Hi folks,

This is the weekly digest for my blog, Irrational Exuberance. Reach out with thoughts on Twitter at @lethain, or reply to this email.

Posts from this week:

- Finding your Staff sponsor.
- Interviewing for Staff-plus roles.
- Notes on compliance tools.
- Mailbag: Advice for someone five years into their tech career?

Finding your Staff sponsor.

As I’ve spoken with more folks trying to reach their first Staff-plus role, most folks run into similar challenges. Many have miscalibrated their own impact, and simply haven’t done the work yet to operate at that level: a Staff Engiener isn’t just a faster Senior Engineer. However, there’s a large cohort who have done the work–they’re visible across their organization and have pulled together a strong promotion packet–but are still struggling to have that work recognized.

These folks are often frustrated by the distance between their impact and their recognized impact, and ask their managers and peers for feedback on closing that gap. They’re told to complete a staff project or to create space for others. For folks who haven’t done the work yet, this is great advice, but for folks who have these checkboxes are a distraction: what they’re really missing is a sponsor willing to push for the recognition of their existing work.

It’s common to view promotion systems through the lens of other systems that have evaluated us throughout our live such as school, but this falsely frames performance evaluation as a solo activity. Whether your company does ad-hoc promotions or uses a calibration process, promotions are a team activity and as Julia Grace, then of Slack, advised me once during a job search, “Don’t play team games alone, you’ll lose.”

Finding your sponsor

The most important member of the team guiding your promotion is you yourself. The second most important person is your organizational sponsor. Lara Hogan has written on sponsorship at length, but roughly this is the person speaking up for your work in forums of influence and when advocating for constrained resources (like budget for salary increases).

While you’ll likely have many different varieties of sponsor, in the context of getting promoted—especially to a Staff-plus role—this almost always needs to be your direct manager. They’ll be the person to take your drafted promotion packet and turn it into the company’s format. They’ll be the person to advocate for your promotion during a calibration meeting as others drill into your qualifications. They’ll also be the person who has to have the honest conversation with you about the gaps you still have before you’re a strong promotion candidate.

While you’ll always need your direct manager engaged as your sponsor, you may need additional sponsorship. If your manager has never promoted someone to a Staff-plus role before, they’re likely going to get surprised or make a misstep along the way. Invest into establishing a relationship further along your management chain. You don’t need to spend much time with your skip-level manager, but if they aren’t familiar enough with your work’s impact to remember it in a meeting two months from now, you’re unlikely to get promoted into a senior role.

Activating your sponsor

The first step of activating your sponsors is being explicit about your goals. “I’m looking to be recognized as a Staff Engineer,” is a great start. Ritu Vincent mentioned this as her top advice for folks seeking Staff-plus roles,

People frequently come to me and ask, “What should I do next to reach Staff?” One of the things that I tell them is to be super open and honest with your manager about what you want from your career. A mistake I made early on in my one-on-ones was telling my manager what I thought they wanted to hear, instead of what I actually felt.

Once they’ve identified their sponsors, many folks see their work as complete: it’s up the sponsor to do the heavy lifting. This usually fails! Sponsors are folks with more organizational capital than bandwidth to deploy that capital, and they’ll help you most when you aligns the pieces for them. Ask your sponsor how you can support their sponsorship. Owning your career isn’t only about asking for things, it is about that, but it’s much more about facilitating those things happening.

Reviewing your promotion packet collaboratively with your sponsors is a great way to facilitate this conversation. Focus on asking for what the gaps are in a way that doesn’t prompt your sponsor to make up an answer. Most folks forget they can answer questions with, “I don’t know,” and instead make up unhelpful answers if you push them to answer questions they’re uncertain about. If you keep getting answers like, “Work on larger, high impact technical projects,” then you’re asking in the wrong way, the wrong questions, or the wrong person.

One starting prompt is, “If I don’t get promoted this cycle, what are some the likely causes?” Another question worth asking is, “What’s the most effective thing I can do to make myself a stronger candidate?” That said, the best questions are very specific and do a lot of the work for the answerer. Think about how hard it is to answer those questions compared to a question like, “This quarter I completed the API refactor, which I thought would demonstrate Staff-level work, but the schedule slipped a lot and it ended up frustrating our product managers because their work got dropped. How could I have handled this project more effectively?” The later question is much easier to give a useful answer towards, even if the answerer isn’t too familiar with the details of the project.

Finally, remember that activating your sponsor isn’t a transactional thing to do once before your promotion. Build a relationship over time, and put in the work to help them when they need your support. Stay aligned with their initiatives. If they need folks to join a working group, volunteer and put in the work. These folks have a lot of folks asking them for things, and they are pretty cognizant of folks who show up right before promotion time. I once had a colleague who rarely visited the office, but a always visited the office the week before promotion decisions were made. People noticed.

What if it doesn’t work?

If you find yourself in a situation where you and your manager don’t work together well, which isn’t quite the same thing as liking each other, then you’re not going to get promoted into a leadership role. Your manager has too direct an influence on your impact and your perceived impact for that to happen. Similarly, you might have an amazing relationship with your manager who then leaves the company. You’re hardly doomed, but your promotion clock will likely get reset as you build a relationship with your new manager. (Sometimes this works out the other way, with your new manager working hard to prove themselves to you by advocating on your behalf.)

You’ll cheat yourself if you immediately try to switch teams or companies after running into friction with your manager. Companies generally don’t allow transfers unless your manager approves it, so you may burn a bridge to nowhere that you’re standing on. More importantly, you’ll lose the opportunity to develop your skill of working with folks you don’t immediately click with: it’s not a fun skill to develop, but leadership always involves influencing and building relationships with folks with conflicting goals and styles.

If you’ve spent six months proactively trying to make the relationship work, then it probably is time to explore moving teams and to perhaps consider switching companies.

Interviewing for Staff-plus roles.

When you decide to interview for a Senior engineer role, you roughly know what to expect. You’ll refresh your resume, work through Cracking the Coding Interview, and do some research on the company to prepare questions. When you go into the interview, you know it’s going to be five-ish interviews composed of a few programming exercises, something about technical architecture, and some cultural, behavioral, or career questions.

It would be amazing if you could start a Staff-plus interview process with similarly clear expectations, but most companies struggle with their Staff-plus interview loops. It might be the same exact interview you’d get for a Senior engineer role. It might be an engineering manager loop with a programming question added. It might be something else entirely.

Getting comfortable navigating ambiguity is a core part of the Staff-plus role, so a particularly optimistic person might view the state of Staff-plus interviewing as a good opportunity to demonstrate your skills. If you’re less optimistic, you might find it a bit frustrating, but a bit of preparation can go a long way in making these interviews more predictable.

Draw your lines

The engineering leadership phase of your career may last twenty years, but if you think of that in terms of roles, how you spend that time will likely come down to four or five pivotal decisions. Each of those decisions is a scarce resource, and you should allocate them deliberately. Before jumping into an interview process, spend some time refining your criteria for the kinds of processes you’re willing to participate in, as well as reflecting on the right company for you.

There are certain signals you’ll get during an interview loop that the company doesn’t quite know how to interview Staff-plus engineers. Because most companies have mediocre Staff-plus interview processes, you shouldn’t automatically opt-out of poorly run processes, but you should consider which of those signals represent a line you’re unwilling to cross.

One line that many folks in Staff-plus roles draw is they’re unwilling to practice interview programming. This often means they are slower or make more mistakes in the sort of algorithmic questions that many companies use to evaluate early career candidates. Folks who don’t practice take that stance because they’ve decided that a company who cares about fast programming is likely to misuse its Staff-plus engineer. Is that a line you want to draw? Maybe, decide for yourself.

Debug the process

After you’ve draw your lines, next you’ll need to figure out the actual interview process used at the company you’re interviewing with. It might feel like asking these questions could push the company to reconsider your candidacy, but it’s always reasonable to ask the recruiting team and hiring manager for more details about your interview process. At the Staff-plus level it’s almost a point of concern if you don’t ask for more details. Companies want you to exceed, and understanding the process is an essential part of preparation.

The three most important things to understand before you start interviewing are:

1. What are the interview formats, including what are they evaluating for?
2. Do any of the interviews require specific preparation?
3. Who are the interviewers?

Once you’ve answered those, then it’s just a matter of preparation. Take notes about how you want to approach the different kind of questions. Prepare materials for any presentations interviews. Briefly research the interviewers to tailor questions to their background.

This is also a moment to debug if you’re in the right process. If your interview panel is composed primarily of early-career and mid-level engineers, it will rarely generate a Staff-plus offer; the panel will be ill-equipped to evaluate your strengths and folks are often resistant to offers more senior than their own. If there are no deepdives into your previous accomplishments and no presentation opportunities, it’s similarly hard to demonstrate the expertise to support a Staff-plus offer.

If it’s the wrong loop but you’re exceptionally good at whatever the loop does measure, then you’ll potentially get a Staff-plus offer anyway. However, if you’re less confident in those incidental measures, then raise your concerns politely and constructive, perhaps point them at resources around designing Staff-plus interview loops. Don’t allow momentum to pull you into a process that doesn’t support your goals.

It’s particularly valuable to understand is when leveling happens within the company’s progress. Some companies advertise roles with level-specific titles, which lets you apply directly to level you think is appropriate. If you’re hoping for a Senior Engineer role, then apply for the Staff Engineer job posting. However, many companies use those as provisional titles and finalize them later; other companies are quite rigid. The only way to know is to ask.

It may feel very unnatural to take more control over your interview process, and in theory you might miss out on some opportunities this way, but that’s a good outcome: your goal is to find the best available leadership opportunity, not the first available opportunity.

Finish well

Even if you skate through the interview process, always negotiatie the details, and remember to finish well. Brief your references on the role’s details. Send followup emails to interviewers. Accept the offered sell chats and bring thoughtful questions into them. In this case, the last mile is the easiest if you take the time to walk it.

Notes on compliance tools.

Recently I’ve been chatting more with Chris Stobie, Calm’s Engineering Director of Infrastructure (obligatory, come work with us!), about how we can get more value from our compliance work. As any company starts selling and partnering with larger companies, the size and quantity of security reviews increase, and fulfilling some of the better-known security regimes is the most reliable way to reduce that overhead.

To learn a bit from the community, I tweeted out curious if folks thought highly of the various related compliance tools and platforms out there, and I've collected the notes here.

Have any of you used something like eg Vanta to reduce overhead of SOC 2, ISO 27001 and HIPAA? Better than ye olde spreadsheet? How *much* better?

— Will Larson (@Lethain) November 19, 2020

Some of the considerations to think about:

• Are you willing to use the compliance work as an opportunity versus just an obligation? If you treat this as purely a burden, you'll get very little out of the process.
• Which regimes do your (enterprise) users want from you?
• Multi-tenant versus single-tenant – how well protected and isolated is your compliance data within these platforms?
• How much of the verification is automated versus just a checklist for you to follow?

Most commonly used tools:

• Vanta
• LaikaHQ
• Tugboat Logic
• ZenGRC from Reciprocity Labs
• SecurityProgram.io
• Drata is a company in "stealth mode" aiming towards this space as well

Open source tools:

• IBM's AuditTree
• StrongDM's Comply

Some useful links and such from the responses:

• John Kodumal – SOC2 is not a 4 letter word
• The Developer's Guide to SOC 2 Compliance
• Using Github Protected Branches to Make SOC 2 Audits Suck Less, and you can read Github's own docs on protected branches
• Lessons learned on our journey to SoC 2 compliance - Clubbhouse

Mailbag: Advice for someone five years into their tech career?

I recently got an email asking for some perspective that was general enough that I thought it might make more sense to answer as another mailbag post. The lightly edited core of the email was:

1. What advice would you give someone five years in their tech career?
2. What should someone focus on in the world of fast-evolving tech?
3. Also, how did you find the right mentors in the course of your career?

These three questions relate a bit, but are sufficiently different that I’ll answer them independently.

Advice five years into tech career

If I could only give one very actionable piece of advice, it would be to adopt the Promotion packet technique, aka Julia Evan’s brag document. Conversely, I can also ramble on this topic for a while.

When you talk to folks later in their career, they’ve spent so much time crafting their career narrative that it can be hard for them to remember which parts of what they’re saying are real and which parts are the story they’ve practiced telling about themselves for the last decade. For example, earlier this year I tried to write up my own career story in a way that acknowledges just how much luck and privilege has played a part in my accomplishments. It’s still a narrative–we’re all public figures to some extent these days–but hopefully at least a relatively honest one.

The best general career advice I’ve written is A forty year career, which tries to think about what our careers can be if we focus away from liquidity events and towards fulfilling work. Of course, this advice is harder for some folks to follow, who experience a tech industry that is indifferent to their continued participation: "How would I approach my work differently if focused on growth and engagement, and if I measured eras not in equity and IPOs but instead in decades? I’d focus on a small handful of things that build together, with each making the others more impactful as they compound over time."

I also wrote up a more generic article on career advice before that, Some career advice, which isn’t particularly good, but has some generic relevant advice, a few that are particularly relevant for someone ~5 years into their career:

• “You’re just getting started. Particularly in tech in the Bay area, you can find yourself in some companies and jobs where you feel like an old-timer even though you’re only ten or even five years into your career. Although it certainly feels that way, rest assured it is not the case. You’re still just getting started, there is still more to learn and new things to do.”
• “Decisions aren’t permanent. Increasingly I believe that there are very few trapdoor decisions. Do you want to become a manager? Go for it. It’s not a neutral event to return from management to engineering, but it’s a very common operation that many folks do successfully.”
• “Learn what you can learn everywhere you go, but don’t stay where you aren’t valued. If you’re lucky, at some point in your career you’ll find a company that values you much, much more than previous ones. Typically this will be because you’ve finally found a place where your values are mostly aligned. If you don’t feel that way, know that there is another company out there, somewhere, that will align with your values and they will value you much more as a result. That said, it takes a while to find such places, so don’t wait to learn until you find one, be a deliberate learner everywhere you go.”
• “Build a reservoir of prestige. Once your resume “looks right”, you’ll have more and easier access to interesting opportunities, including second opportunities if something you try doesn’t end up working out. Even if you enter the industry without much prestige, this is something you can deliberately build over time by working at increasingly well-respected companies, writing online, maintaining relationships and speaking at meetups (perhaps graduating eventually to conferences).”

All of those have been important lessons for me, and in particular, the last two have helped me manage my mental wellness more effectively as I’ve come to understand them better.

Focus in the fast-evolving world of tech?

First, a tangential answer. Titles do matter and it is useful to spend time pursuing them to a limited extent,, especially for folks who don’t look like the stereotypical image of a software engineer. However, it’s also important to remember that titles are not enough. It’s easy to get a senior title in a such a way that you end up stagnating.

Another indirect answer is that unless you have a very clear passion, I’d recommend against specializing too much at this point in your career. I’ve seen folks get framed into a given role and be unable to escape that role for decades. Part of that is, probably, their responsibility for not being more creative in how they switch roles, but there are real forces in play that create career inertia. It’s particularly hard to overcome the financial aspects of that inertia when you have significant responsibilities that make it hard to take a temporary financial hit.

As a final indirect answer–then I’ll actually answer the question–I’d recommend that folks be very cautious about moving from core engineering roles into what I’ll very loosely describe as adjacent roles like TPM, PM, Engineering Management or SRE. If you struggle it can be hard to transition back, but even moreso if you thrive it’s even harder to transition back–how do you step away from all that success? My general advice is to avoid changing roles until you’ve finished what you want to accomplish within your current role–you won’’t always retrace your steps later.

Alright then, so what should you actually focus on?

1. Do more and different interesting and difficult things - these will stretch and shape you in remarkable ways. It’s often the specific projects more than the company mission that will create the most opportunities for growth.
2. Pace yourself - if you’re burning out, fix that. You’ll get the promotion in a year anyway. If your company is fundamentally designed around burning folks out and it’s harming you, leave. You’ll find a better opportunity and if you wait you’ll be a shell of yourself when you’re interviewing or take months of unemployed recovery time.
3. Work on what matters - spend more time working on things your organization values and less time fighting your organization about things they don’t value. If something is very important to you, it’s usually better to find a company that values those things than to try to force a cultural change as a software engineer. There are shades of grey here, of course, if it’s a modest change, then of course try to create that change first.
4. Build a network of peers - peer relationships are the secret enabler to better jobs and success within jobs.
5. Build financial resilience - saving money early in your career creates flexibility for you and those you care about, forever.

Like most advice, this is pretty generic, but if folks ever want more concrete advice, I’m glad to give my thoughts, although what you probably really want is advice from someone who actually knows you and your context, which brings us to the third and final question...

How do you find the right mentors?

Last year I wrote about the strategies I’ve found for Meeting people, which is some general advice on network building. In terms of actually finding mentors, my experience is a bit like what Ritu Vincent’s shared in her StaffEng interview, "What’s been most impactful for me is having a lot of people who I think of as mentors, usually friends, former managers and folks that I’ve worked with. I have a decent number of recurring monthly lunches, coffee chats and dinners with people who’ve worked with me in the past, know me, and I trust. It’s those conversations about career challenges and growth that have gotten me to where I am in my career."

I’ve never found the idea of a capital M Mentor to be super useful for me, but there are dozens of folks in my life who I go to sometimes to get their perspective. The two things that have been most useful for me are meeting folks by working together at medium to large companies (Stripe was… maybe 400 people when I joined an ~2,000 when I left. Uber was ~1,000 when I joined and maybe ~8,000 when I left, Yahoo was 13,000 when I joined and, ahh, 9,000 or so when I left, but I was so early in my career that I didn’t meet many folks), and forming various learning circles and communities. For example, early this year I formed a CTO/VPE learning circle (going really well, although not accepting more folks personally, would strongly encourage more folks to form their own groups like this that meet 1-2 times a week for 1 hour to discuss challenges together) and more recently a TechWriters discord (which isn’t really working yet, pretty low engagement in there, but a supportive place and have met some really impressive folks ambiently through it).

If you are more of a Mentor type, my best advice would be to send a really concise, thoughtful question to a dozen folks you look up to, and then if they respond send them another similarly thoughtful question six months later. Do this three or four times and you have a mentor who does have your context and appreciates how thoughtful you’ve been about their time, and most of those folks at that point would be glad to have a 30 minute video call where they wouldn’t have been engaged enough earlier on.

That's all for now! Hope to hear your thoughts on Twitter at @lethain!