Ryan D. Sullivan

Productivity, Business, and Being a Dad

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The 25 Step Guide to Buying a Mattress Online

… and what it taught me about project management

Jackie and I badly needed a new bed so we set out to explore our options. I expected the shopping process to be a major pain (and it was), but it was also the smallest part of the project.

I was reminded once again that projects are never what they seem on the surface, and there are always more layers to be uncovered as you try and figure out what’s really involved in task at hand.

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Motivation is Lame. Discipline is the Truth.

If you’re anything like me you’re much more prone to looking at inspiring fitness images on Pinterest and Instagram for 30 minutes than you are at picking up your ass and hitting the treadmill for 30.

I struggle with being truly disciplined in everything that I do. I find, especially with my work, I can be incredibly productive on Monday and Tuesday, acceptably productive on Wednesday, and Thursday and Friday are a lot less productive than I’d like them to be.

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How I Manage Notifications for all my Messaging Apps

Holy smokes there are a lot of messaging apps. Right?

  • Email
  • Slack
  • Hangouts
  • Telegram
  • Signal
  • WhatsApp
  • Basecamp

And that doesn’t count all of the social apps that have essentially become secondary messaging platforms like Facebook, Twitter, Snapchat, and Instagram.

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Don’t Be Afraid of Saying “I Don’t Know”

No one can be an expert at everything.

It sounds obvious, but throughout my professional career, I’ve been blessed with the opportunity of working with dozens of individuals who actually did know everything. I mean, they never actually came out and said they knew everything, but I never heard them say they didn’t know everything, so I’m going to go out on a limb and assume that, at least in their own mind, they did actually know all things.

Let’s take a look at a few quick examples:


You all know this bro. He’s the bro that because of social status, or an inexplicable need to be right about everything will swallow a cyanide capsule before he admits that he doesn’t know something about something.

“Hey Chad (they’re almost always named Chad btw), what’s the capital of Kansas?”

“Easy, it’s Wichita”

“Nah, it’s actually Tope—” watches Chad walk in front of a bus to avoid hearing the truth

This is the type of know-it-all that’s tough to communicate with, but it’s not impossible. Because the majority of the the pride comes from somewhere internal, usually finding Chad in a quiet place and genuinely trying to help explain a concept that he doesn’t fully grasp is the best approach here.

Talking to Chad in front of a group is an exercise in futility.

Operating Out of Fear

This is one of those lame situations where someone works in an environment where saying “I don’t know” means you could be at risk of losing employment, or missing out on that next big promotion. This is a sad but very real scenario that I’ve encountered many times before.

The biggest bummer is that because of this fear, the employee either makes statements that aren’t true, or gets defensive, or endlessly argues a point that they really don’t have any business arguing.

“Hey Scott, can you submit a PR on Github for that change?”

“PFFFT Why do you even use Github?”

“Well, it’s the de facto standard for hosting git repositories and is used by the Enterprise and pretty much everyone”

“Alright, I guess I can do it that way after I get approval from my manager” sneaks back to desk and furiously begins googling git and pull requests

This one is really tricky to address. Things probably aren’t going to change unless the overbearing and threatening manager drastically changes things from the top down, and works toward creating an environment of learning instead of a career-long memorization contest.

My kids are pretty damn good at Memory, but I haven’t really ever considered spanking them for missing a match. Although that could make the game more interesting…

I’d do everything I can to steer clear of these types of associations. They’re toxic and rarely end well for anyone.

Complete Lack of Self-Awareness

This is the Mt. Rushmore of know-it-alls. These individuals actually lack the self-awareness to understand that they don’t know everything. They don’t have any external pressure to be right. They genuinely believe that their answer to every question is the correct one.

“Jake, the moon landing was real right?”

“Yeah, real like Donald Trump’s hair. What a stupid question.”

“But it’s really well documented and…”

“Let me stop you right there. I studied 4 semesters at Oxford Harvard Stanford Moon School about the moon landing. End of discussion.”


Jake is clearly a tool who is too busy patting himself on the back to listen to others and learn from them. In his mind, he is the gospel. His word is final, and trying to do anything to convince him otherwise is just a genuine waste of time.

Whenever I meet a Jake, I light a candle in his memory because it’s the last time I’ll ever talk to Jake again.

A Challenge

When you find yourself in a situation where you feel pressured to be right about something, or to give the impression that you know the answer even though you don’t have a clue, I’m going to challenge you to say seven easy words:

I don’t know, but I’ll find out

That’s it. It’s really that simple. So many times when you’re asked if you have the answer for something, it’s not because the person asking is expecting a google-like response. They’re simply hoping for some guidance. If you don’t have the answer, volunteer to seek out someone who does. That’s just as valuable to the person asking as having the perfect answer on the spot every single time.

If not having the answer in real time is going to cause problems with a client or boss, it’s probably time to reevaluate expectations there and do what you can to get things back under control.

How do you respond when you’re put in a situation where you’d like to have an answer but you don’t? Are you a Jake, a Scott, or a Chad? Or do you take the road less traveled and simply admit that you don’t know? That’s the coolest way to approach it, FYI.

The Intricacies of Building a Well-Rounded Support Team

I read a fantastic blog post on the Intercom blog yesterday talking about how Great Support Takes More Than Tech Skills.

It’s something that I’ve believed for a long time, but the way they phrased it really resonated with me. The author, Sharon, talks about how every person on the support team has a very diverse background. One used to be a high school history teacher. Another, a TV Editor. Their support staff all come from very different walks of life, that gives them unique perspective.

In the WP Site Care Year in Review post  yesterday, I mentioned how I loved that our support team was so well-rounded, and how their different points of view play into providing truly stellar support. I hadn’t even read the Intercom post at the time. Talk about living on the same wavelength.

As I thought more about what makes up a great support team, I came up with a few ideas from our own staff.

Every Member is an Individual

On our team we have a licensed social worker, a public radio DJ, a cosmetologist, a legal staffer for Starbucks, and a Brookstone sales associate. They all come from varied backgrounds and bring something unique to the table.

It’s been incredible to watch opinions evolve and empathy rise as everyone brings their own history to the table and presents it to the rest of the team. Some of the early members of the team glean more from my style of support, which is a very “let’s get stuff done” attitude, but I really appreciate some of the styles that have been introduced to our team in the last year.

A bit slower, but more methodical. Not necessarily racing to close tickets, but working on truly understanding the issue before jumping into the dashboard or logging into a server. An approach that, ironically, results in closing tickets faster…

Can you imagine the reaction of a customer who gets a bad haircut?

Or the stress level of working in a corporate entity the size of Starbucks?

WordPress Support seems like child’s play when you have that type of background.

They Give a Damn

I can teach someone how to migrate a website, or code a theme template, but as far as I can tell it’s pretty much impossible to teach someone to care.

And my team cares. I’ve always prided myself in going above and beyond for clients, even when it “isn’t in our best interest,” but some of the actions of my team members put me to shame. They go the extra mile every single day.

When we’re trialing with a potential hire there are a few key things I look at, and none of them have to do with code.

  • How are they at communicating with the rest of the team? Are they using language that encourages collaboration or are they worried about how everything is going to impact them personally? When they log into slack, do all of the green lights go black (yes, I’ve really seen this before)?
  • When do they clock out? Do they walk away for the night with a huge queue of pending tickets, or will they stick with it a bit longer just to let customers know that we’re at least looking into things? Support staff who walk away from helping out clients trigger a definite red flag for me.
  • Where are their loyalties? In the past it’s become clear with a few individuals that Site Care was simply a springboard into other opportunities. To be totally clear, I don’t even have a problem with that. But I do have a problem if one thing is being said and another is being executed. Employees who are clear with where their loyalties always tend to have an above average volume of give-a-damn.

They Know How to Laugh

I can’t overstate the importance of this when working in a support environment. People who take things too seriously are really going to struggle. There are plenty of days that aren’t fun, and the only recourse is to learn to laugh about it, or at ourselves.

No amount of technical knowledge will ever replace the ability to laugh when stress is the highest.

We crack jokes all the time and we’ll be sharing more of them on our company instagram, so check us out there if you’re into cheesy tech jokes about cats or Rick Rolls.

It really upsets me to admit this, but I’m pretty sure I’m the least funny person on our team now. Seriously, I’m not happy about it at all. But what am I supposed to do? I either have to get funnier or fire everyone, and the latter is never gonna happen with a staff that’s this well-rounded.

Any thoughts you have to share about putting together a well-rounded staff? Hit me up in the comments.

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