How to make better decisions

2026-07-13

I published an internal memo on "How to make better decisions" last year. At the time, I was worried that we were hiring too quickly and communication costs were skyrocketing. We had 14 people.

Today, we added 14 new people in a single day, and this memo has become an interesting time capsule for what seems like a very different era of Ivo. I'm sharing the original memo for posterity.

Originally published January 23, 2025

tl;dr

• This is a really exciting time for our company. We're bringing on a lot of new people and we will need to be more thoughtful about the way we work with each other.
• If we want to make better decisions, we need information transfer within the company to be as frictionless as possible.
• Some ways we can improve context for decision making include (1) Reduce Slack DMs; (2) Writing Culture; and (3) Being Close to Users.

Not too long ago — as late as June 2023 — Ivo was just three people. This made communication extremely efficient. We had almost complete context for every decision we made.

Then, we added a fourth teammate. Although we only added one more person and increased our team size by 25%, we actually doubled communication overhead by going from three lines of communication to six.

Still, things were pretty efficient! It helped that we worked out of a dining room table in an Airbnb, which meant that every conversation we had was practically a company All-Hands (now we need to schedule them a week in advance).

Times have changed. If we only include full-time employees, we're now at 91 lines of communication.

If we include all staff (~25 people) we're at 300 lines, and by the end of the year (~75 people) we'll be at 2775 (!!) lines. The increase in communication cost doesn't scale linearly with headcount — it scales quadratically.

This is a huge cost, and goes a long way to explain why large companies seem to move at the pace of a beached whale *cough* *cough* *[REDACTED]* *cough*.

This has two important implications:

• The bar for each hire must be extremely high, because (among other reasons) they must justify quadratically increasing our communication overhead. Our default position for any candidate should be they are a No unless they are insanely great.

  It is not enough that a candidate would contribute positively in some way to the organization; they must overcome the communication cost they add. We should never hire someone because "they are a B candidate but we need to fill the role ASAP", or the more common "I don't see anything wrong with X candidate, therefore we should give them an offer".

  We need evidence of (potential for) greatness; the aforementioned approach gets the burden of proof backwards.

• We should work actively to reduce communication cost and improve information sharing so we can make better decisions.

I'll share my thoughts on (1) one day in a separate memo. The rest of this memo will be focused on Point 2.

Context Sharing

Why should you care about having more information / context?

Every day, you need to make hundreds of micro-decisions. It is impossible for anyone to micro-manage each of these hundreds of decisions for you; you, as the person actually doing the work, need to exercise good judgement.

Good judgement requires a number of ingredients, including intelligence, creativity, experience, clarity of thought, strong internal mental models, some non-conformism (or willingness to "think outside the box"), courage (to override fear-driven lizard-brain style cognitive biases) etc.

But the most straightforward, actionable way you can improve judgement is by having more information to see as many branches in the decision tree as possible.

Good judgement is helpful but insufficient; in many cases, it is more important to be decisive than spending too much time pontificating about the correct course of action. We will very rarely have complete information for every decision.

Most decisions are reversible, and moving fast forces us to make contact with reality more often, thereby giving us more opportunities to course correct where necessary.

Although context is obviously helpful for big strategic decisions, it is even more helpful, in the aggregate, for the hundreds of day-to-day micro-decisions. Context helps you because:

• Your instincts will improve
• You'll be able to work faster; you'll be more confident and decisive
• You'll be able to make better decisions
• You will be trusted with more autonomy

How can we improve context sharing?

Reduce Slack DMs

Strongly bias against using Slack DMs. Public slack messages are helpful for context sharing:

1. Makes conversations persistent and linkable.
2. Opportunities for helpful, serendipitous interactions.
3. There is no additional effort required from the sender.
4. If someone needs to get pulled into a task, they have a full history of the relevant state in that thread.

Much of this is taken from Stripe's policy on scaling email transparency, which I suggest reading: https://stripe.com/blog/scaling-email-transparency

Writing culture

We should be in the habit of writing stuff (both short-form and long-form). Writing is helpful because:

1. It encourages us to think through our perspective and understand it deeply.
2. It's shareable, reference-able, and scalable beyond the people who happen to be within a 20-feet radius of you at the time you say something.
3. People can think through your perspective and respond after giving it some thought rather than reflexively saying the first thing that comes to mind.
4. It's less disruptive to flow state, since the recipient can decide when they want to be interrupted.

For example, in writing this memo, I can communicate my position on this topic to all employees and future employees; because my writing is not ephemeral, I can just say "read the memo!" rather than repeating the same speech.

In-person communication is superior to written communication across many dimensions, so we (obviously) shouldn't discard it — but at the moment we are at least slightly too biased towards in-person conversations rather than written.

Being in the office

There's not much to say on this other than that being in the office obviously helps with context sharing. We shouldn't overly rely on being in the office as a crutch (all points about Writing Culture above still apply).

Too much context

It is possible to share too much context. The main way this happens is when people write or say long, rambling stream-of-consciousness thoughts in a misguided attempt to include as much information as possible (I am often guilty of this).

Good communication is concise. Think about the "user experience" of your communication, where your colleagues are your users — how easy have you made it for them to understand your Ask / Perspective / Whatever, and action the request you've made of them?

Expending effort to make your note concise and readable with thoughtful presentation takes more time — however, the cost of taking shortcuts is that you force your colleagues to expend additional time and cognitive effort to understand you.

There's a good article about being concise here: https://newsletter.weskao.com/p/how-to-be-concise

Being close to our users

Understanding our users will help us make better decisions. Do we really understand their problems? Their hopes and dreams? Their deepest desires? Their opinion on airplane food?

A good way to start developing better instincts about our users is to (a) join customer calls; or (b) watch customer call recordings through Sybill. If you don't have a Sybill license and aren't able to view call recordings, let me know and I'll handle it for you. I suggest aiming to listen to at least one a week, particularly if you are in a non-customer facing role.