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.


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 withMark Mizera.

8 Ideas For Tesla’s Next Software Update

My wife and I taking delivery of our Tesla Model S at Fremont Factory in 2015

I’ve been driving a Tesla Model S for three years now and I simply love it. It’s the first vehicle I’ve owned that gets better with age. With every software update, a new set of tricks and features appear at my disposal. It’s hard to imagine commuting and driving along winding roads now without features like AutoPilot and Forward Collision Warnings (features that were automatically added to my car after I had already bought it).  

Naturally, as a product person, spending several hours commuting in my Tesla everyday, I dream up some feature ideas of my own from time to time. And I’ve decided to share some of them here. According to the six degrees of separation theory, someone at Tesla is bound to have a look.

Who knows?

Maybe something will stick.

Eight Feature Ideas and Improvements For Tesla

1. Curated radio and podcasts

I utilize my commute to stay up on my favorite audio content (news, tech, leadership, …), but the media playback experience can be cumbersome while driving, as you have to know exactly what you want to play and select it specifically. I know from my time spent in the TV industry that people love to be entertained with as a little decision making as possible.

It would make things easier if the car analyzed my listening behavior and curated an ongoing, custom feed just for me. Aggregating both on-demand media (like podcasts), and also recorded segments of live broadcasts that match with my topics of interest — combining the playback ability of DVR and the machine learning of personalized media streams.

Resulting in a linear, Pandora-like talk radio station, with a mixture of sure bets and new suggestions.

2. Instapaper integration

I also utilize Instapaper to catch up on articles I want to read, by listening to them on my commute – but I do this manually through the iPhone app and it’s a bit clunky.

It’d be great if Instapaper could be integrated directly into the Tesla’s media interface, playing the audio transcripts like they were any other digital radio station.

Actually, Instapaper’s competitor, Pocket, announced last week that they are focusing on this read aloud ‘podcast’ use case – so fingers crossed for more attention here.

Listening to Instapaper read aloud my backlog of articles in my Tesla

3. Autopilot and motorcycles

When Autopilot is engaged, the Tesla maintains a perfectly center position in the lane – even when a motorcycle passes by in the gaps between cars, which is not ideal (Note I have APv1).

If the car could sense the motorcycle approaching from behind and move to the side of the lane (yet remaining within the lines), the motorcycle would have more clearance as it passed.

Occasionally, as the motorcycle passes by my car’s front bumper, AutoPilot thinks the motorcycle is another car, suddenly appearing in dangerous proximity, and proceeds to apply the breaks. This can be dangerous if the car behind is not paying attention.

Making this change I think would place Tesla as a loved brand among motorcyclists and as an added bonus, this would increase the percent of miles driven using AutoPilot (driving up that KPI).

My drawing of how Tesla might better handle land splitting motorcycles

4. Fort Knox Mode

When I leave my car somewhere, at the airport for example, I’d like to be sure it’s safe and sound.

The iPhone app could notify me if the car is unlocked, or moved, by someone other than myself. This would come in handy when parking at a valet, too – knowing if the car gets taken out for an unauthorized joyride.

And if there were no notifications, I could be more confident in the safety of “our beloved Tessa” (as it’s known to my children who consider the car part of the family).

5. Cool on arrival

Remote cooling the cabin of the vehicle so that it’s comfortable when you return to it on a hot day. You can do this manually today through the Tesla app but you have to remember to do it. Imagine if instead you could schedule a time you expect to return to the car, or better yet, the GPS on your phone could automatically begin the process once you return to a certain proximity.

6. Commute analytics and recommendations

Departure time recommendations based on traffic conditions. I’d love to plot average commute times I’ve had over the last year or so, and see how they historically vary by time of day and how they are changing. It might advise me to leave 15 minutes earlier than normal on Thursdays, where I could save 10 minutes on my commute time.  

7. Weather

A brief weather report for where I’m going (as entered into the Navigation system). Automatic, unless switched off. For longer drives, this might cause me to grab an umbrella or jacket for the destination.

8. Phone app

Contact Favorites.

We need contact favorites.

When I want to call my wife, I have three options: I can either use voice command (and then select which “Jeanine” out of 3 potentials, and then select between her home and mobile number), or scroll through the 1600 contacts in my phone, or I can dial her number manually. None of these are great options when cruising along at 70 MPH.

With 5 to 10 pre-set “favorites”, you could just tap phone icon and tap the pre-set people.

Also, the “mute” button should NOT be adjacent to hangup. It’s easy to tap the wrong one while driving. For this reason, I tend to use the steering wheel buttons when doing conference calls in the car. Alan Cooper calls this notion hiding the “ejector seat lever”.

Alan Cooper on hiding “ejector seat lever” in About Face 3.

With all that being said, it’s been a great three years driving my Tesla, and I expect nothing but more good things to come.

It really is a kick to have the question, “What will my car do next?” always floating through your head, and I look forward to finding out.

– Preston, driver of a Model S

Preston Smalley produced in collaboration with Mark Mizera.

The Power of Asking For Help

Lifebuoy. Photo: ranieldiaz via flickr/CC BY 2.0

At what point in facing a challenge should we resort to asking for help?

The trick here is the word “resort”.

In spite of our better judgments, most of us wait until we’re stuck in the quicksand of a problem before we turn to someone for advice or counsel. But why wait until we’re desperate to seek out assistance? Why let ourselves get to a point of anxiety and frustration when it’s often altogether unneeded?

Why not, instead, make asking for help a built-in part of our work process?

There’s this metaphor in a book by Stephen Covey I read a while back, about the importance of sharpening a saw between cuts, so that the saw doesn’t get stuck in the wood it’s working through.  

“We must never become too busy sawing to take time to sharpen the saw.”

Dr. Stephen R. Covey

When we get busy, it’s easy to spend all of our time working and grinding away at whatever to-do item is looming overhead. But we should remember to find time to “sharpen our saws”, in the sense of finding ways to get better and more efficient at our work. Allowing us to ultimately get more done.

Asking for help is one of the many ways we can seek to “sharpen our saws” as we’re heading into new tasks. And the earlier we seek assistance, the less likely we are to get stuck.

Broaden your perspective

Leading product management for a team can be a lonely job. Often your peers — like the head of engineering or marketing — can’t relate to the specific challenges you face.

I found myself in this situation back when I was running product for Plaxo. As described in a previous post, I was facing a whole host of frustrating challenges. Fortunately, my boss at the time was super supportive and recommended I join Collaborative Gain, something he had received a lot of value from over the years.

Collaborative Gain is an organization founded by Phil Terry that’s anchored by a semi-annual retreat with “asking for help” as its cornerstone.

As a participant, you join a year-round “council” of 15-20 professionals in your line of work, from different organizations and industries. The council remains stable over time (save for an average turnover of 2 or 3 members a year).

This week marks my 14th retreat with my council.

Around the time of my first retreat I was considering applying Lean Startup methods to try various pivots we might make with the business. It was a big moment for myself and the company, and I wasn’t totally confident in my approach. Through what we call a “Request For Help” I led my council through the situation, and the approach I was considering. They not only gave me the confidence I needed to proceed, but also helped me fine-tune the approach, and advised me on how to best position it to my staff.

We often think our situations are unique. But more often than not, they fit into larger patterns that actually are quite common. Having access to a wider range of perspectives and experiences illustrates this, and allows you to apply the lessons already learned by others.

Ask your boss

External peers really help in diversifying your perspective, but perspective isn’t the only thing we should be asking for help with.  

It isn’t always comfortable for you or your boss, but if there’s something in their power that could enhance your performance, it’s necessary that you make it clear to them. It might be something you need their help fighting for. It might be a new challenge. A promotion. Or a more flexible schedule.

Whatever it is you need, be proactive and make it clear to them.

Hit the books

Pursuing higher education is often connected with career advancement, with the educational virtues regarded as almost an afterthought. A means to an end. But a big reason I went back to school for my MBA was fill-in a personal knowledge gap — to understand how product and business leaders think. One of the most valuable aspects of my time at Haas was applying the HBS Case Method where, again, we gained perspective around what previous business leaders did right or wrong by placing ourselves in their shoes. By covering dozens of cases we racked up experience that would have taken decades to learn first hand.

Of course, education comes in many forms, and you never know what new lesson might change your entire outlook on things.

Ask for feedback

Feedback is a gift, and if you don’t ask for it you won’t always get it. For an individual, it might be 360 surveys. For an organization, it might be employee NPS.

If your boss isn’t giving you regular feedback, or maybe they skipped your recent review — take initiative and ask for it. Present your self-review to them and ask for their assessment.

Whatever format suits your situation, don’t wait till it lands at your feet. Be proactive about identifying weaknesses and figuring out how to work around them.

“We all need people who will give us feedback. That’s how we improve.”

Bill Gates

Early in a career, it can feel like everyone but yourself has it figured out – and if you want to move up, you’ve got to start being the one with the answers. But the people who move up and lead prosperous careers do have something figured out — asking for help.  

Everyone has their gaps. Gaps in perspective, gaps in wisdom, and gaps in a skillset. The gaps really aren’t important though – what’s important is what you do about them.

Asking for help should be an early stage of our routine. Something we do automatically – like muscle memory. Without prideful or timid hesitation.

By viewing assistance, and advice as tools in our wheelhouse, and not just last-resort, life-saving devices, we can save ourselves a lot of time and frustration.

Everyone needs help.

Get it early, and get it often.

Preston Smalley produced in collaboration with Mark Mizera.

Designing A Work-life Balance in The Bay Area

Commute traffic in the SF Bay Area. Photo: thomashawk via flickr/CC BY-ND 2.0

A few years ago my Bay Area commute was really getting to me.

One and a half to two hours behind the wheel. Home around seven thirty in the evenings. Never in time for dinner with my family. My little ones already in bed, having also missed them in the morning as I headed off to work early. It was depressing.

Not what I wanted for my life.

Eventually, I worked it out that I’d stay late at the office two nights a week (bringing leftovers for dinner). Then I’d leave early two days a week, so I could be home by five thirty. It made a huge difference.

More time at home with my family, fewer hours in traffic.

And since then, I went on to make it so I could WFH one to two days a week, for the same reasons. Now, when I’m not traveling to my company’s headquarters in Philadelphia, I’m seeing my family a lot more and actually getting to spend quality time with them.

I noticed these changes in my schedule not only improved my time out of the office, but they improved my time on the job as well. Getting to spend more time with my family has made me more present when I’m on the job – better enabling me to listen and mentor, which is a large part of my role. And getting myself more time out of the “trees” more often – away from the drawing board – also helps me to better see the “forest” of product strategy. A win-win, all around.

Now everyone may not be in a position to dictate their schedule to this degree, but everyone has the ability to be proactive in finding their own personal work-life balance.

So what’s the right ratio of work:life these days?

Writer Jessica Wildfire illustrated in a recent article that widely held definitions of “work” and “fun” aren’t held by everyone – and some people enjoy their work more than they enjoy their peers’ various ideas of fun.

I can certainly relate, deriving great satisfaction from my own work. But there are other aspects of my life, which I also enjoy, that can get pushed aside if I’m not strategic about how I spend my time. And careful not to let work automatically “win” over everything else.  

The challenge is staying competitive amongst those who choose not to fight this temptation. Those who do allow work to always “win”. Perhaps telling themselves that they’ll dial it back after this next release, this next quarter, once they retire. Or those who have no intention of dialing it back at all.

Columnist and Senior Editor at The Economist, Ryan Avent discussed in a recent article the growing trend of seeking passion and fulfillment in a person’s work today, whereas previous generations may have seen it as more of a means to an end. The piece went on to discuss that the more people enjoy their labor, the more time they’re able to spend laboring – in turn driving up the competition amongst individuals pursuing the same trade.

So if you’re someone who seems to benefit from a decent amount time away from the drawing board, and you’re competing against those who may not need as much of a break, how do you stay competitive and make time for other areas?

For me, the remedy is being proactive and strategic in finding ways to ensure my time is being spent where I want it to be, and being intentional about the way I spend my time in each of the areas – work, family, fun, etc.

These are a few things I like to keep an eye on and some basic “hacks” for maintaining my optimal work-life balance.

A Glimpse into My Personal System of Checks and (Work-life) Balances

Keep an eye on the big picture

Even with a self-tailored work schedule that “guarantees” a balance in my schedule, I still find that if I’m not careful about scheduling meetings and events and how I organize everything – my work-life balance can quickly get out of whack.

My answer to this is Calendar Bird’s-Eye View in Google Spreadsheet.

Calendars – whether in Outlook, gCal, or your phone – can quickly “bring you into the trees” of all your scheduled appointments. Making it hard to “see the forest” of how you’re spending your time and coordinating major events coming up (both work and personal).

To keep an eye on the bigger picture of how and where I’m spending my time, I maintain a birds-eye view calendar which shows where I’ll be in the morning/afternoon/evening of each day. I then color code whether I’ll be at my local office in Sunnyvale, headquarters in Philly, working from home, OOO on vacation, or in transit traveling. This way I won’t overbook a work trip on top of an important personal event that week. If the proportion of the colors doesn’t seem right, I’ll immediately know and be able to make adjustments.

Excerpt from my Calendar Bird’s-Eye View Google Spreadsheet

Your desired ratio may be different than mine but having a bird’s-eye view – and one that is easy to visualize, like color-coded blocks, can help you maintain your preferred ratios between work and home/family/etc.

Safeguard your “me-time”

Each and every day will throw a peppering of obligations and distractions at you, so take proactive measures to ensure that certain parts of the day aren’t jeopardized. It’s important in our hectic world that we get some time to think and work on our own projects and ideas – and these are the ones that tend to be most jeopardized because no one else will be advocating for them but you. Software developers, call this “flow” or getting “into the zone” but it’s not just useful for those roles.

Find a means of accountability for the other, also important, areas

This could mean investing money in a new exercise program to supply with an extra bit of motivation (shoutout to my fellow Pelaton’ers!), or it could mean scheduling recurring activities with a friend that you’ll find ways to make time for because you don’t want to bail on them.

For me, a great one I’ve found is signing up to coach my kids’ teams. I found this is the best way to periodically be extra present for their sports. I can’t do it all the time but each year I’ve picked one to do which gives me one more reason to get my work done and get to their practices and games.

Coaching baseball for one of my son’s on a day where I proudly awarded him the “game ball” 

Outsource as much as possible

I once read if you could delegate something and the other person could do it 70% as well as you could… do it.

Why not apply this to areas of life… to the time spent doing things you’d rather allocate toward something else?

I’m fortunate enough to afford the outsourcing of things like yard work and cleaning my pool (with a robot) – activities I’m not wild about.

See if there’s anything taking up your time that could be delegated to someone else, and allow you to focus more on something else.

As important as being smart with your time may be, it’s also good to remind yourself why you’re working in the first place.

A post by my friend and career coach, Larry Cornett really spoke to me last year. When he was experiencing some doubt about where his time was being allocated a while back, he made the calculation that 3 ½ total months of his life had been spent in traffic over the last 4 years at his previous job.

In his post, he writes that this was the day something inside of him “snapped,” and ultimately moved him to rethink how his time was being spent. For Larry, this meant ultimately leaving his corporate career to foster an independent one. It really made me think about why we work, though. All of us, in general.

Whatever your situation – as far as commute, homelife, etc. – we all make a thousand choices every day about the way we spend our time, and where it’s allocated.

There’s no reason not to be proactive with our time and choose how we spend it wisely.

Preston Smalley produced in collaboration with Mark Mizera.

Why Should Leadership Replace Our Personality?

What is a leader suppose to look like?

How do they act? How do they dress? What shows are they watching? Do they watch TV? What’s their workout routine? Beard or no?

Am I meditating hard enough???

Having the opportunity to lead within an organization is a privilege, but that privilege can be accompanied by uncomfortable pressures and expectations – real or imagined. Some of these pressures and expectations are concrete, while some are obscure. Some expectations should certainly be met, while some would be better challenged, and others even ignored altogether. The key is learning to sort through the pressures and discern which ones are coming from external agents, and which ones we’re placing on ourselves, unnecessarily.

While there may be some universal, “best-practices” in leadership, there’s no one-single best way to lead people. We each have different characters and styles, and should take advantage of these aspectsrather than try and hide them in some misguided attempt to be “what a leader should be”.

Be the kind of leader you should be.

Be proud of your personal quirks and oddities, even (and especially) in the face of the surmounting pressures and expectations that come with leadership. Staying true to who you are, and what you believe in, will make you a better leader. One that inspires and elevates their team members and colleagues.

Collected here are a few tips and reflections from my time so far as a leader in business and tech. 

Tip 1: Don’t hide your personal life at work.

Early in my career, I was hesitant to open up much about my life outside the office. When I’d go on vacation I’d leave a cryptic OOO message in my email. Part of me felt guilty for taking off time. Divulging any details of what could possibly pull me away from the office felt like a confession of disloyalty.

“OOO” leaves room for interpretation… Out of office could mean I’m attending a conference. Out to an important meeting. Sent by the company on a secret mission to establish partnerships in China.

But, somehow, I think people just usually assumed I was taking my PTO like a normal person.

Eventually I realized that small, furtive behaviors like this one were really just missed opportunities to share who I was with my team.

Pardon the cliche, but the truth really does set you free. It’s a relieving weight off your back to not feel like you have to switch into different modes in every environment. It can feel incredibly liberating to be open about who you are as a person, and show how that has contributed to your professional path.

I now use my out of office message to give a glimpse into what I’m up to: “Gone Backpacking”, “Skiing Monday”, etc. I feel more authentic by this simple adjustment, and I also think that, as a leader, it’s good let my team members know that I support them finding ways to relax and enjoy these other areas of life, too.

[Auto-Reply] I’ll be out Monday skiing with my wife

Much of what can be accomplished within a company is based on trust. Can you do what you say you’re gonna do? Are you being candid with me? And if there’s a rapport, both parties are more likely to help each other succeed.

By sharing your whole self at work, I’ve found that I’ve been able to more quickly establish trust. And as I’ve done more of it myself, I’ve also found the opposite true. Those that are heavily guarded and private raise questions to me about whether they are also hiding work-related info.

Me as “Madison Bumble-garner” for Halloween at Work (Oct 2014)

Tip 2: Don’t always assume management is right.

Aside from those fields where instant decision-making is the difference between life and death, most organizations provide a means for their leaders to push back and challenge the decisions of management.

Other times you may need to take it into your own hands. Either way, being able to effectively say no to your boss is an important part of leadership.

As you lead others and move up the ranks, it’s easy to lose sight of who you are and become the instrument of an organization. There may be times when you need to dig deep, and keep what’s important to you in sight.

In the end, it’s important to own your actions, and stand firmly behind your team’s approaches.

Tip 3: Listen to your gut.

Some situations feel out of your control. Set in stone. Like when you’re ordered to deliver the message from a higher up authority that someone needs to be let go.  

Even in these situations, be mindful of the process. If the words don’t feel right, find truer ones to employ. If you can’t, perhaps there’s something wrong about the whole situation that needs to be challenged.

On a few occasions over my career, I’ve had to lay people off. More often than not it’s for one of two reasons: (A) a larger restructuring of the company, or (B) a team member simply isn’t a fit for the role they’re in.

In both of these situations, I’ve found that I’ve had to look inward to maintain who I am, and not just act as the management function I’m serving at the time. It’s easy to get lost and resort to corporate non-speak.

Fight this.

I try to own the wording of the messages I carry. And if I don’t like the words coming out, I push up the management chain to come up with a better solution.

When delivering the message of a layoff for reason (B) above, it’s critical that you separate the person from the role. If you think the person could ultimately succeed, help them. Give honest feedback. Provide course correction. Reflect feedback you hear from others (360 reviews are extremely valuable here).

Be a manager.

However, if that’s not working after a reasonable effort, perhaps this person is just in the wrong role at the moment. I’ve found there really are no “poor performers”, just people in the wrong roles. Or the person may have once been fine in this role, but the company requires a different style at this point in time, for whatever reason. In this case, the person would benefit from finding a new role, perhaps even within the same company.

It’s good to think about how you’d want to be treated if you were in the other chair in these situations, and be genuine about it.

“The reality is that no one can be authentic by trying to be like someone else. There is no doubt you can learn from their experiences, but there is no way you can be successful trying to be like them. People trust you when you are genuine and authentic, not an imitation.”

— Bill George, True North

Tip 4: Stay Balanced

While working at eBay for a leadership class that was part of my MBA curriculum,  I had the chance to interview our company’s president John Donahoe. John told me about a story back when he was consulting at Bain and Co. His wife had taken a role clerking for a federal judge, and he had to find a way to bring his kids to school a few days a week. John and his managing director were able to agree with their client that John would arrive on-site at ten o’clock, every morning. To his amazement, the clients actually appreciated his family-oriented choices, and he did some of his best work during that time.

This story really stuck with me. At a time when I was balancing my own work while earning an MBA, and carving out as much time with my family as I could, my wife and I having just had our first child. I continue to take a proactive approach with my schedule today, and make adjustments when necessary. I now work from home one to two days a week, and leave early on one other day so I can help coach baseball teams or simply be present after school and home for family dinner.

Me with my crew one afternoon dying Easter eggs being silly

Albeit I still find ways to make up the work in other ways. Staying late at the office a couple times a week along with a fair amount of travel. But in almost every case I can think of, these “tradeoffs” have enhanced the overall experience of my daily life at work, and at home. And I think it’s led to me being able to find more authenticity in my leadership.

Tip 5: Don’t Take Yourself Too Seriously

At the end of the day, regardless of your role at work, you’re still your mother’s child. You may be a sibling. A parent. A spouse. Friend. Goofball. We all share something in common with billions of other people on the planet. I go on dates with my wife. We make plans with friends. And even just playing with my kids seems to go a long way in grounding me.

There’s nothing quite as humbling than your own kids pointing out your various shortcomings (for me it’s usually my cooking).

These lessons have helped me in my career, and perhaps they can help an aspect of your own. I’m always on the look for tips and secrets that others have found true, and encourage anyone to share them with myself and with others.

Preston Smalley produced in collaboration with Mark Mizera.

Further Reading:

The Unsuspected Danger of Building Good Products

What makes a good product?

Best-in-market technology? Stellar user reviews? Right time of entry? Each of these factors indicates potential, but in truth, a product could have all three of these items going for it and still tank-it in the market. Just ask any of the 75% of venture-backed companies who fail to return their cash to investors.

So what’s happening?

Turns out, a lot of times, people are just focusing too much on quality.

The Difference Between Quality and Product-Fit

Sounds strange, right? Focusing too much on quality. But it’s true. In the early stages of building a product, more attention should actually be allocated towards the overall fit of your product within the lives of your users.

There’s an important difference between the quality of a product and product-fit. “Quality” is how well a product solves a customer issue. “Product-Fit” is a product’s ability to make the customer solve the issue, using your product. And beyond picking your product just once, Larry Page looks for it to pass the “toothbrush test” and be used twice a day.

The quality of a product is important. And quality does factor in to the overall fit of a product. But quality is not everything. Factors like price also play a significant role in the overall fit of a product vs. the other options in the market.

The original Echo was nothing to look at and lacked “skills” but sure found Product-Fit

Take the Plaxo story for example.

As a division of Comcast, the team at Plaxo was developing a product to solve the issue of Contact List disorganization. At the time I was the GM at Plaxo and working hard with the team on this shiny new product: The Plaxo Personal Assistant. It had premium, automated features. Integrated, cutting-edge database technology (Cassandra). Machine Learning. It was a beautifully-crafted product in a wide-open market. To boot, seemingly every working business professional griped and groaned about the issue of Contact List disorganization, and there we were: proudly holding the answers.

And then we went to market…

Our quality was through the roof. Demand was high, and competition was low. What better conditions could you ask for?

Product Page for Plaxo Personal Assistant (2011)

Well, there we stood. And what we got…



… was crickets.

As a product person, this hurt. Everything I had built up to this point in my career had worked. How could I expect people to trust my judgement after a huge failure like that?

Around the same time as this letdown, Eric Ries was gaining traction with his Lean Startup movement. I went to the meetups and heard Eric talking about the hundreds of other failing startups out there. He argued that ideas should be built simpler and proven faster to avoid overinvesting in them. Everything he was describing was exactly my pain at the time.

We invested two years’ worth of time and money developing a high quality product that no one would pay for. Dwelling on quality and neglecting product-fit With Lean methodologies failure still happens, but it happens faster, and allows you to move on sooner to the next idea. Failure becomes a valuable part of the process and not some ominous threat.With concepts like Minimum Viable Product we could’ve spent under six months teasing out these unknowns earlier on in the process. The fact that our price-point was too high and our entire initial business plan needed major adjustments would’ve been quickly evident.

I came away from this experience with a conviction that that overinvesting in a product’s quality, and waiting too long to shift that focus over to its overall fit within the market, is a serious pitfall. Equipped with these new methodologies, we then tried out some other ways of pivoting the business, and they, too, seemed not to fit in their markets. But we had found a way to get to this point in the process in a fraction of the time it had taken us before.

Team whiteboard at Plaxo as we explored possible pivots (2011)

At this point we had verified that there was no way to grow the business and recommended Plaxo be shut down. I expected I would part with the company but the management team at Comcast noticed the value in what we had gone through and asked me to apply what we were learning to their TV business. And so my work at Comcast Silicon Valley began.

We’re still applying the Lean methodologies today for our new product offerings and seeing success with it. Even if that success means failing quickly and getting to those products that do fit in the market and ultimately succeed in influencing the lives of our customers. Ash Maurya’s Lean Canvas is still a great way to flesh out a variety of business models–I’m even using it on a project today.  And never again will I over-build large and expensive products without testing for product-fit early on.

Lean Canvas by Ash Maurya

Preston Smalley produced in collaboration with Mark Mizera.

Billy Bean character in 2011 Moneyball (via Filmofilia)

The Dos and Don’ts of Leading Inherited Product Teams

Know Your Game Plan before Stepping into a New Locker-room

How do you Product Manage teams that know more about a product than you do?

When Product Managers inherit pre-existing products (whether it’s a change of company or an internal re-org) there are a lot of factors that need to be locked-down. Team Dynamics. Product Strategy. Performance Assessment Timelines.

Having a clear game plan in these situations can help you stay on the offensive, and not just feel you’re digging your product out of a hole. Below are some dos and don’ts I’ve picked up along the way after going through this process a number of times myself.

Game plans often need adjustments, but some truths remain constant and can be used to guide decisions as you move forward.

Do: Establish the Right KPI’s

Right as you step into a new product, figure out how the teams are measuring success.

How are we tracking performance? I’ve seen both extremes here. Teams that are drowning in data, and teams with no data at all. What’s the objective of your product? And what is the best metric to measure this objective? Getting to the right metric for your product is important.

I like Dave McClure’s Pirate Metrics, “AARRR!”, as well as Jonathan Kim’s refresher of the model.

What’re your retention metrics? You’re being judged on how much you’re moving it forward – it’s your responsibility to find the best way to measure success.

Define success for your product and illustrate that you’re doing a good job. This is your best chance to setup the goal posts–because if you don’t someone else will.

Don’t: Lead Blindly

Just as you shouldn’t blindly go along with whatever KPI’s were previously in use, you also want to avoid blindly doing what you think execs want you to do. Don’t build products without actively understanding why you’re building them.

Following orders without reason is not a strategy.

Analyze the issues your product is aiming to solve and make data-driven decisions. Read more on How to Say No to Your Boss in a previous post.

Do: Focus Your Strategy

Are the teams utilizing random, or no, feature prioritization? Are there disorganized backlogs? Is there a software methodology in place?

Whatever the current picture, these items need to be established from the outset.

Consider bringing in outside perspectives. Whether it’s a design consultant, or someone who can help to shape your strategy. It helps on multiple levels to seek fresh and objective approaches to the problems the team’s been living with for months or years. While you may be thought of as the “outside” perspective it may be more effective for you to facilitate that process and have an ally.

Seek to build a strategy that’s based on the objective of the product, and centered on customer needs.

An outsider’s perspective in Moneyball really helped Billy Bean (via Filmofilia)

Don’t: Think You Have Nothing but Time

People can tend to think too long-term in these situations. Deciding they need to completely redo the app. Start all over, in a new direction. Thinking, “it may take us a year and a half but it’s going to be worth it once we get there.”

Leaders often underestimate how much time they have. They take a long term, waterfall approach to rebooting the app of the team but fail to realize they need to produce results in the short-term in order to get to make it to those further-out time-frames.

The reality is, as a leader, you’re often judged much sooner than you’d like to be.

Do: Get Early Wins

It’s important to have a long-term strategy and make investments that are going to pay-off in the long run. But it’s also important to get some smaller wins under your belt along the way. Identify ways to move the product forward between now and the three month mark. Then again at the sixth month mark.

These may seem small, but it can signal to the rest of the organization: look, things are changing. Things are getting better. We’re making improvements.

Some of those early wins that you chose to go after can be useful teaching moments for your teams, and they can also buy you time to go after the goals you’ve set further-out. In business school a good deal of focus was spent on “change management” principles like those of John Kotter’s Leading Change: Why Transformation Efforts Fail [$] in the HBR. Around that time, I posted some thoughts on large company inertia on my website as well.

Don’t: Create Toxicity

It may sound obvious, but some leaders who step into an environment with poor cross-functional relations, see an opportunity to create camaraderie around their shared, negative sentiments. It’s “Us vs. Them”. Essentially fanning the flames of dysfunction and creating toxic cross-functional dynamics.

While this may create an instant gel around you and your team, it won’t pull the cross-functional teams together. And until you’re able to unpack that and create a collaborative environment amongst the other teams you have to work with, you’ll be drudging through a negative work environment.

Do: Get In-Tune with Team Dynamics

What’s going on? Are the different functional areas collaborating with each other?

When stepping in to manage a product team a couple years ago I found that Engineering, UX Design, and Product weren’t communicating. They were all completely silo’ed, which wasn’t helping the product. This is a good example of an instance where I brought in an outside perspective who was able to reboot everything and get it humming along. I was given a different area to manage after doing well with that team and to this date they’re still a well-functioning unit.

See what other dysfunctions there may be. Who’s getting in the way? Move them out of the team, or the company – quickly.

Who’s being undervalued? Find the diamond in the rough. Can they take on more responsibility?

Don’t: Think You Have All the Answers

Between implementing all your clever frameworks and reboots, don’t forget to listen to the team members.

Leaders seem especially prone to this mistake – failing to listen to the teams – when a product is failing and they step into fix it. It’s intuitive to think the quality of a product is reflective of the teams but sometimes this just couldn’t be further from the truth. Often you’ll find the team members themselves are frustrated with the product and have a pile of ideas that nobody seems to be listening to.

So listen.

If you were a coach stepping into to work in a new organization, you’d want to understand who your star players are. Who are the people that are going to be creating problems in the locker room? Who’s really talented but has a bad attitude? In sports though, the KPI’s are straightforward.

You’re judged on your wins. In Product, wins can be much more ambiguous. Getting clarity on what type of wins you and your teams should be going after will bring a lot more focus and success to your efforts.

Preston Smalley produced in collaboration with Mark Mizera.

The One Question Your Product Demo Should Answer

Wizard of Oz Experiments, Pixar, and Other Elements of Product Storytelling

Why do we demonstrate products?

Should we be demonstrating products?

What’s happening beneath the surface of an effective Product Demo? Where should we be focusing our energy when creating them?

What makes these things tick?

Steve Job’s memorable Product Demo of the original iPhone (Jan 2007)

Product Demos can do a lot of good for your products. But there is one specific result that a well-crafted Product Demo creates that far outweighs any others.

They answer the simple question:

What’s in it for them?

Direct the efforts of your Product Demo toward showing audiences why they care about your product with the three following steps.

Step 1: Wizard-of-Oz It

As Product People, it’s natural to want to show off our prized creations. We might cavalcade our products through the streets, if the marketing budget allowed it. But, alas, we have to get our kicks during the Engineering Demos, because the Product Demo is for the consumer. And the consumer doesn’t care about the hoops or scrums, sprints, long jumps or high jumps our teams had to go through to make these things.

They just want to know what’s in it for them.

A well-focused Product Demo demonstrates how a product can serve end users. It does not demonstrate the actual product, itself.

There’s a difference.

Watching how a product can serve end users is like watching a highlight reel. The latter can feel like being forced to sit through an entire sporting event in the span of your five-minute demo, if you make the audience follow you through every single screen within your app.

Keep things focused on what’s in it for the audience by crafting the Hero Case of your product. The ideal scenario in which an end user benefits from the product.

The Wizard of Oz (MGM, 1939

This is where Wizard of Oz Experiments come in. As many of us know, a Wizard of Oz Experiment is one in which the subject thinks the computer program their testing is autonomous, but is actually being operated by a hidden person. One of human’s greatest strengths is our ability to imagine. We’re able to vividly picture elaborate scenarios in our heads on a whim and can be so enthralled by these imaginary moving pictures that we forget where we are. Why get in the way of that?

Set up a presentation that transports the audience into the Hero Case. And don’t take them out of it with unnecessary distractions like logins and page loading screens.

Wizard-of-Oz It.

The audience’s ability to visualize themselves using the product will make this type of demo feel realer than the actual thing.

Step 2: Tailor the Hero Case to Every Audience

Just as users aren’t concerned with the inner-workings of a product, not all end users will have the same Hero Case with your product.

In a tweet I have saved, former Pixar Storyboard Artist Emma Coats shares advice about storytelling that bears similarity to this notion.

Just as writers and audience members will have different ideas about what’s interesting, individual audience members will have varying ideas about that, too.

Consider your audience and tailor that Hero Case you present to them to match their profiles. If you’re interviewing with a reporter or a journalist, cater it to their beat. They’ll be doing this later on anyways, so take control of how that message gets shaped. If you go on the air with a local radio host, tie in a hometown, or two.

XFINITY X1 Olympics Product Demo (2018)

And if you happen to be presenting the XFINITY X1 platform for the Olympics to a group of youth figure skaters in Nashville, who really love the twenty year old figure skater Bradie Tennell, it only makes sense to show them how to soak up every second of their hero’s possible screen time. Right?

Plus, there’ll be plenty of other chances to show off the rest of the marquee Olympians (e.g. Shaun White).

In a great piece in the First Round Blog a while back, Rob Falcone argued this in reference to startup pitches, “Your Product Demo Sucks Because It’s Focused on Your Product

Good demos don’t have to be perfect for the product. They have to be perfect for the audience.

Rob Falcone (2014)

Step 3: Storyboard The Hero Cases

I’m a big fan of Pixar. I value a lot of the concepts in Ed Catmull, the president and co-founder’s book on fostering creative environments; and I also just enjoy the sheer awesomeness of seeing a scene from the first Toy Story movie get pitched on a storyboard.

Watch Joe Ranft Storyboard Pitch a Scene from the Original Toy Story

When drafting up the Hero Cases to present in your demos, storyboarding can be a really useful tool. When you label each card that represents a scene, if you will, in a particular Hero Case; the words you write down on the card naturally become the script for the demo. It’s a helpful way to figure out how to paint the picture you want the audience to visualize.

In movies, we don’t usually see characters doing things like chores, or brushing their teeth. Myriad exceptions exist of course, but even the exceptions are intentional. The filmmakers include them to reveal something about the character, or to set up the next scene. But every scene that makes the final cut in a movie is necessary to the plot. And if a scene is not necessary to the plot, it’s cut.

Take a look at the script of your demos and see if any sections don’t pertain to the plot of your Hero. Anything unrelated to the Hero Case is a distraction.

Stay focused, and make it clear to the audience what’s in this for them.

Thanks for reading! Please comment anything I missed or approaches you’ve found to get audiences more engaged. And for more on the Art and Science of Product Demos, check out my field guide to demos:

3 Practices for Building Strong Presentations

Preston Smalley produced in collaboration with Mark 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.


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

3 Practices for Building Strong Presentations

A Product Demo Field Guide

There’s a few components to a product demo. The content of the presentation itself. The nuts-and-bolt logistics of how you’ll physically present your content. And then there’s another aspect you have to plan for — the technical difficulties. The mishaps. The curve-balls.

The unexpected.

Though after having delivered a hundred some-odd product demos, these “unexpected issues” have taken a much more predictable air about them for me. In fact I’m pressed to think of a single presentation I’ve given where at least something didn’t go differently than planned.

We can’t know exactly what to expect during the course of a presentation. But we do know the general types of issues that arise, and we can position our presentations in a way that doesn’t allow these issues to unhinge them.

Below are three different ways to address the factors I’ve found to play a consistent role here. By using these frameworks when planning and producing a product demo, you can avoid a great deal of pitfalls that tend to surface while presenting.

3 Practices for Strong Product Demos

1. Limit the Variables

When planning a product demo, it’s understandable to want to “think big”. You want to wow your audience. Dazzle them. Give ‘em the real thing! And then before you know it, you’ve assembled a Rube Goldberg machine of moving parts. Variables that add extra degrees of risk in the successful execution of your demonstration.

But the thing is, the less moving parts you have in your presentation, the less opportunities there are for errors.

An elaborate show of function is not the aim of a product demo. Effectively communicating why a product is relevant, and how it can impact users should be the aim of a product demo.

Anything that jeopardizes that mission is a liability.

2. Establish Contingency Plans (and contingency plans for those too)

Once you’ve trimmed the fat of unnecessary variables, assess the remaining components and identify any possible stress points.

Play out all the scenarios in your head:

What if the WiFi network at a venue gets overloaded? Personal hotspot? Ethernet cable? Maybe I’d be better off using stored content, and not relying on having a connection at all.

What if the file gets lost? Cloud copy? Hard copy? USB Flash drive? USB-C adaptor for flash drive?

What if the device dies on stage? Backup device? Powered on, plugged in, with the demo up— standing by on another video input, just in case?
It only sounds paranoid until it doesn’t. Just ask Bill Gates…

Each demo has a unique environment and requires its own assessment. Creating an exhaustive set of contingency plans allows you to easily circumvent any “unexpected” malfunctions.

Establish and ready your plan B’s, C’s, and D’s (E’s and F’s if you have them). The more you have, the less stress you’re presentation will take on.

3. Improvise 

It’s true. Even with a structurally sound presentation, and an alphabet full of backup plans at your disposal. The best laid plans go awry.

But that’s okay. It’s part of the gig, really.

Stay loose.

Now, onstage, is not the time to be rigid. Stubbornly trying to execute your original plan, when circumstance calls for impromptu adjustments, will only make things worse.

Equip yourself with the advantage of expecting to improvise. Planning on it. Anticipating the moment when you’ll need to think on your feet, briefly.

By simply realizing beforehand that you’ll likely be called upon to make small adjustments throughout your presentation, you’ll enhance your ability to make small adjustments throughout your presentation. Everything from needing to do your demo in half the planned time, to adapting to glitches.

I can remember a product demo I gave where the audio wasn’t working. Naturally, the product being demo’ed had a feature that allowed the user to ask the device what song was playing. Well, given there was no audio the audience couldn’t hear the song playing. But instead of distracting the audience, from the feature itself, with our technical difficulty, I just talked around it.

Something to the effect of, “Now, if you hear a song you like, you can ask the device… and the song will appear on the screen.”

Looking back, maybe it was better that way. Maybe… by not having the song playing, the audience was able to focus on the feature more intently, rather than on the song itself.

Either way, the presentation was fine.

Improvisation is a small but useful tactic to the smooth execution of a product demo.

Hopefully these concepts seem obvious, in part, to most people. The concepts, themselves, are not the key here. The key, here, is deliberately integrating these features into the preparation and production process. When utilized as a cohesive playbook, these approaches can keep even the most sabotaging of issues from the audience’s attention.

Keeping the focus on the product.

Preston Smalley produced in collaboration with Mark Mizera