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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In mid-November, I was lucky enough to attend the second Support Driven conference, SUPCONF NYC. Held in the middle of lower-Manhattan at the DigitalOcean offices, it was a gathering of support professionals serious about delivering top-notch customer experiences.

For me, this SUPCONF was dear to my heart as I went with the Customer Success Team that I work with at Wildbit. And it was the first time that I was able to meet my wonderful colleagues in person since we all work remotely.

The NYC edition of the conference introduced a new wrinkle: lightning talks. Instead of a more curated talk, these were talks proposed by the Support Driven community. Before the conference, SUPCONF attendees voted on the proposals. The top 5 presented their talks at the conference.

The talks were great as they were short, rough around the edges, but packed tons of information. These will be the some of the first I watch when the videos come out. The presenters and topics covered were:

  • Justin Reist – Leading as an Introvert
  • Matt Dale – How to troubleshoot anything
  • Karl Pawlewicz – Surprise! You’re also a salesperson
  • Kelly O’Brien – You have been eaten by a grue: Self-service lessons from a text-based adventure game
  • Peter Shin – How to think about service like a product designer

The conference also featured a live taping of the fantastic support focused podcast, Support Ops. (For those that did attend: I’d be a dragon. The ability to spit fire? Sign me up!). Chase Clemons moderated and participated on a panel answering questions related to support submitted by those attending the conference. Along with Chase, the group had the full Support Ops crew: Carolyn Kopprasch, Chase Livingston, and Jeff Vincent.

Day 1 was a gut check for me. It was full of important topics in support that have become after thoughts for me. From investing in your team, modeling staffing needs, and building a case to fire a customer.

In my opinion, Day 2 was where the conference shined. I’m going to dive deeper into the topics covered on this day.

The morning of Day 2

Create human relationships with your customers

Think about your memories of your best friend, significant other, or your parents.

Done thinking?

The memories that come to mind are most likely not virtual ones. Snapchat messages are fleeting, human relationships are not. For the relationships that we cultivate in life, the human element is the most important part.

Margot da Cunha covered how creating a human relationship with your customer is invaluable. In the world of SaaS apps, the barrier to switching is low. Sure, you can have sticky features, but there’s something even stickier: a human connection with your customer.

It’s possible to create the human connection many ways. From meeting clients in person when possible to creating one-off demo videos (with audio) describing how to do something in your service.

I’d also love to hear how others are crafting a human relationship with their customers. If you have any thoughts on this, please reach out to me via email or Twitter.

Move from transactions to partnerships

I believe we’ve hit peak transactional support. Meaning, the customer coming to the support person and asking for X to happen and receiving X. This could be from canceling an account, to “how do I update my credit card?” questions. AI is coming, and it’s going to take these types of support requests in some form–And that’s okay.

Chris Hardie from Automattic’s WordPress VIP team covered how they’ve moved from transactional support to partnerships support with their customers.

Moving to a partnership model turns the customer relationship on its head. “I can help you with that” becomes “We can work on this together”. You tie the customers success with your success.

Paired with creating a human relationship, the partnership model of support becomes worthwhile.

Burnout is real

While it’s handy to have Slack, Trello, Gmail, etc. on your phone, it can be hard to leave work after working hours.

On top of that, side-hustles to get a new job to or grow your experience are an important thing for many in 2016.

With all that in mind, burnout is becoming more and more common. Camille Acey hit on this while covering how to continue to seek and validate activities.

She noted the biggest causes of burnout are:

  • Lack of control
  • Insufficient reward
  • Absence of fairness
  • Conflict in values
  • Work overload
  • Lack of community

To avoid these causes of burnout, she’s created a framework evaluating new opportunities that address each cause of burnout. The framework has four pillars to evaluate from: Time commitment, growth possibility, safety (how risky), and whether the opportunity is any fun.

Create a time inventoryAvoids conflicts in values, and work overload: With everything you do, it takes time. Log it. From marriage that’s infinite, to a commitment that is for a local event coming up–It all takes time. Add up your time commitments and decide if you’re available to add more to your plate or take something off to work on a new opportunity. When adding something new to your plate, think: How long does it last, and do you want to do it?

GrowthAvoids insufficient reward: Does the opportunity improve yourself?

SafetyAvoids lack of control, absence of fairness: Do you feel accepted in this community where this work will take place? Will you feel like won’t embarrassed for speaking up?

FunAvoids lack of community: Is it something you enjoy? Is there a tribe for you there? If you don’t enjoy something, it’s not worth doing.

By following these rules, it allows you to check new opportunities while avoiding burnout.

Stop changing jobs

Ben MacAskill is my career spirit animal. While he was in college, where was he working? SmugMug. Thirteen years later where does he work? SmugMug. His talk, which closed out SUPCONF, covered his career journey at SmugMug.

While it takes some of us awhile to find our path, the lessons he learned are valuable to all. Instead of focusing on the next promotion or a job at the well-funded start-up on the other side of town, focus on doing your job great today–The journey is the reward. The opportunities will follow. It’s as simple as that.

Wrapping it up

Support Ops Live

SUPCONF NYC was another great professional event put on by the Support Driven Community. Being in a room with 150 some support professionals got me more excited to do my job. And I learned a lot.

One theme that I saw echoed from SUPCONF SF at this event was data and money. When working with other departments at an organization, you need to speak in their language. That language? Data and money. Want to hire a new support employee? Show through data that you’ve hit the threshold for the workload your current support staff can handle. Have a pesky bug that isn’t getting fixed? Make your case by showing how much money the bug is costing your organization. I know these examples are easier said than done but speaking in data and money is crucial.

SUPCONF will be returning in 2017 with an event planned in Seattle on March 20th -21st. Learn more and get your tickets here.

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All images in this post are courtesy of Ben MacAskill. And a special thank you to Camille for help editing this post.

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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Support is the Home Team

While watching Game 1 of the Word Series, a thought hit me: Support is the home team.

In baseball, the home team has the advantage of batting at the bottom of each inning. They’re able to “answer” and have the last at-bat in a game.

Support teams are there to help solve mistakes. If your team has the last inning mindset, each case that comes in is an opportunity to win. No matter how dire a case might look at first.

When an issue comes in, the team should have all of the tools available to them to answer and resolve the issue. The team should also realize creative solutions are sometimes necessary. Or, if you screwed up, admit and be transparent in ways you’re working to avoid the mistake in the future.

For example:

A case might not be resolvable right away – Sometimes a case might require further investigation or escalation. Take the issue to “extra innings” and let them know what’s going on, keep your customer in the loop, and follow-up when you have an answer.

Shortly after signing up a customer decides they need to cancel their account and asks for a refund – Happily give them the refund, you never know when they might have a need for your service in the future.

If your DNS provider goes down – Find a way to provide your customers IP addresses to keep using your service for critical functions they use your service for.

By the way, I’ll take one ticket to the Cubs bandwagon 😀.


Image courtesy of Startup Stock Photos

Being on top of all things is essential in support. It allows the email queue to stay under control while keeping an eye on live chat. But being on top of it all comes with a bad side. In a 5 minute window, you go from live chat to email, the next email, and back to responding to that Slack message.

With constant context switching, an important skill starts to dull: Focus.

Cal Newport wrote his most recent book, Deep Work on just this topic. He theorizes:

Deep work is becoming increasingly valuable at the same time that it’s becoming increasingly rare. Therefore, if you cultivate this skill, you’ll thrive.

I’ve taken Cal’s thinking to heart. In my role in Customer Success at Wildbit, 40% of my week is outside of the inbox and working on customer success. It’s taken rewiring and weeding of focus skills that have degraded over the years.

I’ve started this rewiring by adopting my own version of the Pomodoro Technique. It’s dead simple too: you work in 25-minute bursts, take a short break, then repeat. In those 25 minutes, you free yourself of distractions.

A Pomodoro is best ran with a clear goal and sub-tasks. In the case of writing, for me, it’s an outline. Between each Pomodoro, I jot down what I did. The log gives me a historical reference to look back at how I’m using my time.

I also find listening to music that I’ve heard over and over is best (Ratatat is a favorite of mine for this). It blocks out audible distractions.

Every Support professional should be honing their focus skills. Focus is the intangible power to get out of the inbox and set yourself apart. There’s plenty of day to day scenarios where this is important; from planning out a campaign reaching out to customers who are detractors or to putting together “when the shit hits the fan” plan.

How are you winning back focus?

Written over two Pomodoro’s

Searching Google from Any App

At work, I find myself always referring to our support docs, guides, and blogs best possible answer to our customers. I also support two different products. To make this search quick I use Google’s “site:” search operator to search an entire products website quickly.

This weekend, at Tiny Bit of Space I created a small script to my my search workflow instant.

The scripted is triggered by a keyboard shortcut available in any app on my computer. It brings up a dialogue box with a field to put my search query then opens a new tab to Google in my default web browser searching for my query.

The script I made, triggered within Tower.