Drip campaigns — How we do them differently at Highrise

I’m not a fan of most email I get. So I read very little of it 🙂


The worse offender is often drip campaigns from companies trying to keep me engaged with their product or service. You know the kind. You signup and then get a series of 6 emails someone wrote years ago that just keep coming to you.

They have some importance, right? There are things where you need some time to digest about the experience of working with a new tool or service that you don’t want to to be overloaded with immediately. You need to signup, get your bearings, learn the mobile app, learn how to do X. It just doesn’t make sense to clobber you over the head with all this at once. So some dripped education over the course of weeks or months is actually helpful.

The biggest problem with drip campaigns is they just feel robotic. There’s no human behind them even though they are often signed by the name of a founder or customer service person trying to “interact” with you. But you can tell. It’s robots all the way down.

So we’ve tried doing these a bit differently here at Highrise.

Change the Templates Every Day

This is the most important part of what we do. You can do this with most bulk email/drip campaign tools, but we use Highrise’s bulk email service to send out the majority of our mail to customers.

Just change the templates. Every. Day.

For example, I have a template that kicks off a series of email. It brings up a few different important aspects of getting started.

There’s a block early on:


That’s all about my day or weekend or family. This block was originally written a year ago, but this is what I delete and rewrite every single day. It takes minutes, often less than one, to mention something current and fresh.

Send replies to the highest priority queue

One of the worst mistakes people make with drip campaigns and other bulk mail efforts is that the replies go nowhere. The sender is “no-reply@wedontcare.com” or if it is a legitimate sender email, no one writes back.

It shouldn’t be this way.

All the drip/bulk mail I send is from my Highrise email address. Replies go directly to me. Often they are “thank you’s” and observations around the personalization of the email in the first place — see above if you skipped it :).

If I need help answering, I just forward them to the Support team at Highrise.

Now you might ask, “But Nate, your email inbox is a mess. 67k unread messages!? How can you reply to Highrise customers?”

Again, this is tool specific, but since I use Highrise, I use our auto-forwarding system and group inbox. I auto-forward my email to Highrise and have it whitelist just Highrise customers. That, combined with our group inbox, gives me a clean, prioritized inbox in Highrise that I keep empty.

But the big takeaway from this is you should use whatever tool gives you the workflow of making it a priority to handle replies to your drip campaigns or other bulk email.

Ask People to Chat

Most drip campaign email feels an awful lot like a lecture. “Here, you should try this.” “Hey again, you should do this.” “It’s been a few weeks, do this other thing.”

So I make sure to open up my email with a question:

Is there anything I can do?

I want to start a conversation here, not a lecture.

Give Them an Out

Emails are of course helpful, but sometimes it achieves the opposite effect.

You write your email trying to guide people through a ton of things they could possibly explore, but email is so direct. It’s not like the manual that comes with your car that you never bothered to read. A new email from you is probably at the top of their inbox. And then another comes.

Give people an out to realize this isn’t mandatory if it’s not helping.

I tell folks:

Also, Highrise is one of those products you can just use even if you lost the manual. But if you need any guidance there’s some resources below.

In other words, “Stop reading and throw this out, if this isn’t for you.”

Just Do It For Them

A lot of products have some kind of setup step. Maybe it’s an import of data. Maybe it’s setting up departments and filling out information for their users.

I’m always surprised more companies don’t just offer to do this for their customers. Your company’s employees, especially the support team, is faster at doing these steps than anyone, and once you get people past these things they are way more likely to stick with you than if they get stuck in setup.

So in our Welcome email we let new folks know:

Here’s some online help for doing an import with Highrise. Or if you’d like some help from us, reply to this email. If you have a spreadsheet of contacts, please attach the spreadsheet in your reply, and we’d be happy to help take care of that for you.

Of course you have to balance this with the size of the support team you have available. But in our case this saves more time than draining it because we don’t have to spend the extra time helping revert a bad import and redoing it if it didn’t work right the first time.


Those are just a few things we try and do differently. Some new things we’re fooling with are actually a customized email for each and every single person.

Alison here at Highrise created this effort and has shown us how awesome it is to send individual video emails to each customer (we use Bonjorno).

It requires the extra time, so it’s a balance to fit it in. But you can get an amazing amount of these out to customers with less effort than most people probably anticipate. It’s worth trying and adjusting if it isn’t scalable for your leads.

P.S. Please help spread this article by clicking the below.

You should follow my YouTube channel, where I share more about how history, psychology, and science can help us come up with better ideas and start businesses. And if you need a simple system to track leads, manage follow-ups, and send bulk email you should try Highrise.


Data is Man-Made


Here’s a secret from the support team at Highrise. Customer support metrics make us feel icky.

Our team doesn’t know our satisfaction score. We’ve never asked any of the people that use Highrise to try those types of surveys.

We can’t give you an exact number for our average response time. It depends. Sometimes it’s 90 seconds, and other times it’s within 24 hours.

We can’t tell you our average handle time for an issue. Our team has a general idea, but no exact number.

These types of customer support metrics aren’t wrong. We’re sure they work for other support teams.

We’re just not sure they’re right for us.

Because there is one piece of knowledge we’ve come to realize: data is man-made.


What do you mean data is man-made?

Data or metrics or stats are all man-made. A human decides what to measure, how to measure it, how to present it, and how to share it with others.

But why does it matter to measure these things? And what’s the point?

A lot of times people avoid these questions when it comes to data. Companies copy what other teams measure, ignoring the fact if it’s important to measure the same things in the same way, or if it’s even important to measure it at all.


But isn’t all data objective?

Many people view numerical data as more trustworthy than qualitative data.

Clayton Christensen, Competing Against Luck

Numbers are black and white. Concrete. You can trust the numbers.

Right?

Nope. Almost all data is built on biases and judgement. Because humans are deciding what to measure, how to measure, and why to measure.

Numbers fit perfectly into a spreadsheet or a graph. A number gives a definitive answer to questions like how much or how many.

That doesn’t mean you should treat those numbers as insights and act immediately. Data shouldn’t be used to prove a point.

Data should be used to fuel your imagination.


Words > Numbers

Qualitative data isn’t easy. There aren’t any formulas or simple math. It doesn’t fit into a spreadsheet. It doesn’t answer questions. It’s not black and white.

It’s colorful. Messy. Qualitative data creates more questions. It’s not simple to present or share with others. It takes some time.

Our support team has found one thing to be true. Qualitative data is worth it. 100 percent worth it.

For example, our team recently updated the filters in Highrise. This update was to an earlier revision to filters we made during the year.

It was driven by one piece of qualitative data from a new user:

Thanks for pointing out those filters. I didn’t even know they were there. Those icons weren’t obvious to me at first.

This hit all of us across the nose. The filters looked better. It was a much more clean than the original design.


The original design vs. our next iteration

We didn’t make these changes just for aesthetic reasons though. The original design had a lot of trouble for most of our users who had more than a handful of custom fields. But how to use the filters wasn’t as obvious any longer.

Folks need to find a specific set of contacts in the city of: Chicago, that have the value: Interested in the custom field: Status, and that are tagged: Potential.

It wasn’t clear how to do that, so our team made a change.


We made it abundantly clear what to click on to add a filter.

Quantitative data didn’t tell us we needed to make this change. It was all qualitative.

Questions from customers and questions from our team. It was a conversation. There is not a numerical value you can put on that.


So what do we measure?

Instead of striving to lower our average response time or improve our customer satisfaction score, our support team is aiming for something a bit different. Something harder to measure. It’s not a number.

As Alison would say, we strive to put ourselves out of work.

Don’t confuse that with us not wanting to work at Highrise. We love it, and love working with our small team.

What we mean is we want to make it easier for people to use Highrise. We want to create a product that is so obvious and so easy to use that we seldom get questions on how to use it.

And when folks do have questions, we want to have resources available to them right away, so they can help themselves. So if someone has a question at 2 am in the morning, and we’re not around, they can find an answer without waiting for us.

Because we don’t believe managing a number is going to improve our support. We believe focusing on customers and what they are trying to do with Highrise is going to make a better product, and better support.


If you enjoyed this post, please click the 💚 to share it with others. Please don’t take this as gospel either. What works for our team, might not work for your team. And vice versa.

Also, chapter 9 of Clayton Christensen’s recent book, Competing Against Luck, was a big inspiration for this post. The entire book is great, and you should check it out.

Best Buy vs. The Apple Store

A recent shopping experience that really surprised me

I was captivated when Apple opened its first set of physical retail stores in 2001. I’ve never owned a retail business, but I worked a variety of retail jobs growing up. What Apple did with retail was different.

I’ve always been endlessly fascinated by retail. Watching people browse, seeing how people choose what to buy, seeing how moving stuff around in a store can have significant effects on purchasing patterns, etc. Paco Underhill’s Why We Buy is one of my favorite books of all time.

When Apple finally opened one in the Chicago area over a decade ago, I rushed over there. I was in awe. What a unique retail experience. Just wonderful.

And for years I enjoyed visiting the stores. Whenever I needed something Apple, I’d go there. I’d rearrange my schedule to shop at an Apple Store.

But in the last few years, the stores have really turned me off. I don’t like stepping into them. They don’t make me feel welcome — rather they make me feel like I need a good reason to be there. Of course I have a reason to be there, but I don’t like the fact that I have to declare it upon entry.

At the door you’re often met by a bouncer who asks you what you need and then directs you here or there. “Please wait by that table over there for a guy with glasses and a blue shirt.” And so you go, awkwardly waiting. Not sure if you can leave your station, lest you miss your opportunity to talk to who you were directed to talk to. Then what?

I find the stores packed with so much Apple staff that you often have to break up a conversation between two staff members in order to ask a question. Now I feel like I’m interrupting someone just to buy something.

Am I being a little dramatic? I’m really trying not to be. This is just how the stores make me feel these days. And it’s not just one store — it’s a handful of stores I’ve visited. Some have been better than others, but there’s a general vibe I get when I walk in that just doesn’t sit well with me. Whenever I go to the Apple Store I feel like I’m on the clock. Like some other customer appointment is pushing up behind me. Hurry up. I can’t explain it beyond that.

Here’s an exaggeration, but not by much: The stores feel more like a deli experience — take a number, wait over there, we’ll call you when it’s your turn.

I recognize Apple is a victim of their success here. Due to unprecedented retail demand, they’ve had to institute protocols to manage the number of people and different kinds of customers. I’m sympathetic to the challenges — it can’t be easy. And they’re probably doing it better than anyone else could. But regardless, I’m just sharing how it makes me feel as a customer.

So just a few days ago my wife asked me to pick up a new iPad for her. She needed it quickly — shipping wasn’t an option. A few years ago I would have hopped in the car and ran down to the local Apple store. This time, I checked Amazon Now first to see if we could get same day delivery. Then I realized Amazon doesn’t really sell Apple stuff so that was out. I could have tried Postmates since they deliver from local Apple Stores, but it didn’t cross my mind at the time.

So I decided to go somewhere I almost never go: Best Buy. There’s one right around the corner from our house. A 10 minute walk, a 3 minute drive.

I walked in. The place was empty. This doesn’t bode well for Best Buy, but as a customer I kinda loved it. I could enter the store without being asked why I was there today. I just walked in and headed towards the dedicated Apple area in the back. When I got there I asked a guy if they had a 128 gig smaller size iPad Pro. He asked what color, I said gold. And he grabbed me one. Done. 5 minutes.

Then I happened to ask the guy if they had the iPhone 7 and if I could switch our service from T-Mobile to Verizon. I figured I’d have to go to an Apple Store to do this (which is why we hadn’t done it yet). Or an Verizon store (which is another reason why we hadn’t done it yet). He said, sure, no problem at all, and he was really helpful throughout the process. So we did that too.

They weren’t happy or unhappy to see me. They weren’t overeager or disinterested. They didn’t stop me before I started shopping. I was there, they were there. It was just a transaction. Smooth, fast, and fair. At Best Buy. In and out in a few minutes.

Again — if you break it down, it’s clear that Apple Stores are doing quite well and Best Buy stores aren’t. So this isn’t commentary on successful business models. It’s just a simple share of a shopping experience I had recently that surprised me. Best Buy feels simple, Apple Stores feels over engineered, too sophisticated. I get why, but why doesn’t matter to the customer experience. It’s either great or it’s not — the why behind the scenes doesn’t matter. Who’s been teaching me that for decades? Apple.

Are you looking for an answer or are you asking about impact?

The question has everything to do with the answer

“What’s one thing you love about Basecamp?”

“What’s the one thing you like least about Basecamp?”

“If you could change one thing about Basecamp, what would it be?”

“Would you recommend Basecamp to a friend or colleague?”

We’ve asked these questions before. They’re ok, but ultimately they’re pretty self-serving. We wanted people to talk about us. What are we doing well, poorly, etc. We were getting answers. That’s what most companies are after when they ask questions — they’re looking for answers about themselves.

But answers are easy to come by. What’s more interesting is impact and outcomes. What kind of impact is Basecamp having on people’s lives? What’s changing for the better at companies that run on Basecamp 3? That’s what I really wanted to know.

So on our latest survey we shifted the question outward. If you want to get people talking, ask them about themselves.

So we asked “What’s changed for the better since you started using Basecamp? and, wow, impact came streaming in. Nearly 4000 people responded in just a matter of days — making it one of our most successful surveys ever. But it was what they said that really mattered…

And about 990 more…

If you read through the responses you’ll see patterns — accountability has increased, people know what’s happening inside their company now, business owners are on top of things again, things are getting done with fewer errors, stuff is going in one place rather than all over the place, people have been able to jettison a cobbled together mess of multiple tools to standardize on one, etc.

None of these are specific features of Basecamp — they are all outcomes. They are the result of impact the product had on a given company’s workflow and lifestyle.

And yes, a webpage that goes on forever with 1,000 quotes isn’t meant to be read from top to bottom. We obviously know that. But if you play scroll roulette, and end up anywhere on that page, you’ll get something good out of it. That, plus the sheer volume of positive outcomes, impacts, and good feels, is the point.

So next time you’re setting out to get some answers, make sure you consider the question first. What’s it going to prompt? Answers about you, or answers about them?


2017’s right around the corner. Going to let your hair burn for another year? Or time to put out the fire once and for all? Business doesn’t have to be crazy. You don’t have to run around with your hair on fire. Get off the conveyor belt or crazy and come over to the calm, organized, sane way to work: Basecamp 3. It’s free to try. Bring accountability, organization, and discipline to your business.

From Inbox Zero to Inbox Comes Second


Often, the work I do feels invisible. I’m not building a feature or designing a website. I’m ensuring that our support team (a sect of tech with an industry standard of high turnover) has the information they need, doesn’t suffer from too much burn out, and is empowered to make their own decisions. Part of my job this year has been to adjust our team’s culture: a shift that has often felt like repeatedly rerouting a ship’s course.

When we lost a successful, tenured employee to Help Scout last December, we suffered a bittersweet loss. Only a few weeks later did we abruptly lose a newer employee, which became a more challenging loss than anticipated. The combination of losing a long-term team member who shaped our team culture and experiencing a contentious departure by that newer team member hit our morale pretty hard. With shaken morale, we also had to work through the busiest time of the year with those two gone and a third person on paternity leave: we were working at 70% capacity at the height of busy season with a stressed-out team.

January is notoriously busy for us and is always a bit of a shock to the system after the lackadaisical holiday season when customers don’t write to us often. The sluggish season offers a nice break for us after another year of work and allows us to bond with each other and our families. Since customers aren’t writing to us, we seldom have a backlog and rarely a queue, which means we can respond to customers within minutes. November and December are often Inbox Zero.

Enter January. Enter 70% capacity. Enter low morale. Enter a swell from n emails to 6n emails. Enter an obsession with an idealized and impossible image of Inbox Zero.

Enter negativity.

Each day felt like a packed CTA train at rush hour in the winter: sweaty, steamy, and uncomfortable. We went from each answering 60 emails per day to answering 150 per day. I couldn’t spend any time on admin work since we were down three bodies, which meant I couldn’t even begin the hiring process until February. I was too busy to work.

Meanwhile, the team felt the pressure of Inbox Zero. Inbox Zero is an arbitrary goal; there will always be another customer email or phone call or tweet. Inbox Zero is a fruitless fight for control. It became an image that tied us to our screens, that swallowed any self-care practices we had instilled over the years. It also became a habit of treating our customers less like humans who needed support and more like screens to get rid of.

By March, we finally hired two new folks: Carrie and Elizabeth. We brought them to Portland and welcomed them to our damaged team by accidentally showcasing our stress. During a 1-on-1 with Carrie, she brought up how disappointed she was by our negativity and stress: we hired her to help alleviate stress only to pass our stress onto her. Carrie opened our eyes to our bad habits and the true depth of our low morale. Together, she and Elizabeth showed us their fresh perspectives and willingness to fight the negativity we had introduced them to. Without them, we might still be spiraling.

But, we’re still a work in progress. While we’re not where I want us to be — there’s some lingering negativity and stress — I see movement. Part of that movement has been to stop following the 37signals hiring standard to “Hire When It Hurts.” That doesn’t work in support. If you’re waiting for The Hurt to tell you to hire, then your perspective is off and you’re expecting your team to carry the weight of another workload. Instead of carrying extra weight, we’re working on creating space for personal projects, better communication, innovation, brainstorming; if you can’t breathe, then you can’t think.

So, during the summer, we hired Jayne. Last month, we welcomed Esther and Janice. Last week, we promoted Natalie, a senior support employee, to help manage the team (we’re now at a total of 14). We hired more and created a new managerial position to help open that much-needed and well-deserved space for the more-tenured employees to relax into.

And, while we lost two people last year, we gained five this year. That’s five fresh perspectives to hold us accountable to our high standards while reminding us to remain human and keep ourselves first: Inbox Comes Second.

Does Know Your Company actually work?


The most common question I hear from a business owner about our software is something to the effect of: “What are the results I’ll see in my company because of Know Your Company?”

In other words, “Does Know Your Company actually work?”

Admittedly, when a business owner would ask me this, I’d sometimes struggle to answer the question. I’d share anecdotes and success stories from our 200+ CEOs and more than 12,000 employees who use our product in 15 different countries (stories of which we had plenty)… but those stories alone didn’t feel like enough. I wanted a bit more data to share.

To better understand exactly what impact Know Your Company has, we conducted a survey with all of our customers — from which 96 CEOs (28% of our customer base) and 143 employees (7.9% of our customer base) across 30 different companies ended up participating. Here’s a breakdown of the size and industry of the companies who participated in the survey:



Based off this, here are our most interesting findings (you can view the full survey results here)…

#1: What Know Your Company does best is create a more connected company.

The most consistent finding that was revealed in the survey responses is that both employees and CEOs feel connected to one another as a result of using Know Your Company.



The consistency of those responses — it is such a high percentage for both employees and CEOs — stood out to me.

In particular, a lot of the feedback we got was about how helpful Know Your Company is for connecting remote teams or companies with several offices. Employees reported feeling especially connected to co-workers they don’t see regularly, and to new hires just joining the company.


Creating a greater sense of connection in a company matters. Studies show that 33% of employees don’t trust their CEOs — but when they feel connected to their CEO, that trust is increased. As the study describes, the more employees trust their CEO, the more-likely they are to be loyal, work harder and speak highly about the company.

Connection between co-workers increases employee engagement, as well. As stated in this HBR article: “Companies and leaders who want productive, happy employees should make it their job to foster more intimacy at the office.”

#2: The more your employees knows each other, the more engaged they are.

Another finding from our survey is an overwhelming majority of CEOs see higher employee engagement and a positive impact on company culture as a result of using Know Your Company.



These results are important, given how critical employee engagement and a healthy company culture are to a team’s success. Without a healthy company culture, turnover increases… and that’s expensive. It costs the average company 150% of an employee’s salary to find a new person to fill that position.

Employee disengagement is expensive, as well. A 2009 Gallup poll of more than 1,000 U.S.-based employees found that for every disengaged employee, a company loses between $3,400 and $10,000 in salary due to decreased productivity.

#3: Know Your Company gives employees a voice.

The survey also revealed to us how much Know Your Company enables employees to have a voice. Almost 8 out of every 10 employees feel the Know Your Company gives them more of a voice. This has always been an intention of our product — to help employees speak up at work — so it was rewarding to see employees’ outcomes matching that intention.


Numerous employees also shared how Know Your Company helps create a safe, friendly environment where they feel more comfortable voicing their opinions. In fact, some employees admitted noticing how employees are more honest, because of Know Your Company.


When employees are given a voice, they can help you overcome your blindspots as a CEO. By contrast, when employees lack a voice, they are more likely to be disengaged. Gallup found that 4 out of 10 workers become actively disengaged when their managers don’t communicate or ask for feedback.

#4: Know Your Company helps you make more informed business decisions.

One finding that I found particularly interesting is the number of CEOs who have used Know Your Company to make more informed business decisions.


Through dozens and dozens of phone calls and meetings over the past three years, I’d heard how CEOs use Know Your Company to improve their companies’ benefits, employee onboarding, marketing, sales, design, product development, customer support, etc. But the survey data gives us the ability to objectively say that this is an outcome that a large majority of our customers are experiencing.


#5: Know Your Company helps employees know what’s going on in the rest of the company.

Another statistic that surprised me was the number of employees who better understand what is going on in the company because of Know Your Company.


This isn’t the primary function of Know Your Company as a tool (the primary one being to help a company feel more connected). But it’s crucial — the bigger a company gets, the easier it is for employees to feel silo-ed from other areas of the company. When employees feel like they’re “on the same page,” it’s easier for them to see how their individual contribution is helping to the company forward. This can lead to increased motivation and a sense of fulfillment in their own work.


#6: The importance of ease – employees love Know Your Company because it’s easy.

The survey also showed that ease of use is one of the core reasons Know Your Company works so well. We didn’t ask any specific questions about Know Your Company’s ease of use or user interface. But, when asking employees, “What’s the one thing you love about Know Your Company?”, there were many comments in this vein…


Overall, the survey we conducted ended up being formative for us. It confirmed what’s really working with Know Your Company (e.g., we help CEOs feel more connected, have more engaged employees, and make better decisions). This way, we can better market our tool (we recently built a page on our marketing site to address this), and make smarter product development decisions that benefit our current customers (we recently built the Agreements feature, in part based off feedback we got back from survey data).

And, it now gives me a much better answer when someone asks me, “Does Know Your Company actually work?”


Big news! We’re now Know Your Team. Check out our new product that helps managers become better leaders, and get the full story behind our change.


P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)

The Curse of Knowledge


“Uh, it’s off Airport Road. You should be able to get there from Umstead. I think or, or maybe go up to Estes?”

I paused again. I was confusing the person asking me for directions more than I was confusing myself.

What was the matter with me?

I grew up in Chapel Hill and went to college there. I lived there for over a decade. I was a local.

And when a stranger asked me for directions, I couldn’t tell them.

I stammered over and over, and told them they might need to ask someone else or look at their phone.

Was something wrong with me?


One of the most rewarding, and challenging, things about working at Highrise is how fast the product changes.

Our team runs on a train schedule. This means every few weeks we announce an improvement or something new.

It could be a big feature like recurring tasks, or something small like a new rule for auto-forwarding emails.

The reward is we’re making the product more useful to ourselves because we use Highrise every day, and making it more handy to customers.

A big challenge is documenting these changes. It’s informing people that use Highrise with what has changed, why it changed, and how to make use of the changes.

The number one resource for this is our help site. It’s a living, breathing how-to guide or user manual.

It’s a beast of a resource to maintain. There are over 100 articles, countless screenshots, and videos.

And with frequent updates, this snapshot or how-to guide of Highrise can go out of date fast.

It came to our team’s realization when updating a screenshot. The settings menu now has a new option for all users (Referrals), and the old screenshot didn’t reflect that.

It was a tiny change. A person new to Highrise might not even notice it. Our team did, so we updated the screenshot.

This change sparked lots of others too. We began to notice videos were out of date by months. More screenshots too.

A pull request with one commit, a change to a screenshot, turned into a two-week project. 277 changes later, our team updated the entire help site to more accurately reflect the product.

What took us so long to realize things were out of date?


Nicholas Epley has a dynamite book on this topic. It’s called Mindwise: Why We Misunderstand What Others Think, Believe, Feel, and Want.

In the book, there is an eye-opening exercise.

FINISHED FILES ARE THE RESULT OF YEARS OF SCIENTIFIC STUDY COMBINED WITH THE EXPERIENCE OF YEARS.

Epley asks you to count how many fs are in this sentence. Start counting.

How many fs do you count?

Is it more than you can count on one hand?

If not, Epley has confirmed you’re a terrific reader, but a terrible counter.

Now count them again? Did you find all six fs?

Don’t forget that the word of has an f in it. See all six now?

Most people, including myself, only found three fs.

Why is that?

Epley explains it has everything to do with knowledge.

He continues, “Your expertise of English blinds you from seeing some letters. You know how to read so well that you can hear the sounds of some letters as you read over them.”

So, because of your expertise, every time you see the word of, you hear a v rather than a f, and you miss it.

Epley points out, “First graders are more likely to find all six in this task than fifth graders, and young children are likely to do better than this than you did as well.”

This is known as the curse of knowledge. Why is knowledge a curse?

Because once you have it, you can’t imagine what it’s not like to possess it.

Knowledge or a level of expertise gives you the lens of a microscope.

It means you notice subtle details a novice might not catch, and it also means your focus is so sharp, you might miss the big picture and you’ll struggle to understand a novice’s perspective.

Epley offers a slew of good examples in the book and elsewhere too.

One of my favorites is how Clorox bought Hidden Valley Ranch Dressing and spent a decade trying to make the original recipe so that it did not need to be refrigerated. All of their internal taste tests of the dressing came back as worse than the original. Or so they thought.

Hidden Valley finally sent a worse tasting version of the dressing to the market, and people loved it. Because not many people ever tasted the original dressing. The consumer’s perspective was way different than the company’s perspective.

Epley writes further, “The expert’s problem is assuming that what’s so clear in his or her own mind is more obvious to others.”


This is something our own team fell into at Highrise. We were spotting tiny changes like typos or a missing menu option in a screenshot, but missing the bigger picture that almost everything was out of date.

Our perspective was way different than someone who started using the product yesterday.

And it’s what happened to me when trying to give directions. I could probably get the stranger to the location if we rode in the same car.

I could tell her Airport Road is now named Martin Luther King Jr. Blvd. And there used to be tons of trees on Umstead Road that the city cutdown. I could point out all these tiny details.

But I couldn’t tell her how to get there on her own.

There was nothing wrong with me. I was cursed.

Cursed by knowledge.


If you enjoyed this post, please click the💚 and share it with others. If you enjoyed the ideas, I recommend reading Nicholas Epley’s book. It’s fascinating. And if you’re curious about what improvements we’re making to Highrise, catch up on our announcements.

Be the Plumber


A 30-something immigrant with no fancy education or consumer product experience started a company in 2003. The product’s first sales came out of the trunks of cars.

9 years later, the company’s products were being snagged by people checking out at Walmart and sales exceeded $1 billion.

How the hell did that happen?


One of the hardest parts about supporting customers is seeing things from their perspective. There were plenty of customers who knew the product better than me when I first started at Highrise 17 months ago.

That’s not a great feeling. Because people are asking you questions and you’re supposed to have answers.

How do you get to know the product better?

You use it.

In my first 12 months at Highrise, our team tried using the product more and more. We assigned tasks for following up with customers. We tracked email with our dropbox addresses. We built support to autoforward in tons of mail.

We were learning the product, but we really weren’t using it as much as we could. Especially for supporting customers.

The majority of my time was spent in help desk software. That’s where I was replying to customers. It wasn’t spent in Highrise.

One day, our CEO, Nathan, asked me what would it take to use Highrise to support customers?

My first reaction was that wouldn’t even work. There is no support queue. It would be terrible and slow us down a ton.

But Nathan knew if we could pull it off, it would mean our entire team would spend a ton more time in Highrise.

By using Highrise, it would become more useful to us and our customers.


But it wasn’t going to be all ice cream and nuts. It was going to be tricky. Rough spots were ahead.

Our team started small. One of the first things we announced was autoforwarding support for Gmail.

All email was being autoforwarded into Highrise. It was a firehose of information. Overwhelming. Noisy.

It became impossible to search and find information. It sucked.

But if our own team was having trouble with it, customers probably felt the same way.

This shitty experience put pressure on us to make it better.

A little later our team built a way to connect Gmail and send emails directly out of Highrise. Our support email address used Google Apps, so we were inching closer to being able to support customers with Highrise alone.

The first version to send email out of Highrise was a bit underwhelming. You couldn’t attach files. No way to CC or BCC others.

It was good enough for us to start using it, but there was still too much friction.

Weeks later we introduced rules including a way to only forward in email from existing contacts. This reduced the noise and made it easier for us to use Highrise. The firehose was no longer always on.

It was still hard to find notes and emails when searching. Tons more email was still in our account. So we improved search and made it easier and faster to find things.

When replying to customers, we sometimes needed to copy others or attach files when replying to customers. So our team made it possible to CC/BCC from Highrise and followed that up with attachment support.

More progress. But still more pressure too. No queue for emails. We had no idea what needed to be replied to or what was outstanding or important.

Next, we introduced a personal assistant. We call it Good Morning.

Good Morning helps us organize and respond to incoming activity that needs attention. It’s our take on a support queue.

Now we were damn close.

We couldn’t tell who was replying to what. Our team sometimes replied to a customer twice because we had no idea someone else was already replying to them. Definitely not ideal.

Our team built presence to see if someone else is responding, and it improved. No more replying to the same customer twice.

By the fall of 2015, our team was using Highrise to reply to every customer email. Something I thought wouldn’t be possible.


5-Hour Energy founder Manoj Bhargava will tell you he grew his product company to over $1 billion in sales with combination of common sense and a sense of urgency. By not doing dumb stuff.

Bhargava claims his company isn’t efficient at all. They just don’t do useless stuff. He cut out everything that didn’t make money, didn’t improve the product, or didn’t make the customer happy.

Business isn’t complicated to Bhargava. It’s just do useful stuff. And avoid useless.

That belief turned 5-Hour Energy into one of the most popular consumer products in the world.

Bhargava, who dropped out of Princeton after one year, doesn’t believe in MBAs. Why? They’re useless.

It’s a simple thing. If you’re going to learn plumbing, go learn from a plumber that has actually seen a pipe. That has fixed a leak.

Not just written about pipes, lectured on pipes, and researched pipes.

I’m not for theoretical plumbers.

Manoj Bhargava, Why a MBA is Useless

Our story is similar. Our team made a commitment to using Highrise more. Instead of being theoretical users of the product, we became customers of it. We depended on it.

We felt the pain our customers were telling us about. It wasn’t pleasant. But it gave us a new insight into what it was like to use the product. It forced us to improve Highrise and to do it quickly.

Sometimes you have dig in and fix it from the inside. It might take a little pain, but it may also be the only way you’ll figure it out.

This post was inspired by this talk from Manoj Bhargava.


P.S. Curious about how we’re applying this to Highrise now? Follow us on Twitter, check out our recent announcements or ask me @cjgallo.

The Lost Coffee Order

A great experience even when things went wrong.


Last month, I sent a surprise gift to one of our customers. In an unfortunate series of events, the gift package never made it to her.

Here’s the email I received from the coffee company I bought the gift from:

I spoke with your customer and she says that they did not receive the package and has spoken with her neighbors to be sure that the box was not delivered to one of them by accident. On the day of delivery, there was terrible weather all across the area, including tornados. Many businesses and all of the schools closed that day, but she says that their office did not close. It is possible that either the postal delivery person was in too big of a hurry that day because of the weather and chose not to deliver the box or there was a substitute delivery person who did not know where to leave the package.

I am very frustrated that this has happened. I am going to re-flavor the coffee (Hazelnut) today (it has to sit overnight) and deliver the coffee/ tea order to her myself tomorrow. I’ll let you know if I get any more information.

Thanks, again, for the order.

Clarke, Highland Coffees

They really did a great job turning this potentially negative situation into a great one. Instead of blaming the post office or leaving me to figure out where the package went, Clark sent out a brand new order. Clarke even shared in my frustration that the experience wasn’t perfect.

Explanation? Check.

Empathy? Check.

Promise to follow-up? Check.

Even though this order might take an extra little bit to get to the customer, I’d still order with Highland Coffees again in the future. It turned out to be a great experience even when things went wrong.


We work hard to provide the same stellar experience with our customers. If you haven’t yet, go check out Basecamp 3!

No Reply Addresses

Go check your inbox right now. I guarantee you’ve got a few emails from a “noreply@myapp.com”. A quick search through mine yielded 28 different no-reply emails from 28 different companies. It’s not limited to only big companies either. Tiny startups use them to send out their newsletters, invites, notifications, etc.

When I get an email from a no-reply address, I know that company doesn’t want to hear from me. They’re telling me that while I need to read this email, they won’t be reading any replies that I want to send them about it. They can consume my time but they won’t spare any of their time for me.

In short, they don’t care.

Sometimes it’s unintentional. A new startup sees that other businesses are doing it so they do. Sometimes it’s intentional because a company doesn’t want to get bombarded by auto-responders about being out of the office. And sometimes it’s justifiable. If your app sends out email notifications for certain actions, like checking off a to-do or sending a message, then I can understand the use of a no-reply email address.

But overall, stay far, far away from them.

You want your customers to be talking to you. You want them sharing ideas and experiences with you. Instead of a no-reply, set it to your support email address. Make sure someone will see any replies that a customer sends. Sure, you’re going to get lots of auto-responders. That’s why your email app has filter and rules you can set up.

Embrace the idea of a yes-reply email address. It’ll keep that communication lane open between you and your customer. It’ll make customers realize that you do value their time and will give them some of yours if they want it.

Your goal should be to talk more with your customers. Switching your no-reply addresses over will be a great first step towards it.