Over the course of the past few years running my startup, it’s almost ludicrous just how much I’ve learnt. From how to turn a coffee-table conversation into a working product, a product into a scalable venture, scalable venture into multi-million dollar funding rounds, etc.
But no single area of learning has been as valuable, scalable or effective as the knowledge of how to manage a team. As soon as you have more than one person working on something the dynamic shifts completely — in ways that are hard to quantify from the outset no matter how prepared you think you are.
It’s a strange phenomenon, since usually you’re hiring someone to fill a gap that you desperately need sealed. Or to pick up some slack that you simply cannot straighten out yourself.
But no matter what, scaling from a solo-operator, or solo-engineer/designer/salesperson to a “team” requires a change in process, clarity and, most importantly, your own psychology.
As a matter of fact, one could make a compelling case that learning how to manage a team is actually an exercise in learning how to manage oneself first — and as an extension, others.
No longer can you (or should you) see yourself as the “hero”, the builder of the product, the linchpin of the organization. You’re now forced to see yourself as a curator of talent, a facilitator of alignment and collaboration, a guiding light when there is encroaching darkness and a steady hand on the rudder when seas get rough.
The following are a collection of principles I have leaned on and continue to lean on, refine, and adapt to the changing environment. Some of them may be bullshit, others may be timeless. That’s besides the point.
The main goal is to put them down for myself, for accountability, for updating, and in the off-chance that they prove useful to others who happen to stumble upon.
TL;DR Quick List Of Principles. Click to scroll.
- People are most often looking for either guidance or confirmation i.e. “Ask before answering”.
- Always apologize first, or make it clear you won’t i.e. “Limbo Kills”.
- Respect and love define a leader — not age, experience, title or role.
- Don’t equate long work for hard work.
- In times of conflict — breathe, empathize, return.
- Before you can win, you have to make sure everyone is playing the same game.
- Things don’t gain importance by words, they gain importance by actions alone.
- Simplicity is not always the goal, complexity is not always the answer
- No management book will ever teach you the real thing. Learn by doing and use knowledge to avoid mistakes.
1. People are most often looking for either guidance or confirmation i.e. “Ask before answering”.
Most people (myself included), though they’d be chaste to admit it, have very high opinions of their own thoughts and decisions. It can be all too easy to fall in love with the sound of your own voice without understanding just what it is that others are looking for.
In most cases people are listening to you to be polite — there are exceptions of course. But in a majority of cases I’ve found that people are looking for one of two things — guidance or confirmation.
There are different strategies for dealing with either scenario but the main principle here is to understand which situation you are in. The way you respond to someone looking for confirmation, who has already made up their mind, ought to be vastly different than those who need your expertise and advise.
It’s not that you should always agree with their decision, not at all, but if you don’t understand that confirmation is what the person is looking for and you begin offering them guidance it’s all too common for your words to fall on deaf ears.
Know which game you are going to play before you prance on the field.
2. Always apologize first, or make it clear you won’t i.e. “Limbo Kills”.
The worst thing that can happen between two team members is not conflict — that’s actually relatively easy to deal with. Usually stemming from miscommunication, talking past each other or — on rare occasions — toxic personalities, conflict tends to lend itself well to mediation.
Situations with conflict also have the added benefit that they are either solvable (a misunderstanding/miscommunication) or unsolvable (fundamental philosophical differences) and you can move on once you understand which is which.
But back to the original point, the actual worst thing for relationships within a team is uncertainty.
When I don’t know where you stand and you don’t know where I stand then we end up at an impasse that kills creativity and collaboration like no other. This is especially true in small, close knit teams.
If I’m in my corner expecting you to acknowledge my position and apologize to me and meanwhile you are huddled in yours, nothing gets done. Tensions flare. Feelings get hurt. Work becomes a chore, life gets hard.
On the flip side if you’re clear in your actions — “I’m sorry, I don’t know if this was entirely my fault but I know there are things I could have done better and I apologize” or “I am not going to apologize as I believe strongly in X, Y Z”.
Either of these two sentiments brings clarity to the situation. It’s quite possible or probably that someone might not agree, but it removes the tension of uncertainty and either shifts the situation more towards empathy and understanding or towards fundamental conflict — which as I mentioned before, is actually preferable to uncertainty.
Limbo kills relationships, partnerships, businesses, and probably house plants. Don’t allow any room for it in the culture you build.
3. Respect and love define a leader — not age, experience, title or role.
Leadership is the process of helping others realize their own potential. It's about providing support, direction, assistance (when needed) and having the insight to know when to keep your mouth shut,
While strategies, tactics, styles and more vary the one thing that does not is the notion that leadership transcends surface level properties. The same way we don't associate eye color, hair, height, or weight with leadership ability, we should also be careful to attribute age, experience, title or role to the same.
While it may be true that most people don't rise to the level of their expectation but fall to the level of their training, where that level of expectation is in the first place will determine how far and deep the fall. The higher you set the expectation, the higher the eventual outcome. People are malleable and have the potential for infinite change, thus putting bounds on growth based on superficial characteristics holds an organization back more than anything else.
A leader is not defined by these characteristics but should rather be defined by the respect and love of the people they lead. While bringing love into a business context is not a normal thing to do, stories like that of Herb Kelleher ("A company is stronger if it is bound by love rather than by fear.") give us indication that the sterile, emotionless bubble business has long been associated with may not be the most effective way to go.
Measure yourself by respect and love and your team, your company, and maybe someday even the world, will thank you for it.
4. Don’t equate long work for hard work.
Long work usually means inefficient process, unrefined planning or lack of understanding the true goal. Of course sometimes with deadlines and the grind of a startup long hours are unavoidable, but in general long does not mean hard (at least, well, not in this context) and sometimes 4 hours of focused, primed, hard work can beat 12 hours of unfocused muddling.
The other important things here is to never expect your team to work more than you do and to not hold people to a standard of working insane hours. Hours do not prove loyalty, they do not prove respect and they do not prove buy-in to the mission.
Asking people to go above and beyond should be a tool that’s used only when it’s needed and therefore a tool that should barely be used at all because at the end of the day building a lasting business is a marathon, not a sprint, and as a marathon runner I can safely say that pacing. is. everything.
5. In times of conflict — breathe, empathize, return.
As a recovering hot head, dealing with conflict maturely and in a matter that de-escalates the situation has never been my strong suit. I’ve had to discover strategies the hard way and have collected advice the easy way all of which effectively come back to the same thing — add an interrupt.
Moments of passion rarely lead to positive outcomes (in this context, at least) so the rule of backing up, breathing (6 deep breaths, lowering that blood pressure), trying to empathize with the person (or people) on the other end, and then coming back to the situation helps almost every time.
A thoughtless Slack message can be just as damaging to a relationship as a rude comment or public shaming, so adding a pattern interrupt is crucial to avoid putting your foot in your mouth as much as humanly possible.
6. Before you can win, you have to make sure everyone is playing the same game.
A company is nothing more than a loose organization of people working towards the same goal. But if there is any crack in this shared reality, any fuzz in this vision of the future that you are working towards, then it becomes difficult to move forward quickly or effectively.
It’s difficult to win if you’re not playing the same game and impossible to play unless you’re all on the same field. Err towards oversharing and over-communicating, especially when it comes to things like mission, vision, culture and roadmap.
As the saying goes, “If you want to build a ship, don’t drum up the men to gather wood, divide the work, and give orders. Instead, teach them to yearn for the vast and endless sea.” It’s the job of a leader to set priorities and to cultivate that yearning by making sure each and every person with you has the same image of the endless sparkling water just beyond their reach.
7. Things don’t gain importance by words, they gain importance by actions alone.
As Ben Horowitz puts it in What You Do Is Who You Are, “Culture is a strategic investment in the company doing things the right way when you are not looking.” The key imperative here is doing. It’s not a passive activity, it’s a conscious and targeted effort.
Paying lip-service is the easiest thing in the world. “Oh we ought to do this”, or “We should look into that”, or “That’s a really good idea, let’s circle back on that!”. Especially in an environment where there is no clearly defined model for behavior, every action and every decision paves the way for actions and decisions to come. What you do really does become who you are.
Future decision markers will look and lean back on the choices made today to justify actions taken tomorrow. In those situations, it won’t matter the words that someone uttered in a meeting somewhere, what will matter is what was done, how it was done and why it was done.
In a startup, actions will always speak louder than words.
8. Simplicity is not always the goal, complexity is not always the answer
The same way there is no general rule is life, there are no general rules in business. Even in this list so far, there are probably many times the principles are either in opposition or are paradoxical. Simplicity, many times, is not what you need, especially in situations that call for a light touch and nuance.
Occam’s Razor, while working for a large number of situations, can also at times be complete horse shit. Take the story of the universe vs. creationism for example. Occam’s Razor would very likely choose the simple story of creationism over the complex and intricate Big Bang, and depending on your politics you may or may not agree (I personally do not).
On the flip side, complexity can be a mask for a lack of clear thinking. Most things in business are simply not that complicated. Most non-deep-tech companies are not in a line of business where complexity is baked in to every aspect of the environment. However, sometimes complexity may be warranted.
A model that’s too simple loses predictive power. A model too complex becomes hard to manage, track and at some point is more unruly than the underlying reality itself. There is a fine line — a balance to strike — between the two and knowing when simplicity is warranted, and when to leverage complexity is a crucial skill for success.
9. No management book will ever teach you the real thing. Learn by doing and use knowledge to avoid mistakes.
The same way reading this list is almost never going to be as useful as having lived the situations that birthed these insights, no book, podcast, book or artifact is going to give you the same insights as experience. Reality is a beast, and the only way to tame it is to put yourself out there, take risks, fail, and — most importantly, learn.
It’s all too easy to get stuck in analysis paralysis and to be too smart for your own good. Whenever you fall in these times, just remember that thinking can be a form of avoiding action and sometimes you just have to eat the frog.
10. I did say this was a WIP didn’t I :)