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:

- Example Call For Proposals submissions.
- How to partner with an executive assistant.

Example Call For Proposals submissions.

If you're looking for a more complete take on this idea: speakerline.io.

I was chatting with a couple folks recently about submitting a talk proposal to TheLeadDev, and it reminded me of something that used to prevent me from submitting talks: I had no idea what a good Call For Proposal submission looked like.

At Stripe, both Julia Evans and Amy Nguyen were kind enough to host recurring sessions where they helped folks craft their first submission for a tech conference CFPs, which – to the best of my memory – resulted in every one of those talks getting submitted, accepted and presented at a conference. This was amazing, but not everyone has a Julia Evans or Amy Nguyen dropping wisdom on their CFP submission, so I started wondering if I could at least collect examples of successful submissions for folks to use as a resource.

First some examples, then some advice on the process.

Examples

All of these were submitted for a Call For Proposal and accepted at a conference. There are a few of my own and a bunch shared by folks on Twitter:

• Big Data at the Intersection of Typed FP and Category Theory which Long Cao gave at Typelevel Summit Boston, March 2018
• Failure Friday! which Doug Barth gave at DevOpsDays Austin 2015. (Scroll below the slides to see the CFP; see all of Doug's CFPs)
• How Stripe invests in technical infrastructure which I gave at SRECon Emea 2019, and started as this blog post
• How to Mend a Broken Identity which Keavy McMinn gave at Webstock 2016
• Implementing Distributed Consensus which Dan Lüdtke gave at SREcon 2019 APAC
• ITV's Common Platform v2: Better, faster, cheaper, happier which Tom Clark gave at DevOps Enterprise Summit 2019
• How we un-scattered our DNS setup and unlocked new automation options which Dan Lüdtke gave at SREcon EMEA 2018
• Managing Uber's Data Workflows at Scale which Alex Kira gave at Strata 2019
• Migrating Github Enterprise safely and seamlessly which Dylan Vassallo gave at GitHub Universe 2017
• Migrations: the only scalable approach to technical debt which I gave at QCon SF 2018, and started as this blog post
• Principles of Awesome APIs and How to Build Them which Keavy McMinn gave at RubyConf 2019
• Service Mesh in Kubernetes: it's not that easy which Lita Cho gave at envoycon 2019
• Tackling Kafka, with a Small Team which Jaren Glover presented at SRECon Americas 2019

In addition, here are a few collections of CFP submissions:

• Amy Nguyen has all her CFP submissions on Github
• Julia Evans also has all her CFP submissions on Github
• Justin Garrison collects all his submissions in this repo
• Speakerline has about eighty CFP submissions as well
• global diversity CFP day has a bunch of great proposals, thanks to Joshua Bezaleel for pointing me towards them

If you have examples, email them my way and I'll add them here!

Process

Before you start writing your submission, identify something interesting you have to say. What's something you've learned that you didn't know a year ago? A topic that's controversial, counterintuitive or important enough that it'll worm its way into folks' heads, changing their behavior just a little bit over the next year?

A lot of folks convince themselves they don't have something interesting to say, but I promise you that you do. (It just might seem boring to you know that you know it really well.)

Once you have an idea, I personally find it extremely helpful to develop the idea into long-form writing. Each of my talks started first as a blog post: (1) "migrations", (2) "investing in tech infra" (3) "evolving process". Writing forces you to develop and structure the idea, and makes writing the summary and outline much, much easier.

Your third step is to find conferences you'd like to talk at. Start by making a list of speakers whose talks have impressed you, then build out a list of conferences they've spoken at. Supplement that list with some Googling and asking on Twitter or LinkedIn. You'll have to do these eight to twelve months before you want to speak, because many conferences close their CFPs long before they start.

As the CFP windows open up for those conferences, write up a submission (be sure to save them all together in a doc so you can tweak and submit for subsequent CFPs rather than rewrite from scratch), and get someone with speaking experience to review your submission before you submit it. Ideally ask a friend or coworker, but you can even just ask on Twitter as long as you streamline the process.

(If you do ask on Twitter, tweet out a Google doc or Gist with the proposal and ask for feedback. Do not turn it into a multi-step engagement where you first ask if anyone is willing, wait for someone to say yes, then fork a copy, ask for their email... this doubles or triples the amount of effort for the person trying to help and makes it much less likely you'll get help.)

Then submit it. You'll find out in a few weeks or so if it was accepted. Even if it's not accepted, I'd encourage you to think about recording yourself giving the talk anyway and posting it on YouTube. Then you'll get the practice, some perspective on what does or doesn't make for an effective talk, and puts you in a better spot to write your next CFP submission.

Conferences without CFPs

It's worth mentioning that there are a fair amount of conferences that rely exclusively on asking folks to talk at their conference rather than drawing from a public submission process.

For example, I never wrote a CFP submission for "Good process is evolved, not designed" talk because I was asked to present. I did write a short summary, but mostly I just sent over the existing blog post that I planned to translate into a talk.

In general, my experience is that if you put yourself out there as a public speaker, then you're going to start getting these sorts of invitations. Start by speaking at meetups and CFP-based conferences, and folks will start reaching out once you have some videos of you speaking that they can watch to get a feel for your style.

Anonymous selection

Many conferences try to improve the quality of selections by ensuring CFPs don't include the identity of the speaker or the company that the speaker works for. On the other hand, many conferences do not do this, and instead are focused on bringing on exciting speakers at exciting companies, believing it will encourage stronger attendance and provide a better experience for attendees.

It's both my personal experience and observation that it's much easier to get started as a speaker when you're working at a trendy company. This is yet another example of how prestige compounds to make everything easier, and if you happen to be at a well-known company, you may want to take advantage of that platform to bootstrap your speaking experience.

If you're not at a prestigious company, you absolutely still can get speaking experiences, but you'll have to be more deliberate at finding an interesting angle. Don't get discouraged, but do recognize you will have to put forth something of higher quality.

Resources

Additional resources for putting together conference talks:

• Nina Zakharenko wrote The Ultimate Guide to Memorable Tech Talks
• Emily Reiderer wrote Notes on preparing a tech talk

Hopefully these examples and notes will help you writing your next CFP submission, and once it's accepted drop me a note with your submission and I'll add it above!

How to partner with an executive assistant.

One of the magic moments you’ll experience as a senior leader is the first time you get support from an executive assistant. Starting at that moment you’ll slowly uncover more and more possibilities that you had – in order to preserve your sanity – intentionally blinded yourself to. It is, you’ll gradually relearn, actually possible to reschedule large meetings, get all those one-off meeting requests scheduled in a timely fashion, and to plan good offsites that bring the team together.

Busy leaders so often drop these sorts of seemingly low leverage tasks, that their organizations are hamstrung not by an insufficiently extraordinary vision but rather by an absence of the fundamentals. Bringing a strong executive assistant onto the team is the most effective way I’ve found to reverse that trend.

That said, it can be unclear when you ought to start hiring executive assistants, there’s a real learning curve to partnering with them well, and it’s common for the executive assistant career path to be ambiguous or absent. Let’s talk through all of these.

This topic is inspired by David Loftesness who brought it up during a recent dinner, where I also learned a bunch from Kimber Lockhart’s experiences. Thanks also to Steffi Hoydich and Jennifer Shorr for reading and suggesting a number of important improvements.

Assistants, administrators and so on

The role of executive assistant goes by a number of different names, and I’ll stick to executive assistant, abbreviated to EA, throughout this piece. I’ve not found any name-of-role distinctions to be particularly consistent across companies except, so I won’t attempt to identify a taxonomy. Similarly, I’ll refer to the folks that are supported by an executive assistant as “leaders.” This is for clarity only, and an entrant into the endless redefining of management and leadership.

When to hire?

The general hiring pattern I’ve seen is that CEOs hire an executive assistant early on, likely before the company reaches thirty folks, but that there is little additional EA hiring until the company gets much larger. Once sub-organizations, e.g. product, engineering or operations, cross one hundred folks, it’s common for companies to add the next layer of EAs. Generally by the time a company crosses 1,000 folks there are five to ten EAs supporting the leadership team.

Most companies never hire the third layer of support even as they grow larger, to the chagrin of folks who are leading teams of hundred-plus nestled within organizations of thousands. Rationales for not hiring vary, most frequently concerns around cost or that hiring additional EAs will create a cycle that requires hiring more EAs. I’ve found that folks leading large organizations without EA support tend to roll their eyes at folks with EAs voting to curtail additional hiring.

The rules of thumb I’d offer up are

1. Anyone leading an organization with more than fifty people should get part-time EA support for offsites and scheduling large meetings.
2. Folks leading more than a hundred should get full-time support, starting with calendaring and extending to a deep partnership.

This is a larger investment than most companies I’m familiar with have made, although Facebook seems to have successfully done something along these lines, but I think it’s a worthwhile investment.

Leveraging support

When you first start working with an executive assistant, it can be hard to figure out what to offload to them. It can also feel weird, since these are often tasks you’ve personally deprioritized – probably because you’ve felt they’re less important than the work you’re doing – and now you’re asking someone to do them for you.

Your homework before you start partnering is to talk to as many executive assistants within the company or at peer companies as you can, try to talk to three or four, and ask them what’s worked for them. Also dig into which kinds of tasks have been most and least effective to delegate. Then do the same thing with three or four folks who’ve been supported by an executive assistant.

Once you start partnering with an executive assistant, your first step is to establish a rapid feedback loop between the two of you. For your first few weeks, you should maintain a daily fifteen-minute meeting at the beginning of the day to tweak coordination based on the day before, align on priorities for the day, and moderate workload. Too much? What can be more efficient or take back for now. Too little? Identify next tasks to transition.

After two weeks, take an hour together to review how the work is going and whether you should reset approach or if you’re heading in the right direction.

Getting a bit more concrete, some sorts of tasks that typically delegate well are:

• Time management - this is both managing your calendar, reviewing time allocation and suggesting improvements (maybe that weekly meeting really isn’t that useful anymore), and also routing requests to maximize focus and minimize interrupts
• Drafting communications - coordinating clean communication, especially for sensitive organizational changes, requires great attention to detail and also ensuring you loop in the right folks
• Recurring meetings - at some point most companies end up with recurring operational meetings, and executive assistants can coordinate the agenda, presenters, timing and action items
• Planning offsites - a great team offsite will gel a team and provide focus in your execution, and an executive assistant can do a great job of alchemizing a general theme into an agenda, a rented room and a date
• All hands meetings - most organizations bring the company together to talk about their work, progress and priorities, and an executive assistant can coordinate the presenters, give feedback on the presentations, run practice sessions, and coordinate execution of the meeting itself

That said, the partnership between a leader and an executive assistant is more custom-fitted than most, and you ultimately you should find the intersection between what the leader needs, what works for both of you, and the executive assistant’s career development.

Being supportive

Executive assistants do a tremendous amount to make their leaders successful, but the social contract goes both ways. Folks whose executive assistants are tremendously impactful approach their relationship as a partnership built on trust and communication. Folks who don’t support their EAs at best get a pair of hands instead of both head and hands, and at worst find themselves rebuilding their partnership with a new EA every couple quarters. While the EA role is to support you, they can’t do that unless you support them as well.

A surprising number of folks get this wrong, so I’ll share the core secret to supporting your executive assistant effectively: support them as you would any other member of your team. Have one-on-ones with them that are about them, not just your schedule. Work with them on their career development. Identify stretch assignments. Give them feedback that helps them grow in addition to feedback that helps the two of you partner effectively.

Leader-aligned or centralized

One of the tricky decisions in designing the role of executive assistants in your company is whether they report to the leaders they support or whether they report into a centralized manager. As is often the case for specialized roles, these different approaches represent a tradeoff between alignment on one hand and career development on the other.

Switching between models is surprisingly disruptive because in the former your first team is the team your leader supports, and in the later your first team is the other executive assistants. Many organizations flip-flop between approaches, which is often a primary source of frustration. Both models can work with proper investment.

In the leader-aligned model – where EAs report directly to their leader – then the biggest challenge tends to be a lack of professional and career development. In the centralized model the biggest challenge is a lack of alignment between leaders and the central organization’s management.

Another wrinkle is whether the EAs support a single leader or multiple leaders. Sometimes you’ll see EAs supporting multiple leaders with very different responsibilities and who have distinct – potentially inconsistent – views on what the role of an EA ought to be. This is a source of considerable stress for folks in such arrangements. One way to reduce that stress is asking your executive assistant to share with you what they’re doing to support any other leaders they are supporting. This has two benefits: first is understanding their workload, and second is that it ends up being an amazing way to learn from peer leaders about practices you might want to adopt!

The model that I’ve found most successful is having the executive assistant dedicated to supporting a single leader who is their direct manager. The EA provides full support to that leader, and limited support to the organization that leader supports. This approach maximizes continuity, creates a clear community and team for the EA to be part of, and also provides support for folks within the organization who often would end up unsupported.

Career development

The most obvious downside of the leader-aligned model is a lack of career path. How do you develop your career in the context of supporting a single leader? I’ve seen a couple different approaches work here, but either way start with the fundamentals: ensure you’re having monthly career discussion in addition to 1:1s that focus on execution.

The first is by working with your manager to develop a career narrative. Identify skills you want to develop, and work together to find projects that develop those skills. Watch the leader you support, understand where they’re spending time, and find the intersection of taking work off their plate and the skills you want to develop. This approach can culminate into a Chief of Staff style role as the organization grows.

Another approach is treating the executive assistant role as a stepping stone role, building expertise and relationships within the company, and after a year or two transitioning into a different role. I’ve seen folks move into business operations roles, program management roles, customer experience roles, and a handful of others. Depending on your personal goals, it can be an effective way to slingshot into a successful role with your internal network and existing business context flattening the new role’s learning curve.

Exceed the precedents

I’d offer two major points to take away. First, most organizations underinvest into making their executive assistants successful, which unsurprisingly makes them less successful. Second, most organizations underinvest in hiring executive assistants, which limits the leverage their existing leaders can bring to the company. Don’t be afraid to buck both trends.

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