When to Ask Forgiveness and Secretly Build a Product Anyway

It feels counterintuitive to keep something secret at work. And yet we all see situations where organizations kill really good ideas. Organizations with and without models for disruptive innovation in place. If an idea is perceived to detract focus from the current top-down directives, it’s likely to face insurmountable opposition.

You can’t get the green light to build an idea without some sort of proof. And often you can’t get any proof without actually building it.

So what do you do?

Give up?

Not if your idea is a baby tiger, you don’t.

Yawning tiger cub
New ideas are like “baby tigers” that need your protection [photo by?tambako]

Baby Tiger Ideas

Tigers may be an apex predator, but baby tigers need protecting until they’re more developed and able to fend for themselves in the wild. The baby tigers are those ideas that could be unstoppable, if only someone would see their potential and protect them.

A while back at eBay someone spotted a baby tiger and a group of us took it upon ourselves to work together and protect it until it grew into a $2B business.

It was 2008.

“Mobile”? hadn’t quite taken off yet. eBay’s mobile site was underperforming in comparison to desktop. Management decided to fire the whole team. Forget about this mobile thing, our focus should be on the core business. Soon after this, Apple made an announcement to a select number of developers inviting them to participate in a new service they were preparing to launch at WWDC: the App Store. Some of these developers were at eBay.

Well luckily for eBay, these developers saw the opportunity in this and formed a band of renegades to get it built. One of these people was a designer on my team who came to me about the project. We got all of her other work covered by other team members and she was able to focus solely on the app so we could have it built in time for the launch. By the time the launch came around and the app was built, the project was shown to management and they were quickly on board with the whole idea.

Steve Jobs introducing eBay as an App Store launch partner (WWDC July 2008)

The eBay iPhone app was a major success, and a significant factor of the success came from the opportunity of being featured as part of the App Store launch – which lead to even further exposure and positive relations with Apple that helped as this whole “mobile” thing really took off. In 2010 while only 12% of top 500 Internet retailers had mobile-optimized Web sites, 7% had mobile apps, and only 2% had checkout features. eBay accounted for 50% of mobile eCommerce in the U.S. that year and 70% of that came from the iPhone.

These unexpected opportunities come up, and you really have to know how to spot them and take advantage of them.

Here’s a few things to think about when doing this.


Release an idea into the “wild” of an organization before it can defend itself, and it may very well be killed before it ever stood a chance.

Think about what dangers your idea may face when it’s proposed. What aspects will be scrutinized? What if it’s brought up to the C-level? How will it do then?


Often there can be a mismatch between the actual scope of something, and how much required effort various stakeholders perceive. If an organization’s general wisdom is that a feature is impossible or a lot harder than it really is, it will likely get killed.

Build your PoC or proposal in a strategic way so that it can specifically invalidate these kinds of assumptions.

Putting in the Hours

It may be necessary to put in some extra time to lay out the groundwork for your idea in any off hours you can find. Take advantage of opportunities like company Hack Days, where employees are encouraged to work on personal projects and share what they’ve done. Occasionally I’ve seen folks use these moments to share ideas they’ve worked on outside the office as well – whatever works.


But remember, it may not be wise to show all of your cards until your hand is ready to be played on the table of internal appeals. Mind the lasting importance of first impressions. It may be to your advantage to keep aspects of an idea behind the curtain until you’re ready to withstand its potential critiques.


If the opposition you’re aiming to circumnavigate is within your personal management chain, there’s a high risk of resentment and retaliation (however the idea pans out). Be mindful of what you broadcast and who may be involved and affected by these efforts.?


Seek out assistance and support in these situations.

People often gripe about middle management. But middle management can actually be a valuable asset in coordinating these, sort-of, guerilla collaboration-efforts when it appears necessary.

If you’re in middle management, don’t underestimate the liberty you have in your role to facilitate these projects. And if your approaching someone in middle management about an idea, find a way to contextualize it in terms they’re likely to sympathize with.

We all have to take some risks in life.

Don’t let your ideas get thrown to wayside without a fair fight.

Preston Smalley produced in collaboration with Mark Mizera. A version of this article was featured on the homepage of Medium in October 2018.

Don’t let your organization kill your next baby tiger. Learn from an example when keeping secrets at work paid off for everyone.

What’s on my iPhone

As a product design guy, I try out a lot of iPhone apps however the list of apps I actually use everyday is quite small. To keep things interesting I’ll skip built-in apps like Mail, Phone, and Calendar to focus on 3rd Party apps (especially appropriate as most expect Apple to hit the 1 billion downloaded milestone today).

  1. Facebook App – I find the user experience better than the web version as it seems to get at the essence of enabling me to keep up with what’s going on in my friends lives. It avoids all apps, advertising, and modes that plague the web version.
    What’s missing:
    Enabling me to phone my friends, sync with my phone contacts, and the ability to leverage my location to find my friends. 5/11 Update: All there now.
  2. New York Times App – First, I’m a NYT junkie and I love that I can get my fix while on the go. They’ve done a great job extending the NYT brand into the app and formating the stories for the form factor.
    What’s missing: After several updates it’s still far too unstable. With OS 3.0 I hope they enable the day’s stories to be pushed down to my phone everyday at 5AM–it’s charging and on wi-fi, why not? Finally, I’d like to be able to tweet stories directly from the app.
  3. Mint.com App – As we all tighten out belts, I find it extraordinarily useful to have the pulse of my balance sheet and cash flow on a regular basis. As a mobile extension of the web service, it does a good job summarizing where my money’s coming and going as well as showing me “alerts” when irregular events occur such as a large purchase.
    What’s missing: I’d like to be able to dig into changes in my 401K (chart of how it’s trending, which holdings are up/down), be able to re-categorize transactions, and “predict” my cash flow out a couple months based on past data and budgets. 5/11 Update: Many added.
    12/09 Update: The latest app adds re categorization.
  4. eBay App – I’m glad that with the 1.2 version of the app we’ve finally got a stable version of the buyer experience. I can check on items I’m watching, bid or buy items, as well as do quick price check searches.
    What’s missing:
    Disclosure: the design for this app is on my team so you’ll have to settle for… “stay tuned” 🙂 5/11 Update: While I’m no longer at eBay, the addition of mobile selling and RedLaser is great!
  5. Google App – Enables me to search the web and my contacts quickly–even allowing voice search.
    What’s missing: It needs to search more things on my phone, especially my email. I’d also like the app to expand on results from certain sources (e.g. wikipedia entries) similar to Yahoo Search Monkey so that I don’t have to goto the page. Safari browsing should be built into the app so that it doesn’t need to be separately launched.
  6. Dropbox App (added 02/10) – Syncs my files across both my Mac and PC as well as making them available in the cloud which I can access via the web or thru this iPhone app. Now no matter where I am I can access my key files.
    What’s missing: Search 5/11 Update: Now added.
  7. Twitter App (added 05/11) – Follow the latest news from influencers in my industry. I also use the search feature to stay up-to-date on what people are saying about Plaxo and jump in on the conversation.
    What’s missing: Ability to integrate with my bit.ly account and rank the “search” feature by the influence level of the tweeter.
  8. HipChat App (added 05/11) — An instant messaging client based in the cloud used at Plaxo. It allows you to stay in touch with your co-workers easily and quickly. I receive a push alert any time a message is sent to me.
    What’s missing: I’d like to be able to look back further in time and be signed in on both my phone and my desktop client.
  9. Skyfire App (added 05/11) – A better web browser (than Safari) for your phone. About 70% of the time I have a page not work in Safari it works here.
    What’s missing: Ability to make it the default browser for the phone (Apple’s problem) and making it work with more websites.
  10. Plaxo App (added 05/11) – Okay, I’m biased. But seriously it syncs your contacts over-the-air with the Plaxo cloud which in my case is connected to my Mac, Gmail, and my iPad.
    What’s missing: You’ll just have to wait and see… 🙂

What apps would I like to put on my home page but just aren’t available?

LinkedIn App – The current 1.0 app misses the point and tries to copy Facebook with a news feed approach. What I want is an app that replaces my built-in Contacts app with rich information about everyone I talk with everyday (role, history of previous calls/sms/emails, names for their spouse and kids). When I’m networking with new people, I want to be able to exchange business cards wirelessly (leverage OS 3.0 bonjour). I should be able to look up LinkedIn profiles using just a name and phone number. Finally, I’d like the app to remind me to follow up with key contacts I want to stay in touch with when it’s been too long.
12/09 Update: The 3.0 version of this app shows the LinkedIn Product team is commited to building a solid app. They added the biz card exchange feature and many key features from the website.

Skype App – The current 1.0 app is helpful (especially when traveling to make cheap VoIP calls) but is held back by two key limitations: lack of push events and VoIP only over WiFi. Time will tell if the carriers dial-back on the 3G limitation, but OS 3.0 will enable the Skype app to tell me if someone’s sending me an IM or trying to call me–a huge breakthru.
05/11 Update: Adding VoIP was a big win and I’m now a fan.

TomTom App – My TomTom 300 device is dear friend of mine and navigated me all over Italy. That said, I would part with it if TomTom could provide me with Turn-by-Turn voice directions, rerouting, and offline maps (thus enabling it work anywhere with GPS). It looks like OS 3.0 will enable this now it’s just up to TomTom to come thru with their long rumored app. I’d pay $75 for this one and would sell my device on eBay.
05/11 Update: Love the app and use it EVERYDAY. While it’s pricey ($50 + $20 for traffic) it gets me home 10-15 minutes faster than I would otherwise by finding the best route “right now” based on traffic.

PowerPoint App with Dongle – This one’s simple, I’d like to be able to connect my phone to an LCD projector via a dongle and project a presentation. Why bring a powerful laptop when a simple device like my phone can do the job. This doesn’t have to be built by Microsoft and perhaps the Slideshare or Air Sharing folks might come out with it first–or better yet a micro-projector that does it all.

Fitbit App – I’m on the waiting list for the first fitbit exercise/sleep device now due out early this summer. What would make this experience one better is if I could track what I eat directly on my phone without having to remember later when I get to my computer. It also could show me a summary of key stats (like Mint) which would be interesting to check-in with daily (e.g. how did I sleep last night?).
12/09 Update: I got my FitBit in Nov and after 2 weeks returned it. It didn’t offer much analysis and the sleep tracking feature was not very accurate. Good idea but mediocre execution.

What apps do you use everyday? What apps do you think are missing?

Preston Smalley discusses his most used iPhone apps: Facebook, NY Times, Mint, eBay and Google as well as the ones he wishes existed or were better: LinkedIn, Tom Tom, Skype, PowerPoint, and Fitbit.