One-on-ones with executives | Hacker News Reader

One-on-ones with executives

lethain.com

149 pointskiyanwang73 comments

One thing I've noticed is that a lot of colleagues don't know how to give good situation reports. One common error, especially amongst engineers, is to start from first observations and work towards a conclusion. This is exactly how one should think about technical problems, but it's not a very effective way of communicating, especially when you're trying to relay information up a chain of command.

Here's how I learned to give a situation report during my brief stint in the armed forces:

1. "I am" (identify yourself & other parties involved; give location where appilcable)

2. "I see" (What is on your radar? What's the problem? What situation is developing? Which milestone have you reached?)

3. "I'm doing" (How are you responding to what you see?)

4. "I want" (How can your interlocutor help? What resources do you need?)

The mnemonic for this is rather funny: "I'm lost. I can't see shit. I'm doing fuck all. I want to go home."

I think it works rather well in civilian life, too: "I'm working on $FEATURE. I'm noticing that page load times have doubled. I'm caching the results to try to reduce that a bit. Could Bob have a look at the database indexes?"

This seems like good advice. This is pretty close to the "STAR" framework I've seen used(Situation, Task, Action, Result) - explain the context briefly, what you're doing, what you're doing to accomplish the thing you're trying to do, and what the end result of it all is.

> a lot of colleagues don't know how to give good situation reports.

Another thing that can help, both written and in face-to-face communication, is using the Inverted Pyramid. Let's say the person in your 1-1 has an emergency and you have to cut it short after 5 minutes. In those first 5 minutes you want to get the most important information across. In the next 10 minutes, you give supporting details, and in the final 15 you can geek-out on the nitty-gritty.

I like the analogy of math proofs. It isn't an account of the discovery process; no reader of a math journal is after an account of the author's inspiration and thought process, save that for your bio. The proof is the finished product of all that work.

Execs only care about the proof. They're not asking out of curiosity.

Summarizing up-front is hard because it works the opposite of how many peoples’ brain works; if you don’t have a summary drafted, one good way is to run through everything verbally and then summarize at the end. This also plays into the natural narrative-creating tendencies.

So it’s good to recognize that this is a cognitive habit and it might require practicing a different approach, or preparation.

Another military term I’ve heard for written comms is “Bottom Line Up Front” (BLUF) which translates to a proactive TLDR. Similarly, this is a very useful tool for helping people consume your written comms; it allows readers to figure out if the content is something they need to deeply engage with or skim, rather than forcing them to skim the whole thing to figure that out for themselves.

The common theme here is that there is lots of value in providing a concise summary, so that recipients have to do the minimum amount of work to extract the first level of detail of information. This allows the first level of detail to travel further in the org and means the org is going to be better equipped to make good decisions.

>Another military term I’ve heard for written comms is “Bottom Line Up Front” (BLUF)

Yup! I've also heard this phrased as "start with the punchline, then explain the joke".

It works fine for written communication. In case of a long email, write a tl;dr and cut-paste it to the very top. That's what I do.

100% this.

And if your email includes an ask of any sort from the recipient, be sure to make the ask in the very first line (and summarize it in the subject line).

Then spend the rest of the email with the details around the ask.

I was taught basically this same method as the "Princess Bride" plan:

Hello, my name is Inigo Montoya (who I am)

You killed my father (why I'm reaching out)

Prepare to die (my ask / expectation)

Ha! This is very good.

Nobody cares who you are. The better approach is:

1. prepare to die (gets their attention)

2. because you killed my father (explanation)

3. I am Inigo Montoya (background info)

Beware of things that "work" in movies. I've been led astray by that too many times.

BTW, ever wonder why movies start out with an action sequence that often has little to do with the rest of the movie? It's to get your attention. Let's face it, you and I watch the first couple minutes of a movie to decide if we want to invest more time in it or click to the next Netflix movie. (Do we care who the director is? Nope.)

Much in life works the same way.

I think you may be missing the point. It's a mnemonic, not a rationale.

Mnemonics almost always imply an order. My point is the order is backwards, even though people naturally assume that the first step is introducing oneself. They naturally assume that their name is the most important thing because it is the most important thing to them.

But for other people, one's name is the least important thing, because of course what it most important to them is what affects them.

Once one realizes this principle, you'll see it in action everywhere.

Who is involved in what tends to be very high on the list of important parameters.

To your point, though, you'd of course tailor this to your audience. For example: you might say "marketing" or "the engineering team" instead of "Tom, Dick and Harry".

If you're a celebrity your audience has heard of, yes. Otherwise, no.

Agreed. I think your counterpart is too focused on the person's _name_ rather than the contextual _role_ that the person occupies.

If someone is coming to me with a question, it is extremely helpful to know up front who they are (with respect to their role, not so much their name) in order to immediately start narrowing down the relevant contextual parameters that will be framing my understanding of their problem and my response. I don't want to read a wall of text while thinking of how to respond from an engineering perspective, only to discover at the end that the person lacks technical aptitude.

I volunteer as a CERT (community emergency responder, green helmets) and this is how we're trained to relay information to the incident commander. It's been eye opening to see how much you can do with just a weekend of training. And how it fits into everyday life.

Would you tell us more how that training translates in business/management? Are there good training materials we could look at online?

Now do an OPORD brief

Saw this an hour ago, just used it with my skip-level, worked well. +1 lol

I'm so glad to hear it! Enjoy your new powers! :)

Agree. But in my experience, you have to bring the ask/need/most important detail to the first line.

1. Greeting, of course 2. The ask or most important detail, standing on its own line. (The exec can rapidly say yes or offer feedback if they agree on the face of it, or read on for more detail.) 3. Then do the I see, I'm doing, I want, etc in more detail.

I think execs managing a tremendous workload appreciate if you can invert to this "thesis first before anything else" style—it took me a while to learn this, and I also appreciate it when partner teams who send stuff to me for review follow this style. I think boils down to time management, triage, and giving rapid yes/nos, but you still need to show your work, but if you make your email harder to action it'll get delayed in processing or even forgotten.

Of course, relationship management matters too.

I think we're in agreement. To be clear, there is no expectation that these items arrive in any particular order. What is important is that they all be present. Ordering is situation-dependent.

So to your point, yes, this is typically how I would write an email. In fact, the "I am" part of an email is often adequately covered by the 'From' address.

On the radio, in contrast, I would explicitly say something like "This is four-two, actual" before proceeding with the rest.

I think the "Loyalty Check" meeting, despite its name (and claim in the blog post), is a meeting that should happen at well-run companies. There are few things worse for a company than for layers of mid-senior leaders to be not bought into key initiatives. Checking for/ensuring/reinforcing alignment with these key initiatives is one way how strong companies out-perform average or weak ones.

Rename "Loyalty Check" to "Alignment Check", change nothing else about the meeting or intentions, and it's a positive thing for companies.

This is absolutely true. Checking if their reports are going to be impediments to their goals is critical for managers, especially if those goals were themselves aligned with THEIR managers. You don't want to assign significant responsibility to someone who might drag their feet on something.

Agreed. These meetings can certainly end up being as cynically founded as the version posed in the post, but they're often also useful opportunities for execs to make sure that communication of the ultimate intent that led to the proposed work has made it through to the folks who will be tasked with doing the work. Understanding the business goal of the work makes it much easier to accurately weigh the inevitable tradeoffs that come up in projects without needing to run everything all the way back up the chain.

Hmmm, it seems to me that if an executive is reaching across the organization for that kind of thing, that's a bad sign. It means the executive doesn't trust their leadership team (in the case of a skip-level) or their peer organization (in the case of a dotted-line meeting).

That said, bad signs don't always mean bad things; as the author indicated a "Loyalty check" can range from "Just wanted to check in on how things are going and hear some detailed updates straight from the folks at the coal-face" (very healthy and normal) to "So-and-so is getting ready to betray our entire organization and I want you to plug this anonymous USB key into their computer".

"Trust, but verify"

If the executive is consistently reaching across the organization that's a bad thing. If they do it once in a while to ensure they have made good staffing decisions, that's a good thing.

> Trust, but verify.

I don’t like that “but”. It implies trust and verification are opposites. To the contrary, verification is there to ensure that trust is not hurt in case of a mistake, misunderstanding, or whatever. “Trust and verify” is much better.

Thank you for this. "Trust but verify" never made any sense to me at all. If you have to verify, then there is no trust.

Ensuring that there hasn't been a misunderstanding makes a lot more sense. "Verify" is still a misleading word in that equation, though.

I got the attention of an exec at a meeting a few years ago when I asked about opportunities intra-office and wanted to apply to some positions at headquarters (I worked from a satellite office). This was pre-COVID and aside from the public conversation with the exec in the meeting with 200+ people, I’d only hear from him via the chain of command.

I got encouraged to apply to a few jobs at the main office and when I talked to managers there, everyone acted strange and uncomfortable about it and it was obvious nobody wanted someone working “remote” on their team. Eventually they said “oh we’re not hiring for that position this year”. Drastic way to keep remote people out.

But the exec never heard from me or solicited feedback so he wouldn’t have ever known this. So his initiative was dead in the water.

This was when I was more junior. Today I’d just have shot him an email giving him a status report on my experience but in my experience a lot of “ground level” folks are terrified of interacting with execs 5 levels above them in the org.

A follow up meeting with me would have definitely revealed what was going on and he could have taken some action.

Many execs lament junior employees being afraid of them. I bet you could have safely sent that email.

Yeah, the term "Loyalty Check" gives it a weird connotation. There are some executives that just want to hear "Yes" to their initiative, but, (1) the good ones don't, they prefer to hear corrective feedback late rather than not or all, and (2) if you offer corrective feedback and it isn't taken into consideration, it helps inform you about the kind of executive your working for. Loyalty should run both ways.

Had a "recruiting" call with a CTO yesterday. Halfway through the call he tells me 1) they're not recruiting, and the position I applied to doesn't actually exist, 2) they're going to run out of money in 15 months, and 3) he "just likes to meet people in the industry" and maybe they'll open a position up. He didn't do anything to steer the conversation after that and it just ended awkwardly.

I think people deify execs too much. A lot of the time they're just as clueless as the rest of us.

I think treating "execs" as a category upon which judgment can be passed is a mistake.

Every company has different standards. Execs as a general population aren't genius or clueless. You have to get specific about the sub-group.

For example, execs at Amazon are likely to be significantly above average in competence. Execs at a 6 month old startup might be anywhere across the spectrum, hard to know.

100%. Execs are people too. Some effective. Some not so much.

That being said, I would use this article to understand 1-1s with effective execs.

there's a book written in the 60s called the Effective Executive which I enjoyed reading.

If a CTO at a company with only 15 months of runway is just doing random recruiting calls then rest assured they have little significance in the company, or the rest of the company has resigned to letting the business fail.

Isn't it pretty normal to do recruiting with a 15 month runway?

(Obviously, not normal to do recruiting if there are no positions open)

15 months seems pretty dire imo. The CTO should probably be spending time figuring out what's going wrong. Recruiting with only 15 months of runway feels like they're trying to distract themselves from other fires. This is especially true given the other details provided (not actually hiring, no position).

15 months seems pretty standard for an early stage startup.

Not in my experience, unless you're very close to raising your next round. 20-30 months is about what I'd expect from a Series seed company in between rounds. 15 months is essentially 1 year. It's going to take 6 months to raise more money from start to finish. That means your actual runway is closer to 9 months. Now of course, they could be excluding current and future revenue, which a lot of companies leave out from runway (rightfully so), but if not, 15 feels low.

As things change during this recession, I could see many Seed stage companies pushing to operational break even. If you can keep your annual costs below $1m, and scale to $1m in ARR, you're going to be far better off than companies that have to raise to keep going. If you can grow and sustain the business for another 24-30 months, you'll avoid the game investors are playing now of "let's see how low we can get this valuation".

It depends on the industry and the level of the conversation. If you're in a specialized field in which as CTO you are not an expert, and you're speaking with a competitor or at least someone else in the field, a detailed interview can offer quite a bit of information. It can be used to validate your approach, your tech stack, etc...

Of course typically when you play that game you don't actually admit that you're not hiring and you're running out of cash.

> Try to figure out why the meeting is happening before you’re in the meeting. It’s much easier to prepare if you understand why it’s happening.

As a general rule for Executives, whenever you want to talk to ICs even if Senior ICs, _always_ provide a one-liner on the topic.

So many times I had the secretive email or IM from VPs or CTOs "Can we talk? When is a good time for you?".

Often they have an agenda in their heads but not expanding on it is anxiety inducing for someone working under you in the hierarchy.

It's similar to that rule of thumb that you don't joke about firing someone if they are your direct reports (or even if they are not really).

If you don't have a relationship with the executive you should ask for an agenda and clarity on the goal of the meeting. You should say "you need the context so that you can prepare and ensure a productive meeting". Even if there is a one or two sentence description you should ask for more info. This does two things, first it helps you prepare and 2nd if they don't provide an agenda you get some forewarning that something is going on. Worse case they say no, best case they see you habitually doing good prep work.

I disagree with this advice. At least in the US, I think it could easily be interpreted as anxious or rigid. Or even just make you seem too junior. Leaders need to be able to handle ambiguous meetings.

if you flip the script you'd never ask an exec you don't know for a meeting without giving context. This is common courtesy if you do it without seeming demanding.

"Looking forward to our discussion. Can you give me a bit more context for the meeting and an agenda? This way I can be sure to have enough time to properly prepare. Thanks..."

would you say no to that?

This is a perfectly reasonable email to send, with the expectation that the EA may well ignore it.

No, but I'd likely say "I haven't met with you in several months, and I just would like to check in with you how things are going. What are your concerns, what makes you happy, what are we missing. This is intentionally freeform, with a focus on whatever is important to you".

There won't be an agenda, because it predetermines possible outcomes.

But it's probably worth considering that even skips for exec-level folks are usually quite senior and should be able to handle an ad-hoc conversation. It's not an approach I'd choose with more junior folks.

The hypothetical reply you gave is still useful, IMO. It's important to distinguish between "there is an agenda, but it hasn't been communicated" and "there's no agenda, just an open free-form conversation" cases.

It would also be good to ask your manager for insight into the meeting since they may already know, and if not then they should be able to find out.

This is an excellent article on the nuances of corporate politics without assigning judgement to it - it's simply the nature of the beast with corporate and has some very clear laws to it when viewed at the right angle.

Nice one -- will look at some of the author's other posts. :)

If you haven’t read Will Larson’s writing before, congrats - you have just stumbled upon lots of great content! Not many people write content specifically targeted at the Senior->Staff transition.

He has a book called Staff Engineer which is partly “best hits” from the blog and partly expanded material, which is a good place to start; I find it a bit more focused and well-ordered than the blog (which I also dig, to be clear).

Will absolutely look into the Staff Engineer book; personally prefer dead tree books to anything digital if there's the option. Thank you sincerely for giving me the heads up!

One small point on which I'm sure the author would agree is that an executive meeting can shift around between the three. Especially a pre-scheduled skip-level.

It can start with some Mentoring, the executive might hear something interesting and do some Fact Finding, and then become concerned enough to do some amount of Loyalty Check.

IME, this rule is the one that will keep you grounded through such an experience: "Also try to be kind: my rule in this situations is to always assume what I say will be inadvertently shared with the person who it’s about."

You might call it the Mercury rule; right next to Golden!

> Try to figure out why the meeting is happening before you’re in the meeting.

Any meeting invitation should make it clear what the meeting is for, so people can come properly prepared. And for group meetings (obviously not an executive 1-on-1), knowing the agenda might allow you to skip the meeting altogether instead of wasting your time.

Internal meeting culture at most tech companies is absolutely unhinged. I didn't _really_ notice this until I started my own company. Before that I was an executive at a startup, and having a day full of meetings was par for the course. Now that I run my own company I can say that 99.99% (maybe 100%) of internal meetings are unnecessary. I'm using the word unnecessary instead of useless as I think internal meetings can be productive, but in almost every case can be avoided. Instead, rely on internal communication and writing to discuss ideas. The feedback isn't immediate, but it doesn't have to be. Decisions can be made quickly without having a meeting. You just have to set your company up so that they don't rely on quick decision making.

> I can say that 99.99% (maybe 100%) of internal meetings are unnecessary.

Absolutely.

And there's a corollary rule of thumb -- anything useful in the meeting will happen in the first 15 minutes. The rest is just time-wasting.

Yeah... I'll never have a 1-on-1 with an executive. Although I did supposedly win a team lunch with my company's CIO. Their admin has yet to set that up and it's been like 5 months, so I'm guessing that won't happen.

They’ve forgotten, but if you reach out to the admin to remind them, odds are extremely high that they’ll make it happen.

Oh, we've talked on a few occasions about it. We even settled the details of it.

Frankly, I don't care. I don't see the benefit to the team eating lunch with the CIO. I'm not special. I won't get "discovered" or whatever.

Maybe that attitude is why you haven't been "discovered" ;)

Take the meeting, it'll be good for your career.

Nah, it doesn't matter. They only care about who puts in a ton of extra hours.

As an exec, I don’t care in the least about hours. I do care about results and outcomes, of course, but if you achieve more for the company in 2 hours per week than what someone else does in 40, you are more valuable to the company.

My company is big on "engagement" and they measure that in extra hours.

Ugh. I think a lot of engineers could deliver more in 30 well-focused hours while being well rested than those same engineers could do in 50 or 60 hours per week. More hours for creative work (beyond a certain point) doesn’t generally give more value.

I am an exec at my company. I really do not care about the hours you put in. I care about the results that get out. Basically, I care about what you are able to EXECute. I will admit tho that it is easier to do more when working more, but the time is not what I measure.

My company is big on "engagement" and they measure that in extra hours.

If you speak with executives, you'll find that the explicit game is not the real game. In other words: if you find yourself being measured by the official measures, you are already losing.

It's easy to be cynical about this, but it's a universal truth, even outside of work life. Knowing the difference between the official game and the game actually being is part of being competent at whatever it is you're doing. Often, the real game is better, healthier and more productive than the two-dimensional rulebook you're given.

That really isn't true. I second the opinion that you should take that meeting. It's part of the job. It's how you make sure you're working on the right thing, and that execs know it.

That said, it's totally fair to not want to climb the latter beyond a certain point. But, you seem a bit bitter, so perhaps that's not your case.

The author omits that these meetings are extremely dangerous for technical staff, and must be treated as such. The most likely outcome of such a meeting, if there is any, is negative.

Most importantly, any information requested should be provided only after whatever slant is expected has been identified, and then only such as to confirm that slant.

It helps to think of corporate management as direct analogs to communist party representatives. They cannot send you to the GULag, but they can fire you, and will, in a heartbeat.

I've been through hundreds of one-on-ones, and I hate them to this day. They're the sort of meeting I dread the most.

Mostly because I never know what the the executive is wanting to get out of the meeting, and have never figured out how to find that out.

Ask? If you dont know what the meeting agenda is, its a waste of time. If they're not sure tell them what you want out of it. If you really dont care about anything like career progression or finding out about the organization I'm sure the manager would be glad to stop having one, but its your chance to shine and/or find out what you want.

I've asked. The answers are always vague. I don't know what I want out of it. If I want something, I'll have already reached out anyway, so it seems to me that the meeting is really for them.

> its your chance to shine and/or find out what you want.

Except, of course, for all the other communication that happens!

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