LLenny's Podcast
← All frameworks
StrategyAmi Vora (CPO at Faire, ex-WhatsApp, FB, IG)

The Hill Climb

Name whether you're optimising a local hill or crossing the valley to a bigger mountain — then price the valley.

Difficulty
Advanced
Time to result
~months to results
Steps
5
Confidence
95%

A mental model for the local-optimum vs global-optimum decision. You are standing on a hill you have optimised well. Off in the distance is a mountain you can't see the top of. Reaching it means climbing down, crossing an unknown chasm, and climbing back up just to reach the altitude you already had. The framework's real payload is expectation-setting: it tells you that the slog is not a failure signal, it is the valley, and it is supposed to feel like this.

Origin

Vora's own metaphor, drawn from the optimisation concept of local vs global optima. Her canonical instance is the desktop-to-mobile transition, where companies with excellent desktop businesses could see the mobile mountain but had to make painful trade-offs in the core business with no guarantee of arriving.

Core principles

  • 01Continuous improvement of your current system is real progress — and it is capped by the height of the hill you are standing on.
  • 02The cost of the mountain is not the climb; it is the descent plus the unknown chasm.
  • 03Crossing means giving up something that is working well without a guarantee you arrive.
  • 04Most of the time the answer is yes, go — but the value of the model is knowing where you are, not what to pick.
  • 05The valley is survivable only if you can still picture the summit.

How to run it

  1. 1

    Locate the hill you are on

    Name the system you are currently optimising — the product, the business model, the career, the org design — and be honest that you are near its top.

  2. 2

    Look for the mountain

    Identify the distinctly better way of doing this that you can see in the distance but cannot fully evaluate. You should be able to see that it is higher, but not see its top.

    Pro tip If you can see the top of it clearly, it is probably another hill, not the mountain.

  3. 3

    Price the descent and the chasm

    Be explicit about what you have to give up in the working system, and about how much of the crossing is genuinely unknown. Accept that you climb back up just to reach where you already were, with more climbing left.

    Watch out Teams price the summit and forget the descent. The trade-offs in the core business are the actual bill.

  4. 4

    Decide, then pre-brief the valley

    If you go, tell the team in advance that things will get worse before they get better and that this is by design, not by failure. Set the expectation that you will slow down what you are doing now.

    Pro tip The metaphor is doing team-communication work here: it converts a demoralising slowdown into a legible, expected phase.

  5. 5

    Hold the summit picture through the slog

    When it feels like a slog, check your position: are you in the valley? If so, the feeling is confirmation, not evidence against the plan. Remember what the summit feels like — the problems solved, the life better in these specific ways — and keep walking.

    Pro tip Write down concretely what the summit looks like before you descend, while you still have the optimism to describe it.

    Watch out A valley with no articulable summit is just a decline. If you cannot describe the summit, you should not have left the hill.

In the wild

Desktop to mobile

Companies were excellent at desktop and could see the mobile mountain far off. Getting there required real trade-offs in the core desktop business and a fundamental rewiring of how they worked, with no guarantee the mobile bet would pay off.

The ones who accepted the valley crossed to a much higher peak; the ones who kept optimising the desktop hill topped out at its height.

Personal moves

Vora applies the same model to new jobs, new relocations and new relationships — anything where you give up something that is working pretty well without knowing whether you will reach the top of the next mountain.

She uses it to locate herself: 'this feels like a slog because I'm still in the valley', which converts discouragement into a status report.

Common mistakes

Mistaking the valley for failure

The descent looks identical to decline from the inside. Without the model, teams abandon the crossing exactly when the discomfort proves they are on track.

Refusing to leave a hill you have mastered

Optimising the current system feels great and produces visible wins. That's precisely why local optima are sticky — and why the mountain gets claimed by someone with less to lose.

Is it for you?

Best for

Leaders facing a platform shift, replatforming, or business-model change where the existing thing still works and the new thing is unproven.

Not ideal for

Situations where the current hill is genuinely under-optimised — climb it first before mounting an expedition.

From the transcript

for me the hill climb is all about like the difference between local Optimum and a global Optimum

26:30

you have to decide like are you going to take the risk of climbing down your Hill Crossing like an unknown Chasm and then climbing…

27:30

a lot of companies were really good at desktop and you could see the m Mountain like way out over there

27:30

the thing that gets me through the valley is remembering what the summit feels like

00:30

From the episode

Making an impact through authenticity and curiosity

Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG)