Defending your big bets | Timestamp Karaoke

## Q: I work at a big company and my team and I keep trying to launch a “big bet” project (one with a lot of upside but that’ll take a while to build), and our resources keep getting pulled away. Any advice for maintaining support for a big bet?

I like to think of a “big bet” project like a highly-experimental new weapon that you’re trying to smuggle to the front. There are forces at play that want this project squashed, and if you charge ahead without the proper support or make any missteps, you’ll get discovered and taken out.

The solution is to create “cover fire.”

You do this by consistently shipping small but consistent wins: moving your KPIs, hitting goals, and showing progress. With this cover in place, you’ll be able to smuggle the big bet through and emerge on the other side with a game-changing new product.

I’ve done this time and again, and I’ve found this strategy to be the only way to consistently maintain the buy-in and resources necessary to work on a long-term project at larger companies, on most teams.

Tactically, my rule of thumb is to spend 80% of my team’s time on short-term low-risk incremental wins, and 20% on high-risk, long-term bets. This way, we can continue to move our KPIs while bringing our big bet alongside. Here’s how that might look on a roadmap:

This doesn’t need to be nefarious or secretive — in fact, I recommend you share this strategy with your manager. The whole idea is that your team doesn’t go for long periods of time without showing any impact on the business (which your manager will also appreciate).

Why does this work? If you only work on long-term big bets, without showing any direct impact on the business, it’s difficult for leaders (and people in general) to give you the benefit of the doubt indefinitely. Resources are scarce, and there are always going to be higher-urgency and more-important needs. By showing steady success, you:

1. Don’t give anyone a reason to mess with your team 2. Build trust in your team’s ability to execute 3. Earn the right to take bigger bets

Even you do have the trust and cover of the current leaders, people and priorities change. When there are new fires, people will come looking for non-essential projects in progress to pull resources from. If your project hasn’t shown any concrete benefits for a while, and the upside is uncertain, it’ll be easy picking.

Note: This advice applies mostly to larger companies, and to the average team. Some teams are top-down designated to work on long-term high-risk projects, in which case this is less likely to be an issue. Similarly, at early-stage startups, most everything you work on is a high-risk long-term big bet. If this isn’t an issue for you, don’t sweat it.

Bonus advice for helping your big bet see the light of day

[While working on this post, I put a call out on Twitter](https://twitter.com/lennysan/status/1363549295815835656) asking PMs, founders, and leaders what has worked best for them to allow their “big bets” to survive to launch. Here are my favorites additional pieces of advice from people who’ve been in the thick of it:

#### “Keep it small/avoid too much attention until ready.”

— Sriram Krishnan, PM ex-Twitter, Snap, FB, Microsoft

#### “Code wins. Demo end-to-end prototype that works for some critical path. At this stage lots can be smoke & mirror though have (good) answers when asked about it Have clear next steps that also might "work" for that demo.”

— Jason Warner, CTO GitHub

#### “[Create a] small hungry entrepreneurial team. Clear mandate. Independent operations. Carved out headcount.”

— Tomer London, co-founder Gusto

#### “Make sure the proposing happens \before\ quarterly planning & the bet is set to launch\after\ at least one quarter has completed. This allows time for all the annoying but essential bits like stakeholder management, adequate resourcing, relentless comms, change management, etc.”

— Zoelle Egner, ex-marketing at Airtable, Box

#### “Keep the emphasis on the *why all along.”*

— Anand Chandrasekaran, EVP Product Management at Five9

#### “[Bring] an appetite for disruptive ideas, a little bit of funding (seed), some healthy skepticism to motivate the team (expectation was most things we try would fail) and some air cover to prove out product-market fit.”

— Robleh Jama, Director of Product at Shopify

#### “Culture. It’s all culture first, execution second. Laying the groundwork, helping drive coalition, ensuring we had the right behaviors to adopt the new ‘thing’.”

— Ben Perreau, Principal, SYPartners

Don’t miss the full thread for much more great advice.