The Support Side of Downtime

There used to be a panicked feeling that would set in when we’d have any sort of outage or issue in Basecamp past — that stomach-dropping, heart-palpitating, sweaty-palmed feeling. But on November 8th when I awoke to a 6am text spelling out Basecamp’s downtime, I wasn’t worried. Before I finished reading the full text, I remember thinking, “Oh, they’ll have it sorted out before I can finish making coffee.” But as I continued reading and began to understand the estimated downtime to be at least two hours, my adrenaline hit.

The first thing I wanted to do was check on the support team. Were they in panic-mode? How sweaty were their palms? How many customers had they talked to already today? How close to capacity were they?

And by the time I received the alert and logged on (coffee brewing while I said Good Morning, thank glob for remote work), Basecamp had been in read-only for about 30 minutes, three times my prediction. Despite the stress of a lengthy downtime, knowing that we’d have a few hours of this status allowed us to settle in and accept our predicament. We had time to get into a flow and trust ourselves to talk our customers through this.

Really, what I realized when I logged on was that everything was absolutely under control on the support team. And of course it was: for the past two years, our team has been conducting crisis drills with each other. Once a month, we rotate responsibility for these drills and each person is responsible for coming up with their own style of drill. They’ve become quite the gif-filled, fun time! We work from a playbook (hosted on GitHub in case Basecamp is down) that acts as a living document we can update as-needed. We’re currently in the process of using our experience from the read-only outage to revamp and reassess the playbook to make it even more accessible, comprehensive, and succinct — no small task, mind you!

Keep reading

People, Not Robots: Bringing the Humanity Back to Customer Support

(Adapted from a keynote I gave at Lean Digital Summit in Lisbon this month.)

Good help is hard to find. I dread calling the credit card company, the phone company, any service provider, including and maybe especially SaaS companies. I anticipate talking to someone who is poorly trained, under-paid, powerless, and miserable. I anticipate their frustration rubbing off on me. I anticipate arguing to get my needs met. And that’s if I can even get a real human to talk to me. The people standing in the way of good help aren’t the customer support representatives themselves, though. Corporate culture, the bottom line, and rotten support for service roles has ruined how folks get the help they need.

I’m not alone in this. I’m not the only consumer who approaches support defensively, with their hackles up. Before we dig in, I want to tell you about a customer of ours — let’s call her Nancy — who, like me, had low expectations. She wrote to us asking for a lower price (which we didn’t have).

One of our reps, who has been at Basecamp for almost five years, wrote her back to politely tell her that we don’t have any lower plans to offer her.

Here’s what they wrote to Nancy:


Her response back was a little bewildering:


Three words! A sentence fragment! End of transmission. I saw this and recognized something interesting. Nancy was replying as if she were on hold with an automated service: Say ‘Account and billing’ for our accounting department. Say ‘Technical support’ for our technical department. I’ve been greeted by too many of those automated services and have more than once simply repeated the word “Human” until a person got on the phone with me. I swear, it works more quickly! Anyway, I recognized this in Nancy, so I jumped on a call with her. She immediately confirmed my suspicions and told me that she thought that the person who originally responded to her was a robot — and she then read the whole email to me in a robot voice to further her point. She also told me that because she thought she was speaking with a robot, that her three-word response was an attempt to get the robot to understand her. In short, she was speaking the robot’s language. To her, Basecamp was nothing more than beeps, algorithms, and machinery. We were no longer a group of humans with families and hobbies and struggles — we were machines that didn’t deserve even a full thought.

So how did we get here, to this point where our customers assume we are not even human? This was Nancy’s first interaction with us, so she had no context or history with us that would have lead her down this inhuman path — something else, outside of Basecamp, made her believe robots are the general first responders. We all know that capitalism has made the bottom line more important than the people. We need to reject these late capitalist temptations in order to protect our customers, our people. The people are why we’re here, the people pay our salaries, the people use our products. Don’t be fooled into thinking that anything other than people can support your customers.

Nancy, like myself and so many of you, drew from her previous experiences with customer support. So many companies put up some automation, a chatbot, some AI that ends up standing in the way of customer service and support. Nancy, by the time she emailed us, was already fed up with this culture, this treatment. Frankly, I’m fed up with it too. I never want to sit on hold listening to shitty music, pressing menu buttons, entering my account ID. Like Nancy, I want to talk to a human. I want us to get to a place in our industry where I know that when I contact a company, I’ll speak with a well-trained, cared-for human.

Because I live by the Golden Rule, to treat others as I want to be treated, I need to formalize how I want to be treated in order to better help our customers. What do I want? I want to talk to a well-trained, compassionate, and intelligent person when I have an issue. I have never in my life wanted to work out a problem with an ill-informed person. I never want our customers to feel that way about us: either that they cannot get a human to speak with them or that the humans who are speaking to them are simply unhelpful. Place yourself in a compassionate position — how do you want to be treated when you need to contact a company with an issue? What’s your ideal scenario? Start compiling your values so that you know what’s important to you.

Once you’ve figured out how you want a company to treat you, it’s time to look in the mirror. Are you treating your customers the way you want to be treated? Would your friends and family receive decent help from a decent human? Would you rest assured knowing your neighbor would be treated compassionately and timely if they needed help from your company? To put it shortly, are you proud of how your customers are treated? Does your company stand up to your own expectations?

If not, that’s ok. I want to help.

Now that you’re coming to grips with your own values and expectations, it’s time to open up a direct line of communication with your customers. Not an answering service, not an auto-reply, not an automated recording or menu, no bots, no AI. Figure out what you can manage. Email is the best way to gauge this.

Here’s what our support page looks like. It takes one click to get here from our homepage. We’re not hiding behind a “contact us” link at the very bottom of a page.


If you scroll down, there’s a text box below this that you can fill out to send us an email that goes directly to support@basecamp.com. We also show you roughly how long it’ll take for us to respond to you. On a normal day, we answer 100% of emails within an hour of receiving them. 90% of those, however, are answered within 30 minutes.

That quickness, that attention, didn’t happen overnight. It was an iterative process that took about a year or two. We kept adjusting our methodology, each time failing a little better. When I started at Basecamp, we had four people answering emails. We all lived in the same timezone and worked roughly the same hours. At 8am on a Monday morning in Chicago, we’d have 600+ emails waiting for us. We rarely answered an email on the day it was received. Now, we have fifteen people stationed from West Coast US to East Coast Australia. We answer emails 24/7, save holidays and company meetups, with folks working roughly 9am-5pm five days per week. No one works in a call center. We train and support our own employees. We are connected to each other through Basecamp. Our team is the face of Basecamp.

I’m showing you this so that you can see how easy it is to talk to someone at Basecamp. We’re not hiding behind a device or a bot that’s trying to convince you that we care. We actually do care. We really do care. We know that our customers want to talk to us. They don’t want to wait on hold or have some AI device convince them that their problem is simpler than it really is. They want our expertise, our consult. When I call our customers, they aren’t asking me Yes Or No questions — they are giving me their stories, their narratives. They want me to understand their daily workflows and needs so that I can consult and problem-solve with them. I want to help our customers succeed — hell, it’s in my own best interest that our customers succeed not just at using our product but at their business so that they can continue to pay us to use our product. Part of helping them succeed is hearing their stories. When people can speak their truths aloud, then they are better able to process those truths. That means that when we give our customers the opportunity to speak to us, to tell us their stories, then they understand their workflows better. If you understand your truths and workflows better, then you can do better work. When you employ a bot or use an automated service, you’re sending the message that you’re too good to talk to your customers yourself, that they don’t deserve your time or patience or thoughts. Your customers want to talk to you, and you should want to talk to them.

Let me show you just a glimpse of the feedback we get at Basecamp after we have conversations with our customers.


So, you see that our customers (who aren’t different than yours) want to talk to a real human. A real human! They want to have a real conversation with another person. It’s not just that they are happy that they got to talk to another human — it’s that they are surprised that they did. Like Nancy, they assumed we were robots. Why? Because so many companies have failed them, treated them like a burden so that they learned robots are now being employed to help customers. This happy surprise that our customers get after realizing our humanity isn’t exactly a good thing, it’s not exactly flattering. The bar is so low that all we have to do is be a real human. What we’re doing at Basecamp isn’t ingenious. We’re simply understanding our own capacity for answering emails (60–75 per person per day) and doing that in our own voices. We’re simply allowing a team of people to have human conversations with our customers. It’s sad to me that our fellow humans expect so little from us. We only have ourselves to blame!

Check out this hilarious clip from the latest season of Bojack Horseman, in which one character is struggling through her day and needs help from a customer support rep. Diane is carrying a lot of emotional baggage with her and needs a human touch, someone who can empathize and alleviate some of that burden. She’s instead met with a robot.

It’s funny and we laugh (it’s dystopian but honestly not all that absurd), but this is a daily reality for so many people who simply need a human conversation, someone to guide them through a difficulty (even if that difficulty seems frivolous to us). A harsh reality played out here is that, too often, service providers like this are not trained to actually help a person in need.

It’s not just that a human conversation is what our customers want and deserve. Our relationship to our customers should be more symbiotic — we need just as much from them as they need from us. Sure, our needs are different, but think about how we know to grow our product, where the holes are. At Basecamp, we talk to our customers. We interview them. We listen to their feature requests, their rants, their raves. We don’t simply look at data and clicks (we do that, too!), but we also have real conversations with real people. Real humans!

It may seem cheaper to employ chatbots and automation, and that’s because it is. It’s not a good thing when cheap is synonymous with flimsy. You’re sacrificing intel, product knowledge, connection, and culture. It’s not worth the sacrifice. Your human support team connects daily with your customers, your customers who not only carry with them the money you need to stay in business but also the knowledge of how to improve your product.

So if customers want to talk to humans and if customers have product knowledge to glean, why are we seeing so many companies employ these automations and bots? One of the reasons is simply that we’re a society that’s obsessed with technology and profit and the intersections therein. Maybe we should all reread Frankenstein?! But I also think that a more compelling reason is that support teams, in general, are not treated with the dignity and respect that they deserve. That creates a culture of apathy and causes high turnover rates. Turnover frustrates managers and hiring committees: Why won’t people stay? This job is too draining. Let’s get bots who don’t complain and can’t leave. Apathy frustrates your customers who will find another service provider who can support them genuinely. I can tell you from experience that it’s not the work itself that makes people leave; it’s not the work itself that creates apathy — it’s the culture.

I’ve been supporting Basecamp customers for over seven years. Three others on my team have been supporting Basecamp customers for over seven years. Several others have been doing this for nearly five years. Collectively, our team has been supporting Basecamp customers for 64 years. It’s rare when someone leaves. So, I’ll repeat myself: it’s not the work itself that creates high churn and apathy in support positions; it’s how the employees are treated.

We all need to start placing higher value on the team that works directly with our customers. That means finding people who are preternatural helpers, first and foremost. What are preternatural helpers? People who enjoy problem solving with others. People who want to cull all sorts of knowledge for themselves and others. People who run to a problem instead of away from it.

Our team is made up of librarians, educators, personal assistants, fraud specialists, and IT professionals. All of these kinds of helpers, in order to succeed in this field, must be strong writers. You need a team of people who can communicate effectively in any form — that means that their written word must be passionate and strong. You need to hire people who can devise a way to gently say no, to kindly show a user how to accomplish a simple task without making them feel stupid. You need to hire people who are capable of handling difficult conversations with grace and candor. You need to hire people who can translate customer conversations into new product features or even new products themselves. Writers can do this because they can conjure these tones and emotions in strangers. Writers can identify, organize, and synthesize information for your customers to understand easily.

It’s a red flag to me when I receive bad support. The red flag is always for the company itself. It’s rarely the fault of the person trying to help me. Rather, these situations show me that the management, the company at-large abandoned this person. It’s a systemic failure, not a personal one, due to poor training, poor wages, no stake in the company (cultural or financial), no trust or autonomy. It’s honestly so easy to remedy.

Once you find the right folks (those polymath writers haha), you need to write and maintain effective and thoughtful training documentation that sets your new hires up for success. You need to constantly support your team. That looks different for each person you hire, so you need to get to know each person individually. Employees deserve regular reviews, regular feedback, opportunity to share their feedback, 1–1s, team chats. You need to listen to your team to know where you’ve failed so that you can atone and reconfigure. Let them guide you as much as you guide them. Your support team deserves competitive wages that can support them in a career — support work is not a stepping stone to another career; it’s its own career. They deserve retirement security, paid time off, childcare, healthcare. I could go on. If you want to treat your customers well, then you have to start treating your support staff well. If you value your customers, then you better value the folks who talk to your customers. Otherwise, you’re setting your customers up to fail and waving that red flag.

Once your team is comfortable and confident, you need to start giving them time away from the queue to process all the information customers gave them, to maintain documentation, to teach and interview customers, to learn new processes, to advance their skills.

Each support representative should have their own project for which they are responsible. On our team, each person spends one full day each week on working on Research & Innovation, a kind of Personal Development. They write help documentation, programming documentation, teach classes, interview customers, write blog posts, do social media engagement, learn programming, etc. I don’t decide what each person works on — I help them come to their own decision. This management style gives them a sense of ownership and dedication, a stake in a team so that there would be a true gap, perhaps even a systemic failure, if they left. Your support staff should not feel expendable. Help them feel essential by trusting them with their own passion project. Let your team show you better methodologies, better processes. Let them suggest protocol. Give them ownership in their work.

Try to remember that you started this process. You shifted the culture. You hired the right people, you trained them effectively. Now trust them. If you don’t trust them, then you took a wrong turn. People will soar when given the freedom. They will be grateful and hard-working, dedicated and loyal. They will challenge your company and make it a better place to work. I can’t say the same for robots.

The immeasurable value of customer friendly policies

A while back we bought a duvet cover from Brooklinen based on, of course, a glowing Wirecutter review. We’ve been happy with it (it’s super comfy!), but sometime in the last couple months the teeniest, tiniest of holes appeared in it.

This wasn’t a big deal, but this tiny hole could eventually turn into a big gaping tear sometime in the future, so I wanted to get it fixed up. Thankfully, Brooklinen offers a lifetime warranty.


I sent them an email with a few details, and with zero fuss we had brand new replacement duvet sent to us for free. And on top of that, they told me to just keep the torn one so I didn’t have the hassle of shipping it back.

And with just that one small interaction, they’d secured me as a customer for life. The product is great, their service was outstanding, and the prices are fair (especially given how they stand behind their products). Why would I even bother shopping around in the future when they’ve done right by me in every way?

In absolute terms they lost a bit of money on this single transaction with me. But beyond the short term, they’ve setup potentially thousands of dollars of future sales from both me and word of mouth goodwill. I know I’ll be back for sure.


On the flip side, I recently ordered a couple pillows from Tempurpedic. They’re a well known brand in the bedding space and on the high end of the price scale.

I honestly didn’t think much about their warranty and return policy when I bought the pillows. I had just come off the Brooklinen experience and just kind of assumed a high-end brand like Tempurpedic would be as good if not better on the customer service front.

I gave the pillows an honest shot for about a week, but they just weren’t for me. There was nothing defective or wrong with them, but I found them uncomfortable. I decided to return them.

Wups! Their return policy clearly states that they don’t accept any kind of returns on pillows.


Now to be clear, this is 100% my fault for not checking the return policy before buying. And this also isn’t a product defect. They are well within their rights as a company to have a policy like this to protect their business. Objectively I have no problem with any of that.

But subjectively I was surprised and a little irritated. It left a bad taste in my mouth, especially coming off the Brooklinen experience and knowing they have a far more generous return policy (as do Leesa, Casper, and others in their industry). Surely they could be more lenient with this policy to take care of their customers?

Now could I have emailed them and finagled my way into a refund? Yeah, probably. But it hardly seemed worth the effort. From just reading their policy, I got the feeling — right or wrong — that emailing with them was probably going to be a huge pain in the ass. I didn’t bother.

All said and done, I doubt I’ll ever buy another Tempurpedic product again. I wasn’t really happy with the product and on paper the company didn’t seem to really care if I was happy. Why would I ever support this company again with my dollars?

They landed $80 from me this one time, but it sure seems like they missed out on a long-term relationship with a customer.


At Basecamp we try to be ultra-clear about our refunds. Yeah, we’re not making multi-thousand-dollar physical products, but treating customers the right way and making them happy is our golden rule.

We’re happy to make our customers happy. 😃

And beyond what our public policy says, there is a singular philosophy that we follow when helping out customers at Basecamp: if you have even the slightest doubt on what to do, just do right by the customer. The trust and respect we gain by making a customer happy — even if it means “losing” a few bucks today — is immeasurably more valuable in the long run.

How to manage all-hands customer service

The evolution of “Everyone on Support”


At Basecamp, we’ve been running an initiative called Everyone on Support for nearly five years now. Each person in the company, whether a designer, developer or podcast producer, spends a day every eight weeks or so responding to customer emails. As Emily wrote a few months in, EOS quickly proved its worth: Direct contact with customers gave people a new perspective on our products, first-hand experience of the problems users were facing, and a reminder of what we were all working towards together. Lessons were learned, bugs fixed, and cross-team relationships were strengthened.

And then we got busy. With customer requests climbing, the support team lost some important people, and those that remained developed an unhealthy obsession with “inbox zero”. Our stress was infectious: Folk would turn up to their EOS shifts eager to help and leave deflated because they’d barely made a dent in the email queue. Each of them had a dedicated support team buddy to ask for help, but rather than “bug us” with questions, they’d spend hours down help-page rabbit holes. And on the rare occasions that things were quiet, they got bored because we weren’t leaving them with anything to do.

Something was very wrong, but the support team was too busy to notice. We didn’t have time to check in with each other, much less the people who were joining us for the day. We’d started Everyone on Support with the best intentions of not turning our coworkers into part-time firefighters, but that’s exactly what they became. Month after month, people would show up, grab the kind of requests they’d seen before, respond to as many as they could before their eyes started to swim, and clock off feeling bad because they hadn’t kept pace with the pros.

We hired some wonderful people, and reset our expectations for the support queue. While we took the time to train our new members, we paused EOS for a few months. That meant that we could put our whole focus on training, and take some time to think about how to do all-hands support right. As part of fixing our unhealthy behaviours, we carved out some time for “research and innovation”. I spent that time working out how we could invite our colleagues into the new, healthier space we’d created for ourselves. Here’s what we did, and what we learned.


Clear expectations are everything

Right from the start, we wanted to be clear about what Everyone on Support is. We put together a guide to outline what we expect from our guests and from their buddies on Team OMG (our pet name for the customer support team at Basecamp). A doc called What is EOS? What is EOS NOT? reaffirms our original goals for the scheme and how we’re going to achieve them together. It also reassures folk that they aren’t fodder to paper over cracks in coverage. We’ll work together to ensure their shift will be interesting, useful and fun.

Hands-off all-hands

As a bad manager in a previous work life, my initial impulse was to impose a solid structure onto EOS. On their first support shift, each person would respond to X number of login emails, then level up to billing issues, before starting to look at feature requests, and so on. I drew up a detailed syllabus, and asked for help fine-tuning it. Jim pinged me, and we had a great conversation, including the following question:

What does the loosest implementation of this look like?
The company as a whole has been moving towards a more structured way of working for a while, but a lot of Getting Real and Rework are about doing less. How can we capture that spirit in EOS? What’s the smallest amount of work we can do to give the most support to the folks doing EOS?

I decided to scrap the syllabus. Using metrics risked the kind of anxiety around speed people had experienced in the past. Being too prescriptive would suggest that there’s only one way to succeed in support. And neither of those things got us closer to our goals for EOS.

I turned my gaze to the work we’d done to onboard the new members of the support team. OMG had done a great job of building a loose framework to support the learning of the newbies, and that felt like a better fit for what we were looking to do with Everyone on Support. I salvaged some bits from the abandoned syllabus, and repurposed them. When EOS would start back up again, everyone would have a collection of resources and some advice on handling common cases.

Basecamp is a company which values independence. The best approach was to give everyone everything they need to succeed, and then get out of their way.

Communication is key

Basecamp’s support team are thoughtful, kind humans. Instead of telling them how to manage their charges, I encouraged them to talk it out, and discover the way that person works best.

I suggested that each EOS day start with a discussion about what our guest supporter wanted to do, and end with a catch-up about how it went:

Your job is to help ensure that your buddy has fun, learns something new and feels good about their shift. Creating the experience that best works for them is going to come down to good communication.

A two-way street

Team OMG is full of good listeners (it’s our job!), and we’re as interested in learning from our coworkers as we are in teaching them. When updating our buddies list, I tried to pair people along shared lines of interest. Time zones made this tricky, but I’ve managed to connect support folk interested in research and product development with specialists in data and design, and the two-way insights have started to flow.

One size does not fit all

When training new OMG team members, we recognise that everyone learns and works in their own way. That’s something we’ve built into our approach to Everyone on Support: for some people, we pick emails that will be of interest and provide hints as to the answers; for others, we leave them to it, and stand by in case they have any questions.

Once someone’s comfortable with email support, it’s up to them how they spend their time with us. If something fits in a single day, and is going to benefit our customers, then it’s a good use of a support shift. People on EOS have squashed bugs, launched customer research projects, improved our internal tooling, leveled-up our external documentation… and that’s just the start!


Everyone on Support is a work in progress, but it feels like we’re going in the right direction. For six months now, we’ve been running a much more chill, cheerful — and constructive — version of EOS. I’m going to keep steering it with a light touch, and check in with people, to see how they feel about where we’re headed. Basecamp’s approach to all-hands support aligns with our values and how we choose to work as a company — so you may not be able to apply everything here to your own initiatives. We didn’t get it right on our first try, and we’ll make more mistakes in the future. It’s worth it.


Do you offer all-hands support? How does your approach differ to ours? Or are you thinking about rolling out something similar in your organisation? And what concerns or challenges are holding you back?

Let us know in the comments! 🖤

Don’t Be Fake


Hey, are you crushing it? It seems like everyone is constantly crushing it in the business world. But maybe it would be better if we were honest about our flaws, talked like ourselves, and aimed to be genuine instead of super polished. In this episode of the Rework podcast: A Basecamp customer support representative shares tips on writing emails like a real human being; an inherently artificial industry gets a dose of reality; and two startup founders try an experiment in radical transparency to save their business. Stick around until the end for some poetry. Yes, poetry!

How we do support at Highrise

When I joined the Highrise team in May of 2016, the support team wasn’t a team at all: it was a single person. Chris did everything, from answering emails, to maintaining our help site, to recording how-to videos. Just the emotional output from being “on” empathetically all day every day can be exhausting, so I came along to help.

After a few months of me getting up to speed we realized that while there were certain times that it made sense for both of us to be helping users, like first thing in the morning, for a portion of the day one of us answering emails was sufficient. So we started asking ourselves, what was the best way for us to not only help our users and teammates, but to take care of ourselves as well?

As we started brainstorming the best way to accomplish that, we began by going through all of the other areas of Highrise we wanted to help contribute. The help site and all of it’s written and video content was always our responsibility, but we realized there were other ways we could help with the “extra” bandwidth we found ourselves with.

Onboarding emails for new users. Spending time coming up with and implementing different ways to build relationships with people. Writing more. Helping out with product testing and QA. And just generally being there for other teammates who could use an extra hand.


Chris and I spent some time going through different ways we could divide our time. We settled on a time frame that would help us not only recuperate emotionally from being on, but enough “off” time to really dig into other projects and interests we have.

Any project that you really need to dig in and complete needs more than just a 3 hour chunk of your week.

What did we decide to do? A week on support, and a week off.

The week you are on the support inbox, that is your #1 priority. The expectation we set for users is that we’ll be here from 8am-5pm CST, so when you’re on the inbox, that’s what you cover. There’s still time to sneak other little things in there, but we pride ourselves on giving replying to customers as soon as we possibly can, so when you’re on, you’re on.

When you’re off the inbox, that’s the time to take care of bigger projects. It’s amazing to be able to write and tackle other things without having to constantly go back and check the inbox.

I personally use the time to take care of myself a little bit more too. It’s a great time to catch up on reading and learning, meeting up with users or colleagues to chat over coffee, even just taking a walk in the middle of the day to let the brain relax and think.

This system has worked incredibly well for us. Both Chris and I approach the job refreshed after a week “off”, and can give customers the best version of ourselves, which they wholeheartedly deserve.

We also get to scratch the other professional itches we have, while simultaneously helping our other teammates out as well.

Some may say that their inbox has a perpetual backlog, and they need all hands on deck at all times. Which is understandable, I personally have experienced that on many occasions. But even if your support team is 10+ people, finding room to start on a “small” version of this plan could pay off huge dividends.

If I knew I had every Wednesday afternoon off from the inbox to recharge my empathy batteries and tackle some other passion projects of mine, it completely shifts my mindset, and can very easily stave off burnout.


Will we always work this way? Maybe not. We’re already exploring other options for seasonality, and things may change when a third person joins our team at some point in the future.

You may be hard pressed to find two people who care more about helping users than we do. However, to take care of others, we know we have to take care of ourselves first.

Oh, and what app do we use to help customers? Highrise, of course.


Building the Best Relationships We Can

Maslow had it wrong. To get it right, we have to move social needs to the bottom of his pyramid.

-Matthew Lieberman (Professor of Social Cognitive Neuroscience at UCLA and author of the book Social)

Babies would die without their caregivers at birth. Study after study show the pain and ill we go through when we are isolated from others like us. As humans, we are wired to connect to one another.

However, instead of connecting, we seem to be heading the opposite direction. On the streets and in restaurants people are looking at their phones instead of the person right next to them.

Businesses strive to make everything quicker, faster, and automated. Sending automated welcome emails with generic information to everyone who signs up. Introducing artificial intelligence to weed through support inquiries instead of having someone read and respond to your query.


It’s important to us here at Highrise to help people build great relationships. For many of our users, Highrise is an essential piece of that equation.

But what about us? How is our relationship with our users?

We try to make the welcome you get when signing up for Highrise a bit unique by changing the templates every day, asking people to chat, and a few other tweaks our CEO Nathan covers in detail here.

But we want to go even further. What else can we do?

Now, when you sign up for Highrise, you hear directly from me.

And by “directly from me”, I mean you see me, you hear me, and I address your individual needs based on what you’ve told us about you so far.

You get a personalized video.

I personally greet you and ask you what you specifically need. And how we can help solve the problems you are having with your business.

The results so far have been really, really positive. And while making the human connection is the most important thing, we are hearing some really incredible feedback too.

First of all, holy crap. I’ve never gotten a video as a welcome message from a SaaS product before. I’m really impressed.

What an AWESOME email and video. Highrise is killin’ it! I really loved how personal this was.

Thanks Alison. I appreciate the thought and effort!

Hey Alison, that custom video for me was just mind blowing. Do you try to reach out to every customer that way? So impressed.

We are still a few weeks away from finding out whether or not these videos have an effect on our conversion rate. But one other huge factor is at play too: the memory of someone who cares. — Even if Highrise isn’t a good fit now, you may recommend us to friends, or even come back when the time is right. But most importantly, you might remember the human that took the time to make the connection with you.

As experts in helping people build great relationships, we keep learning too!


Bargain for Bugs

Comic from xkcd.com

I found a bug . . .

When you receive an email from a customer that starts like this, what is your first reaction?

Disappointed? Are you anxious? Shocked?

The support team at Highrise is often skeptical. Why?

Because sometimes what you think is a bug isn’t a bug at all. It’s an expectation.

We’re firm believers that the best answer is a question.

Because if you expected X, and got Y — that’s not a bug. It’s an expectation. What did you expect to happen is a powerful question.


For example . . . .

I found a bug. When I filter by the tag Chicago and I only see four total contacts. There are several other people associated with the companies tagged Chicago so why does it only show four?

Please advise on when this will be fixed.

This was an email our support team received over and over again. When we began asking the question: What are you expecting to happen?

We found that the customer expected to filter by the tag Chicago, and for that filter to include all people contacts that belong to companies tagged Chicago too. However, this isn’t how Highrise was built to work at the time.

Unless, you also tagged all the people contacts with Chicago, your filter won’t include those people contacts. Only the company contacts.

This wasn’t a bug afterall. Highrise was working as it was intended in this example. The problem was that intention didn’t match most customers’ expectations.

This was an email our support team received over and over again. This isn’t a bug. It’s only a difference in expectations.

This failure of expectations led to our team to make an adjustment. Instead of the intention to only include people if they have the same tag, our team made it so if people contacts belong to a company contact, those people contacts inherit those same tags. We call it company tags.

Not a bug, but a failed expectation led us to improve Highrise using company tags.

I’m not here to argue the definition of a bug. Or to make a case that bugs don’t exist in Highrise. Or to say if a customer assumes there is a bug, that they’re wrong.

Of course, they’re not wrong. And bugs exist in all software too.

All I’m suggesting is before giving in and adding to your bug report, ask a question.

What are you expecting to happen?


Enjoy this post? Smash the 💚 to share it with others. And if you need to track leads and manage follow-ups, please check out Highrise. Your address book doesn’t do enough, other CRM software tries to do too much. Highrise is built to do just what you need — no more, no less.

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.


Honesty is the Best Policy


Downtown Vegas’ fire-breathing mantis & Staying on the set of The Real World Season 31

Two weeks ago Highrise had a company meetup in Downtown Las Vegas. It’s only seven of us, so you can imagine what traveling and meetups do to our customer support.

We have two people dedicated to customer support. They stagger their travel so when situations like this arise, someone is still on the ground answering email. Still, there are moments during a meetup like this where we can’t be as good about our response times on our support queue as we want to be.

What do we do?


We typically do our meetups in Chicago, and once in Boulder, CO in April. We got stuck in CO when the airport closed for a day due to snow [more on that crazy story here 🙂].

This time, Las Vegas came to mind as a place we could go in April and not have to worry about weather problems.

I’m also incredibly inspired with the effort Tony Hsieh, the CEO of Zappos, has put into resuscitating the Downtown area of Las Vegas. I highly recommend it as a place for meetups (Pro tip: use the Real World Suite as a place to work during the day).

So we mainly stuck to the Downtown area of Vegas, but we did take advantage of some of the fun things also on “The Strip”. For example, we saw Cirque du Soleil’s Love.

And we also went to a fancy cocktail bar overlooking a gorgeous human-made waterfall.

This bar came from a bunch of recommendations, but when we sat down something was off. The table was a little wobbly, so I looked underneath it and saw what appeared to be blood.


Can’t be. Maybe someone just stepped on a raspberry and it hasn’t been cleaned up yet.

The experience remained “off”. It took about 20 minutes before anyone even came over to our table to take an order. The person finally taking our order only uttered 3 words: “Are you ready?” We all ordered water too. But even after another long wait for drinks, the water never came. We had to reorder that too.

A little later, someone working there dropped a glass behind me. They cleaned up half of it and left the rest. It seemed as if they saw the rest of the glass, but they didn’t do the work to sweep what wasn’t in easy reach.

I heard people, sitting down behind me, later step on the pieces.

Maybe it actually was blood under our table.

To top off the night, the bill came with an automatic 18% gratuity, likely because there were 7 of us. This place didn’t deserve anything close to this gratuity. But… we’d already spent too much time there for me to wait around to talk with someone about it. I just wanted to leave.

So why was it like this? The biggest cause we noticed was that the main waitress taking all of our orders was the only one working tables and serving drinks. She was slammed. Clearly she was too busy to handle this well and that’s not her fault.

But what’s interesting to me is how some simple a handful of words would have made all the difference.

If she had just said, “I’m sorry for the wait. We’re slammed today and my backup hasn’t shown up yet.” Our entire experience would have improved with those expectations.


At Highrise, when our support can’t be as top notch as we want it to, we make sure we tell you about it upfront.

Here’s what our help site looks like when we’re on a company meetup:


The yellow alert about our limited support is built into the custom made site so it’s easy to throw up in situations like these. It doesn’t go up often — the bi-annual company meetup, Christmas, an unexpected crisis.

But the effect has been tremendous. Instead of getting upset emails about a temporary slowness to our response times, we get email telling us to enjoy our holiday or time together and letting us know they appreciate the heads up.

It’s a strong lesson for those folks out there who are constantly trying to hide how things are really going. They make it sound like they have an international team running the business when really it’s just a solo entrepreneur making it all work. Or they pretend everything’s going great, even though everyone is clearly aware you’re barely getting by.

Pretending it’s something different doesn’t make it better. As your customers, we can tell. You might as well be honest. Exceed expectations every time you can. And set them appropriately when you can’t.

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 and follow-ups you should try Highrise.