Hiring a sales VP and expecting them to also serve as an account manager is like hiring a restaurant manager and expecting them to also be the chef, or hiring an F1 team principal and expecting them to race the car. If you're limited in budget, hire the chef and manage the restaurant yourself, or hire the F1 driver and manage the team yourself; asking them to do both is setting them up for failure. How so? When I think of organizational expectations for a tech company, I use the following guidelines, visualized in the graphic: Individual contributors: they focus on completing their tasks using their skills & experience. They might or might not deal with customers and generally don’t get public/media exposure. They tend to work on daily or weekly horizons. Managers: they lead ICs, define tasks, manage conflict, are closest to the field, and know what good IC work looks like; they will often deal with customers, but might not get to communicate with the public/media. Their work’s time horizon is weeks/months. Directors: they lead managers, define high level deliverables, help execute strategy, and know what good teams look like. They tend to interact with senior stakeholders at customers and will often communicate with the media. Their time horizon is months/quarters Vice Presidents: they lead directors, define strategy at their level, and are involved in corporate planning; they know what good execution looks like. They will typically interact with customer VPs or CxOs., and their media presence tends to be authoritative and influences the company’s public perception. Their time outlook is quarters/years In short, a sales VP is not a super salesperson, she has a distinct role: you can’t have her meet a CIO in the morning then respond to an RFP in the evening. The wise investment is to fractionally or contractually build the sales strategy, and prioritize hiring the IC. What are your thoughts? How do you think about and prioritize roles?

Dear startups, stop hiring VPs of Sales in APAC. Regards, VPs of Sales. You’ve secured funding, established your presence in the USand Europe, and now you're eyeing APAC for expansion. Naturally, you hire a VP of Sales, expecting them to be a coach/player, add a few support roles, and wait for success. Six months in, progress is minimal. A year later, with only a few leads, your board questions the APAC investment. Soon, APAC gets cut for being "not worth it." We know, the APAC is appealing on paper with its high population, growth,and stability. But it's different from the US or EU - there are traps! Appealing on the outside, tough on the inside: the largest economies, China, Japan, and India, are hard to penetrate due to local preferences, cultural/language barriers, and fierce competition. Australia is easier but small in scale, and ASEAN markets, with the exception of Singapore, are less developed. You think you've cracked it open, but not really: APAC's wildly varied cultures, development stages, and business practices make it hard to replicate success. Unlike the US or EU, there’s no unified cultural, legal, or language frameworks. Success in one country doesn't mean success in another The initial investments are easy, until you stall: hiring a VP of Sales expecting them to handle both strategy and hands-on sales won’t yield the best ROI. The roles of VP and account manager are mutually exclusive, making the hire poor at both. So what’s a startup to do? Consider one of the following: Bullish Approach: if markets are solid and you can afford it, hire a full team (VP, salespeople, channel person, marketing/BD) in 2-3 countries. Expect minimal revenue in year one and some traction in year two. Cautious Approach: experiment with the market by hiring an account manager for each country, managed remotely by HQ. Strategize for 1-2years with lower investment and risk. Eventually, hire a VP or promote aneffective AM for the role Hybrid Approach: use a fractional leader for strategicinput a few days a week. This gives you the best of both worlds: keeps costs down and resources fit for purpose. What have I missed? Share your thoughts in the comments.

A ladder only has one path. There is only one measure for a ladder: how high you are. To reach a step you have to have had climbed the one before. A ladder goes only in two ways - up, or down. Ladders are boring: once you've figured out how to climb a step, you know how to climb the next one. You can't overtake someone on a ladder, going up or down. Once you're on top of a ladder, to climb another ladder, you first have to climb down. A wall has many paths to climb. You might reach the top or you might not, but wherever you end up, there's always an interesting journey behind you. Climbing walls are like solving puzzles: out of all the possibilities, which one can you take? There are many skills required to climb a wall, climbers will rely on some skills more than others - and that's ok. You can climb the same wall 10 times and still learn something. If you're climbing and you're stuck, you can back down a bit and try a different path. Many people can climb the same wall at the same time, and reach the top. You can move sideways on a wall. Some people stop midway on a wall and just enjoy the view - and that's ok. The way to the top is not a ladder, it's a wall.

As we come to the end of year, it’s not a bad idea to reflect on the year that’s passed and think of what we’re going to do differently in the coming one. I’ve been focused on improving my cycling, and learned that to go faster I have to go slower. If you think about the common maxims of exercise, the phrases “push yourself”, “work harder”, “you can do it!” might come to mind. It makes some intuitive sense: if I want to go faster, I just need to power through whenever I feel tired or slow. But as many of our intuitions about the world prove to be, it’s somewhat incomplete. Pushing hard might get you results, but they’re less durable and could lead to injury and burnout. The more optimal way to get results is to mix Zone 2 and VO2 max training. Z2 training is working out hard enough to be short of breath but able to hold a conversation it generally feels easy, almost boring. VO2 is your body’s ability to use oxygen while exercising, and you train that by high intensity workouts. A good visual representation is a pyramid: Z2 is the base and VO2 max is the height: you’re aiming toward is maximum volume. Things get interesting when you see the recommended mix: 80% Z2 and 20% VO2. The vast majority of your training needs to be “easy”. What struck me further about this is how readily this idea can be transferred to the world of business. A common theme that’s emerging with business leaders is to crack a tough problem, it’s not sufficient to keep tackling it. Self-aware leaders take breaks – they go for walks, they talk to their colleagues, they read a book, they work on other problems, and return to the tough one armed with rejuvenation and potential new insight. These business Z2 activities, that keep you mildly challenged but not burned out, are the rich foundation on which creative and insightful breakthroughs are built. And I think this can be taken even further: as one specializes in one’s career – becoming more senior, focusing on an ever more niche area in the business – one can’t ignore what’s happening outside of that niche business. If your specialized expertise is the height of the pyramid, it’ll topple very quickly if it’s not built on a wide foundation of more general knowledge. Learning about many things that are not at the core of what you do is not a waste of time, but an essential part of self-development. Having wider knowledge allows you to develop context, nuance, correlations, parallels, and lessons that can be applied in your business. In fact I believe building a higher pyramid is not even possible without a wider base. I’ll close with the final element of a good exercise program: rest. Your body needs time to build muscle, replenish its energy stores, clean up waste, and set you up for the next workout. Your mind is the same: it needs its breaks. So I hope you’re all taking some time off to take your mind off of work and spend it with family and friends. Let me know what you think of this, whether you like to mix things up or keep pushing to the limit.

Note: this is a somewhat personal entry that many people found useful. I share it here because who knows who might need to hear one of the points below. October 1st 2023 will mark two months since I’ve been out of work, and part of my process of self-reflection has been many 1:1 meetings. Those meetings have taught me that there is a strong third wave coffee culture in Singapore, and that I can handle 3 cups of coffee before it starts affecting my sleep. I also learned other important lessons, five of which are worth sharing: I’m not alone in my job search. There are many people out there “between jobs”, recently let go, been away for a while, or taking one form or another of sabbatical. Two points starkly stood out: first, even if someone is currently gainfully employed, many have been through a redundancy at some point in their careers. Second, as is true of most social media posting, people on LinkedIn only share good professional news. Many individuals who are not currently employed, even months after the fact, still have their most recent roles on LinkedIn. That realization was comforting, taking away the stress and “why me” mentality that first came with losing a job. It’s not about me. Companies are profit generating machines and as such cannot always care about their employees. Individuals care, managers care, HR cares, but their emergent phenomenon known as a company has no empathy or humanity; many decisions are taken based on the bottom line. When the decision is taken to reduce headcount it’s rarely about performance and impact, it’s mostly about satisfying some arbitrary targets set by shareholders. Going it alone is not necessarily better for me. I had always imagined that business owners have it better off – no unexplainable decisions to follow, no shareholders to drive quarterly results, and you can work your own hours. The reality, however, for most small business owners, at least until they hit scale, is a life of constant hustle. One of my friends described his contractor role as “feast or famine” – a stressful state that I don’t think I’d enjoy. That said, it is also a state that many thrive in. I need a thicker skin because finding a new job is a numbers game. There will be many more misses than hits. When I used to give advice to other job seekers, I used to liken the process to dating; there are many single people out there, but for the right people to meet each other, it must be the right place, right time, right status, right mental space – for both parties… finding a job is exactly like that. I’ll need to find a role that requires my experience, in a company that appeals to me, in the city I live, and they need to find me compelling enough, and be ready to hire, and actually complete the hiring process. There will be many false positives, and lots of ghosting, and many “thank you for your application, while your profile is strong, it didn’t fit” emails along the way. The search will take time, but I will eventually be OK. Patience will need to be my friend. In addition to all the challenges in point 4, senior roles, by definition, are rare, and in uncertain economic conditions, tend to become lower priority (the roles either consolidate or get double-hatted). But once I do find something, I’ll look back and see a bump in the road rather than a cliff that I fell off, and most importantly, be all the richer for the interesting and inspiring people I’m getting to meet along the way. Have you been through a redundancy before? What lessons did you learn from it?

I, like many of you here, struggle with recruiting talent. When I’m meeting candidates, one area that I keep thinking of is their ability to lead. When I share these thoughts with my colleagues and peers, saying that we don’t have enough leaders, I sometimes get comments like, “We have enough managers”, or, “We need more ICs”. We do have enough managers, but what we don’t have are enough leaders. What do I mean when I say that? It’s normal to confuse management for leadership. We call managers leaders. We call boards of directors or the C-suite the company’s leadership. We expect new managers to show leadership. But really those two concepts, while linked, are quite different. To keep it simple: management is a corporate function, but leadership is a human behavior. I can make someone a manager by giving them the role, but I can’t “make” them a leader. Management is about reporting lines, and team outputs, and the “housekeeping” of a team. The specifics of the role are usually in the job description. And while good leadership helps make a good manager, it is not critical to it. And most importantly, you don’t need to be a manager to be a leader! So what exactly is leadership? My favorite definition is this: leadership is about getting systems unstuck. With systems I mean interactions of people & processes trying to get things done. At work – and in life – we often find ourselves in situations where things are just not working, and leadership is identifying and taking the actions that could move things forward while bringing people and teams along the journey. If we think of leadership in that sense, you’ll agree that leadership is an individual exercise. Anyone can practice leadership; no one needs to make you a manager for you to look around you and try to fix problems. Leadership also applies outside of work: when dealing with conflicts with neighbors, family issues, the irate traveler at the airport: what can you do to move things forward? Good leaders identify “stuckness,” how to “unstick” it, and take action. The word “system” in the definition implies the inclusion of other people. While it’s good that an individual can solve their own problems, leadership comes into play when there are other people involved. And since leadership is not necessarily about management, you’ll find that effective leadership relies on communications and influence, to move others to help with getting things unstuck. Good leaders don’t force their opinions but bring others to consensus. Leaders can’t lead if no one wants to follow them. As humans process information, our minds build models into which the information is slotted. This means that while we’re communicating and discussing, we tend to process and interpret based on our understanding, not necessarily on what the speaker meant. In practical terms, this will lead to mismatched expectations, and statements like “I thought you were supposed to do this”. A big part of leadership is making sure that the common understanding of a discussion is as clear as possible, , to ensure everyone knows who needs to do what by when. Leaders understand ownership and hold themselves and others accountable. We have a tendency to fall in love with our ideas, thinking them more valuable because they are “ours”. We might also link our value to them, that somehow having good ideas makes us good. But we also all make mistakes. Recognizing that we’ve made a mistake could be a great opportunity: it’s a chance for us to learn something new and grow. It could also be a hindrance: if we’ve come up with an idea that turns out to be mistaken, we might hold on to it even more tightly, refusing to acknowledge the mistake and digging our heels in. Leaders know better; they can admit their mistakes, are flexible with their thinking, adapting to new facts and opinions as they become clearer. In a deeper sense, leaders can separate their ideas from who they are. Leaders know mistakes will happen, and accept them in themselves and others, and recognize them as opportunities for learning. In summary, leadership is about behaviors and actions we can all take. In contrast to management, you don’t need anyone’s permission to practice leadership. Leaders find ways to “unstick” systems in their everyday lives, and the lessons of leadership apply always everywhere. In fact, when I think about it, I find that the more leaders I hire, the fewer managers I need. So what are your thoughts about this? What am I missing?

You’ve always wanted to be a manager. You know you’re hard working, achieve results and think you can make a difference. You learn that a manager’s position is open internally and raise your hand – you want that promotion. Considering your track record, you’re a shoo-in. Congratulations, you’ve just been made a manager! So, what next? Your first instinct might be to dive right in, call a meeting, set objectives, and expectations, etc. But what if I told you that becoming a manager is not really a promotion, but a career change? “Career change?”, you ask me, “What do you mean? I’m still doing what I’m doing, only I have people reporting into me.” While you might remain in the same part of the organization, your job now is completely different. Let’s take a step back. As an individual contributor, your work output was almost 100% within your control: you wrote your own code, compiled your own reports, analyzed the data yourself, or built your own presentations – whatever your job was, the final result was up to you. When you became a manager, all of that was taken away from you and put in the hands of your team. So the question is no longer, “How do I perform well?”, but “How do I ensure that my team performs well?”. You might think, I’ll set clear expectations and guidelines, and everyone will follow them. Let me spare you the pain, this is not sufficient and will not have the effect you want. As a high performer yourself, reflect on what drives you. Is it what your boss tells you? Corporate strategy? Customer feedback? From experience, I’ve seen the most successful high performers intuitively take all the above, add a bit of personal value and vision, and blend them into something unique. As a manager, you’ll have to find a way to get your team to do the same. In addition, once you understand that your role is about getting the best out of your team, you’ll start seeing all the skills that made you an excellent individual contributor cannot be one-for-one transferred to your new role as a manager. And that’s why becoming a manager is not a promotion, or more accurately not just a promotion, but a career change. Now if you agree that new role is not more of the same, what does a high performing manager do? The first thing you’ll be faced with as a new manager is… management! I’m referring here to the day-to-day: assigning tasks, reporting up, approving things. While that’s part of the job, it’s the less critical part of it. The real meat of the job is what I mentioned earlier: how do you inspire your individual team members to perform? I invite you here to think of the good bosses vs. not so good ones you’ve had and reflect on why you feel that way. I’d wager a guess that the good ones will have typically drawn a clear picture of where the organization is going and how to get there, they would’ve given you space to grow and learn, given you feedback that’s timely and direct, and spent a lot of time listening to you and getting your input. There’s a term for all these behaviors: coaching. And while you might shudder at the thought because your experience with coaching was either the dreaded quarterly or annual reviews or know the word as a euphemism for bad bosses publicly criticizing their teams, the proper way of doing it is regular, two-way communication that’s focused on performance. To be absolutely clear: if you want to be a great manager, coaching and mentoring are not part of your job, they ARE the job. It’s not reports, it’s not approvals; it’s  ensuring your team can deliver to their highest potential. I will leave you with this; unlike promotions you might’ve had before, becoming a manager is a career change and, if you rise to the challenge, a change in mindset. It will be difficult because it doesn’t build much on your previous experience. It might initially feel overwhelming and reverting to the strengths and strategies that you got you here might be tempting but fight the temptation! They simply will not work here. The one idea that always grounds me when I feel I’m drowning is this: being a manager isn’t about you, it’s about your team. When they succeed, you succeed. Literally. If you use that as your guiding principle, the rest will come to you naturally. Welcome to your new career: the messy, unpredictable, emotional, and sometimes contradictory world of managing people! Please do share your experiences in the comments, I would love to know how the transition to management went/is going for you and the key takeaways you’ve learned from it.

Note: this is was originally published in 2017, so please forgive the dated examples. One of the challenges of working in the IT industry is the rise and fall of buzzwords. During the rise, everyone wants to get on the bandwagon. Even companies that don’t have anything to do with the buzzword will want in, so they’ll find something to link them to it. Mind you, buzzwords are not trends. Trends represent where technology is headed; actual, concrete products or technologies that affect our lives. Buzzwords are concepts or technology practice words that everyone gets excited about. For example, the Internet of Things, artificial intelligence, and blockchain, are examples of technology trends. Even though there’s hype surrounding them, and some of the definitions here aren’t clear (with Internet of Things leading the pack in ambiguity), trends tend to refer to actual things. Buzzwords, on the other hand, refer to concepts that become popular because they’re new, or have been accused of transforming a company, or are related to successful companies, etc. In the context of this article, buzzwords are words that don’t refer to physical things, carry definitions that are seldom clear, and they tend to be used incorrectly/out of context on a regular basis. More recent buzzwords I’m hearing would include disruption, digital transformation, agile, and others. I am not a fan of buzzwords. There are several reasons I don’t like them. First, using words that are not well-defined removes accountability from a conversation. I can say whatever I want if what I’m referring to exists clearly only in my head. Second, reducing complex concepts to soundbites (or single words, in this case), creates the inaccurate impression that they’re a simple thing we should all be doing. If it is something worth talking about, considering, or evaluating; if it’s taken a place in our consciousness, it can’t simply be a one-word concept. Third, and I think is the most important reason, some these buzzwords are being used to build corporate strategies. While there is no way to remove these words from the general consciousness, we can perhaps ground the more common ones in realistic definitions and applications. In this article I want to talk about my favorite buzzword. Disruption. In the last decade or so, I don’t think any conference, talk, blog, or article that talks about technology in any way has not used the word disruption. It’s been applied to everything from TVs to cleaning products. At the rate the word is used, we will all be immortal cyborgs living on a space station orbiting the nearest star in 6-9 months. We obviously will not – so what gives? I think it helps to look at three angles: first, what is disruption, second, what is not disruption, and third, why its overuse. First, what is disruption? The word was first used in the business sense in a 1995 HBR article where the Joseph Bower and Clayton Christensen introduced the concept, which I’ll clumsily summarize here (there really is no alternative to reading the article and the more recent follow-up entries). The authors noticed something interesting: the more market leaders focused on their customers, the less innovative and more susceptible to losing their market leadership they became. The authors contended that it is this focus on existing customers that makes it impossible for companies to make business model innovations that rely on the current customer base, because said innovations would, by definition, eat into their current value networks. This creates a niche of unserved customer needs that only other (often less established) players to target that niche by introducing an innovation or technology that overturns current business models – disrupting them. Disruption in the original sense is a novel approach to serving value that makes current business models insufficient, and by definition, making them less valuable. A key point here: new technology isn't necessary for disruptive approaches; it's the business model and customer base that defines disruption. So, what is disruption not? Disruption is not innovation; at least, not only innovation. Incremental improvements to products and technologies can’t be disruptions. A company that makes a new version of an existing product can’t be considered disrupting, if the new product serves the same set of customers in the same way. In fact, a company coming up with a truly disruptive productive is committing suicide, since it’s killing its current revenue stream. See, disruptive technologies will start out small and slow, (which is why they are almost always ignored by the big players), and slowly gain relevance. That means that a company running blindly into self-disruption will run into trouble. Before I turn to third angle, perhaps it’ll be illustrative to introduce some examples. A textbook example of disruptive technology in the last decade is the iPhone. At the time of its launch, Nokia was the world leader in mobile phones, cranking out devices that got incremental improvements every few months. They weren’t exactly dumb phones, but they weren’t groundbreaking. The iPhone, on the other hand, was a computer first and a phone second. It had apps, it had an app store, it had a large display, and a responsive touch screen. What it didn’t have: copy-paste, Bluetooth, MMS, and a friggin’ keyboard . Hardcore Nokia & Blackberry fans rolled their eyes in Apple’s general direction and continued tapping away at the physical keyboards (myself included). What’s interesting is that Apple didn’t introduce any new technology here, they just recombined existing elements into a new experience that made the escalation of features in other phones irrelevant . Now to third angle: if disruption is so well-defined, why its casual overuse? The small reason is the definition is not clear in everyone’s minds. The big reason, however, is that disruptive technologies have made their inventors a lot of money. Every company wants to be seen to have the potential to introduce the next big thing; disruption has become aspirational. Unfortunately, just because you call something disruptive, it doesn’t make it true. In fact, when I hear that word used to describe a product launch, I’m immediately ready to hear an incremental enhancement, not true disruption. Again by definition, a company cannot self-disrupt, though it can create disruptive divisions. One final note on the word’s overuse: even if applied with good intentions, the word’s very definition makes it difficult to apply to the immediate present. If we return to the definition, it points to a niche customer base that’s not served by the current value network, and that it starts small, under the radar of established players. The definition doesn’t guarantee a disruptive product (not every niche customer base will become disruptive); it’s almost impossible to tell with certainty that a product will be disruptive, even it ticks all the boxes. One can say that a product is disruptive only after the disruption has happened.