Interview with Raymond Lai Co-Founder, CTO of Mitterra Ecommerce Solutions and Author of This is Professional Services

Published on Mar 9, 2018

6 min read

image for Interview with Raymond Lai Co-Founder, CTO of Mitterra Ecommerce Solutions and Author of This is Professional Services

Location: Toronto, Canada
Current role: Co-Founder, CTO of Mitterra Ecommerce Solutions and Author of This is Professional Services blog

What is your background and how did you get into management?

I’ve always been a people person. My academic background is a blend of business and tech tech: mathematics, information sciences, and organizational theory, though I contribute my multi-disciplinary background to a complete lack of focus. I just couldn’t choose so I decided to do them all.

My entry into a coaching/management role was really out of necessity. At the time my team had a revolving door or non-technical managers who were assigned to our technical team. It was hurting the team, as these people really had no idea what we were doing, and by extension, what we should aspire to do. I decided to gradually take over more and more of the team leadership responsibilities over time until someone decided to make it official. It was either continue to bare the terribleness of poor leadership or learn as I go. I chose the latter.

What are the biggest challenges you face?

The biggest challenge I face is really myself. A lot of the time I step back and question if what I’m doing is leadership, and what I should be doing to really benefit and lead the team. That mentality has paralized myself a many times, and I found the most effective way to beat that funk is to reach out to my mentors and peers to just talk things out. Sometimes I get inspired, others I feel validated, but 100% of the time I find myself ready to tackle the next challenge.

What is my approach to hiring?

Fit over skills, definitely ( Every organization has a scorecard of barebones skills, but I find that when push comes to shove, skills can be learned by anyone who has the drive to. I have a couple of litmus tests, but the “after work social” test is something I personally believe in: If I don’t mind spending an hour or two (or more!) after work with a person engaged in lively conversation, then that’s a person I think I’ll have fun working with. If that person can join in on an after-work social with the team, then that’s a person I think the team will enjoy working with. A professionally cultural fit with the team is essential to having a cohesive team that has the drive to do great things (

What is your advice for managers who are just starting out?

Question: Do you want to be a manager or a coach? A manager is fixated on metrics and ensuring the team completes their tasks and processes to reach those metrics. A coach defines a goal, and inspires the team to reach that goal.

And a caveat: I’m in no way an expert, but here’s my advice:

  1. Define your goal – Goals aren’t tasks. Goals aren’t processes. Define a big, hairy, audacious goal (thanks to the book “Built to Last“), make sure the team understands that goal, have the team agree that the goal is the most important thing for them to achieve in the upcoming time period, and drive the team towards it
  2. You are not the smartest person in the room ( – Not by a long shot. You’re probably the dumbest person around and the most expendable that can be removed from execution duties to take on leadership duties. Your team is your biggest asset: use them for idea generation, idea vetting. If they tell you your idea is the worst ever, they’re probably right so it’s important to listen.
  3. Stop doing. Start leading – Your job has transitioned from doing to leading. That means you drop every client, every project, every bug fix. Your job is to listen to your team pains and solve them. Your successes are measured by what your team does, and not what you do.
  4. Be a goddamn good human being – You’re a coach/manager, not royalty. You’re in a position to serve others, and if you view your team as a tool to serve you, you should rethink your promotion. Treat everyone the way you like to be treated, and don’t have a “managerial attitude” where you sit high up and scream orders.

What’s your work day like and how do you manage your time, emails, etc.

The first thing I do every day is to pour through communications from my team, and prioritize the stuff that will help them get through the day easier. My day really starts when everyone is in the office. I greet them, ask how they’re doing, and get a sense of their worries and problems. I take action based on how my team feels as their biggest obstacles, and if a problem needs to be tackled right away, I schedule the right people to begin tackling that problem.

Emails, phone calls, meetings, reports… all that is important but I fit that in between the important stuff: Your team and solving the pains they’re experiencing.

The one thing that I’d like to do (and not enough of), is to take inventory of my daily goals. At the end of the day, I write down what I want to accomplish the next day, and I review the entry from the day before to make sure I actually have reached it. If I’m feeling depressed because I continuously miss my goals, that’s an indication there’s a big problem that needs solving that’s taking up a lot of my time, and it forces me to step back and re-evaluate.

What’s a personal habit that contributes to your success.

Be a good human being. Smile. Be positive in the face of utter negativity. Just generally be a person that others can feed positive energy off of. As a leader, the team is acutely aware of team direction and organizational problems based on your behaviour. Being honest is important, but being positive allows people to realize that no problem is too big to tackle and take down as a team.

Share an internet resource or tool that you can’t live without

The entire SAAS suite of tools from Atlassian. I’m a huge fan of documenting our processes so we know what we’ve done in the past and learn from, but I HATE documents. Documents are so lonely, so impersonal. When you want to share a document, you have to consciously select someone and give it away ONLY TO THAT PERSON… it’s exclusive and doesn’t promote team learning and growth. A wiki-like confluence allows a team to document at their own pace (and their own styles), and it’s shared amongst the team in an open and collaborative way. JIRA is absolutely fantastic too… you can do so much with it. Spend a little time to understand custom workflows, post-functions, and custom fields and you’ll realize that JIRA can handle almost anything process-related.

If you can recommend one book to managers, what would it by and why?

My previous employer got me into Patrick Lencioni’s series of business-related fables. They’re short reads and are super sticky. Each book gives you a new tool in your leadership toolbox that is easily understandable and implementable. My favourite book is called “3 Signs of a Miserable Job”, which recently changed its name to “The Truth About Employee Engagement: A Fable About Addressing the Three Root Causes of Job Misery”. I guess Patrick changed the name to be less negative, but the original name was so sticky and impactful. You can find it on Amazon here.

Where can we go to learn more about you?

I’m a huge professional services nerd. Not a lot of people know what professional services is, and it’s not a well-defined discipline, so I’ve decided to start writing a manual. I write it mostly for myself so I don’t forget the lessons I’ve learned in the discipline, but as some of my friends have pointed out, I cannot be the only person who is in the same boat. I release new articles every Thursday on the topics of professional services, technical leadership, and inter-team dynamics at You can also find me on LinkedIn at Shoot me a message! I promise to respond.

This series asks engineering managers to share their experiences with the intent of helping other engineering managers learn and improve. Have someone you want to see featured or questions you think we should ask? Contact me.

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