Ry Sullivan

Vox pipiare en deserto | CPO @MeetSnappyGifts | Former @cartainc, @Klout, @driveshift, @GoldmanSachs | @dartmouth & @HarvardHBS alum | Proud WV native

[Ry Sullivan @rysullivan]

Learning from the San Francisco blackout today: the @Waymo fleet should get pulled off the road immediately for SF citywide events. Almost all the gridlock on the roads is Waymo cars stuck at intersections. If this were an emergency like an earthquake this wouldn’t work at all.

[Ry Sullivan @rysullivan]

1000 DAYS!!!

What can I say, I’m kinda proud 😝

#nytxw #crossword @nytimes @NYTGames

[Ry Sullivan @rysullivan]

Shout out to ⁦@RecParkSF⁩ for the awesome new stairs at the top of Twin Peaks!

#runSF #SanFrancisco #running

[Ry Sullivan @rysullivan]

My feelings solving today’s #NYTXW:

Ugh, this is going to be a slog…

So that’s interesting…

OK, that’s kinda impressive too…

Alright, this is seriously COOL!

Major kudos to @davidkwong for an impressive, devious, and fun grid. Hat tip to you, sir! 🎩

[Ry Sullivan @rysullivan]

I ❤️ Arnie Slot.

[Ry Sullivan @rysullivan]

I guess my wife and I are one of the last people to walk on the bouncy walkways of @flySFO’s Terminal 3 after our late night arrival Monday night. It’s closing this evening, and we’ll miss its bouncy novelty after long trips back to the city. 🥲

https://t.co/svhHnSKGi3

[Ry Sullivan @rysullivan]

My hometown is an #NYTXW clue! 🤩

[Ry Sullivan @rysullivan]

Who could have predicted this…

[Ry Sullivan @rysullivan]

@PeterJ_Walker Or why not make abandon the alphabetic naming convention altogether for something more fun? “Series Awesome” or “Series Get Our First Customer”? Simple sequentiality is boring!

[Ry Sullivan @rysullivan]

I miss away goals.

#UCL

[Ry Sullivan @rysullivan]

Everything about the rental car business still feels like a scam. Hidden fees, extra extra insurance, inventory switcharoos, etc…. How has this not been fixed?

https://t.co/zdDuvYsB7n

[Ry Sullivan @rysullivan]

@KarlTheFog showing up in the Friday #NYTimes crossword! 🌁✏️

42A Phenomenon nicknamed “Karl” in San Francisco

[Ry Sullivan @rysullivan]

Running in San Francisco is like running in a dream. 🌁🌇🌃 #SF #RunningWithTumiSole

[Ry Sullivan @rysullivan]

Hit 5,000 lifetime miles in the @nike Run Club app on one of my favorite stretches up Twin Peaks. Milestone with a spectacular view! 🏃‍♂️⛰️🏆💪

[Ry Sullivan @rysullivan]

The Klopp Era at @LFC has been such a joy for the last 8.5 years.

I think this quote from Dr. Seuss best captures my emotions this morning.

Thank you, Jürgen Klopp!

[Ry Sullivan @rysullivan]

Klopp leaving Liverpool??? No no no! Best coach I've ever seen! 😭😭😭 #klopp

https://t.co/BlErWrbf5l

[Ry Sullivan @rysullivan]

The way Paramount/NBC shows @premierleague games across @peacock and @NBCSports is terrible... Sometimes it’s on one, sometimes on another. And requiring a cable provider vs an online subscription in 2024 is way behind the times.

Is everything moving to Peacock at some point?

[Ry Sullivan @rysullivan]

@ESPNCFB: What do think? An improvement?

[Ry Sullivan @rysullivan]

College Football is Broken. Here’s How to Fix It. https://t.co/Dvk1Wkq6x9

[Shreyas Doshi @shreyas]

As a senior executive, you care a lot about your teams moving fast.

So when a team misses its committed launch date, you show great displeasure.

You demand more accountability.

You make an example out of this team.

Other teams see this.
They are not stupid.
So they learn.

And from now on, every single team hits their committed launch dates.

You are very happy.
I can see it.

But my friend, I am so sorry to tell you:

You are no longer moving as fast as you were before.

Plus, what you ship will no longer be as high quality as before.

And over time you start to see this too.
You are not stupid.

Even though everyone is hitting their launch dates, something has changed.

Things seem to be moving slower than before.

And you have no idea why.

So you call meetings.

You set up check-ins.

You set up processes.

But despite all your efforts, nothing changes.

That gnawing feeling that you are no longer moving fast persists.

That embarrassment of seeing your teams ship a shoddy experience is all too common now.

And you have no idea why.

The answer is right there.

You are no longer moving fast because of YOUR communication.

Instead of creating a culture where teams have intrinsic motivation to move fast — because they are energetic and they care — you started punishing the odd case where a team misses its aggressive target date.

And so, by doing that you sent a message to everyone: Don't be very ambitious, because the reward for ambition is punishment.

I know that isn't the message you wanted to send.

But by doing what you did, it is the only message you will send. 100 times out of 100.

What could you have done instead?

When that team missed its launch date, you could have sent a positive message instead of punishing the team's leaders.

You could have used this opportunity to build & maintain a culture of aggression and ambition.

You could have said:

"I understand why you missed the launch date.

I'd rather that you stay aggressive and sometimes miss the date than being conservative and always hitting the date.

I don't want you to stop being aggressive by default.

And we want more teams to be like you."

At this point, you are either seeing the value of this approach or you are trying to find reasons to reject it.

And your reasons are quite flimsy, such as: "But what about launches that have an external commitment?"

You are smart. You can figure that one out.

But okay, let me spell it out for you:

1. Most launch dates should not be committed externally. So don't commit dates for most launches.

2. A few launches need external commitments (to customers, or regulators, or partners...)

3. For the launches in # 2, sure, commit a conservative launch date that you are almost certain to hit.

4. But even for those, ask the team to devise an aggressive internal target date. It's okay if they slip this date. But it's important to have that aggressive internal target.

Why? Because remember Parkinson's Law:

Work expands to fill the time allotted for its completion.

Have you ever noticed how teams always struggle to hit their launch date, no matter how conservatively they've set them?

Yes, that's because of Parkinson's Law.

Look, I know it's easy to have dogma around "always hitting dates".

Dates are an easy, but incorrect proxy for your teams' velocity, ambition, and energy.

Though if you still want to maintain your fascination with hitting all dates, I am not sure I can (or even want to at this point) convince you otherwise.

But then I also guarantee that you will spend your entire career managing teams that move slower than they really can and/or ship lower quality products than they really can, and you will spend your entire career setting up check-ins, processes, spreadsheets, and carrots/sticks trying & failing to solve a problem that you created in the first place.

Best of luck to you!