Packing a Workspace

This is my sixth and final post for the 6 week Support Driven writing challenge. For this post, the topic is “Share your workspace with us”.

I’m a remote worker, because of that, my physical workspace is in flux. Most days are spent either at home or a local coworking spot. Because of that, I wanted to capture what I keep in what I call my desk, my backpack.

I do have one rule for where I work: The space must be quiet and private. No open office and little time spent in coffee shops.


Here’s what’s pictured above:

  • Standard issue MacBook Pro and charger.
  • Ear buds.
  • A notebook to write down thoughts.
  • Blue/Black Pen. Like a TV remote, I’m always losing one of these. Currently lost is the blue pen.
  • USB cable.
  • Clicky keyboard & mouse. Not always on me but a must have.
  • Water bottle.
  • The book I’m currently reading, Getting Things Done.
  • A local magazine, Little Village.
  • The desk, a Crumpler Backpack.


  • Snacks/lunch.
  • Coffee mug.
  • Sweatshirt, mittens, and hat. (it’s getting cold)

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An Archetypal Week

This is my fifth post for the 6 week Support Driven writing challenge. For this post, the topic is “Tell us about a typical day in your life”.

I split my week and days between working in Support and working in Success. Support is what you’d expect: Answering emails, live chats, and Tweets. Success is working on proactive content, researching how customers are using our products, and campaigns reaching out to customers.

Before Work

I wake up anywhere between 7:30 AM – 9:30 AM. It depends on what I have planned for the morning. I might meet up with a friend for coffee, go to the gym, or sleep in as long as I can.

For breakfast, I’ll have a bowl of greek yogurt with granola. Before I log on for work, I’ll make a fussy cup of coffee with a Chemex or AeroPress.


I start my day around 10:00 AM. I’ll hop into Slack to say hello to my team (we work remotely) and glance at Basecamp for what I missed.

At that point, I’ll turn my focus to what my role is for the day, support or success.

Support Days

My Support days are Monday, Thursday, and Friday. As you might expect, these are days where the work is done as it shows up.

When I load up Help Scout for the day, I’ll do my best to prioritize the cases in our queue: Are there any extremely urgent situations, are there any replies to European customers that I need to get out right away (to give them a chance to respond before their day is over).

From there, it’s heads down in the queue till lunch. I’ll also turn on Live Chat to have that available until 5:00 PM.

Lunch will happen between 1:00 PM – 3:00 PM. After lunch, it’s back into the queue.

For 3 hours I’m on alert monitoring shift for our transactional email service, Postmark. While on my shift, I’ll catch-up on my Pocket queue between alerts.

In my last hour of the day, I’ll follow-up on any Basecamp posts and finish up any to-dos. On Thursdays, I’ll write down any wandering thoughts from my previous Success days.

Success Days

My Success days are Tuesday and Wednesday. These days are much more focused than a support day. I’ll put Slack in DND (do not disturb). And I’m getting better at quitting Slack for a couple of hours.

As I said in the intro, Success is much more proactive work. Our goal in Success is to make our customers better developers, not just better Beanstalk users.

That’s where the content comes in. Maybe we find ourselves having to teach customers Git often, to help out with that we can create a Getting Started with Git guide. It can be blog posts, guides, or help articles.

Research is looking at all the data available like support requests and behavioral analytics. We try to find wedges here to make our customers more successful. Maybe there’s a pitfall we see people falling into. With that information, we can suggest product improvements or content to create.

A campaign would be reaching out to customers who haven’t reached MVE (minimum viable effort, i.e., the point of realizing the value of a product). It could also be reaching out to customers that we’ve identified that are at risk for churn. For example, I am planning to reach out to customers in a suspended state (payment is failing).

As you might be able to tell, there’s a lot of possibilities for what a Success day can look like hour by hour.

After Work

Around 6:00 PM I’ll start shutdown procedures (close the laptop lid) and end my day. There are no set plans for after work.

On days that my beautiful wife works, she won’t get home until 8:00 PM. The days she works I’ll cook dinner and on her days off she’ll cook dinner.

Some nights after work I might meet up with friends to watch a sporting event, or we might have a friend over for board games.

I’m a night owl and will stay up later than my wife. I’ll work on a project like this blog post or become terrified of technology by watching Black Mirror.

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Stacking Up Support

This is my fourth post for the 6 week Support Driven writing challenge. For this post, the topic is “What mediums does your team do support through? What are the pros and cons to each of these mediums?”

At Wildbit, our support stack is mundane, and that’s good. It means we’re not overwhelmed, and we can deliver exceptional support while being a small team.

We have the channels of email, live chat, Twitter, and are testing phone support. Along with help docs and guides.


I love email support. To me, this is the bread and butter of helping customers.


You can assume every customer has an email address. There are no extra accounts for them to learn and services to learn to interact with you.

Each customer is unique. Email support allows you time to make a response specific to the customers unique needs. For a tricky case, you can spend 10 minutes researching, and the customer doesn’t know the difference. In live chat, they’d be asking “are you there?”.

For the tricky cases, you can spend 10 minutes researching, and the customer doesn’t know the difference. In live chat, they’d be asking “are you there?”.


For the customer, it can be difficult. If they’re coming to you, that means they have a problem. If you can’t get back to them quickly, it becomes a little terrifying with comments like:

Is there a phone number I can call?

Do you need more information?

Did my email get lost?

Live Chat

We have live chat on our marketing pages and in-app. It can be fun as you’re going over pricing/features, and at the same time teaching someone Git.


The immediacy cons of email are all resolved with live chat.

A human connection is easy to make with a customer over chat.

It’s easier to judge the tone of a conversation compared to email. It allows for a more enjoyable exchange with a customer.


An immediate, non-transactional answer can be hard.

I support developers. Teaching someone complicated topics or working through complex errors over chat is often mentally draining.



Like email, the barrier for a customer to ask a question is low.


I’m not a fan of Twitter support. Tying a Twitter handle to a customer is hard.

Replies are “cold” with only 140 characters available to a question that deserves 140 words.


This is an experimental feature two of my colleagues are starting this week.

In their email signatures, they include a Calendy link to schedule a phone call for phone support. We’re not sure how this will go, the best part is if it’s successful, it’s a win. If it’s not, we can remove the link from the signature and move on.


The most human of all popular channels.


In a twenty-minute phone call, you can only help one customer, with email or live chat in the same period you can assist 4-6 customers. Your team has to in a position to handle the volume or limit access.

Some answers are best answered over text.

Self-service (docs and guides)

We have two types of self-service content: Docs & Guides.

Docs are product specific information. Guides are product agnostic. i.e., in theory, a competitor could link to them as a great resource for information on a topic, and a guild should provide value even if you aren’t using one of our products.


The difficult how-to you get often? Turn it into a doc, and it can help the next 5 customers with the same question.

If your support team isn’t 24/7, it offers something in off hours.

Best practices? If you’re living and breathing your product you probably have some best practices, share them as a guide!


Docs can be a crutch.

Creating a help doc doesn’t solve all problems. The fewer help docs, the better. If you have customers reaching out to you frequently about the same problem, it can be a sign there needs to be improvements there. This isn’t to say help docs aren’t important but it is dangerous to fall into the trap of creating X amount of help docs a week.

Simon Ouderkirk and Carolyn Kopprasch have written great posts on the dangers of self-service docs.

A parting thought

A piece of advice I once heard: Never add a new channel until you’ve mastered one for 6 months. i.e., if you were starting a support team on day one, you wouldn’t have email, chat, and phone.

Pick one, master it, and add more later. If you can deliver an amazing customer experience in one channel, it’ll go much farther, than a bad experience on many channels.

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My Thinking Space

This is my third post for the 6 week Support Driven writing challenge. For this post, the topic is “Describe your ‘Thinking space’ – What do you do, or where do you go, when you need to sort through thoughts.”

My thinking space is found walking. When I have a hard problem that I’m thinking through, it’s done walking. I’ll frequently pair my lunch with a 15 to 30-minute walk to clear my mind.

Most of my thinking will be on how to respond to a tricky support case, a message I want to post to my colleagues, brainstorming ideas, or thinking through a project that I’m working on.

For the deeper thoughts, I write them down days before I’m ready to share anything. That means drafting something up. It’s raw and not intended for anyone else to read, it could be a simple list on paper or a more formal written out draft.

The draft allows me to get my thinking out of my mind. During mental downtime or when walking, I can return to those thoughts and not fear about forgetting something.

When I’m ready to work deeply, I’ll employ Pomodoro to focus.

From my lunch walk today. Can you feel the winter chill?

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This is my second post for the 6 week Support Driven writing challenge. For this post, the topic is “What tools do you use to manage your tasks and time?”

The tools that we use can become a black hole of conversation for me. I love to talk about what gadgets, apps, and services people are using to get things done.

With that said, I find that tools aren’t one size fits all. Just because Basecamp works for me, it doesn’t mean it’ll work for you. Because of that I’m going to focus on non-traditional tools that I use to get things done.

Being a detective

Being a detective is a mindset. Others might classify it as simply “curious”. It’s the thinking that the answer to any question isn’t going to be staring you in the face and you need to dig for it.

With a Customer Support hat on, it’s taking a reply with no information given to you and finding the answer. For example, with a message of:

Hi, I can’t log in. Can you help me?

Assuming you have an admin panel to look up customers you can turn that into a response that thoroughly answers any questions the customer might have to log into their account. And add in customer account specific data like their account URL (since you’re a detective, you looked that up).

With a Customer Success hat on, being a detective is realizing that you’re going to ask hard questions about how your customers use your service. Take the time to shut off distractions, pull up a spreadsheet, and take a fine comb over the app-data that you have.

Site search

I created a tool to make searching the web easier. It’s a keyboard shortcut to pull up an AppleScript that searches Google for a particular keyword that I enter (to a predetermined domain).

I created this because I support two products. Along with that comes searching blogs/guides/help docs if I’m not sure on an answer. This helps me be a detective more efficiently.

While creating a tool yourself might be too difficult, simply using Google’s “site:” search operator allows you to search a website with ease.

Here’s how my site search tool works in action:



On a weekly basis, I meet with others in a mastermind group. An official definition of mastermind groups would look something like:

Meetings where people who help each other to succeed through their advice and assistance.

It’s peer mentorship, where each member is on the same level–There isn’t the idea of a more knowledgeable person helping someone less knowledgeable, we’re all helping each other.

It’s a good way to learn how others are solving a similar problem. You can seek opinions on a hard problem you’re working through. Peer accountability to do something as simple as writing this blog post can also be created by a mastermind. Privacy is also important to create a place where you and others can discuss your challenges in a safe place.

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Chase that Ghost

This is my first post for the 6 week Support Driven writing challenge. For this post, the topic is “Our history shapes us – what path led you to Support? Was it a planned career? Or did you happen upon it?” I revisit the Origin Story I wrote for the 2015 flavor of the #challenge.

… I didn’t set out to become a Support Professional.

  • Me (2015)

When I look back at my professional history, I realize that I was on the path to becoming a Support Professional from the beginning.

One of my grandfathers serviced typewriters and other machines for a bank, this type of role that would become “IT.” Growing up, my dad managed a support desk. My mom calls me her help desk for when she has a question about her iPad. This type of work is in my DNA.

When I was in college, I shunned a non-help desk internship, for a help desk position in the Political Science Department. And since graduating college, I’ve only held roles in the support industry.

Becoming a support professional was no accident. The accident was thinking that I could be something else.

Going into my college career, I choose Civil Engineering as my major. Becoming an “Engineer” was something I aspired to be. Chemistry and I could never get along, so I quickly transferred to a business degree. After graduating, this would haunt me for the next ~5 years as I chased the ghost of engineering.

After college, I joined a big bank working in their support department. It was hard work, being in a phone queue for 8+ hours a day, working with loan officers trying to close deals while having technical issues, and adhering to strict metrics. Looking back it was good for me, I learned how to get pushed around by people and bounce back 5 minutes later, and I learned how to work with people in stressful situations. It has become the foundation of my career.

The first job after the big bank gave me the opportunity to create a title. “Oh, Fancy!” I thought. I gave myself the title of “Support Engineer.” At the time I was so excited, here, the guy that couldn’t get through chemistry still had “Engineer” in his job title! The next job was similar–my title still included “Engineer,” yay me!

Fast forward a few years and my job title at Wildbit is “Customer Success” and I couldn’t be more proud that it doesn’t include “Engineer.”

What changed? After discovering the Support Ops podcast, Support Driven, and reading numerous books I’ve adopted a Customer Centric view for my career, I realize that being an “Engineer” has no notion of anything that I’m good at and was a dream that 18-year-old me was chasing.

Today, I’d much rather have a “Be So Good They Can’t Ignore Your” philosophy and work from there. I’d prefer working hard in the weeds, and value learning over a job title.

Each day, I’m going to become a better support professional. Some days, I might learn new thoughts on Customer Success, others it’ll be how to handle an email better, and sometimes it’ll take me in a direction I never expected as I learn more. For example, I’ve been reading “Setting the Table” and it’s opened my eyes on what hospitality means and why it matters when making a great customer experience (Hint: It starts by empowering your colleagues).

As I think about my future, I remind myself a great blog post Gregory Ciotti wrote, titled “If You Aren’t Cringing, You Aren’t Improving.” Just as I want to cringe at the “Origin Story” post I wrote over a year ago, I’ll cringe at this post someday–And that’s okay! The only way to keep cringing is to keep improving.

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