any potential cognitive dissonance.

The road to being an engineering leader is long and hard. It does not have to be lonely.

Thank you again for reading! If you are in this position and do not feel like you are in a position to talk to anyone in your company about it, please reach out. I would be happy to spend some time learning about your situation and your struggles and I am happy to share my perspective.

See you all next week!

They say people do not leave jobs, they leave bosses. I think that reflects 50% of my reactive career decisions over a 20 year span. And if you looked at my LinkedIn profile, that is an unfortunate number of bosses.

So how do you know how you have a good boss?

Is it because you get free pizza when you are hungry?

Is it because you get a good raise every year?

The sad thing is that most of the things that people like about their boss are the opposite of traits of a good boss. You might be getting a lot of things that make you comfortable, and appear to be valuable on the surface. In fact, the better the perks you are receiving, the more likely you are probably working for a bad boss.

I am going to give you the characteristics of what I see in a good boss and hopefully at the end of this short article you will sit down and ask yourself if you have a good boss or a bad boss.

For me a good boss does three things.

1. Makes sure I have the tools to do my job
2. Lets me know what his concerns are with his job
3. Grooms me for the next step in my career

That probably sounds abstract and nebulous. I will try to break it down.

Item 1: Having the tools to do my job.

Every time I have managed people and I am needed to moderate some sort of disagreement between two coworkers or two different teams, I always make a big deal about it. I always tell people “the last thing you want me to do is make this decision for you” and sometimes I have to privately sit down with a person and explain “You were hired to solve problems, and I am concerned you are spending more time making them”. That is never a pleasant conversation. When I am coming into a role I want to make sure that my boss has given me the ability to do what needs to be done. Do I have hiring authority? A budget? The right people already on a team? The right tools for me to be effective? If something is missing, I need to be able to go to my boss and make sure that I can get those things or else be empowered to create a solution on my own. This is harder than it sounds, but I have been asked a few times to join a company with constraints on my job that make success impossible. I have learned to avoid that situation.

Item 2: Lets me know what his concerns are with his job.

I am probably worse at this than I want to be, and I am sure many people are. The last thing you want to do is to let people who need to believe in your leadership know that you need anything in particular. I have learned to start trusting people with this more and more as I have evolved, and also made it clear when it is something that is a professional concern or a personal limitation. Let’s be honest—none of us are perfect. Sometimes people on our teams do not help us as much we would like them to, and sometimes the solutions to problems are not easily attainable. Being able to separate personal issues from structural business problems is hard, and it is worth having a conversation with people you are working with to make sure those get resolved. This is a lot harder than it sounds in reality but it is valuable because…

Item 3: Grooms me for the next step in my career.

A friend of mine flattered me recently when we agreed to meet for coffee. I asked him why he always makes time in his bay area visits to get together and he pointed out that he considers me a “best athlete” problem solver. I really cherish that feedback.

I often go out of my way to hire “best athletes” for most of the teams I build as opposed to “best athlete” candidates. For the work that I do there are too many unknowns to focus on “best fit”. If I go and find the best person to solve a specific problem for a specific product, nine times out of ten they are going to struggle when we have to pop the clutch and prioritize some sort of crazy emergency issue related to marketplace shifts. This may be a unique problem to startups but I have yet to regret choosing “best athletes” in hiring.

A big part of the value here is in working with the people on your team and getting them to take on more and more responsibility. There was a period of time in my career when I became very mindful about my role and my responsibilities. There was also a period of time, prior to that, when I was a ravenous bulldog intent on doing my job to the best of my ability and chewing through any obstacle in my way to get my work done, often leaving a trail of chaos and bewilderment in my wake.

To anyone who was affected by the latter, I am deeply sorry. In the case of the former, I often ask myself “how do I make sure that if I get struck by a meteor, the company I work for will continue to succeed”. I know that is dramatic, but it is valuable to ensure there is a succession plan for the organization. I have done some minor team rearranging, and also some random schedule adjustments simply for the sake of ensuring that meaningful work can happen without me. As an engineering manager, for example, I was accused (correctly, and fairly) on a few occasions of missing specific meetings on purpose, just to test that people can manage on their own. “Szeder is meddling with the warp core again” was how my peers stated it, and I cannot say it is wrong—but if you continually try to explore space at warp four, you will never need to know what happens if you urgently need to go warp ten.

I hope this was an enjoyable read. I have had some bad bosses in my time and honestly, whenever I manage people I look in the mirror some days and ask myself if I can see previous managers peering back at me. Maybe that critical self-reflection is the best feature of all for a boss to have.

So what do you think makes a boss a good boss? I would love to know!

It is interesting to look at an internet product or service on its one-year, five-year, and ten-year anniversaries. Let’s take LinkedIn for example. I have a low six-digit LinkedIn user number, which means I was in the first 150k customers. A few years into its existence, I decided I was getting enough value and that I would pay for a premium membership. A few years after that, I decided I was not getting any value for what I was paying and I cancelled my subscription. Somehow in the middle of that experience I went from being their customer to being their product.

There is a similar sort of feeling I get when I play online games. I have played World of Warcraft off and on since The Burning Crusade Expansion. We had a two-to-three season run with Fortnite in our household where even my wife would jump on the PS4 and squad up.

This weekend was the first time I reopened Fortnite to take a look at it in a long time. I gotta admit it was a pretty alien experience.

So what happened? Let’s try to figure that out.

Fortnite’s early seasons did some very interesting things. They attracted a reasonably casual audience. You could log in every day and pick up a new quest. The quests were largely simple and you had a window of multiple days to complete them. The advantage to this system was that if you were terrible with shotguns, for example, then you could let that quest time-out over a couple of days and you would still get other interesting quests on a daily basis. The threshold of risk and commitment was exceptionally low for a pretty significant payout. I think this was a magical system and if it was on Yelp, I would give it five stars.

A curious thing happened next. A competitive battle royale game that was a better “gamer game” came out called Apex Legends. It was by all of my measures a better product, except it was not as popular as Fortnite. We can only guess at the reasons for that. While the gameplay felt better, the graphics were clearly “less cartoony” than Fortnite. Also, they had a pretty rigorous meta system that I considered more challenging and required more risk and a higher degree of commitment to be successful.

I think you can probably see where this is going.

I must not be the only person who thought their meta system was better. It made itself felt a few seasons later inside of Fortnite. The more complex meta system was more “gamery”, and as a family of filthy casuals we just did not find it appealing.

While I can appreciate the thought process that went into it, on the surface you could make a snotty comment about doing “fast follows” on less successful games. I do not recommend racing another company to second place if you are already winning the race. I do know that we went from an eye-popping amount of cosmetic goods purchases each month to zero very quickly.

I mentioned World of Warcraft earlier as a business that struggles with the same issue. There is this dichotomy between the casual gamer and the core gamer. I will say that World of Warcraft has done a better job of servicing both groups at the same time than most live online games out there, which is a tremendous feat.

Believe it or not, this has something to do with LinkedIn. Much like there are casual gamers and core gamers in online games, there are also different kinds of professionals who use a service like LinkedIn. Initially LinkedIn catered more to a casual crowd and focused on empowering and rewarding people for building and maintaining networks. I remember having conversations with people about how high the bar used to be to get someone to accept an invite to your network. LinkedIn figured out that the casual network building also serviced another customer with deeper pockets: The hiring manager. At some point there was a transition inside of LinkedIn to provide greater product support for the higher margin business. 

At that point there is this weird free fall in feature development for customers you have, in favor of making features for customers you want.

It is a difficult place to be and, unfortunately, it is a common one. I have found that if you stare long and hard enough at any successful internet company, they go through a painful transition like this every three to seven years. I will tip my hat to Apple here. I think they have probably done the best job of managing their customer expectations over their multiple transitions from business to business. 

I think that most consumer internet companies struggle with this when they get to scale because of the pressures of public companies and investors. Nowadays I generally do a pretty good job  at realizing when I stop getting value from an internet company, and I turn off the cash-and-eyeballs spigot pretty quickly.

The most painful application I use today that has undergone this kind of transition is Google Maps. Before I say anything further I want to acknowledge freely that I should probably use a different Google product like Waze. There is some stubborn get-off-my-lawn part of me that refuses to use two different mapping applications from the same company. Is it a form of philosophical protest? I do not know. I do know that any time I get selected for feedback and reviews on my experience with Google Maps, I am very unkind in my feedback.

What makes Google Maps so painful for me is the street-by-street directions. I generally have a route mapped out for me on my phone when I travel. Sometimes I will very safely open up the street directions so I can figure out the exit number, or street name for my next turn. Yes, some of us do not have navigation systems built into our cars yet. You can fax me your disappointment later.

The part that burns my soul is when I do open up the application to get the listing of directions, someone inside of Google put me into some sort of A/B test group that indicates that the most important thing that I need to see is an ad for ride-sharing, a parking garage, and a nice little bar graph of how busy the destination is.

The name and number of the exit that I am looking for is accordingly buried deep under the fold (that means it is off the screen for all of you UI/UX language impaired readers).

That is correct. The most important piece of information I consistently need immediately requires an additional swipe to bring up into view.

I am cheerfully including a screenshot of this horrible state of affairs for your viewing pleasure.

Somewhere along the way Google Maps, much like Fortnite, stopped thinking about me as a customer.

I am writing about this because it is a pretty insidious problem. Not a lot of businesses think carefully enough about the customers they have while they are chasing after customers that they want.

When you get into work tomorrow I hope you sit down and think about this.

Are there applications and services you are using that used to be great products and suddenly feel frustrating?

Are you reading feedback from customers that indicate that maybe your own product is one of these?

I could argue that this is a consequence of businesses being heavily fixated on growth. I also think that this is a systemic issue that affects most companies, and that it generally does not get significant mindshare.

Now that I have made you all aware of what is wrong with your once-favorite applications and angry at the lack of mindfulness in thirsty growth-mongering businesses, I want to thank you for reading along! I try to focus on engineering leadership topics, and I cheerfully admit I went a little off topic today.

Let me know by comments, faxes, or carrier pigeon if you approve or disapprove of the randomness of this week’s conversation.