Given that reflection, 50 hit me harder than I thought it would. It’s triggered some meaningful shifts for me and setting myself up for the decades ahead.

(#7) “Or at some point not even work, just help.”

I was just thinking out loud on this one. I had been working so hard, at Apple, leading product marketing for AI. This AI wave is incredible and one of the rare moments for a new peak wave in my tech career. This is the fourth. (Internet → Social → Mobile → AI).

Helping Apple ship amazing products was a life dream for a kid who got his first Apple ][+ in the early 80s and took a Mac LC II to college.

But turning 50 made me reconsider the difference of working and driving things at one company, vs helping lots of companies and people become successful — which I had gotten to do as a VC. I realized that it’s hard to do a full time job and help others. I would occasionally take 9pm calls or 7:30am Saturday calls with founders and friends to help but it was always an extra.

I knew I first had to to hit the major milestone of launching a much improved Siri for Apple, a true capstone to my time there.

But I also decided it was time to make that shift and spend my time helping lots of startups realize their dreams vs only working at one company. I feel so lucky I found a path to join A16Z to do so.

From one small thought, it triggered a lot of change. But I’m so excited about what the next years bring, and this is an incredible time for the next wave of consumer products.

(#27) Could be better at spending more time with all of them [my family] and telling them how important they are to me.

This also got me thinking about how I hadn’t visited my parents in Seattle in a long time. I made that happen multiple times and we had some meaningful conversations. We also shared some family celebrations.

I’m still so lucky to have them in my life and need to do this more often. Another goal for this upcoming year!

(#31) But for the Seahawks and Mariners — I am a deep fan, even when living in the Bay Area. In my lifetime there has been literally one championship between them.

Ok, I’m a huge Seattle sports fan. The Mariners — well they got close last fall, but not even to the World Series, and then had just a terrible season this year. But the Seahawks. Wow. They ended up having a great year, kept rolling through the playoffs and made it to the Super Bowl. People told me that seeing your team win the AFC/NFC championship at home is one of the best feelings in sports. I went up to the NFC Championship in Seattle. They won! The Super Bowl was in our backyard here in the Bay Area. I got to take a Waymo to and from the game, from home. It was incredible to see the Seahawks win.

Bucket list fulfilled!

(#19) I also really love listening to Broadway musicals. And have gotten to see original cast of Rent, Titanic, Spring Awakening, Hamilton, Dear Evan Hansen, Come From Away, Maybe Happy Ending. Will aim to keep expanding this list.

Writing this down helped me remember how much I really do enjoy musicals. And I hadn’t seen many since the pandemic. Got to 6 in the past year including the original cast of Two Strangers Carrying a Cake Across New York (it was delightful!). And a couple I went to alone! My new mantra is do more of the things you love.

I have more queued up for the next year. Very excited about the world premiere of The Interestings which will happen in Berkeley, and taking my mom to a special musical that will premiere in Kansas City in August 2027.

(#37) One thing I realize looking back is how easy it is to focus on benefits and be naive and even ignorant of negative impacts and externalities. As products reach billions, even a 1% issue can affect tens of millions. This is important and something I wish more had focused on earlier. And with each new wave, we make similar mistakes in the race to get to benefits quickly.

The AI wave is incredible. Over the next few years I believe we will transform how we learn, work, share, shop, discover, explore, get things done and so much more. AI will transform nearly every user experience to be so much more natural to use and interact with. Just with language — how we communicate and work with each other. We’re so early and there are so many exciting things happening.

But I realize even more now the importance of doing this right. A way that brings everyone along on the journey and how to make sure we make the world better.

(#44) But if I am being honest with myself, I wish I had chilled out and stayed longer at each job. Growing with a company that hits escape velocity is a rare thing in our tech industry. There have only been dozens of these opportunities across my entire career.

While I do wish I had stayed longer at every job, I’m coming to terms with the reality that I didn’t. Even Apple I thought I’d be at longer.

But as a trade, I’ve been so lucky to be at so many important companies navigating through very critical transformations from something just starting to work to a durable system that will keep growing and scaling.

Seeing many ways to make these leaps prepared me even more to help the next wave.

And we’re in one of those waves where we’re going to see so many things hit escape velocity!

What a time we’re in.

(#50) First 50 years have been incredible. On to the next!

First 51 years have been incredible. On to the next!

I came up with a way to extend the hunt for another hour or so with a great puzzle activity. It turned out to be a really great morning.

I created a whole new puzzle where each egg contained a piece of a puzzle that turned into a home scavenger hunt which eventually led to one big prize. Was a total of ~50 pieces / eggs.

Step 1: Take Close Up Pictures

Go around the house and take ~8 pictures of areas of the house very close up. Macrophotography. Get so close up it is hard to recognize what the object or location actually is, but when you finally identify it, it clicks! World Magazine, which I used to get as a kid, always had a page at the end with photographs like this which inspired my idea. Another example https://www.businessinsider.com/close-up-photos-everyday-objects-2018-11

For example: this was inside one of our Lego constructions

Step 2: Print out these pictures

Step 3: Turn each into a puzzle

Cut up each picture into 7–8 pieces. Make sure your cuts have some shapes to them — it makes it more fun. And as you cut across the photographs, see if you can make it tricky to figure out just which fit with each other. Since one step of solving is just sorting which photo group is which.

Step 4: Set up internal scavenger hunt

Select one location / photograph to be the master location. Hide the prize here. And then take the pieces of this photograph and hide one piece each at the other 7 locations.

Step 5: Set up egg hunt

Take all of the other puzzle pieces and put each one into an egg. This is the most tedious step. Now hide the eggs all over your house / yard. If you do them inside, just make sure you don’t get near any of your scavenger hunt locations.

Step 6: Let them at it!

Their first step will be to collect all the eggs. Make sure they are all found.

Then they will have to sort and assemble the puzzle pieces into the different photographs.

Once assembled, they can find the location of the puzzle pieces for the final photo.

Then they assemble the final photo, identify the location, and receive the prize.

Have fun!

I wanted to expand on the first point and asked ChatGPT to do so. It did a great job with some key insights. But it did miss the importance of making sure you build relationships with the people you work with so that you understand them, they understand you, and you want to keep working together. Every bit of work has bumps and disagreements — but you want to earn the right as a great partner to work through those together to get to great outcomes and not a bulldozer who insists on getting their way without listening, processing, sharing reasoning, and getting to a shared outcome. Anyway on to what ChatGPT advises:

In a world where quick fixes and instant gratification often dominate our decision-making, there’s a valuable lesson to be learned: “Earning the right to do the next thing is more important than doing the right thing once.” This concept reminds us that sustainable success is built on a foundation of consistency, perseverance, and a long-term perspective.

The Illusion of Instant Success

In our fast-paced society, the allure of instant success can be overwhelming. We’re bombarded with stories of overnight sensations and shortcuts to achievement, which can give the impression that you can skip the hard work and go straight to the top. However, such stories are often the exception rather than the rule.

The Power of Building a Foundation

To truly succeed in any endeavor, it’s essential to focus on building a solid foundation. This involves dedicating time, effort, and energy to mastering the fundamentals, honing your skills, and learning from your mistakes. It’s about putting in the work and gaining the experience that makes you proficient in your chosen field.

The Role of Consistency

Consistency is a critical component of earning the right to do the next thing. Consistently doing the right thing, even when no one is watching, is what separates those who achieve long-term success from those who burn out quickly. Whether it’s in your career, relationships, or personal growth, staying committed to your goals is key.

Learning from Mistakes

Mistakes are an inevitable part of the journey towards success. Earning the right to do the next thing also involves the willingness to learn from your failures. Instead of dwelling on your mistakes, view them as valuable lessons that help you grow and improve. It’s often said that the path to success is paved with failures — it’s how you respond to them that counts.

Delayed Gratification

Earning the right to do the next thing requires a willingness to delay gratification. While it may be tempting to take shortcuts or opt for immediate rewards, this approach can lead to short-lived success or even failure in the long run. By staying patient and understanding that real success takes time, you position yourself for sustainable growth.

Short-Term vs. Long-Term Gains

In many situations, individuals who focus on short-term gains may achieve initial success, but they often struggle to maintain it. On the other hand, those who prioritize long-term goals are more likely to achieve lasting success. It’s not about a single moment of brilliance; it’s about consistently performing at a high level over time.

Embracing the Journey

Earning the right to do the next thing is not just about reaching the destination; it’s about embracing the journey. Every step, every challenge, and every effort contributes to your growth and your ability to take on new opportunities. When you focus on the process, the destination becomes all the more satisfying.

Conclusion

In a world where the quest for quick wins and instant success can be tempting, the concept of earning the right to do the next thing reminds us that lasting achievements are the result of consistent effort, learning from mistakes, and a focus on long-term goals. Success is not just about doing the right thing once; it’s about building a foundation that allows you to do the right thing time and time again. So, embrace the journey, stay committed, and remember that true success is earned, not given.

Should I start angel investing?

So the first thing I always tell people is venture investing is a very easy way to lose a lot of money. Most startups fail and never even return the full amount invested in them. The earlier you go, the more risk. The last few years have seen a massive rise in secondary markets that you could buy into, and valuations are quite a bit down from the go go period of 2019–2021. I guess the same is true for public markets.

Given all this, only invest money you are ok with it going to zero. The best way to get started is to invest in your network — people you know or people they know starting companies who want to give you a chance to invest. You can try angelist or republic or other paths like that, but i think those tend to have some adverse selection. My general advice to people in tech is invest your money in safer broader things, until you really have enough you are willing to just lose it

Should I work at a VC firm to learn about startups and investing? What if I like building?

A job at a VC firm should never be the first time you are visiting startups or hanging out in their offices. Do the work ahead of time. Get to know friends with startups, visit them in evenings, jump on weekend phone calls, jam, help if they need it. An entry level VC role is usually not recommended, but it can be fun if you are already doing all of this as a hobby (I sure was!).

But be warned, it is very much not building. Based on your (3), i would say the most fun you can have is having a great building job and occasionally advising or angel investing in companies on the side. This way you still build as your core day job, but enjoy the side hustle of getting to help startups. For me — I spent 15 years at startups (LinkedIn Facebook twitter when they were all much smaller) before becoming a full time VC. I did that for 7 years but I missed building so returned to operating about 5 years ago.

A friend recently asked my advice as they are interviewing their first product manager for their company. They wanted to understand what areas to probe, what to look for, and how to craft their interview loop.

Here’s what I shared:

For product roles — it’s a great question. This article is nearing 20 years old, but it was critical to me when I was early in my product career and in many ways I still haven’t found a better one: https://www.bringthedonuts.com/essays/productmanager.html

In general, my guidance for a small company is you want the first product person you hire to be someone who’s been around a team like you before, and in at least some part of the space you are in (b2b, consumer, fintech, etc) so that they aren’t coming in cold. You don’t want them to be so senior that they keep telling you they need a team, but it’s not a bad thing if they have managed a few PMs before. Then again, it’s not a bad thing if they haven’t, as long as they have managed projects with 20–30 people on them.

For questions, there are three areas I like to probe:

(1) Experience and ability to articulate the narrative.

Basically I like to ask them to explain their resume and why they are here now excited about this opportunity. Should take just a few minutes, but give you a good sense of how they think about themselves. Then… ask the to describe a project they are most proud of the impact it had on their customers, or the business. They should be able to trot out a cool thing they worked on, what impact it had, and the challenges they faced going through it. If it’s compelling, you can probe and really understand their role on the decisions (how much was dictated to them vs what they figured out or advocated). People who can’t do this… it’s wild how bad some of the answers are.

(2) Self-awareness.

My favorite question:

“Product managers need to be good at a lot of different things. We all have strengths and weaknesses. Of these areas, which are you best at, and which are you weakest at?
(1) vision and storytelling — being able to communicate what we’re doing / should be doing and why.
(2) working with design to craft great user experiences
(3) working with engineering to solve gnarly problems.
(4) execution and process — finding the milestones and keeping the team really organized to deliver.
(5) metrics and iteration — once something’s launched, evaluating feedback and coming up with new ideas.

What I look for here is people being rational about what they are best and weakest at. We all have them. If they try to say “I’m good at all, I just say “come on… we all have strengths and weaknesses”. When I answer this personally, I say I’m great at vision/storytelling and explain why, and then I say I’m also pretty strong at metrics and iteration and coming up with ideas as we learn things. I then say I’m weakest at process and organization — there are a lot of people far better and more organized than me, but I can still keep something operating and getting done.

(3) Curiosity and creativity.

A couple of directions here , but you really just want to see how the person thinks about product and brainstorms things. You want someone who you are excited to riff with if they join your company. You could ask “if you joined us, what is the first problem you think would be really important to tackle and how would you approach it”. Or you can ask something about another product like “if you could fix Uber Eats’ recommendation service to suggest better dishes for you, what would you try first”. Or “How would you build a referral program for Netflix? Referrals are so big for other services, and on Netflix they all just share passwords”. Or any idea of a product you think about!

Noun: a person who is under medical care or treatment.

(Source: dictionary.com)

Thinking back to the beginning of 2021, no one wanted to be patient, or a patient. We had been sitting around 2020 in the swirl of a pandemic, a stock market yo-yo, a political roller coaster with the election of Trump and Biden.

By the beginning of 2021, I felt everyone wanted to move on fast. Well except for the beginning of the year Jan 6 when some people wanted things to stay the same and we had that awful moment at the Capitol.

2021 was supposed to be the year everything got back to normal. The vaccines were going to come out, the pandemic was going to fade, we could all return to the office except those who wanted to just work from home forever.

But it hasn’t happened that way. We’ve had to all be patient. And sadly, too many were patients of the noun variety. While we talk about survival rates, I know a few too many who lost close family and friends due to COVID which makes all the stats and “risk” much more real.

You can see the impatience in people wanting to get rich fast too this year. First there was the GameStop and other meme stocks. And then crypto and NFTs and no one wants to be patient to get rich slowly when you can make millions over night buying the right cartoon image before someone else wants it.

Parents have had to be patient all year waiting for their kids to get vaccines, lest they risk their kids become patients. Though fortunately for many, schools reopened at least more or less, with masking etc.

But we end the year similar to how it started. Confusion. Patience. Impatience. Is Omicron going to blow through fast (I sure hope so!) because I am impatient to get back to the real world being much more the real world we had before.

This is going to be a giant imprint on the entire generation. I don’t think the world has gone through anything together like this since the Great Depression and global wars. Those generations were permanently changed. Ours will be too. Whenever someone sneezes near you, it might feel like a mini bomb went off. Certainly will affect our kids forever.

Given that everyone else is going through the same ups and downs and traumas of the past two years, the best thing we can do is be patient with anyone we meet. Be forgiving. And take just enough precautions that we don’t turn others into patients.

I have recently been talking to a number of founders and co-workers about this era and realizing that (a) I’m now old and (b) how few of them were in the industry, or even aware of what was going on then. One recently reminded me he was 4 years old in 2001.

It was such a fun and wild time. Companies like Lycos and TheGlobe.com became multi-billion dollar entities on hope, promise, and revenue from selling products to each other and back. As big as the tech / internet bubble was, the telecom bubble was even bigger with higher highs and higher lows, and much of the over-investment in capacity has been utilized time and again since then (and got really cheap for a few years in between too).

Most things that felt like hype back then, are realized today. Technology and the internet are truly mainstream. Billions of people have connected to the internet in the past hour. Instead of it just being about potential, there are now many trillion-dollar and multi-hundred-billion dollar companies that we depend on almost like core infrastructure now.

But, what’s similar is the belief in the future being much bigger than today, and people around us making gobs of money. In some ways crypto feels the most similar to the dot com hype era — where we talk a lot more about the potential, even if the usage isn’t quite there yet. I do wonder what are the Amazon, Yahoo, eBay, and Google in the crypto world today. And this applies to other really important future areas like space, autonomous vehicles, and more.

I wanted to see if there were any great books or movies to dive in deeper so I asked on Twitter and assembled the results below:

Josh Elman on Twitter: "Are there any iconic books or movies about what really happened during the dot com bubble (and really telecom bubble) and crash? I am looking for both great non fiction overviews of what happened, and fictional or cultural retellings. / Twitter"

Are there any iconic books or movies about what really happened during the dot com bubble (and really telecom bubble) and crash? I am looking for both great non fiction overviews of what happened, and fictional or cultural retellings.

Books:

Non Fiction Overviews:

• How the Internet Happened by Brian McCullough — a great overview on the development of the internet and what the Dot Com era accelerated

Non Fiction Collections of Stories:

• F’d Companies by Philip Kaplan — Philip’s website FuckedCompany.com had all the gossip and stories in that era
• The New New Thing by Michael Lewis — focused on James Clark and a few related stories
• Nudist on the Late Shift by Po Bronson — a collection of iconic stories from the era
• Once You’re Lucky, Twice You’re Good by Sarah Lacy — a collection of stories from Web 2.0 founders who came out of the bubble

Non Fiction Focused Stories:

• There Must Be a Pony in Here Somewhere: The AOL Time Warner Debacle and the Quest for a Digital Future by Kara Swisher
• eBoys by Randall Stross — the story of Benchmark and the VC industry
• How to Castrate a Bull: Unexpected Lessons on Risk, Growth, and Success in Business by Dave Hitz — the story of NetApp and more
• Boo Hoo: A Dot Com Story — how Boo.com burned $135M in one year

Fiction:

• Bleeding Edge by Thomas Pynchon
• Moral Hazard by Kate Jennings

Blog Posts:

• Tren Griffin on the Dot Com Boom and Bust
• Tren Griffin on the Telecom Bubble

Movies & Documentaries:

Overviews:

• What Happened - 2001 Documentary — shared by Mark Cuban

Stories of Specific Companies:

• Startup.com — the story of GovWorks (pay your government bills online!)
• E-Dreams — the story of Kozmo.com (just like Doordash today)
• Riot On! — the story of Riot Entertainment (an early mobile phone)

One thing that surprises me a bit is there aren’t more iconic books or movies made about that era. One reason I suspect is that while the dot com peak was hit in March 2000 and it started falling hard from there, it wasn’t until the tragic events of 9/11 that the era really felt closed. That was such a transformational event I think there have been a lot more content created about that instead. That day still was the most transformational moment of my lifetime until the COVID pandemic.

It reminded me of something my brother recently unearthed and that my Dad used to make cool programs on the Vic 20.

Amazing how the circle continues.

1 rem “greeting to grandparents” copyright 1982 by donald elman
2 clr
10 a$=”{red}{red}{cyn}{pur}{grn}{blu}{yel}”
15 poke36879,12
20 poke36878,15
30 print”{clr}”;
40 fori =1 to 22
50 gosub 3000:gosub 4000:print b$”S”;
60 nexti
70 fori=1 to 21
80 gosub3000:gosub4000:printb$”S S”;
90 nexti
100 fori=1 to 21
110 gosub 3000:gosub 4000:print b$;”S”;
120 next i
130 poke36876,0
140 fori=1to1000:nexti
150 s1=36874:s2=36875
160 s3=36876:v=36878
165 print”{home}{wht}”
170 fori=1 to 4
175 readsl
180 forj=1 to sl
190 read p,d,g$
195 pokev,15
200 poke s2,p
210 printg$;
220 forn=1 to 200*d:next n
230 poke s2,0
240 forn=1 to 20:nextn
250 next j
260 print
270 next i
275 ifvs=0then300
280 poke v,0
290 fori=1to1000:next
300 print”{home}”
310 fori=1 to 4
320 print”{blu}S {cyn}S{pur}S {yel}”
330 next i
335 ifvs=1thenvs=0:goto340
336 vs=1:goto165
340 print”{home}{down}{down}{down}{down}{rght}to {wht}grandma & grandpa”
350 gosub3500
360 gosub3600
380 print”{rght}{red}{down} S S S love S S S S”
390 pokes2,232:pokes1,239:pokev,7
400 gosub3600
405 print”{down}{down}{rght}{pur}joshua, {grn}adam, {cyn}linda,{down}{rght}{rght}{rght}{rght}{rght}{rght}{rght}{wht}don & {yel}vic”
410 gosub 3500
420 gosub3600
430 fori=1 to 750:next i
440 print”{rght}{blu} oh”;:pokes1,239:pokes2,0:pokes3,0:pokev,13
442 fori=1 to1200:next i
450 print” yeah!!{blk}{up}{up}{up}{up}{up}{up}”;:pokes1,240:pokev,4:pokes2,0:pokes3,0:gosub3600
1000 fori=1 to 2000:next i
2000 data6,225,1,”{rght}we “,232,1,”love “,235,1,”you, “,237,1,”grand”,235,1,””,232,3,”ma”
2010 data5,225,1,”{rght}and “,232,1,”grand”,237,1,”pa, “,237,1,”too”,235,4,”;”
2020 data6,225,1,”{rght}in “,231,1,”san “,232,1,”di”,235,1,”e”,232,1,””,231,3,”go,”
2030 data5,225,1,”{rght}the “,231,1,”sky’s “,235,1,”sure “,235,1,”{cyn}blue{wht}”,232,4,””
2040 data6,225,1,”{rght}so “,232,1,”for “,235,1,”this “,237,1,”tr”,235,1,”i”,232,3,”p”
2050 data3,232,1,”{rght}we “,237,2,”thank “,238,6,”{yel}you — {wht}”
2060 data4,238,2,”{rght}oh, “,237,1,”grand”,235,1,”par”,232,2,”ents”
2070 data3,235,2,”{rght}{grn}we “,231,2,”{red}love{$a0}”,232,6,”{pur}you!!!”
2400 pokes1,0:pokes2,0:pokes3,0
2500 end
3000 n=int(rnd(1)*7)+1
3010 b$=mid$(a$,n,1)
3030 return
3500 pokes3,235:pokes2,231:pokes1,240:pokev,7
3510 return
3600 for n=1 to 1500:next n
3610 pokev,0:forn=1 to 500:next n
3620 return
4000 poke36876,int(rnd(1)*128)+128
4010 form=1 to 10:nextm
4020 return

All credit to Adam Elman for saving the code and getting it to render on a Vic 20 Emulator after all these years

Apps are amazing. I use at least 15–20 apps every day to get information, connect with my friends, capture memories, make memories, order food, order everything, and more. I always enjoy learning about and trying out new products. So many times though, I get let down.

Here’s how it usually goes: I am excited. I set aside time to focus on this new app a friend eagerly invited me to or maybe one I found via an article or an ad. I open it. I go through a short little onboarding flow that asks me for my name, email, a TON of permission screens, and an attempt to find my friends by uploading my address book. I usually say no. I get dropped into the main screen of a new product I’ve never used before with some tabs, a settings menu, and a whole lotta information and words I don’t understand. There might be one tooltip or a few on the screen. But, I usually have no idea what to do next. Sometimes I call my friend who shared it with me and ask them what’s the deal? They explain it to me again and I try a little harder. I figure it out and try a few things. Sometimes it catches, but usually it doesn’t. All in all, I end up with hundreds of apps all over my phone that I don’t use again. Thankfully with iOS 14 they are starting to organize those for me and get them out of my way.

But there is a better way!

Onboarding can be the most welcoming part of your product. It can turn people who are curious about your app into your most committed users. It can turn doubters into superfans. Great onboarding is a superpower of your app. Great onboarding is what engages your users. It takes the users on a journey of entering your product and getting to know your product. It helps the users make decisions and set up the product so they can get the most out of it. And for users who decide it’s not for them, they can figure that out as they go along rather than just get confused later and bail.

The moment someone is trying your product is the MOST ATTENTION you ever get from that user. Take advantage of it.

I have learned that longer flows are better than shorter flows. This doesn’t sound right, but trust me, it’s true. Well, it’s true as long as the steps are simple, clear, and progressively build on each other to tell a story. Each step in a flow should be a very simple question to help the user set up the product. In each question and answer, the user should get one step further in their understanding of the product and its capabilities too.

How you measure onboarding can significantly change your approach. Too many people measure the success of onboarding of one flow (A) vs another flow (B) simply by how many people complete the flow and get to the “end.” The only true end of onboarding is when a user is habitually using your product. The best way to successfully measure onboarding is to understand how many engaged users each flow creates. You can do this by looking at the % of active users from those who started the flow one day, one week, or one month later. You may be surprised that an onboarding flow with a better “flow completion” rate may significantly underperform one that has fewer people complete the flow. Because in the latter case, the users who do successfully complete the flow are much more prepared to use the product and are more motivated and excited to use it as well.

My favorite Onboarding Exercise

The best way to make your onboarding better is to try it. Try it often. Every few weeks at minimum. Think of yourself as one of your user personas, or a dumb user rather than you, the expert who knows your product very well. Question every step. Act confused. Think about how nervous someone is about doing something wrong with your product. Think about how nervous someone is about giving all of their information to a product they have never used before. You can take all of these feelings and make it so much better.

Here is an exercise I like to run to improve an onboarding flow:

Participants:

This exercise takes three people from your team. One person plays the “novice user” who is about to onboard to your product. One person plays the “coach.” One person is the “note taker.”

Preparation:

1. Come up with a story for the novice user for how they discovered the app — eg from a friend, an ad, etc., and what they have heard about the app — usually just a little description or blurb. (You can run this with true novice users who aren’t familiar with your product. But I would run the exercise a few times internally before you do that.)
2. Make sure the person playing novice user is willing to forget everything else they know about.
3. Make sure the coach and note taker can see the novice user’s screen, and can hear the novice user. This can be done in person or over video.
4. The note taker should be in a good, comfortable position to take notes.

Process:

The novice user talks out loud as they go through the onboarding. They call out anything that makes them nervous. They ask about anything confusing. They share anything that pops into their head through the process. If they get bored, or feel disinterested or turned off, they share that too. We all have stories in our head when we use software, and the novice user narrates this the best they can.

The coach can jump in at any time. If the novice user is nervous, the coach jumps in to calm their fears. If the novice user is confused, the coach explains. If the novice seems unmotivated to go on or stuck, the coach provides encouragement. The goal of the coach is to get the novice user through the flow and excited to keep using the product over and over.

The note taker captures what’s being said, where the novice user raises questions, and what the coach provides. They specifically capture, in exact words, what the coach says that effectively smooths things over. Words matter. It’s critical to use words that make sense to your customer not just to your product team.

Polish:

Once you have run a number of these sessions, you should see a few patterns. You should know what parts a novice user is mostly likely to get stuck on. You should have a sense of what things a coach says that would be most likely to make the novice user more comfortable. You should know where extra motivation is required. You should know what words make sense and which sound like jargon.

Go back to your designs and change these sections. Add steps if it will create more clarity and better educate the user. Tweak the order if you found the coach always explaining something that would happen later in the process earlier. Or if the coach said “you don’t need to worry about this right now”, move that later in the flow or take it out. Add descriptive language that the coach often had to provide verbally. Add confirmations and success messages that the coach had to add like “yes, everything was done correctly!” People love to receive affirmations through a process.

Then run this again!

Pressure Test:

Once you have built an onboarding flow that you think will make customers comfortable, well set up, and motivated to use your product, now you should really go back out and test this.

Find a bunch of users who have never used your product and ask them to try it out. Don’t give them more than a sentence or two of what your product does. If your product is already known in the world, then don’t tell them anything.

The most important question to ask these users after completing your new onboarding is:

“What do you think the product does?”

If their description after going through your onboarding is pretty accurate, then it means you are onboarding them well. If they didn’t run into many obstacles or nervous moments, it means you’ve learned from running through it.