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 bytambako]

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.

Timing

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?

Framing

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.

Patience

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.

Tact

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.

Cooperation

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 withMark Mizera.

How to Say “No” to Your Boss

Or Worse: Your Boss’s Boss

It’s a product manager’s worst nightmare:

An Exec gets an idea from a teenager that lives next door. Imbued with optimism, the higher-up urges you and your team to drop everything and put all hands on deck. This is where we should be focusing right now.

Great.

Well, not only do you disagree with the efficacy of this proposed feature, but you’ve also seen the train wrecks these situations can cause. Teams get frustrated by being told to do something without understanding why it’s important. Execs get frustrated by a lack of production.

Your instinct is to push back.

But is there any good way to say “no” to your boss? And if there is a good way to do it, is it ever a good idea in the first place? For me, the answers are: yes, and definitely.

If you’re in a leadership role, working within a hierarchy, being able to say no to your boss can actually be an essential skill for success. If done correctly, it can make you a better leader, a more valuable employee, and a more reliable teammate.

Plus you’ll never actually have to say the word “no” to your boss.

Here’s how:

1. Stop Thinking in “Yes” and “No’s”

The first step in effectively saying “no” to your superiors – when it seems necessary – is to stop thinking in “yes” and “no’s”. This part’s really about good listening.

When a superior gives a sudden order, it’s natural to analyze the order itself. But by immediately jumping to that step, you’re missing the bigger picture. Before rushing to give this person an answer, ask them some questions about the idea they’re proposing.

Create a dialogue with them and, eventually, your team members.

2. Identify the Issue

Just as great art often comes from pain and suffering, great ideas often come from problems and difficulties. But in a business, some issues are more important than others. Find out where this idea came from. What customer issue would this feature be solving?

The issue at the root of an idea is more important than the idea itself. An idea may be interesting, but if the problem it solves isn’t that important, than the idea really isn’t as valuable as it may seem.

3. Enable Your Team Members to Weigh In

Once you’ve identified the underlying issue, go back with your team members and evaluate the problem. adult-analyzing-brainstorming-1080865

Bring in the data: Are we losing customers from this issue? Might we gain users by solving it? Are we already solving it? Might this new idea, in fact, be a better solution?

If it becomes evident that this issue is significant, take a moment to explore other viable solutions, and weigh them against the original proposition. If, on the contrary, the underlying issue is revealed to be insignificant, it’s probably best the feature not be built.

4. Sleep On It

Whether you found the underlying issue to be significant or insignificant, take a page from old wisdom and sleep on it.

Even if you manage to complete this process within the same business day, you don’t want this person to feel like they’re being brushed off. Aside from the notion that you probably owe it to this person to give their idea at least a full day or two’s worth of consideration, you never know. This part may surprise you.

You might have an idea yourself. Someone from your team may send you an overlooked piece of data they stumbled across.

I could’ve used this advice earlier in my career. There was a instance at eBay years ago that I can remember clear as day. While figuring out how to enable users to find items that accepted PayPal, an Exec suggested we have the logo pop up on every search result that featured the service (already accepted by 95% of sellers). At the time I was a very-much green UX designer and I’m thinking in my head, this guy wants to make the website look like the sidewalls on a NASCAR track. Only the problem was I wasn’t just thinking this in my head. I actually jumped out of my chair and shared my reaction. At the time I was so green I didn’t even understand that my actions were unadvisable. It just seemed so wrong I had to stand up.

drawing of eBay search results on a whiteboard illustrating a PayPal logo listed next to every item for sale.
Whiteboard drawing of proposed eBay Search Results with PayPal logo on EVERY row (2002)

I realize now that while my stance may have been justified, there was a better way to go about expressing it.

If the circumstances allow it, give yourself a chance to process the findings before presenting them.

5. Present a Data-Driven Decision

Most of all you must follow up.

Never assume that, if you’ve found the idea to be something you shouldn’t pursue, that you just leave it there. If you don’t follow up with the Exec they will naturally think you ARE pursuing the idea. And if they ask you about it later, you’ll be on your back-feet in terms of reporting on your earlier process (steps 1-4)–and will need to start over.

In the end, you can let the data speak for the decision.

Demonstrate that you’ve analyzed the issue at the root of the idea. You’ve explored viable options. And ultimately you’ve landed upon the solution that best aligns with company goals.

And if this means essentially saying no to an Executive’s idea, at least you’ve followed a judicious and egalitarian process. You’ve done what you’re paid to do.

A good executive will be able to see that.


Preston Smalley produced in collaboration with Mark Mizera

280 characters = Navel Gazing

Twitter’s move to test doubling the character limit of tweets this week can’t help but remind me of internal discussions we used to have 10 years ago at eBay around Item Title length. In hindsight those discussions were pure navel gazing and distracted us from the core issues our business faced. I fear Twitter is doing the same today.

55 Characters

eBay Search Results

eBay Search Results (circa 2008)

In the beginning when Pierre Omidyar built eBay to help his fiancée collect Pez dispensers on eBay (spoiler alert: this was startup lore more than truth) he placed a limit on the number of characters a seller could use in their title: 55 characters. This stuck for a number of years however sellers would often complain that they would like more space to describe their item. As we discussed it internally at the company several reasons emerged as to why it would be a bad idea:

  • It would erode listing fees like adding a second category (doubling listing fees) or adding a subtitle (50 cents). Remember these listing fees made up about a third of eBay’s revenue at that time (balance was final value fees, paypal transaction fees).
  • It would make search results less relevant. eBay at the time worked on a pure title search and so by allowing sellers to add more words would mean some items only tangentially related to the keywords would appear (thru keyword spamming).
  • It would be harder to visually scan. Both the item page and search results would be harder to read with a longer title. In face there was some concern that even the search results loading time would be adversely impacted.

eBay Logo Circa 2008And so it went on. The topic was discussed at length and always controversial. Eventually in 2011 the company decided to expand it to 80 characters to align with Amazon and other online retailers platforms. At that point the search infrastructure had improved tremendously and was able to still provide relevant results. Did it fundamentally change eBay’s business in the end or help in its battle with Amazon? No.

So what’s the big deal for Twitter?

I think the lesson here for Twitter is one of putting heir energy and focus on topics that really matter. For example they should focus on the fact that Twitter is a two-sided marketplace of publishers and readers. Publishers are looking for audience and to get their message out. Readers are looking for interesting topics from the general (celebrities, politicians, news) to the more nitch (product management, design). And yet the way it’s positioned is not nearly that clear–and this 280-char test isn’t helping.

Ironically Medium, who already has a much clearer two-sided value prop and now business model, is doing exactly this.

Getting Products out from under the MIDDLE of the Bell Curve and Exceeding Expectations (SVPMA)

Given the key role Product Managers play in creating the environment for their teams… what must they do to avoid the bell curve of mediocre products that unfortunately are the norm? I shared my perspective as the guest speaker at the SVPMA (Sept 3, 2014) based on my own experiences and other authors/speakers that I trust.

Presenting @ SVPMA

I discussed specific ways to set clear goals and establish the right metrics. Dipping into my eBay days, I shared a little known story of the importance of asking for forgiveness rather than permission in driving innovation that resulted in the launch of the eBay iPhone app.

Some other takeaways from this talk include:

  • How to focus on the right, few, customer adoption metrics (e.g. AAARR). More is often not better and can distract from the main goal
  • How defining your product’s purpose often improves working relationships with designers and engineers so you aren’t left arguing about the “what” or the “how
  • How to avoid getting in the executive micromanagement web especially if they are distracted by the “flavor of the month” or “pet feature” ideas
  • How to drive stealth projects or go through quick business case or product prototyping within a big company.

I was pleased to host the event at Comcast Silicon Valley where I work.

A full review of the talk posted on the SVPMA website.

Why Design Matters – P&G

I recently was invited to speak at P&G headquarters in Ohio on “Why Design Matters”. It was a leadership summit of their Global Business Services division which supports all the brands and employees worldwide. For me it was a great chance to reflect on what aspects I see as critical to design and what can get in the way.

Here are the slides. I plan on adding the audio slidecast soon.
UPDATE 6/15: Slidecast now available.

View more presentations from Preston Smalley.

My next chapter

I’ve decided to wrap up 7 great years at eBay and will be leaving in a couple weeks. I’m proud of the design team I’ve built there and wish them and all my colleagues the very best as the eBay Marketplace completes the turnaround that’s well underway. Since finishing my MBA I’ve been interested in making a more formal transition to product management as well as building experience within a smaller organization.

I’m joining an old friend of mine, Justin Miller, who’s now CEO at Plaxo, to head up the Product Management team as it’s Senior Director. I’m looking forward to joining the leadership team to focus on the renewed vision of building a truly smart, socially-aware, and pervasive address book.

UPDATE 4/30: I’m hiring a Product Manager to head up Plaxo’s growth areas (Position filled) and there is also an opening for a lead designer. If you or anyone you know is interested in hearing more, let me know.

Recent April Techcrunch interview on the future of Plaxo:

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?

You too can do a “World of Good”

Yesterday eBay launched a new marketplace for buying environmentally friendly and fair-trade goods from all over the world called World of Good.
World of Good Logo

In the same way you know the groceries at Whole Foods are sourced from vendors who practice environmentally sound and labor friendly practices, this site provides a “Trustology” on every seller which helps you as a buyer make a sound choice. By buying goods on this site you know that you’re supporting people making a living wage or artisan’s in the third world proudly practice their craft.

Congratulations to my friend and classmate Robert Chatwani who’s the “founder” and GM for this effort as well as Seema Shah and Myra Liu who led the design of it.

You too can do a “World of Good”

Yesterday eBay launched a new marketplace for buying environmentally friendly and fair-trade goods from all over the world called World of Good.
World of Good Logo

In the same way you know the groceries at Whole Foods are sourced from vendors who practice environmentally sound and labor friendly practices, this site provides a “Trustology” on every seller which helps you as a buyer make a sound choice. By buying goods on this site you know that you’re supporting people making a living wage or artisan’s in the third world proudly practice their craft.

Congratulations to my friend and classmate Robert Chatwani who’s the “founder” and GM for this effort as well as Seema Shah and Myra Liu who led the design of it.