West Coast, Best Coast

West Coast, Best Coast

Back at Christmas, I surprised my wife with a family road trip through the west coast. Fly into Vancouver, rent a car, then drive all through the Rockies and fly back from Calgary.

My wife had never been to British Columbia before, nor had she driven through the Rockies. Willow had never been on a plane. So it would be an adventure for everyone.

While our flights were booked, the actual itinerary was left intentionally blank. The only things that I knew for sure, were that we’d go whale watching in Vancouver.

I’ll do another post with some pictures, but the TLDR of the trip is:

  • Whale Watching: no whales spotted, just seals & sea lions. Still awesome
  • Stanley Park was beautiful and gigantic
  • Whistler was just as pretty as the last time I was there
  • Four Seasons Whistler was GORGEOUS and their outdoor pool was nice and hot despite the cold weather 😎
  • Kamloops could have been skipped
  • Kelowna is gorgeous and I LOVED the vibe. I could definitely live there
  • Had a BBQ with some great friends, which was such an awesome highlight for me
  • Banff is such a cute and tiny little Village
  • Fairmont Banff springs looks nice from the outside/lobby, but is definitely not worth the money to stay at
  • My daughter was a ROCKSTAR on the plane

Pics to follow.

April Update

April Update

Since my last post, we had four birthdays in our house. Willow, Me, Rascal (dog), and Rupert (cat).

Weather is still horrible (cold and wet), why do people say they like spring? They don’t. They like the last couple weeks of Spring. The rest of it is just cold, grey, and wet.

Until we meet again…

Until we meet again…

2109 days, 5 countries, countless moments.

A lot has happened since I started working at Automattic. We lost our house in a fire, had a child, travelled, weathered a global pandemic.

When I joined, there were a ~240 Automattians, but it still felt like a small company. Fast forward to today and Automattic has grown to 2000 employees. All working where ever they want in the world, within a fully distributed company.

I learned so much during my six years years. Met so many amazing people. Travelled to places I would have otherwise never seen.

Today I signed out of work for the last time. I had five weeks to prepare for this and going into today, I was ready. But when I closed my laptop it hit me… and I was not ready.

The tears are a great reminder that six years ago I made the right decision joining Automattic. They’re a reminder of all the great experiences and people I met. Next week I start a new adventure, but for right now I think I’ll spend a bit more time reminiscing,

Cheers Automattic and until we meet again ❤️

Should you use tiered customer support?

This week someone asked me if I thought tiered customer support was a good thing.

My answer was No … and also Yes.

This is because it depends entirely on the purpose and how it’s implemented.

It’s all about the $$$

Most companies implement tiered support as a cost-savings measure. It can be hard and expensive to hire support staff that have the “total package”.

People that have great soft skills, while also having a high ceiling for hard skills are rare. They are harder to find and more expensive to hire and retain. For this reason, many companies resort to hiring (or outsourcing) an initial layer of customer support that is only meant to handle the easy stuff. By only handling easy/one-touch interactions, it reduces the entry barrier dramatically. Your hiring pool broadens exponentially and training/onboarding becomes faster and cheaper.

So what’s the problem with this?

It’s typically a recipe for a bad customer experience. Yes, that tier 1 team can handle the quick and easy stuff. However, what about anything outside that? For anything else, it often turns into a barrier for customers where they look at tier 1 support as something you have to navigate/fight past in order to “get someone who knows what they’re doing”. This further perpetuates the “Can I speak to a manager” culture.

Because the intention here is cost savings, the time and resources aren’t put into training and developing tier 1 support. As a result, your tier 1 support will often end up giving out incorrect, conflicting, or frustrating advice when asked about something that they haven’t been trained on.

Wouldn’t the Tier 1 support just forward anything they don’t know to Tier 2?”

Sometimes. But often not.

Because this is all about the money, these sorts of team structures are often incentivized around preventing escalations. Escalations cost more money, so the focus will be on volume and not creating escalations. Plus you haven’t invested as much as you should in soft-skills training (again, it’s about the money). So now you get templated answers that lead to a frustrating experience and the team becomes more of an obstacle than an aid.

Can tiered support be done well?

At the start is said Yes and No. So there has to be something we can do?

Take away the financial benefits.

If you are doing tiered support because it will save money, it’s an inevitable ride down the mountain chasing dollars. You’ll cut more and more corners and the customer experience will be poor.

However, if you are doing tiered support for the purpose of providing a great customer experience – you can actually improve customers’ overall experience.

Depending on your service or product, there is likely a certain degree of niche knowledge. This is important stuff to know, but may be difficult or time-consuming to train for.

This could be things:

  • Rare use cases that are outside the norm
  • Technical skills like reading/writing code
  • Due simply to your support having a huge scope. If you selling 200 unique products, it’s not likely your team will be an expert on ALL of them at the same time.

In these situations, it makes sense to break that knowledge up. Have different groups of people specialize.

There are three very important pieces to making this setup work.

  1. Notice that I said “groups of people”. You should never rely on a single person as the sole source of information for anything in your company. Knowledge silos can be deadly to a team when someone leaves the company. There should always be redundancy.
  2. Everyone on the team should have the same core training and development. And everyone should be equally empowered. There shouldn’t be a difference in the experience a customer has, based purely on the nature of their question.
  3. Always minimize transfering a customer. But when you need to, it should be done early in the interaction and should be done in a seemless and positive manner.

The same person that asked me this question, also asked if I could point to companies that I felt do this well. Nothing came to mind at the time, aside from companies I had worked with – which obviously has a level of bias. However the more I thought about it, the more it made sense that I didn’t instantly have examples. This is because of point number three above. If done well, this should be transparent and feel natural to customers.

Easy transitions

If your team all has the same core training, development, and empowerment – they are capable of making a great experience for a customer.

They’ll be more aware of their blind spots and when to ask for help.

They’ll also be more aware of what specialized knowledge other teammates have over them.

Being able to recognize when a interaction should be handled by someone else comes easier. In those situations, you want to act on that right away. There’s no point in having a customer go through a 10-minute conversation with you if you know you ultimately can’t help them, but someone else can.

How you move that customer within your team is important.
No one wants to feel tossed around.

A handoff should always be positioned as a benefit to the customer. Champion your colleagues as “specialists” for that specific type of question and frame your language around connecting the customer with the most knowledgeable person.

To support those handoffs, you also need to ensure that your team infrastructure supports a seamless crossover. If you need to pass a customer to another group whose SLA is 10x another group, that’s a problem. You need to train up more people to support that queue, otherwise, customers are just being handed off into the abyss.


Creating specializations within your support team is a great way to stimulate the team with new learning opportunities, foster cross-collaboration, and scale your support requests.

If done properly, you can create a system that is totally transparent to customers, while also improving the overall experience.

Willow: Mommy is really good at cuddling! And she smells good. And she sings to me good!
Me: What am I good at?
Willow: You give me treats and I eat the treats.

So I’m just a food dispenser now I guess…