Reflections from a first time Operator

  • Avoid speaking negatively about others (even when it’s deserved)

    When you speak down about a person to a third party (i.e., someone who doesn’t know them), it will often reflect negatively on yourself. The weaker the relationship between you and the third party, the truer this is. If the person you’re speaking with hasn’t formed their own opinion, they are unlikely to believe you with certainty. And if they hear you speaking poorly about someone they haven’t informed an opinion on, they might wonder, will this person speak poorly about me to others?

    Here are some common examples.

    1. Speaking poorly about another colleague. Let’s say you work on the sales team, and Dan is an ineffective salesperson. He’s sloppy. He doesn’t close deals. If you’re Dan’s colleague, there might be a temptation to speak negatively about Dan to other team members. Either the person will know Dan and already have formed their own negative opinion of him, at which point hearing it from you will only make you seem like a bully. Or they won’t know Dan, and they’ll wonder why you’re speaking negatively about your colleague, regardless of whether it’s true.

    2. Speaking poorly about a former colleague. Let’s say you start a new job in customer support. During your onboarding, you’re paired with a colleague James who is consistently talking about how terrible a former team member – Taryn – was. Because you never met Taryn, and don’t have your own opinion about her, you’re likely to be skeptical and wonder why it’s a topic of discussion. Even if Taryn was really bad at her job, James is likely to seem gossipy or rude by making it a point of discussion.

    3. Speaking poorly about a former boss or employer in an interview. If you’re interviewing for a new job, it’s likely you’re dissatisfied with your current boss or company. But spending a lot of time in the interview speaking negatively about it isn’t likely to win any favours. That doesn’t mean you need to pretend a bad situation is great. But it does mean to avoid making the topic a focus of the interview.

    P.s., I’m making some domain and hosting changes to the blog. For the next few weeks, you won’t be able to reply directly to this email. If you want to send me a note, you’ll need to send it to daveowencord@gmail.com directly. Thanks for your patience.


  • The Three T’s model for struggling employees

    Every people leader will be faced with the challenge of managing a chronically underperforming employee at some point. A lot of time and energy can be absorbed by underperformers. It can be tough to determine WHY someone is struggling. A myriad of reasons exists. Generally, it’s worth spending the time to try and identify the cause. If we understand the root cause, we can create a plan to address it. But sometimes it’s impossible to determine the why and we’re stuck struggling with what to do.

    Several years ago, I learned about a simple framework to help define a path forward for underperforming employees called the Three T’s, which stands for Train-Transfer-Terminate. The concept being, if someone is persistently underperforming in their role, in most cases you can pursue one of three options:

    1. Train them. Perhaps they are underperforming due to a lack of training and knowledge, which is preventing them from doing their job well, despite their best efforts. Investing time and energy in training is always worth the time; it’s a high return activity. Sometimes an employee won’t realize where their knowledge gap is and you’ll have to suss this out yourself. If you can tell someone is engaged and working hard, but continues to underperform, it may be a sign additional training is required.

    2. Transfer them. A very capable and engaged employee can struggle or fail when placed in the wrong role. Sometimes the problem isn’t the person, it’s the role they are in. If you can tell the person has the right attitude and capabilities, transitioning them into an alternative role can allow them to thrive. That could be a different role and accountabilities on the same team or a new role in an entirely different function within the organization.

    3. Termination. If training won’t solve the problem and you believe the person is in the right role, but they persistently underperform, then you must terminate them. Leaving someone who is failing in a role is unfair to them, unfair to their colleagues, and unfair to the company. Obviously, these are difficult decisions. They are not made easier by inaction.

    Because we are talking about people, situational context is critical and nuance exists. The “three T’s” model isn’t perfect. But it’s a relatively simple and easy to remember mental model to help diagnose the problem.


  • A Life Worth Living

    I like to alternate between reading fiction and non-fiction. Lately, I’ve been on a big biography kick for non-fiction. Mostly, I’ve been reading about successful entrepreneurs. I’ve always enjoyed stories about people’s lives and combined with my interest in learning about what makes certain businesses and operators successful, it’s a fitting combination. I recently finished “The Snowball” by Alice Schroeder, which is a biography of Warren Buffet. I really enjoyed it. She provides a more complete picture of his life than the carefully curated public image.

    In the book, a direct quote is included from Warren’s response to a student group asking about his greatest success and greatest failure. The quote really stuck out to me. I’ve included it here:

    “Basically, when you get to my age, you’ll really measure your success in life by how many of the people you want to have love you actually do love you.

    I know people who have a lot of money, and they get testimonial dinners and they get hospital wings named after them. But the truth is that nobody in the world loves them. If you get to my age in life and nobody thinks well of you, I don’t care how big your bank account is, your life is a disaster.

    That’s the ultimate test of how you have lived your life. The trouble with love is that you can’t buy it. You can buy sex. You can buy testimonial dinners. You can buy pamphlets that say how wonderful you are. But the only way to get love is to be lovable. It’s very irritating if you have a lot of money. You’d like to think you could write a check: I’ll buy a million dollars’ worth of love. But it doesn’t work that way. The more you give love away, the more you get.”

    There’s some irony in reading that quote from someone who spent their life relentlessly accumulating wealth. Regardless, the spirit of the message certainly resonated with me, and in some ways, because of Buffet’s relentless and successful pursuit of wealth, he’s uniquely well positioned to make such a statement. You can never have too many reminders to prioritize those you love and the quality of your personal relationships above all else.


  • Getting feedback when you’re the Boss

    Receiving feedback when you’re the boss can be challenging. If you’re responsible for performance, compensation, and have the authority to fire someone, then you’re in a position of power. And if you’re in a position of power, you’re unlikely to get candid feedback from direct reports by asking them outright. Even if you’re not someone’s direct boss, but are in a leadership position, it can be challenging to get candid feedback by asking. And the bigger the gap in position, the more pronounced this is likely to be (e.g., the CEO can’t simply ask a junior employee for feedback and expect an authentic response).

    You can always pick up on implicit feedback indirectly through your interactions, but that’s less valuable than receiving explicit feedback. Some organizations have formalized processes in place to facilitate upwards feedback (e.g., ‘360 degree’ reviews), which can be valuable tools but are insufficient in totality. Whether you have a formalized 360 review process or not, there are some tactics I’ve found useful in facilitating a feedback conversation as the boss.

    1. Ask the question “what would you do differently in my shoes?”

      This feels safer to respond to than “what could I be doing better?”, even though you might receive a similar response. It can be asked generally and in reference to a specific topic or decision.

    2. If your direct report previously had a boss in a similar position, try “what are 1 to 3 things you admired about your previous boss that I might be able to learn from?”

      I’ve found this to be highly effective, albeit there’s some nuance in that your direct report might admire something you already do well or isn’t as relevant for you.


    3. If your direct report hasn’t had a boss in a similar position, you can try “Is there a previous leader you’ve particularly admired? If someone comes to mind, is there anything I could learn from their leadership qualities?”

      Similar but less useful than #2, as it becomes more general.


    4. Ask your direct report “What advice would you have for me on this topic?”

      This works well in drawing candour but is likely only in reference to a specific topic.


    5. Ask your direct report for 1-3 things you should ‘stop, start, and continue’.

      Phrasing it in a simple and common performance framework can make the question more approachable but I’ve had limited success with this one, likely because of the explicit nature.


    6. Ask them outright. “I’m keen to learn and improve. What are some areas for improvement you can share with me?”

      Due to the power imbalance and dynamic this may not uncover much. Even with folks you have a high degree of psychological safety and trust with. It may work better with more direct personalities.

    If you read this and have any other good suggestions to share, I’d love to hear them.


  • Don’t Settle

    When I moved to Calgary, one of my first tasks was to find a barber. I got a strong referral from Amin and ended up seeing a fellow who did a really good job cutting hair. But he was unbearable in a lot of ways. He’d consistently start ~15-20 minutes later than my appointment. He’d pause mid-haircut to take a phone call or text. He’d talk at me (not with me) for the entire appointment. I’d usually say less than 10 words but be in a ‘conversation’ for nearly 45 minutes. It was painful. And I went to him for almost three years.

    Even though I had intentions to make a change, I was lulled into complacency, because the haircut itself was good and it usually fell to the bottom of the priority list to seek something better. It took COVID as the catalyst for me to find someone new. And after I did, I was mad at myself for waiting so long. Now I get as good a cut and have a way better experience.

    The older you get, the more professional services people you start to accumulate in your life. I’m not that old, and my list is already long. I’ve got a family doctor, dentist, barber, accountant, veterinarian, massage therapist, real estate agent, contractor, carpenter, landscaper, bike service person, house cleaner, dog walker, and dog sitter. And I have probably five stories like the barber one, where finding someone great in the service category and leaving someone who wasn’t has made a huge difference.

    Nearly every time I’ve changed service providers, it’s been a result of some outside force – like my person moving – instead of something I’ve done deliberately. And every time I think, why didn’t I find an alternative sooner. Finding amazing professional service providers can have a meaningful impact on your life. I was reminded of that this week; don’t settle. It’s worth spending the time to seek someone great.


  • Always Connected

    Airplanes were a last bastion of being truly off grid. No service and completely inaccessible.  Sadly, that’s changing quickly. It seems the majority of planes are now equipped with WiFi, as well as free in-plane text messaging. The airlines are servicing our need and desire to always be connected.

    This makes me sad. I have always loved being disconnected on an airplane. There’s something calming about knowing you’re completely unreachable for a set period. No temptation to scroll or chat or respond to anyone. It’s an easy place to leave distractions behind and it’s always been one of my favourite places to read or get focused work done. So it’s a shame to see the last mile become connected. I know using connected services is a choice that requires opt-in but the more convenient the service becomes, the more deliberate a choice needs to be to avoid using it.


  • What role does Luck play?

    I had a wonderful professor in University, Denis Shackle, who facilitated a classroom survey on our belief in luck, destiny, and fate. You had to respond to questions like “I am able to influence the outcomes in my life” and “Fate plays a large role in whether I will be successful or not”. The higher your score, the more likely you were to attribute events and outcomes to fate, chance, luck, etc. Dr. Shackle used the survey to convey a message and a warning: Your mindset plays a major role in your ability to influence the outcomes in your life. And a low score is great, but a score of 1 might indicate an unconstrained ego.

    The average class score was ~20 and I scored ~5. I have always been a strong believer in an individual’s ability to significantly influence their life, almost to an extreme degree. I generally subscribe to his philosophy and line of thinking; if you have the mindset that your life will be dictated by luck and out-of-your-control chance, you’re less likely to take ownership for your actions. Conversely, if you believe in your ability to act and influence your life, you’re more likely to feel empowered to do so.

    Luck is defined as: success or failure apparently brought by chance rather than through one’s own actions. Yet, you hear people attribute outcomes to luck all the time. “I was lucky enough to get into the PhD program!”. Never mind the years of schooling, intense study efforts, and preparation required. “I’m so lucky I have a good boss. She finally gave me the promotion I’ve been hoping for!”. Forget the many projects you delivered with exceptionally high-quality, the times you went above and beyond for your clients, and the tremendous impact you had on the company.

    So does that mean the outcomes in people’s lives can entirely be explained by their actions alone? Not quite. There are tragic examples of bad luck, such as being diagnosed with a certain illness or cancer. And importantly, there is one hugely influential aspect of your life that I believe fits squarely in the definition of luck: your genetic makeup and the family you’re born into. You don’t get to pick your parents and your upbringing is entirely out of your control. And, you still have the power to influence your life regardless of how lucky (or not) you are on the family front.


  • Showing up for your team

    At some point in your professional career, your team will go through a challenging period. It’s natural for there to be ups and downs at work, as there are in life. Through some of my own mistakes and trial and error I’ve come to believe there are certain principles that resonate with teams when addressing challenges, regardless of the cause.

    1. Address the issue head on. Never shy away from a problem. If you see it, your team sees it. If you proactively address it, it will be better received than if your team has to raise it with you. Never put on an overly positive air or insinuate the situation is better than it is. Pretending it’s all good, if you don’t feel that way, is sure to be poorly received. People pick up on inauthenticity and it reduces trust in you and raises questions about your judgement.
    2. Be as transparent as possible. The more information you can share about the situation the better. Calibrate what you share based on the maturity of the team, and in some cases, limit information to respect people’s privacy. For example, if I’m speaking about financial performance with a more junior team, I will likely use higher level references and go into less detail than I might with a senior executive team. But generally, the more you can share the better. It contributes to the team’s professional development and breeds trust.
    3. Share how you’re feeling and discuss the plan. It’s ok to be vulnerable, even if you’re feeling stressed or anxious. Vulnerability based trust is powerful. And if you’re feeling that way, the team has probably already picked up on it. But make sure to pair those feelings with a clear sense of direction and ideally an action plan. Hearing your leader say “I’m really, really stressed about the timeline for our new plant opening and I’m worried we might be delayed” is scary if that’s the end of the message. Hearing, “I’m really, really stressed about the timeline for our new plant opening and I’m worried we might be delayed. I’ve put in an order with two alternative suppliers for the key part we need and have reached out to our facilities in Mexico as an alternative backup. I should have more information next week on where we are” is better.

    Every leader will be put in the position of managing through a challenging time with their team. How you do so and communicate will leave a lasting impression. More so than how you navigate the good times.


  • Come Home Early

    For many years and trips, Julia and I maximized every minute of vacation. If we traveled by plane, we’d seek the last returning flight Sunday evening. We’d return from a trip, exhausted. Maybe unpack, maybe not. Go to bed and get right back to work the next morning. It always made for a rough re-introduction to the rhythm of work life. But we always got the most out of the trip – one more morning in the sun, one last good meal, or one more opportunity to explore our destination.

    Then a few years ago, I started to convince Julia to take an earlier Sunday return flight. Come home in the afternoon. Or at least the early evening. We’d have a bit of time to at least unpack, have dinner at home, and plan for the week ahead. Still a rushed turnaround but a softer transition.

    More recently, we started to take it one step further: return from vacation on the Saturday. Sacrifice one day of vacation travel for the benefit of an entire day at home to re-orient before returning to work. You get a full day at home and two good sleeps in your own bed. You have a whole day to fully unpack, do laundry, grocery shop, and complete whatever chores you have. You can review email, Teams/Slack, or whatever other work you need to, at a calm and leisurely pace. It makes the Monday morning return an easy one. We did this recently on return from vacation in Hawaii and while I feel less ‘fun’ admitting it, I love doing this. Coming home early is worth the sacrifice. I woke up Monday morning fired up and ready to be back.


  • One Year Anniversary

    This post marks the one year anniversary of publishing Dave’s Take. I am thankful to have started. While I have some gripes with the weekly cadence, described below, the experience has exceeded expectations.

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  • Growing up

    When you’re a child, adults seem to have this air of authority about them. In addition to their large stature, they have many years of lived experience. They establish formative rules – bedtime at 9 pm, no dessert until you’ve eaten your broccoli. You ascribe a certain degree of credibility to them because they are adults. And you generally assume they have their life put together because they are old.

    Then at some point, as you mature and become an adult yourself, the shroud of authority starts to lift. You realize there are a whole bunch of completely clueless adults out there who are just doing their best to get by. This is one of the more fascinating transitions in life. You discover that age is in fact not correlated with maturity after a certain point, and you stop ascribing this higher sense of moral authority to old(er) people.  

    A close friend of mine, James, recently shared with me, “adults are just doing their best with the tools they have available to them. And sometimes those tools are inadequate for life’s work”. I really liked that. It’s a nice way of accepting that even gramps can be a reprobate.


  • No one likes a shit sandwich

    One of my first jobs was a Snowboard instructor. When I was 16, I spent my winter weekends teaching at Blue Mountain through a ski and snowboard club called Ravens, which transported kids to Collingwood from Toronto. During my first year, I taught beginners – mostly kids aged 8 to 12 who had never been on a snowboard before. Anyone who has learned to Snowboard knows the first few days really suck. You spend a lot of time on your bum, hands, and knees. It’s a lot of getting up and falling down while you get comfortable balancing on your edges.

    Instructing beginners involves demonstrating the basic elements of how to turn and providing a lot of feedback. You’re constantly pointing out what to do differently and trying various tips to see what lands with the learners. “Bend your knees!” “Keep your back straight!”

    Becoming a level 1 instructor is fairly easy. I had to demonstrate a basic-to-intermediate riding competency, and then learned varying techniques, tips, and training tricks as part of an instructor’s course. During the course, I received my first introduction to the shit sandwich feedback method. The shit sandwich feedback method goes like this: start by giving a compliment or saying something encouraging (top bun), then give some critical feedback (shit meat), before ending with some nice words (bottom bun). “Hey Sarah, you’re doing great out there! Next time, make sure your knees are wider than your ankles over the board. You’ve got this!”.

    Fast forward a few years. My first job after University was an Investment Banking Analyst and in my second year I was tasked with leading the summer intern training program. Before the interns arrived, I participated in a brief instructor’s session where I was surprised to be re-introduced to… you guessed it… the shit sandwich feedback method! Exact same concept, very different application.  “Hey Max, love that you’re digging through the company’s annual report! Next time, don’t forget to check if they have any Restricted Stock Units outstanding when you’re calculating the fully diluted share count. Great initiative though – you’ll get it next time!”

    If you’ve ever had a manager use the shit sandwich feedback method on you, you’ll know it gets old, fast. The pattern becomes obvious and as a result, you ignore the inauthentic initial compliment (top bun), the real feedback becomes diluted (shit meat), and the positive finisher doesn’t feel genuine (bottom bun). If you’re a manager, cut the buns and deliver the shit straight up. People generally want to improve and if you’re going to give someone valuable feedback, go bun free. There are plenty of other opportunities to share praise, encouraging comments, and positive feedback. At a minimum, remove one of the buns. Your team members will thank you for it.


  • An Ambitious(?) Candidate

    A friend recently described a hiring situation where he was evaluating an extremely ambitious candidate. Let’s call the candidate Mark. Mark exuded high energy, had a positive attitude, and was curious to learn about his potential career trajectory at the company. Mark met with several senior leaders and the reviews were mixed. Who doesn’t love an ambitious candidate? But was Mark TOO ambitious? He seemed obsessed with what it would take to secure a promotion, and he hadn’t even received the job! Is self-improvement and professional growth his motivation or is it only receiving the next title? Will he be an eager, high-performer or will he be focused on the wrong goals for the wrong reasons?

    My perspective is nuanced. I strongly believe ambition is a positive employee trait and often correlates with strong work ethic, a desire to learn, and a commitment to producing quality work. But when that ambition causes an obsession with securing a promotion, raise, or some type of transactional reward, it often results in an employee who is high-maintenance and misaligned with the team’s objectives. Employees who are ambitious for all the right reasons will also want and need transactional rewards like promotions and raises over time too and that’s healthy; it just won’t be the sole motivation.

    So how do you determine if an employee or candidate’s ambition level is beneficial or not? It’s difficult. Generally, what has worked well for me is understanding the motivation. If Mark believes a promotion is a key proxy and milestone in his own growth and development, that’s positive. If Mark is seeking a promotion for external validation, that’s cause for concern or at least further discovery.

    One of my favourite interview questions is “what does personal success look like to you, one year from today? Describe to me some of the ‘truths’ you need, to feel you’ve had a successful first year.” Once they respond, I ask a follow-up “respond to the same question but now the time period is three years”. Responses are usually telling as it relates to motivations. I’m concerned when the candidate says, “success is being a Manager in one year and a Director in three”. I’m more positively inclined when a candidate says, “success is learning and mastering my role, building strong relationships with my peers and colleagues, and delivering quality work to clients”.


  • Situational Leadership and task competency

    I recently completed a course called Situational Leadership Essentials. Situational leadership refers to a framework by which a leader can assess someone’s competency at performing a specific task and attempt to tailor their leadership approach to match that individual’s task competency. Let’s say someone on your team is extremely competent at a given task, has completed it many times before, and has exhibited a high degree of mastery, then the leadership style you take is going to be a lot more hands-off. You should be encouraging, observing, and supporting, but not getting too deep in the weeds.

    There is one critical nuance, which I keep reflecting upon. And while it seems fairly obvious in hindsight, it really struck me during the course. That is, you need to flex your leadership style based on the specific task, not the specific individual. You can work with someone who is extremely competent, has deep expertise in their role, is an all-around high performer… AND, if that person is performing a task for the very first time, you still need to adopt a much more directive leadership style.

    On self reflection, I believe I’ve often defaulted to taking a more hands-off approach with individuals who are high-performing and have deep expertise in their role, providing a lot of autonomy, without necessarily differentiating my style based on the specific task or objective they might be working on. While this approach has generally worked well, there are certainly opportunities where a more hands-on approach for a new task likely would have resulted in a better experience for the individual, and ultimately a more efficient path to the desired outcome.  


  • Paper & Pen

    Since I started working, I’ve always taken notes in a hardcopy notebook. Real paper! It’s generally inefficient. My writing is hard to read. Once a notebook is full, I throw it in the recycling and so the content is gone forever. I’m usually jotting down short form notes or simple reminders, so interpreting what I wrote even a few months ago can be challenging or impossible. A notebook is one more thing to carry when I travel.

    And despite all of this, I love it. I have tried digital notetaking at various times, most recently on the Microsoft Surface, and I find the experience is a poor substitute. The pleasure of physically writing is real.

    While most of my note taking revolves around to-do lists, the single most powerful thing about physically writing is distilling my thoughts. Often, that feeling of “I have a million things I need to get done” will translate into only a few important to-do’s once it’s down in writing, making it much more approachable. If I’m trying to think my way through a complicated topic, writing all the thoughts going through my mind down on paper will have a hugely calming and clarifying effect.

    A few years ago, I started keeping a notebook on my nightstand. If there are times I can’t sleep and it feels like there’s too much on my mind while in bed, jotting down a few quick notes is an easy way to download those thoughts and leave them on the page. It’s been a great aid and tool for me.


  • Self awareness is only half the battle

    Recently, I completed a refresher course on DiSC. DiSC is a popular behavioral self-assessment tool used to understand and measure individual behavioral types. I was first exposed to DiSC through a University course on organizational behavior and found it to be eye opening at the time. After completing a short survey, the software was able to generate a report with many reasonably accurate descriptors of my personality and tendencies. While the insights are far from perfect, it was and is a fascinating way to enhance one’s self awareness. Interestingly, the report I recently received is nearly identical to the first one I received almost 15 years ago; a testament to the idea that your personality and innate tendencies do not materially change over time.

    I believe a major component of professional development centers around a heightened degree of self awareness. Emotional Intelligence is defined as the ability to manage both your own emotions and understand the emotions of people around you… and unlike your personality, is an influenceable skill that can be learned, practiced, and improved upon over time. By better knowing yourself and how you react to various social situations, you’re better able to consciously manage your actions and emotions.

    There are all kinds of tools and courses designed to help enhance your self awareness, including popular ones like the aforementioned DiSC, as well as others such as Predictive Analytics or Myers-Briggs. While each tool has its own pros and cons, the fundamental theme is consistent: by better understanding yourself and your leadership style or innate personality traits, you are more likely to be an effective professional.

    Too often, I have seen folks undertake the self-learning process without translating it into behavior change. Better knowing yourself and how you work is great but if you don’t actually modify any behavior with your new-found knowledge, you won’t reap the rewards. And translating self awareness into action is the more challenging part of the professional development journey because it requires actual behavior changes in addition to knowledge alone. Like any learned skill, behavior change take practice and repetition to master.

    While it’s worth celebrating the act of undergoing these forms of training, it’s more important to focus on the actionable changes that heightened self-awareness unlocks.


  • Type 2 Professional Fun

    Two weekends ago, Julia and I went to Skoki Lodge. Skoki Lodge is a backcountry cabin just over 11 km North of Lake Louise, situated in the Skoki Valley. It’s a log cabin originally built by a group of Banff Residents in the 1930’s to cater to ski-tourists. Today, it’s relatively untouched from the original structure and for only ~$700(!) a night you get a truly rustic experience, including no running water or electricity. Fortunately, your stay includes high quality meals and you have amazing access to various trails around several nearby mountains.

    Part of the Skoki adventure is getting to the cabin. You ‘pick your own adventure’ and can hike, XC ski, or alpine ski tour/split board in. Having never been before, not knowing any 1st degree connections who had been, not finding great information online, and receiving poor instructions from the 60-year old ski bum who checked us in at the base of the village, we were woefully unprepared. We brought classic XC skis and no skins (i.e., grips for the bottom of your skis that allow you to climb uphill without constantly slipping backwards), not realizing that much of the journey is a steady uphill climb. From the trailhead, you climb ~500m and must get over Deception pass (~2,500m elevation), which feels like scaling a mountain. Everything you need you carry in on your back so we each had a ~25lb pack on.

    The combination of the wrong equipment, severely underestimating how hard the journey would be, and -25°C weather, all combined to make it one of the more challenging physical activities I’ve ever completed. It took us 5.5 hours. I burned nearly 3,000 calories. When we were maybe ~2/3 of the way in, looking uphill at Deception pass and realizing due to the lack of skins we would be walking up the entire way, I was reminded of the concept “Type 2 Fun”, a former colleague, Matt, had explained to me several years earlier. Type 2 fun describes an activity that can be uncomfortable or extremely challenging throughout, but which you find enjoyable in retrospect.

    Now that a few weeks have passed, I can confidently say the trip squarely fits in the Type 2 Fun category. I’m incredibly grateful we did it, even though a lot of it sucked in the moment. This got me thinking about whether the concept of Type 2 Fun can be applied in a professional context. And I was reminded of my experience at Onex working on the SIG investment.

    SIG Combibloc is a multi-billion dollar aseptic packaging company headquartered in Switzerland. With a small team, I worked on evaluating the investment for nearly a year, of which six months was particularly grueling. For the six months leading up to the acquisition, I literally did nothing but work. I worked 7 days a week, usually for as long as I physically could. With very rare exceptions, I’d arrive at work Monday to Friday at 9 am and leave the office between 2 and 3 am. On Saturday and Sunday, I’d arrive at ~10:30 am and leave at ~3 to 4 am. I spent 5 weeks straight living out of a hotel in London. I travelled to various manufacturing facilities in Germany, Switzerland, and made a 24-hour trip to China. I gained 15 pounds and the week after we signed the deal, I became severely ill. The experience had a lot of suck in the day-to-day… but in retrospect, it was one of the most rewarding professional experiences I’ve ever had. I’m incredibly grateful for it and remember it fondly, and a decade later am still proud of the work we did.

    I’ve also had many experiences of working under similarly hard conditions, which I have absolutely hated, look back with zero feelings of gratitude or joy, and know with certainty that many of those unhappy and long, hard work periods were key drivers to making a career change. So what made the SIG experience different? What are the characteristics that can make an experience, which might be really challenging or difficult in the moment, later fit in the Type 2 Professional Fun bucket? For me, it was a sense of deep accomplishment after the fact (i.e., you worked hard, but you knew the hard work was meaningful and had purpose); enjoying the company of those you’re on the journey with; and having a sense of self-improvement or betterment because of the associated learning from the experience. I believe if those characteristics are present when working through a really challenging period, you’re likely to look back upon it fondly even if it wasn’t enjoyable at the time.

    Importantly, the ability to recognize in the moment the potential future benefits of your current suffering, can make it much more tolerable. That was certainly the case for how I felt ~2/3 of our way into the journey to Skoki.


  • Positive vs. Negative motivation

    People can be driven and motivated by a wide variety of reasons, some of which tend to be positive, and some of which tend to be negative. Both can be extremely powerful forces.

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  • Is it for you? Or them?

    Running is one of my favourite forms of exercise. It’s a great physical and mental outlet. We live near the Bow River in Calgary and I’m fortunate to have excellent access to amazing running routes. I can practically run indefinitely East or West along the Bow. When I’m in Toronto, I typically stay with my parents and also have great access to running routes in the Cedarvale ravine and along the Kay Gardner Beltline. Both these routes are typically quite busy with other runners, people walking, and some cyclists.

    There’s a generally followed, unspoken rule of running etiquette, which is that when you pass by another runner, you give them a short nod and/or a smile and a small wave.* It’s a nicety, for sure. I am definitely a regular ‘waver’ along the trail. So, what do you do when you give someone a polite small and wave… and they completely ignore you. Direct eye contact was made for sure. But they just keep on going. As insane as this sounds, this used to piss me off. My self talk would be something along the lines of… “what is fucking wrong with this person? They can’t wave back?”.

    One day, after getting no response to a smile and wave, I was reminded of an important principle: you can’t control someone else’s actions. You can only control your own. Am I waving at someone because I need a wave back? Or because it feels like a nice thing to do when I’m out for a run? Is the wave for me? Or is it for them? Once I remembered the wave is for me, I stopped caring about whether I got a return wave or not.

    This is a micro-example of an important theme. A lot of time and mental energy can be exhausted worrying about someone else’s response or actions, which you can’t control. Sometimes it helps to ask yourself: are you doing it for you? Or are you doing it for them? So long as you feel good about your own actions, you can feel less emotionally invested in the response (or lack thereof).

    Here are a few other common, perhaps more relatable, examples: You send out a well thought out note on a topic you care about. No one responds. You make a post online. No on ‘likes’ it. You give someone advice or feedback. They ignore it. You request a meeting with someone. They decline. In each case, you can choose to be upset with the response (or lack of), or you can be satisfied with your own actions.

    *Amusingly, in Calgary, this occurs probably 75% of the time based on my non-scientific anecdotal observations. In Toronto, that number is probably closer to 50% or maybe a bit below.


  • Sending Signals

    A blessing and curse of holding a leadership position is the ability to both intentionally (blessing) and unintentionally (curse) send a strong signal or message via small actions. The more senior your role or perceived responsibility, the more significant this impact is likely to be, and it’s particularly pronounced for members of the senior leadership or executive leadership team.  

    As a leader, your words carry substantial weight. Once you’re aware of this, you can absolutely use it as a tool. It can help you enforce messaging and desired behaviors. Small actions like what topics you ask questions about and what agenda items you consistently discuss can help re-enforce your messaging on priorities. Your actions can be used to signal organizational priorities.

    To use an example (intentional). Let’s say a critical priority for your organization this year is Sales and you really want to enforce that. Simple acts like making it a perpetual agenda topic at team meetings, referencing it at big company events, talking about it in 1-2-1s with your team, with your colleagues, and with anyone you interact with in the organization, will re-enforce its importance.

    To use an example (unintentional). You meet with a client and they ask you when a particularly bespoke product feature is going to be available in the software. For the next six months, you routinely check in with your product team on the status of this feature. Without really meaning to, you elevate its importance and find it’s been pulled forward in the priority list, even though you probably wouldn’t have made that choice if it was laid out in front of you.

    Once you’re aware of signal sending, you’ll realize that sometimes you need to take action even when you don’t really feel like it or want to. Maybe you’ve told the team that this year, it’s critical to be present at the major conferences in your industry. But you also had a newborn 6 months ago, and you haven’t taken much vacation lately, and these conferences are spread all across the country. Regardless, you show up and attend because your actions speak louder than words. Your actions send the signal and re-enforce the message: these conferences are important.

    Sometimes you can use hyperbolic or exaggerated versions of actions to really send a strong signal. There is a famous story of a customer returning tires to Home Depot’s customer service desk… at a time when Home Depot didn’t even sell tires. The Chief Merchandising Officer at the time accepted the tires and gave the customer a refund in full. Then he chained those tires above the customer service desk to exaggerate the point “the customer is always right here”. The cost to Home Depot was small, but the value in sending that type of a signal, which became cultural lore, was extremely high.

    *I heard the Home Depot story several years ago and it may not be literally accurate but the spirit of it is intact.