Reflections from a first time Operator

  • Halfway reflections

    This post marks the 26th week of publishing Dave’s Take. As I originally wrote, the initial motivations for publishing a weekly bog were: a) because I miss writing, b) to codify my professional learnings, c) so I could produce my own work artifacts, d) to state opinions publicly, and e) to take on a project that was definitively outside my comfort zone.


  • Things that shouldn’t work and do

    There are a number of things I’ve seen work quite well at work, despite the fact that they really shouldn’t. For some reason, this really amuses me. The list below is not exhaustive but provides a few common examples.


  • Having fun at work is a good thing

    It’s important to have fun at work. Not every hour, day, or necessarily every week, even. But overall, you should be able to find opportunities to interject some fun into your work. Successfully completing challenging professional goals is difficult so being able to find humour and cultivating a culture where levity is normalized is incredibly important. Having some fun is an important aid and complement to hard work.

    Additionally, a huge amount of your time is spent working. If you’re able to find elements of fun in it, it makes your entire work experience that much more positive. While that’s not a revolutionary concept, it’s something you rarely hear spoken about as an explicit objective, despite the fact that it can be a really important feature of a healthy work culture.

    There is a key distinction between the concept of having fun with your colleagues and becoming personal friends with them. Being ‘friends’ with your colleagues is certainly not a pre-requisite to having fun and enjoying working with them. I have worked with many colleagues that I wouldn’t want to spend meaningful time with outside of work, and yet have really enjoyed the experience of working closely together with over many years. I see people rightfully be wary of how close of a relationship they develop with a boss or direct report (and occasionally peer); however, you can remain colleagues and still have a lot of fun working together and from my perspective, that’s not only ok, it’s also a wonderful thing.

  • Go above and beyond when it matters most

    Sadly, at some point in your career, you are going to have a peer, boss, or direct report face some type of tough personal challenge. What that is will vary greatly, but you will know it when it happens… it could be the passing of a family member, a natural disaster that displaces them, or a really bad illness.

    When this (unfortunately) happens, it’s important to Go Big. Go above and beyond. Demonstrate compassion when it really matters. Beyond the altruistic reasons, these are the milestone moments that people remember long into the future. When you’re down and out, those that step up and support you make a meaningful impression. And this is a case where actions speak much louder than words: approve their time off, cover them while they are gone, intercept that pesky client or sales prospect so they don’t have to think about it. It will mean something.

    My business partner, Amin, is exceptional at this and I have learned a lot observing how he handles these types of situations. To use a very minor/micro version of a personal example. In early 2021, Julia and I got COVID. This was still in the earlier period (pre-vaccine) when it was scary, and there was still a stigma around it; most people in Canada didn’t have a 1st-degree connection that had been infected. In the first 24 hours, Amin and his wife Maleka asked if they could help in anyway: we of course said no, not to bother, we would be fine. The next day, unannounced, they showed up in the backyard with a huge bag of goodies (some of our favourite foods, medicine, etc.). This really stuck with me: taking action to help goes much further than simply offering it. Demonstrating compassion through action without burdening the recipient with the need to ask is going big.

  • A reminder can be as powerful as a lesson

    When first starting at Avanti, I was really eager to brush up on my leadership skills and did a ton of reading and listening to help accelerate the learning curve. There’s a wealth of knowledge available via books and podcasts. I sought out and found many gracious folks willing to provide informal mentorship. I also joined a professional peer-group and signed up for 1-on-1 CEO coaching. Overall, I found a lot of value across a broad array of resources in approaching many situations for the first time.


  • Time: our most precious resource (3 of 3)

    The concept of being deliberate and intentional with how we spend our time is equally as important within the framework of our professional lives. To work on something meaningful requires big chunks of uninterrupted time. It’s nearly impossible to create something that is high quality when you’re only able to dedicate brief periods of time to work on it.


  • Time: our most precious resource (2 of 3)

    While there are exceptions, I believe people are fairly good at doing more of the things they really love and doing less of the things they really hate. Are you obsessed with trying new restaurants? My guess is you’re going to find yourself eating out a lot. Do you absolutely hate your boss, your company, and your role? That kind of recurring negative experience is probably a pretty good motivator to make a change.

    Unfortunately, much of our experience falls somewhere in between really good and really bad. There is lots of ‘ok’, which is one more reason it’s so important to be intentional and deliberate about how we use our time. Returning to the job example: let’s say you don’t hate your job, but it’s not a great experience; it’s ok. There are some pluses and minuses. It can be easy to remain in an ok place for years despite there being a significant opportunity cost. Time spent doing something ‘ok’ could be time spent seeking and finding something good (or great).

    Obviously, our rampant use of social media is well-discussed and documented. It’s another example, which for most people probably fits in the ‘ok’ bucket. If you planned out your day, would you consciously set aside [1] hour to be on [Instagram/Reddit/Twitter/Facebook/etc…] each day? Probably not. But it’s not that hard to unintentionally do.

    Another way time can quickly be absorbed unwillingly is due to social pressure and obligation. Have you ever gone to an event, met someone for a coffee, or taken a phone call, when you really didn’t want to but felt obligated? I certainly have (and still do, occasionally). If you highly value your time, it’s important to build the muscle of respectfully saying ‘no’. Saying ‘no’ can be incredibly liberating and is a key skill set in taking control of how your time is spent.

  • Time: our most precious resource (1 of 3)

    In 2014, my best friend, Barry, died in a tragic motor accident while traveling in Vietnam. This week would have been his 34th birthday. It is sad and cliché, but authentic to say, that this is the first genuine appreciation I felt for the phrase “life is short”. Ever since, I have spent a lot of time… thinking about time.


  • Unmet, unspoken expectations are not broken promises

    Unmet, unspoken expectations can breed resentment. It happens all the time. Let’s say you’re having a conversation with your direct report, Robyn, about a new billing process that was recently implemented, and you both wholeheartedly agree it’s not working. It’s causing your clients a lot of frustration. Robyn says she has a few ideas on ways to improve the process and she’ll make sure to sort it out. Two weeks go by, and you keep hearing new stories from other folks in the organization about upset clients complaining about the billing changes. Then, you start getting annoyed with Robyn. She said she had ideas, and she was going to take care of it! Of course, you never actually explicitly discussed when she would take care of it. In the meantime, Robyn has four other projects on the go, which she believes are much higher priority, and accordingly, she has planned to tackle the billing process issues at the end of the month. So Robyn has no concept of your slowly building resentment because neither of you actually spoke clearly about what the expectation was.

    Setting clear expectations is an undervalued and incredibly important skill set. So often, we create our own version of expectations, without explicitly clarifying them. We leave a conversation with someone, each having a very different set of expectations for priority, importance, and timeline.

    There’s so much written about the value of providing your team members with autonomy and avoiding ‘micromanagement’. If you’re onboarding a new employee and speaking to them about how they like to be managed, there’s a good chance you’ll hear that they do NOT want to be micromanaged. Which makes sense of course. However, there is a huge difference between setting clear expectations and micromanaging someone.  

    I know my own aversion to micromanaging my team has on occasion led to the unintentional consequence of being too vague on expectation setting, which is ultimately problematic for everyone. Being extremely clear and mutually agreeing upon deadlines (including specific dates and times), and quality and scope of work expectations, can save everyone a headache and avoid the resentment that is bred from unmet and unspoken expectations.

  • Mood follows action

    I’m an emotional person. I can be prone to over-analyzing situations, and people’s intent and actions. There are lots of benefits to this – it’s easy for me to empathize and read social situations and I’m fairly good at predicting people’s behavior – there are also clearly some costs, such as taking things too personally and allowing emotion to interfere with logic.


  • Asking for help demonstrates confidence and self-awareness (2/2)

    A continuation from last week…


  • Asking for help demonstrates confidence and self-awareness (1/2)

    There is a cliché phrase “don’t bring me a problem, bring me a solution”, which taken literally, sends the wrong message: “if you’re struggling, figure it out on your own”.* This concept is often celebrated. As a result, particularly with new leaders or folks who are in a new role, there tends to be a desire to try and always present an air of confidence – “fake it until you make it” – and mask the extent of overwhelm or struggle that might initially be experienced. It’s silly, since every professional has experienced some degree of insecurity or imposter syndrome throughout their career and especially when taking on a new role, challenge, or learning a new skill set.


  • Start with the most important item

    The meeting starts. You have one hour and 8 topics on the agenda. You look at the list and say… “let’s start with what T-shirt colour we want for our new swag order, that should be really quick”. 45 minutes later you decide black is a safe choice and move on to item #2. 10 minutes later you open your outlook to see when everyone has time for a follow-up meeting to cover items #3 through 8, including such topics as “how do we save client X?” and “next year’s fiscal budget”.


  • What will your best people think?

    Within every organization, and team… and sometimes a group of friends or family… there tend to be one or two folks who are prone to drama. These folks would never admit it, but they relish in the ‘water cooler’ talk. Of course, it’s a spectrum and ideally if it’s within an organization, you work towards creating a culture where this behavior is recognized as trivial; however, it always exists to a certain extent. There’s a reason many people love reality TV – it’s entertaining!


  • Invest in the Best

    While working in private equity, I started to notice a phenomenon: within a portfolio of investments, the ones that received the most attention, energy, effort, and mindshare, were always the worst performing companies. The worst performing companies were more likely to miss budget, disappoint customers, and make errors of strategic judgment (or some combination). The management teams at these companies required significantly more direct involvement, and on some occasions, had to be replaced. It was a lot. Sometimes these intensive efforts would continue for years. And unfortunately, all of the extra effort, time, and energy seemed to rarely turn a significantly underperforming investment into a great one. Most of the time, it was about fighting to protect the initial investment.


  • 6 vs. 9

    My experience as a people leader, and from working with and speaking to many people leaders, is we often default to a normal distribution when it comes to performance evaluation: if we’re evaluating people’s performance out of 10, we’ll say most people are a 7.5, maybe there are a few 9’s or 10’s, and while we hope it’s a rare case, there might be a few people at a 6 or below.


  • Experience and expertise are very different.

    It took me a long time – much longer than I would like to admit – to realize there is a significant difference between experience and expertise. In my first few years at Avanti, I regularly made the mistake of wrongly inferring more years of experience would translate to a greater degree of expertise. While there should be a strong correlation between the two, it’s certainly not a given.


  • Judgement: The Antithesis to Curiosity. (2/2)

    We judge people for all sorts of things: their appearances, where they grew up, their educational and professional background, how much money they have or we think they have, if they are single, if they aren’t single, etc. etc. We’re particularly judgemental when we first meet someone. And despite it being a fairly unattractive behavior, it’s seemingly human nature. We all do it.


  • Curiosity: The Introvert’s Safety Blanket. (1/2)

    I’m fairly shy when I first meet people and prefer to get to know someone a bit before opening up. Those who know me well likely don’t realize it, but I generally identify as an introvert. Because of that initial shyness, I’m regularly placed in social situations that can be uncomfortable or sometimes anxiety inducing.


  • How it feels.