Bold-Move Leap (Not Moving Is the Risk)
When you need a step-change, make the committing bold move all at once — because playing safe is itself the risk
- Difficulty
- Expert
- Time to result
- ~months to results
- Steps
- 4
- Confidence
- 90%
To create a pivotal leap, sometimes you must make a committing bold move rather than a hedged incremental test — and let go of things that made you successful. monday.com became a multi-product company by launching five products simultaneously instead of quietly testing one on the side. The mental reframe: not taking bold risks is itself a risk, and inertia toward incremental value is the danger.
Origin
Daniel Lereya's account of monday.com's strategic shift from a platform sold as a project-management tool to an explicit multi-product company built on that platform.
Core principles
- 01Not taking bold risks and not making bold moves is itself a risk
- 02A hedged single-bet test can teach the wrong lesson if you happen to pick the loser
- 03To make leaps you often must let go of things that were successful for you in the past
- 04People want inertia and incremental value; leaps require deliberately overriding that pull
- 05Reframe who your customers are to justify moves that disturb current success (most of your future customers aren't customers yet)
How to run it
- 1
Spot the latent behavior worth committing to
Notice when users are already stretching your product into new jobs (building CRMs, dev-cycle tools, etc. on top of your platform) — that's the signal a bigger strategic move is available.
- 2
Choose the committing move over the hedged test
Instead of quietly launching one new thing on the side to see if it works, make the bold, visible, all-at-once move. monday.com announced five new products simultaneously to force a pivotal leap in perception — internally and in the market.
Pro tip A simultaneous, committing move changes the competitive landscape and the internal narrative in a way a cautious side-test cannot.
Watch out A single hedged bet risks a false negative: if you pick the one product that fails, you might wrongly conclude the whole strategy (e.g. 'multi-product') doesn't work for you.
- 3
Absorb the friction deliberately
Expect and accept heavy internal friction — confusion for users, conversion worries, multiple go-to-markets, sales navigation, pricing complexity. Decide to proceed because the leap is the point.
Pro tip Use mental models to cope: e.g. 'most of our customers are not customers of Monday yet,' which licenses moves that disturb current success.
Watch out The friction is real and 'really really hard' — many people at the company resisted; don't mistake resistance for a signal to abort.
- 4
Learn and collapse what doesn't hold
After the move, keep what proves itself and fold back what doesn't need to be separate. Some of monday.com's five products succeeded (Monday CRM outgrew the core); others were collapsed back into the main product.
Pro tip The leap's value is the learning and transformation, even for the parts you later reverse.
In the wild
monday.com was a platform sold with a project-management go-to-market, but users were building CRMs and dev tools on top of it. Rather than launch one new product quietly on the side, the team announced five new products simultaneously — over objections about user confusion, conversion, marketing, sales navigation, and pricing.
→ Monday Sell CRM grew faster than core monday.com had; some products were collapsed back into the main product; the move transformed both internal perception and the competitive landscape in a short time — and avoided the trap of concluding 'multi-product won't work' from a single failed bet.
Common mistakes
Defaulting to the safe incremental path
Choosing inertia and incremental value feels safe but is itself a risk — you can work hard for a year and, looking back, not be able to name what you actually did. Playing safe forfeits the leap.
Hedging with a single side-bet
Testing just one new product on the side and doubling down only if it works can produce a false conclusion: if that one bet fails, you may wrongly abandon a whole strategy that a broader, committing move would have proven.
Is it for you?
Best for
Founders and senior product leaders at a successful company facing a strategic step-change (platform to multi-product, new category) where incrementalism won't create the needed leap
Not ideal for
Situations where a failed bold move is existential or unrecoverable, or where there's no strong latent signal that customers already want the new direction
From the transcript
“We actually announced five different new products simultaneously on the same time”
“not taking bold risks not making bold moves it's a risk for itself”
“if you want to do lips many times you need to let go of things that were successful for you in the past”
“just imagine what would happen if we would choose one of them and it wasn't the successful products and our conclusion can be that multi…”
“most of Monday's customers are not customers of Monday yet”
From the episode
Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR
Daniel Lereya (Chief Product and Technology Officer)