Reading “The Manager’s Path”

Jay Shirley
11 min readApr 24, 2017

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O’Reilly recently published this book by Camille Fournier. I made sure to grab the book as soon as I could even though I was slow to start reading it. Blame “How to Read a Book”.

The Manager’s Path is interesting because it combines a lot of knowledge I’ve picked up from various books, blog posts, or talks and stitches it into a somewhat chronological path. It’s familiar content but it does create an a clear learning path up the management chain. In short, I loved the book. The voice of the author shines through, and countless times (even when she talks about her negative feedback!) I was wishing I had (or will have) an opportunity to be on one of Camille’s teams.

I’ll write a bit about the excerpts that made an impact and my thoughts or what I hope to get out of the knowledge. First off, the meaning of “Manager” as Camille defines it:

Your manager should be the person who shows you the larger picture of how your work fits into the team’s goals, and helps you feel a sense of purpose in the day-to-day work.

A delightful person once told me that the leader’s role is to hold the vision, ensure the team has the resources to succeed, and manage the culture. This is very compatible with that but provides more actionable steps. If the culture is one in which everyone feels a individual sense of shared purpose, I’ll be pretty happy.

Being an introvert is not an excuse for making no effort to treat people like real human beings, however. The bedrock of strong teams is human connection, which leads to trust.

This hit me pretty hard. I think for most of my life I allowed myself to ignore people because I hid behind my introversion. I had an enlightening moment where I realized that I wasn’t an introvert, I was just an asshole.

Good managers know that delivering feedback quickly is more valuable than waiting for a convenient time to say something.

Related to “treat people like real human beings”, it’s not enough to deliver feedback but to take a brief pause before so the feedback can land appropriately and as intended. Thinking on this, I would say that bad feedback is better than no feedback, but briefly prepared feedback is best. There’s almost always time to take 60 seconds to collect thoughts, so I need to remember that “quickly” doesn’t mean “immediately”.

Use your manager to discover what’s possible where you are, but look to understand yourself in order to figure out where you want to go next.

Know Thyself. I haven’t been doing a good job of this for a while for a variety of reasons. This was a great reminder that my growth is my responsibility. I don’t believe in work-life balance, but work and home life is integrated. My manager is not Jack Sparrow’s Compass, only I know what I most truly want and I have to get all the data points available to know how to get there successfully. My manager is just one more data point but a very valuable one. Supporting the team members means to provide data points for them to succeed on their own personal and professional missions.

While many people think creativity is about seeing new things, it’s also about seeing patterns that are hidden to others. It’s hard to see patterns when the only data points you have are your own experiences.

I work for Stripe and love it. Stripe got to where it’s was not because they did something entirely brand new (quite a few of us have written similar systems to Stripe, just never as a product). They saw a pattern of repeated, difficult work and figured out how to abstract it out and create a valuable product.

It’s my job to always seek out data points. It’s also up to me to combine those and, along with my team, see the patterns that may point to great opportunities. I feel this is in the spirit of Jeff Bezos’s philosophy: “We go down dark alleys to see what’s on the other side”. You have to know which alleys make sense, and that’s all about collecting data.

Teams often fail because they overworked themselves on a feature that their product manager would have been willing to compromise on.

Thinking about the root cause here and connecting it with the points above, I’ve seen this most when communication is restrained, usually because of lacking empathy or listening (the manager should practice this and coach others). It’s a pattern and one of the data points I’ve seen is when people don’t ever push back against the work.

Now that I’m in an infrastructure role, this feels both easier and slightly more difficult. Often the engineers building things out aren’t having the same conversations I have, and they may lack the data points to find the opportunity if I’m not doing a good job. It’s a struggle to make sure I’m providing the right data but not overwhelming them with irrelevant information.

Another approach that many experienced managers use is to help their new reports create a 30/60/90-day plan. This can include basic goals, like getting up to speed on the code, committing a bug fix, or performing a release, and is especially valuable for new hires and people transferring from other areas of the company.

We have a reasonably good onboarding standard, but it hasn’t been a 30/60/90 day plan and can be hit or miss. I’m going to be trying this plan with the next couple of people joining the team. I’ve done this for myself, independently, and it’s been very valuable.

Forcing yourself to be specific will steer you away from writing reviews based on underlying bias.

I believe feedback should be specific, actionable, and able to be revisited. I love that Camille calls out bias here. Sometimes we give negative feedback just because we don’t like the person. Being specific and working on an actionable plan with the person works even when we like them. Though if we don’t like the person it can be really challenging to want to work with them, but if you can’t do that you shouldn’t be a manager.

I feel I struggle with giving feedback on a regular cadence, despite believing feedback is crucial to success in life. Something to work on…

Don’t let people skip over the good stuff in order to obsess over the areas for improvement, as many will want to do.

I have mixed feelings on this personally. It is good advice and I need to know my feelings are local only to me. In this case I shouldn’t, perhaps, treat people the way I want to be treated. One of my strengths (according to Strengths Finder anyway) is self-assurance. I really don’t need to hear about the good stuff unless it’s in the context of “This was good, do more of this and it will be great”. I don’t feel areas of improvement are a bad thing, but I always try to keep my strengths in the foreground. Some weaknesses can remain untouched and my strengths can make those weaknesses irrelevant.

The kind of toxic drama that is created by these energy vampires is hard for even the best manager to combat. The best defense is a good offense in this case, and quick action is essential.

This is an interesting quote. Sometimes treating others as real human beings means you have to be strict (or even harshly) towards one to benefit a larger group. This is the classic railroad switch. Is it ok to fire one person for the emotional benefit of the rest of the team? I need to make sure I look at everyone as real humans, not just the person causing the problems. Chances are the person creating the toxic drama is miserable on their own and working with them will be a challenge. I just need to remember to brace myself and ensure I’m taking care of myself through a tough situation.

You can make [things] worse by undermining your peers in front of your team, so even when you are frustrated with them, try to stay positive and supportive of their efforts in public.

This is something I’m working on and feeling pretty good. Relentless public positivity just makes things more fun, too. This is especially true when the situation is bad and I’m (trying, anyway) teaching this to my kids. K’naan’s Smile is my theme song here. One thing I’ve been searching for is where it is safe to vent and be honest about my feelings. If I share my feelings, relatively unfiltered with my manager is that constructive? Do they validate or dismiss those or think worse of me for having negative thoughts? It’s a data point worth having to know how much filtering and collecting around negative thoughts needs to happen before sharing privately. In the end, I want some place I can vent frustrations because that’s how I can be positive in public.

…even most introverts want to have a feeling of relatedness with their team. Assuming you don’t have any of the “people drama” problems listed earlier, small efforts in this area can warm the group up considerably

This is important and there is no standard recipe here. Sometimes what works for a group will completely backfire with another. Disregarding the people drama, ensuring that there are continuous small efforts to improve the feeling of relatedness is the best way to improve collaboration and enjoyment of day-to-day work. Small efforts are hard, though. They feel meaningless and often times have no immediate feedback to know if they had any impact. I struggle the most on not giving up on small efforts in important areas when there is no immediate feedback. It’s too easy to just stop thinking about it.

So, yes, shielding your teams from distraction is important. Or, to put it another way, helping them understand the key important goals and focusing them on those goals is important. However, it’s unrealistic to expect that you can or should shield your team from everything. Sometimes it’s appropriate to let some of the stress through to the team. The goal is not to stress them out, but to help them get context into what they’re dealing with.

Again with a challenging implementation! I try to live by the principle of fewest surprises. This means things should be as predictable as possible. If I shelter everybody and then something urgent comes along I’ve failed. That’s not predictable. I try really hard to catalog the inputs and then make sure I continue to check-in, and if something looks potentially problematic I raise it to the team. I’m happy with this process but there’s definitely room to improve. It’s quite reactive and takes up a bit of time. It isn’t always a useful approach for future project work that is ambiguous (where is where we should spend the majority of our time).

Creating a safe environment for disagreement to work itself out is far better than pretending that all disagreement does not exist.

Constructive disagreement is a frustrating concept because it sometimes feels that it simply can’t be taught. I’ve noticed there’s two sides to unhealthy disagreement: first there is aggressive disagreement and the other is capitulation. Reading Crucial Conversations was extremely helpful for me, and I recommend it for anybody caught up in these situations.

Your goal as a manager, however, should not be to be nice, it should be to be kind.

This is another challenging line to walk. A related struggle is my attempts at being assertive but not aggressive. Constant reminders and prepping before important conversations. When I feel I’m struggling with aggression, I’ll repeat “Wish [them] to be happy” before a conversation that may go down that path. I need to find an equivalent mantra for “be kind, not nice” (maybe that’s a good enough mantra).

The real goal here is psychological safety — that is, a team whose members are willing to take risks and make mistakes in front of one another. This is the underpinning of a successful team.

Constructive disagreement, open dialog, ability to question priorities, and making risks is exactly how I think teams operate at peak performance. Mihaly Csikszentmihalyi found when people believe they’ll succeed they are bored and disengaged. If they believe they can only fail they’ll disengage and feel hopeless. I recently went through this, and due to other people I was able to feel optimistic and so far things have worked out.

Without psychological safety people will not challenge themselves and always sit in “boredom”, which is another way of staying safe. This is the 37 pieces of flair area, aka “working just hard enough not to get fired”.

You have 10 productive engineering weeks per engineer per quarter

Be selective about what you bring to the team to estimate

My favorite part of running sprints is that we don’t have to put a lot of upfront estimation thought into things we aren’t going to do for a while. I hate sprint planning because we often times miss doing quick wins because we, without verifying, think some tasks are more difficult than what they truly are.

After reading The Toyota Way I feel it’s important to spend time up front to understand the problem and really understand the solution. There are two parts to any work: first is understanding (including the effort the solution requires) the problem and the second is estimating the impact and opportunity of the solution. Thinking of this in terms of Urgency and Importance, I try to plot things mentally like this:

I wrote about this model previously — Eisenhower was good at this stuff.

I feel bad when I suck at being an engineer, but sucking at being a manager would be a choice I inflicted on other people. That’s not fair.

Slow. Clap.

Shortly after I transitioned into managing, I was involved in a discussion that I didn’t put a lot of thought in. Later, my manager pulled me aside and said, “Bigger boats have bigger wakes.” People took my comments in that discussion much differently than I intended.

As a manager your wake will capsize people and it happens behind you. I think all the bad managers I’ve worked with never see the trail of destruction they leave behind so it’s a surprise to them when things are dysfunctional. I worry about this a lot. Making a wrong decision is forgivable but only if I look backwards at the consequences and act accordingly.

If you have the authority to say no, and you don’t believe something should happen, do yourself a favor and don’t agonize over the process. You’ll be wrong sometimes, so when you discover that you were too quick to say no, apologize for making that mistake.

This is an area I’m working on improving. I’ve received some great feedback over the last couple of years that I’m too quick to apologize when I make a mistake, and people don’t feel an emotional connection. There’s two components to this and apologizing for a mistake is only one. The other is to acknowledge the (often times emotional) impact. I was only doing the former.

Leaders who are strong team players understand that the people who report to them are not their first team. Instead, their first team is their peers across the company.

This is something I need to continue to remind myself. My first team is amazing and I’m extremely fortunate to work with them. This group is going to be who I learn best from, just as when I was an engineer I would learn the most from the strongest engineer on the team.

I have many other highlights and thoughts, but this is long enough for now. The book is excellent, the knowledge is easily transformed into actions. I’m better off for reading it.

I have a lot to practice.

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Jay Shirley

Striving to be a man of gallantry and taste. Champion of progress and improvement. Working at @Stripe and constantly working on myself.