Reflections from a first time Operator

  • The Battlefield

    Generals, I’ve established a war room. Quickly, gather your X1 Carbon Lenovo’s, refill your branded waterbottles from the San Pelligrino tap, and meet me in the glass board room overlooking the city. I’ll have my assistant cater kale salads, and together, we’ll defeat the axis of evil aka new procurement agency that is coming after our pricing. And if we don’t make it, well, it will have been an honour to serve with you all.

    War metaphors are often used in business. We have the war room (meeting room). We are in the trenches (mostly excel). We are in a knife fight (for better packaging). We must protect the front lines (of service agents). We are going nuclear (with bright colour branding).

    And I must admit, these analogies are actually pretty helpful and commonly understood, so they are useful in conveying a message. But sometimes I like to remind myself that the repercussions of being wrong in my war room are different than being wrong in a real one. That’s not to say my work or corporate work in general is unimportant, but it is good to recognize the relative significance of it. And not to take it too seriously.

  • What’s more important? Being liked or being respected?

    Over time, leaders tend to make different decisions based on what they care more about: being liked or being respected. It took years and many lived experiences, not all positive, for me to operate more intentionally with respect as the objective. The reality of managing to be respected over being liked is much harder than the concept. At some level, I believe every person – and professional – has a desire to be liked. For some people that desire is naturally very strong and for others it’s more modest. But I believe it’s present in all.

    Here are several examples of situations I’ve lived through or have seen firsthand where the desire to be liked can conflict with being respected.

    1. You have a direct report that is excellent at their job. You get along with them great. They haven’t yet mastered the role, but they believe they have. They want to be promoted and have made that clear. You really want to support them, even though deep down you know they aren’t ready for a promotion. You promote them anyway. Initially, they are thrilled. Unfortunately, they are set up to fail and you ultimately end up having to fire them, or they become uncomfortable enough and dissatisfied from struggling in the position that they quit. This whole scenario erodes the cultural trust in the organization’s promotions because it’s apparent to others they weren’t ready.
    2. Your direct report is fantastic at most things but horrible at public speaking. You’ve built a strong relationship, and they’ve reported to you for years. They are a very sensitive individual. You always give them praise when they do a great job… but you never tell them how bad they are at public speaking. You’re worried it will hurt their feelings. In the short-run, that’s great – no hurt – but over time, their career is limited because they don’t have an opportunity to improve.
    3. You have a new, junior employee on your team. They’ve taken the initiative to put together a plan for one of the team’s key initiatives: reducing your product’s shipping times. They are incredibly enthusiastic, and you’re thrilled they are going above and beyond expectations. When they present the plan… it’s awful. It makes no sense and completely misses the mark. You don’t want to dampen their enthusiasm, so you tell them it’s not bad, just needs a few tweaks. Unfortunately, they have the wrong impression and continue working on it despite you knowing it will never be used.

    Often, making respect the goal leads to harder conversations and choices in the short-term, but benefits the individual, team, and company in the long run.

  • Design for the majority

    Since moving to Calgary, we’ve organized an annual ski trip with my in-laws. We usually head somewhere driving distance from Alberta, so often Inner BC: Fernie, Golden, Revelstoke, and Red Mountain (Rossland) have all been destinations. This year we went back to Fernie, and it was our first time taking a ~weeklong road trip with Henry. With Frankie (the dog), Henry (the baby), and all the ski gear, we pretty close to maxed out our vehicle (Tiguan) for space. Now, for years, my in-laws have been joking that at some point we’ll need to buy a Suburban. And for years, I thought that was a joke. But I think it’s become a bit more serious.

    I hate the suburban. It’s a stupid looking car. It’s humungous. It’s expensive. It looks like a bus. But clearly, it’s very practical if you are hauling a lot of stuff and a lot of humans. The nature of these conversations about getting a suburban is tied to a very specific event: an annual ski road trip. An annual road trip to ski is probably the most space-consuming trip we make as a family all year. At no other time do I need to fill my car with that much stuff. In fact, 95% of the time we use the car, it’s more than sufficient for space. I have been left thinking; do you purchase an oversized vehicle to satisfy 5% of your usage? I think the answer is no. Generally, you should design your life around the majority of use cases and solve for the exceptions as outliers (e.g., perhaps we rent a suburban once a year?).

    One principle I value when it comes to creating a new product or policy is to design for the majority. A habit I picked up from working in an investing role is to attempt and identify uncommon outcomes; identifying uncommon but potentially significant outcomes was a valued skill. That mindset – naturally considering hypothetical scenarios – has sometimes made it hard to balance my desire to design for the majority when designing new HR policies (do we create the overhead to satisfy a rare but possible need?) or providing feedback on software development (do we solve for that uncommon, but very painful use case a client has?).

    I’m still working through my opinion on this, but where I’m circling is to start by designing for the majority, yet consider the potential frequency of uncommon events and the severity of their outcomes to determine when an exception is needed.

  • Take the time

    I was recently speaking with a friend who is negotiating a job offer. The discussions are going well and it’s highly likely they will reach an agreement. One of the discussion points is start date. The company is eager for him to start as soon as reasonably possible, though they have indicated a willingness to be flexible. Because they made a point of expressing their desire to have him start immediately, he’s not planning on taking any time off between jobs. So his plan is to take only a weekend off between finishing at his current company and starting his new job.

    I did the exact same thing when I started at Avanti. I finished working at Onex on a Friday and began working at Avanti on a Monday. With the benefit of hindsight, I consider it a mistake worth learning from. There wasn’t even pressure on start date, but I had this self-imposed sense of obligation to begin immediately. My discussion with Amin about joining Avanti spanned several months so when it finally came time to start, I felt behind and was eager to begin immediately.

    Nearly seven years later, I’ve come to look at a brief break between jobs as special time worth protecting. Unlike a vacation, you truly have zero professional responsibility and can relax and unwind in an unmatched way. Assuming you move jobs infrequently, it’s also a rare opportunity. Even a week off can feel meaningful. I’ve had the experience only once, in 2013, and remember it fondly.

    Over the years, I’ve also negotiated start dates with numerous folks as the employer. I’m confident how well an individual has worked out and their impact on the company has never been determined by whether they started immediately or asked for a week or two of transition time. Especially for senior or executive roles, where ideally you expect to have a multi-year working relationship, I can say with confidence no one will remember the exact start date after a year has passed.

    Always take some time between jobs when you have the opportunity to do so.

  • The end of 2024

    The end of December is one of my favourite times of the year. There’s a collective quieting in the work world, which makes it significantly easier to detach and disconnect. There’s no professional ‘fomo’ or sense that your team, clients, or business are rumbling on without you. It’s a lot harder to disconnect during a normal course vacation when you’re the only one off. I love the drop-off in emails and notifications this time of year.

    I’m a sucker for the festive decorations in storefronts and outside of people’s houses. There are generally lots of social things happening, and people tend to be in a good mood. Lots of good meals to be had. I know not everyone does, but I’ve always had a fond association with Christmas and Hanukkah, which makes the holiday season a treat.

    I also enjoy closing the chapter on the year and the finality of an ending calendar period. January represents the hope and excitement of a new beginning. I always spend ~30 minutes this time of year jotting down reflections on the year past and goals for the coming year. I try not to formalize it too much. Whatever comes to mind, I make note of in bullet form. Over time, it serves as a point-in-time collection of what was top of mind each year. I started doing this in 2019 and it’s a lot of fun to go back and re-read previous years.

    I hope everyone finds some downtime this holiday season and I wish you all an exceptional 2025.

  • Best reads of 2024

    With 2024 coming to an end, I like to do a look back and reflect on the year about to pass before starting to think about the year ahead. I read some great books in 2024. Below I’ve listed some of the highlights, in no particular order.

    • Snowball, by Alice Shroeder.

    I love business biographies. This year I read ones on Michael Dell, Yvon Chouinard (Patagonia’s founder), Jamie Dimon, and Warren Buffett. The Buffett one was my favourite. He has a carefully crafted public image and I thought this book did a good job of providing a more balanced overview of his life. He is a unique individual with a fascinating story.  

    • War and Peace, by Leo Tolstoy.

    Last year I decided I wanted to tackle one famous piece of literature a year and started in 2024 with War and Peace. “Tackle” is the right word since it’s a long and dense read. I ended up enjoying it more than I expected. What I found fascinating, is how consistent the themes in human nature are. I kept thinking, here I am reading a novel written by a Russian author in the 1860’s and the humour, interpersonal conflict, familial and marriage dynamics, are unbelievably relatable. With the breakthroughs in AI and so much discussion on the acceleration of technological change, I took some comfort from being reminded that while technology changes humans remain largely the same.

    • War of Kings, Brandon Sanderson.

    If you’re a fan of nerdy, fantasy novels, the Sanderson series is very good. A definite ‘page-turner’ and super enjoyable. This felt like Lord of the Rings or Game of Thrones level quality.

    • Far from the tree, by Andrew Solomon.

    I read fewer books on parenting than I expected to with Henry being born this year. One book I did read and recommend, was Far From the Tree, which covers the topic of how families accommodate children with physical, mental, and social disabilities and differences. It was pretty eye-opening and empathy building.

  • Sometimes, focus only on the good. Ignore the bad.

    I was at an event earlier this year where an older woman (the boss) opened her speech by expressing gratitude to her Associate (the employee) for all the heavy lifting required to organize the event. It was intended to be a sincere thank you. And it mostly was… except, one of her talking points included a sarcastic joke about an error made on one of the printouts. It was meant to be a light tease but it did not land well at all. It came across as mean spirited and you could absolutely tell the employee was offended.

    It reminded me of an important lesson my dad taught me a long time ago: in some situations, you need to focus exclusively on the good and ignore the bad. When I was around ten years old, I bought my mom a combo pack of scented perfume from Shoppers (good boy). It was some sort of 5-for-one pack, I think private label brand?, and probably intended for tweenage girls. Not my best gift, but I was young, so good intentions. My mom put it under her bathroom sink and it was never opened, which with the benefit of hindsight of course makes complete sense. But I noticed. And next year on her birthday, I was writing out her card and came to my dad to tell him I had come up with a witty comment to include. Something along the lines of “I hope you like this gift much more than the perfume that’s never been opened”. Fortunately, he pointed out that when you’re celebrating someone (e.g., it’s their birthday), you want to focus exclusively on the good. As simple and silly a story as that is, it really stuck with me.

    Adding sarcasm, or a back-handed compliment, or even teasing (if done in poor taste) to a genuine and sincerely intended message will at best water it down. When you’re announcing someone’s promotion, or giving a toast at your friend’s birthday, focus on the good and best parts of that person. Don’t use it as a chance to bring up an issue you might be having with them. It’s not the time or place for that.

  • Can taking pride in your work be a problem?

    I generally believe taking pride in your work is a hugely important characteristic commonly found in high-performing professionals. When you take pride in your work, you care. You are more likely to go above and beyond. You are likely to re-read before hitting send. Taking pride in what you do also correlates positively with effort; you’re going to put more in because it matters to you.

    For these reasons, I like hiring people and working with people who take pride in their work. There are two watch-outs, though. First, when someone takes immense pride in their work, it can occasionally lead them to strive for perfection. Perfection is impossible to achieve. There’s a gap between excellence and perfection, and in almost all scenarios ‘excellent’ is a sufficient bar to strive for. Usually, I start to wonder if someone is falling into the perfection trap if they always deliver extremely high-quality work but consistently struggle to keep up with the pace of deliverables, if they deliver work after a reasonable, mutually agreed-upon deadline has passed, or if they can only hit the deadline by working an unreasonable amount. Second, is when I notice someone struggle to get started on a new project or work deliverable. The desire to deliver a work product close to perfection can lead to inaction by creating this intimidating invisible barrier to start.

    Fortunately, I’d much rather work with someone who struggles with these challenges than someone who doesn’t give a shit. With coaching, it’s possible to educate someone on the declining marginal benefit of taking something close to ‘perfection’, and make them feel really, really good about delivering something that’s (just) excellent. There’s still a lot of pride to be had and finding that sweet spot between quality and effort is an important learned skill.

    Part of building good professional judgement over time is knowing which projects and work products require more or less time and effort and whether the investment is likely to impact the outcome. For far too long, my desire to take pride in my work resulted in me investing too much effort into deliverables where the quality didn’t necessarily impact the outcome much. Spending an hour honing the perfect email proposal to an executive at a client, who you can reasonably predict might skim the email and say “let’s hop on the phone” may not be the best investment. I try to remind myself of the intended outcome of what I’m working on to help calibrate what level of effort should go into it, despite a general desire to produce something I can be proud of.

  • Learning Styles

    I recall being taught the concept of learning styles at some point in school. The idea is everyone has a certain learning style that works best for them. The four main learning styles are visual (images, charts, diagrams), auditory (spoken information, podcasts, discussions), reading/writing (engaging with text-based input, writing notes, working with written instructions), and kinesthetic (hands-on experience, physical activity). They aren’t intended to be mutually exclusive and ideally can be combined for best effect.

    When I first learned of the concept, I don’t recall identifying strongly with any style. But in the past few years, I’ve come to really appreciate how much better I learn and retain new information when there’s a visual component. It seems so simple it’s kind of silly, but it’s a pronounced difference for me. If someone can SHOW me something, or draw it, or share a visual, it helps immensely.

    I started to become more aware of it when I was working 5 days a week in the office. Amin and I spent a lot of time chatting through things in each other’s offices and we both had whiteboards on our walls. Amin is a natural teacher and I came to realize how helpful it was for him to draw things on the whiteboard as we were discussing. Having moved to an almost entirely distributed work environment, I’ve had to adjust accordingly. Now, I find I’ll often ask someone to share their screen so I can actually SEE what they are talking about. And if I have any significant planning work, or need to come up the curve on a technical or complex topic, it’s essential I can draw it out or see it in front of me.

    I did a bit of googling on the concept as part of writing this post and there’s a lot of criticism of the Learning Styles concept. Apparently, it might be pseudo-science and the empirical evidence is lacking. I didn’t dig deep enough to validate one way or another nor do I necessarily care. I’ve learned for myself, finding ways to incorporate visuals into conversations has made a meaningful difference and being aware of it has real value to me.

  • Ode to Dog

    Julia, Henry, and I returned to Calgary at the end of last week after a ten-day stint in Toronto and Halifax. Coming home was satisfying for many reasons, and none more important than to see our three-year old Bernedoodle, Frankie. I grew up with family dogs – a Lab named Maisie and a mini goldendoodle named Molly – and always expected at some point we’d add a dog to our family. But I always saw that as a longer-term plan; ideally, we would have kids and bring a dog into the picture once they were older. Fortunately, Julia persuaded (forced) me to join the COVID trend and choose one earlier than I likely would have otherwise. I’m so grateful she did.

    If I reflect on changes that have positively influenced my life in the past few years, finding Frankie is top of that list. In many ways, dog relationships are simple; they love you unconditionally. Their needs are relatively straightforward: play, exercise, food, treats, affection. You always know where you stand with a dog. Yet, their personalities are incredibly nuanced and varied. They can be loving, funny, sad, playful, anxious. Sometimes they can be assholes. Within an hour of getting home and seeing Frankie on Friday, she ate the sandwich off my desk while I went to get a glass of water. And she was very pleased about it.

    For how fun they are, they are also a serious obligation. We travel often and rarely with her because I refuse to put her in a plane cargo hold. That means consistently finding someone to take care of her. We’ve been incredibly fortunate to have a great group of close friends who willingly take her. People often say it takes a village to raise a child and I think that’s sort of true with a dog as well, at least it has been in our case.

    Frankie is such an important part of my life I can’t imagine living without a dog ever again.

  • A key leadership outcome

    A few years ago, one of our functional leaders departed and I was debating my options with a friend and advisor. I could either seek an external hire or consider a stretch promotion for an internal candidate currently leading one of the smaller teams within the function. The internal candidate was doing an excellent job leading her team and we believed she had a lot of potential. We had planned to provide her with more scope of responsibility over time but not on such an accelerated timeline. I was a bit nervous about putting her in the seat. It would be a big increase in demands and challenges.

    In the discussion, my friend focused on one question: “Can she increase the sense of urgency and accountability on the team?” I’ve come back to that question many times since. While there are many important leadership qualities, that’s a good and simple summation of a key desired outcome from putting a strong leader in place.

    I try to remind myself of that question whenever it comes to promotions, new hires, and role changes. I also like to reflect on whether I’m fostering those outcomes across the organization.

  • Systems & Routine

    My favourite form of exercise is running. In addition to the physical health benefits, there’s a tangible mental benefit. It helps me de-stress, regain focus, and spark creative ideas. I regularly connect dots or draw important insights during a run. Not once have I ever regretted the decision to go for a run. Despite all the benefits, committing the time can still be challenging. Particularly as the days become shorter and winter arrives, the invisible barrier grows. It becomes harder to get up early and go out in the dark and cold, or to sacrifice family or social time after the workday, even though I know how important it is.

    A few years ago, I had the realization that I needed a system in place to ensure I would get out and run even when I didn’t want to. That system was a rolling formal race commitment. if I sign up for a race, it takes away the ongoing mental decision making: to run or not? I know if I sign up, I will practice. The motivation isn’t my finish time or to set a new personal record. The motivation is to consistently get out and run.

    Signing up for a race is my way of instituting a system to support my habit and the behavior I’m trying to pursue. Finding systems that aid the behaviors you want can be powerful. Particularly when you’re tired or out of decision-making capital, having healthy systems in place can drive better behaviors. Lately, I’ve been thinking about what other systems I can put in place professionally to reduce the burden of discipline and accountability. I have certain routines I follow, like starting the quarter with a clear idea of what I want to accomplish. And starting each week with a clear list of objectives. If you have any good ones, please do share.

  • Healthy

    For pretty much my entire life, I’ve been fortunate never to suffer any significant injury or have any severe health challenges. Except for a few bouts of COVID, I have rarely been sick if at all over the past few years. Then at the start of October, I caught some type of lingering virus and cold that lasted a few weeks. And right as I was finally recovering and feeling back to myself again, I caught a rough stomach virus that totally debilitated me for several days.

    Since, I’ve been thinking about a quote I heard (or read?) somewhere:

    “Health is a crown the healthy wear but only the sick can see.”

    It really hit home. I hate being sick. It sucks not feeling able to do the things you want to do. And yet it’s so hard not to take feeling healthy for granted, because feeling healthy consumes zero mental energy. I am finally feeling healthy again and trying to remind myself to be grateful for it.

  • Say – Do ratio

    The single most important piece of professional advice I’ve ever received and now regularly offer is to maintain a high “Say-Do” ratio.

    The “Say – Do” ratio refers to the ratio of how consistently your actions match your words. I first learned about the concept at Onex during a Lunch and Learn session with one of the most respected CEOs in the portfolio of businesses at the time, Kirk Hachigan. He had dramatically improved performance at one of their largest companies in a very short period and was a bit of an internal celebrity. His answer to the question “What is the single biggest differentiator you’ve seen across executives you’ve worked with during your career?” was a high Say-Do ratio.

    Though simple, there is immense power in operating with a high Say-Do. Consistently delivering on your stated commitments earns you tremendous respect and trust from your peers. It a) breeds trust, b) boosts credibility, c) encourages accountability, and d) improves team alignment. Leaders with high Say-Do ratios have the added benefit of being perceived as more competent.

    Most people are familiar with the concept. What’s underappreciated is that the power of Say-Do comes from maintaining as near 100% a ratio as possible. The gap between 75% consistency and 98% is dramatic in terms of the signal it sends to your team or organization. I use 98% because I think perfection is unrealistic.

    This concept can and should be taken almost to an extreme. Obviously, if you have committed to your team or boss a delivery date on a big project it’s important to meet it. But it’s the micro interactions that matter in terms of consistently demonstrating high Say-Do and cultivating a reputation for trust and follow through. Did you mention to your boss you’d send them an interesting article and then never deliver? Of course, as a single occurrence that’s no big deal. It happens all the time. But if you can be the type of person who demonstrates near perfect follow-through, it will have a material positive impact on your career. As a leader, demonstrating consistent follow-through helps breed a culture where that becomes the expectation, which has a positive multiplier effect on organizational accountability.

    For how simple it is, it’s difficult to persistently deliver on. There are constant distractions that get in the way of follow through; it takes a heightened awareness and real discipline to deliver.

    As incredibly important as a high Say-Do ratio is professionally, the spirit of it applies equally to your personal life. The quality of your relationships will benefit from being a person who follows through on your word with your friends and family.

    I’ve sometimes heard alternative versions of the same concept. For example, “always be the team member that doesn’t need progress to be checked in on”. That’s a wordy way of saying keep your Say-Do high.

  • Deciding what to read next

    These days, there are far more high-quality movies, TV shows, podcasts, blogs, and books to consume than time allows, which makes filtering important and more challenging. Particularly with books, I often struggle to decide what to read next. If all the options you’re considering are positively reviewed and come strongly recommended, how do you choose? Of the last five books I’ve read, all had a 4.5+ review on Amazon and each was personally recommended by someone I respect. And I easily could have gone without one of them (maybe two).  

    I was reminded this week of a great tip, which is to listen to a short interview or podcast from the author around the time of release. Fortunately, over the past decade, it’s become common practice for authors of popular books to do a tour as a Podcast guest as part of their book launch. Listening to the author provides a helpful sneak peek into the content, as well as a feel for the author, without requiring a significant time investment. If I enjoy the podcast and finish wanting more, it’s a positive indicator I should read the book. If I feel the podcast was enough, I can confidently pass on the book.

  • Scripted Speaking

    I grew up terrified of public speaking. I can recall my throat tightening before having to make a presentation in class and feeling my heart race. These weren’t big public venues. I’m referring to the typical forums for speaking when you’re young: group presentations, drama class, clubs, etc. To combat my anxiety, I would script out the content and memorize it. That way, at least I didn’t have to worry about what to say.

    I think unintentionally, scripting added to my apprehension. If you forget a scripted line, or word, it throws you off entirely. While giving a presentation at the front of a 70-person class in University I forgot one of my lines halfway through and completely froze. After about 5 seconds, which felt much longer, I had to retreat to my desk to recover my script. Once you’ve lost the line, it’s almost impossible to get it back; particularly while your stress levels are rising, and your classmates are all staring at you.

    When I entered the professional world, the nature of my work regularly thrust me into situations where I was forced to speak in uncomfortably large settings or with people who seemed intimidatingly important. Fortunately, it was only ever in reference to content I had either prepared myself or was familiar enough to feel confident speaking to. While still nerve wracking, it helped me build more public speaking confidence and over time I started to ditch scripting.

    Now, if I’m going to speak in front of an audience or in a large group setting, I prefer to be completely unscripted. I like to have a strong handle on the content. And I still prepare. But that might be as simple as reflecting on the takeaways I want the audience to have or the key points I’m trying to convey. There’s a cost to presenting this way. I’ll often forget one or a few of the points I’d ideally have made. Or I’ll word something a bit awkwardly. Or I’ll need to pause for a few seconds to gather my thoughts. But I’m a firm believer that even if you only deliver 75% of what you intended, it’s better to ditch the script.

    When I hear someone give a speech or presentation that is obviously scripted, I find it challenging to stay focused on the content. There is something less authentic about it. Intonation and body language tend to be more muted. If you’re used to scripting or planning out every word of what you’re going to say, I’d encourage you to start cutting back on having a precise script. And like so many skills that are hard to master, you only improve through repetition. It gets significantly easier over time. I still get quite nervous before speaking in front of a large audience, or when the stakes are high, but only to a fraction of the degree when I was younger.

  • Dining in Toronto

    We recently returned to Calgary after spending nearly 6 weeks in Toronto. Despite having been in Calgary for over 6.5 years now, Toronto still feels like home. I had such an enjoyable time catching up with family, friends, and colleagues. The end of August and start of September is the best time to be in Toronto. The evening weather is still warm, patios are still open, and people are enjoying the last taste of summer. This visit was special in that we introduced Henry to so many of the people we care about. My Cousin Rebecca got married and the wedding was a blast. And importantly, we managed to get to my in-law’s cottage on Kennisis Lake for a week, which is one of my favourite places to spend time.

    I live to eat and one of the best parts of being back in Toronto is trying new restaurants. Last year we went a bit crazy going out practically every night and so this visit we tried to be a bit more selective. We ate at: Casa Paco, Conejo Negro, Immigrante, Nobu, and Union.

    Casa Paco stood out relative to the rest. It was an exceptional meal and a place I’m keen to return to. It’s so rare to have a meal that delivers excellence across atmosphere, food, company, and service. Eating there felt like sitting down in a cozy living room, being served by a caring and dedicated master of craft, enjoying consistently delicious food with unique wine to complement, and it was our first meal leaving Henry at home (with his grandparents). I highly recommend making a visit, particularly on Sundays, when they do Paella.

    After enjoying building out a tracker for places we’ve eaten in Calgary, last summer I decided to do the same in Toronto. If you’re interested in seeing my Toronto list, you can take a peak here. And if you have any good recommendations, please share!

  • Mercenary

    I’ve come across an employee a few times that I deem to be a “mercenary”. This is an individual who produces good work but takes an entirely transactional view of their role. Likely, they are misaligned or uncaring about the organization’s broader vision and exclusively care about achieving goals for their own purposes as opposed to accomplishments for the benefit of their team or the company. Importantly, this person may be entirely likeable and easy to work with; this is not the prototypical ‘brilliant jerk’, which is routinely discussed.

    Reconciling what to do about the Mercenary can be extremely challenging. Not only are they seemingly producing high-quality work and accomplishing goals, but they get along well with others. So, what’s the problem? Inevitably, once they no longer perceive sufficient benefit in the transaction, they will leave, and when they do, they will leave behind a Beverly Hills sized walk-in closet of skeletons. If someone is entirely self-interested, they will take every single shortcut to achieve their goals as quickly as possible, often at the expense of longer-term considerations. Over a brief period, this can be misleadingly positive. Many of these minor short-cuts and trade-offs will be hidden, but unfortunately, they will compound over time. And once they are gone, the effort required to clean up the unintentional negative consequences can be material.

    Here is a practical and well-known example:

    • You have a Sales person or executive who realizes that committing to unrealistic deliverables, or embellishing (but not lying) will help her win more. So she does it regularly and closes many deals. Awesome. Fast forward six months, and those customers are now disappointed in what they purchased and end up leaving for a competitor shortly thereafter. And of course, by the time those unhappy customers start surfacing, she’s on to her next gig. It can be tempting to turn a blind eye to the behavior even when you’re aware of it because of the results, but the long-term negative repercussions will certainly come back to bite you.

    Usually, it’s fairly apparent when you have this type of employee on your team. As hard as it can be to reconcile, it’s important to either engage with and develop alignment with them or cut your losses.  

  • Partnership

    Next week, after six and a half years, I will become the sole CEO at Avanti and Amin will transition into a Chair role. I am incredibly fortunate to have the type of partnership, in the truest sense, where we can complete a role transition of this nature and continue to want to work closely together.

    About 9 months ago, my friend launched his own investment firm. In the investment memo, he had a sentence that stuck out to me: “[investment firm] is the only place [partner] and I intend to work for the rest of our careers”. I imagine there’s something satisfying about knowing with certainty you’ve found the last job you want to have in your career. I’m not sure I can say the same. I love working at Avanti and hope to be here for many years, but having only just turned 35, I can’t say with certainty it will be the last role in my career.

    One thing I am certain of is I want to work closely with Amin in some capacity for the rest of my career. I’m grateful for that. It’s not easy to find someone you share a common set of values with and can enjoy working with after many years, including through many highs and lows.

    In many ways, a business partnership resembles a marriage. Aside from Julia, I have spoken with Amin more than anyone else over the past 6.5 years, including family and close friends. Making it a successful partnership has required intention and effort, like all meaningful partnerships.

    I first met Amin in 2011 when we both moved to San Francisco for work. Our respective roommates were mutually connected from school and we became fast friends. I believe the fact that the initial connection was social and we enjoyed spending time together has been important in making the professional partnership work well. If you’re going to spend countless hours working closely together, you must enjoy one another, and you must have a more complete understanding of the person you’re partnered with than the professional picture alone provides. Throughout our time running Avanti, we’ve continued to spend time together socially, which has had compounding benefits to the partnership. And it doesn’t hurt that Amin ended up marrying someone much cooler than he, that Julia and I both very much enjoy as well!

    There are two distinct factors that stick out in terms of making the partnership a success.

    The first factor was investing significant upfront time in preparing for how we would work together. We began the partnership by discussing a set of realistic scenarios that could lead to future conflicts. Some more mundane (e.g., what if I want to hire someone and you don’t like them?) and others more imaginative (e.g., what if the business does ok; not great but not terrible and one of us wants to sell the business and one of us wants to raise growth capital and keep going?). Working through those scenarios when they were hypotheticals enhanced our ability to navigate them when they became a reality. It also provided an understanding of how we might respectively approach and react to situations during times of conflict, and helped elucidate what matters most. Most of the scenarios never surfaced and I’m glad we discussed them, regardless.

    The second is vulnerability-based mutual trust and humility. We both have egos and take pride in our work. And we’re also willing to accept when we’re wrong and receive feedback with an open mind. That is much easier when a deep mutual trust exists. When you know someone is challenging your thinking with the desire to get to a mutually positive outcome, even the most difficult conversations become possible.

    While our roles are changing, I look forward to continuing to work closely with Amin and value the multi-faceted role he will continue to play as a friend, colleague, therapist, mentor, and advisor.

  • Objective performance measures

    One trend I’ve observed over time is high performing employees are particularly drawn to quantifiable and objective measures of performance. That seems intuitive. You sort of expect those who take pride in their work and want to excel at it to want measurable proof as validation. I initially assumed this to be driven by external forces: those who are great want to be able to show they are great and receive the external recognition and validation that comes with that. While there’s probably some truth to that, the desire for objective performance measures goes far beyond. Below are additional reasons I’ve noticed.

    1. Clarifies expectations and accountability. When targets are clear and measurable, there’s less room for misinterpretation between an employee and boss. Great employees want to know what is required to be excellent.

    2. Validation of improvement. Using a measurable performance metric over time can validate you’re consistently getting better. The same way it’s satisfying to set a new best personal best half-marathon time, it’s satisfying to validate you are consistently improving your output at work. That is for intrinsic reasons.

    3. Relative performance. Using consistent, objective measurement ensures a manager is aware of who is performing on a team and who is not. From my experience, it’s extremely frustrating when you have a colleague, or worse a boss, who is performing really poorly and you aren’t sure if anyone else realizes. Having more objective measures provides some relief that poor performance will be surfaced and hopefully addressed.

    4. Facts over feelings. When performance is being measured objectively, there’s less concern that favouritism or feelings are strongly influencing performance outcomes on a team.

    It’s not always possible to quantify success measures in every role. In those cases, the more objective you can make the qualitative measure (e.g., think “SMART” goals), the better.

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