70 learnings from Slush

During my time at Slush, I had a habit of sitting down and reflecting twice a year. Instead of keeping these in my Notion, I thought sharing some of my learnings might be valuable for someone.

For context, I started at Slush in 2018, working on partnerships (also helped with the program here & there), led the engineering, marketing, and partnership teams as COO in 2019, and finally was CEO through 2020 & 2021.

When I look over my notes from those four years, there are three areas that I’ve repeatedly reflected on: management, leadership, and operations. My notes get particularly rich from the past 2 years. That time included one cancelled Slush, a complete pivot from event to online community, and a return to a physical event last December. It was, and will quite likely remain, the hardest and most teaching period in my life.

So, on management, on leadership, and on ops – with a hint of crisis – here are selected 70 things that the past four years have taught me.

  1. As a C-level, especially as CEO, aim to be the Chief Question Asker (CQA). Give space for others to speak up and be curious. From Day 1, your title affects how seriously people take your words more than you expect.
  2. I’ve found it to be important to activate the creative, left-brain in everyday work. Our systematic and logical right-brain is actively in use in hectic, execution-oriented work life. Thus, taking time off and having space to ponder is helpful in order to generate new ideas and "aha" moments. A practical way to do this: allocate “thinking time” every week to your calendar or copy how Bill Gates does it.
  3. Speak openly about your worries and challenges with your team. This alone, if done well, gets you a long way towards the kind of agency and focus that you need from your team. People tend to run in the right direction when they have a full view of what surrounds them.
  4. An organization that pulses faster makes things happen faster. As a CEO, find ways to increase the tempo. Draw short-term targets from your long-term goals, manage your team’s energy, compress cycle times whenever possible, celebrate small victories, and arrange retrospectives to reflect on progress and direction. Anything that builds momentum. Frank Slootman (Snowflake CEO): “Somebody would ask me if he could get back to me about something next week, and I would reply ‘how about tomorrow morning? Might be completely unreasonable, did not matter. The point was to change people’s sense of urgency.”
  5. Seek actively for advice but take them with a grain of salt. Always apply your own thought-process to reflect the advice. One my mentors once said: “The advice comes from knowledge. Knowledge comes from generalizing and condensing past experiences. Experience come from making decisions, especially bad ones.”
  6. Nailing the company values and operating principles takes time. Be prepared to reserve 6–8 weeks for the whole process. Get these done before you start running.
  7. Forming psychological safety in teams is the most important job to do as a leader. Low trust leads to endless invisible small frictions between teams, wasted time, and conflicts. You can increase it by facilitating well-managed encounters between people. The level of trust can also be increased by promoting empathy and understanding of others’ work across the team. Gaining more trust is a slow process, whereas losing trust can happen in seconds.
  8. At Slush, we arranged monthly “open thoughts sessions” where everyone can voice their concerns, questions, or wishes. This had several benefits: it built a culture of transparency, created a safe space to discuss difficult topics, and often helped us to spot underlying problems early. Companies that rally around a Founder-CEO tend to run CEO office hours. I believe that this was a good modification that reflected the more democratic nature of Slush.
  9. In 1on1s, listen deeply, be present and take notes. There's tremendous power in deep conversations. Reserve at least 45 minutes, be on time, and send your questions 2–3 days prior to the meeting. When you’re the senior person in that setting, aim to spend the majority of time on topics suggested by your team member. I’ve found it useful to start 1on1s by asking the simple question: “what’s on your mind today?”. More often than not, you’ll spend >50% of time on that one question.
  10. The biggest challenges were usually caused by my inability to deliver constructive feedback or take action early enough. In other words, actively running towards the pain. Ben Horowitz’s article “Which Way Do You Run?” resonated throughout my time as CEO and changed the way I approach unpleasant thoughts or actions. Whatever challenge or concern, run towards it as fast as you can.
  11. The difference between a truly exceptional leader and a good one is that both know what to do but only the exceptionals will do it. Usually, this is related to painful decisions.
  12. Always write a job description and set clear targets before you start hiring. If you don't have these, finding the right person, giving feedback, or firing a person is extremely hard.
  13. Ultimately, your culture is defined by two actions: hiring and firing.
  14. “Who you are is not the values you list on the wall. It’s not what you say in a company-wide meeting. It’s not your marketing campaign. It’s not even what you believe. Who you are is what you do.This is another fundamental learning from Ben Horowitz that crystallized during my time as the CEO.
  15. If transparency is an important value for you and your organization, make everything as transparent as possible. Share everything (excl. sensitive people-related topics) with your team: board decks, financials, worries, and highlights. Levels, a metabolic health startup, has taken this to the extreme. Levels shares almost all of its thinking publicly. That includes all-hands meetings, founder working sessions, and their Tesla-inspired strategy.
  16. Invest time in offboarding when you have to let your team members go. Help them find new opportunities, find interesting people who they could talk to, be available and occasionally ask how they're doing. This might feel like an extra in the midst of the pressure but it's worth it. I was inspired by how Brian Chesky and Airbnb approached their layoffs in 2020: “to take care of those that are leaving, we have looked across severance, equity, healthcare, and job support and done our best to treat everyone in a compassionate and thoughtful way.”
  17. “To be careless in making decisions is to naively believe that a single decision impacts nothing more than that single decision, for a single decision can spawn a thousand others that were entirely unnecessary or it can bring peace to a thousand places we never knew existed.” - Craig D. Lounsbrough, Flecks of Gold on a Path of Stone: Simple Truths for Life's Complex Journey
  18. Type 1 & Type 2 decisions (Bezos). Type 1 decisions are irreversible e.g. if you walk through the door and don’t like what you see on the other side, you can’t get back to where you were before. But most decisions aren’t like that – they are changeable, reversible – they’re two-way doors. If you’ve made a suboptimal Type 2 decision, you don’t have to live with the consequences for that long. You can reopen the door and go back through.
  19. If you have a decision that's irreversible, take your time, but commit to a timeline upfront. Floating is the worst as it decreases motivation and burns money.
  20. If you must lay off people, make sure you lay off enough people to avoid doing it a second time. It’s a painful process and doing it twice might be devastating to your culture. (As hard as it was at the time, I’m happy that we succeeded at this in early 2020.)
  21. If you must lay off people: overcommunicate. You easily fall into the trap of assuming people understand the logic behind the decision or in general, are up to date, when they are not. Communicate all the time in different formats: company-wide emails, Slack messages, and face-to-face. For context: we laid off people in March 2020 due to the COVID-19 pandemic. At that time it was not obvious that the pandemic would continue after the summer and would affect our annual event in November. In other words, our team had every reason to question my decision.
  22. When things go from bad to really bad, you as a leader should highlight the importance of focus and hope. While people will see through naivete, you should help people understand that change is always an opportunity to do something new and better. Brian Chesky’s quote captured how it felt to lead in 2020: “So much of getting through a crisis is thinking you will get through a crisis. And if you are in a position of leadership, your own psychology becomes the psychology of your team. Believing leads to curiosity, and curiosity opens the door to creative solutions - exactly what you need when the going gets tough.”
  23. When there is a lack of momentum, focus on small wins. Slowly ramp up these wins to gain the momentum back.
  24. People think about trust as almost an on/off kind of thing. You either trust someone or you don’t but it’s actually more gradient than that. Tobi Lütke’s (Shopify Founder & CEO) concept of the trust battery proved to be useful tool to think about trust: “If people meet each other, especially in a curated context like a company, like both of us start working here, and we both got hired, so we both ran through the gauntlet of how to be hired here, so that means we probably will trust each other, let’s say, 50% right off the bat. Then we have these interactions, we have a meeting like the one we just talked about, the combatant idea, or we just talk about an idea, we come up with something even better, we work well together. This slowly charges, right? I think it’s useful to have this metaphor between people because it allows you to sort of talk about the trust that exists between two people without actually becoming personal.” Note: At Slush, our core value is “trust by default”. When it’s truly implemented to your culture, it’s one of the most empowering forces for your team.
  25. When meeting older, more influential people than you, do not appear “busy” or out of breath. Instead, come in early, prepared with facts, and propose a crystal clear call to action. Ask meaningful questions - more experienced people appreciate your interest in things that are relevant for them.
  26. The Golden Triangle: Referral from a familiar, trusted person is the single most effective way to get to influential people. In practice, you need to get a referral from someone who is close to the person you want to talk to. Leveraging this lets you reach out to someone outside your network as if you had already met and established trust. Basically, your network grows by one degree of separation, which is an exponential increase.
  27. ”It’s nothing personal, it's only business”. Business is always personal, but not private. I believe consumers rally around a cause or a story or some personal connection that they have. Own your contacts, and treat them well.
  28. Things really start to happen when you’ve won several people’s hearts over, not only minds. In order to do that you have to be an authentic example of your own agenda and talk about your goals repeatedly.
  29. Time kills deals. Be quick in your answers for the most important relations and keep them in the loop. Maximize the time that the ball spends in the other person’s court.
  30. Understand that your biases, ways of working, and culture might benefit a certain type of individuals while it might be nonoptimal for others.
  31. When building a product, you must be intellectually honest. It's very easy to fool yourself to believe in something. While you are focused on executing your product vision, critically review new information and if needed, adapt.
  32. “People need something to do, something to look forward to, and something to love.” - Mårten Mickos (Hackerone CEO) in a call late 2020.
  33. A functioning team needs at least: a vision (what we aim to achieve), a mission (reason for existence), short-term targets, clear responsibility areas, and ways to build trust.
  34. It's really important to create clear responsibility areas. As a leader, make it extremely clear who's responsible for what, who reports to whom, and describe what success looks like. Failing at this leads to misaligned interest, confusion, and eventually decreased motivation.
  35. Create a system to facilitate feedback. It may feel "forced”, but it's actually necessary to make it a company-wide habit. As a leader, be an example of how you would like to give and receive feedback.
  36. Hire people who are clearly better than you in at least 1-2 areas that are required to do the job. When recruiting a team, look for sets of 1-2 skills that complement each other and, put together, cover each critical skill area that the company needs. Bear in mind that personalities can also complement each other.
  37. As a CEO, it's often difficult to understand how a normal week looks through the eyes of an employee. You might talk to everyone regularly and know what's happening, but many team members will not. Find ways to build clarity across the company and across teams. For example, having a short laidback afterwork on Friday is a useful complement to your formal all-hands. For context: Slush all-hands are weekly 1 hour sessions at 9 am on Mondays.
  38. Keeper test: ask yourself who from your organization you would fight hard to keep if they were planning to leave, and who you would not. This helps increase the talent density.
  39. Talent density matters because high-performers want to work with other high-performers.
  40. As a CEO, be thoughtful about what you say and when: people might not question your opinion as much as it would merit.
  41. As a leader, be mindful if your team members cancel your 1on1 meetings. This tends to start happening when things get hectic. However, these are usually the times when your team members need you the most. It can also hide underlying challenges from you. Make sure that you have at least a short chat if the 1on1 gets cancelled.
  42. Onboarding matters. A well-planned and executed onboarding process for new hires builds your culture more than you imagine. Naturally, it also helps people get up to speed faster.
  43. Hiring takes longer than you would expect. Rule of thumb: multiply your first estimate by pi.
  44. Product-market fit usually solves all problems. Prioritize actions that get you closer to it over actions that deal with the consequences of not having found it.
  45. People want to be part of an organization that is winning. Marc Andreessen: “Companies that have a retention problem usually have a winning problem. Or rather, a “not winning” problem. The typical case is a company that used to be a hot growth company, but the growth has flattened out, causing the stock to tank and everyone to be in a bad mood. Or, alternately, an older big company that did really well for a while but more recently hasn’t been doing so well, causing the stock to tank and everyone to be in a bad mood. In other words, a company in transition—from winning at one point, to not winning now. The only way a company in that situation can retain great people is to start winning again.”
  46. When you are unsure where to go, go somewhere.
  47. Ask your team members to give motivational speeches. Often (especially during difficult times), they work much better than if the company leadership would do it.
  48. Think of your team members and ask yourself: do you think they are motivated? Are they operating at peak capacity and capability? If the answer is no, ask yourself why? Then ask them. Based on the answers, fix the underlying challenge together. Usually, the reason is some combination of the following: unclear responsibility areas, unclear targets, insufficient compensation or learning (tasks are too easy, repetitive or the person does not see how they relate to where they want to be headed).
  49. People who are unmotivated or not high-performers have a massive negative impact on people who are. Help them or get rid of them as fast as possible.
  50. As a CEO, talk to your customers. You don't have to (and shouldn't) do it most in your team, but you absolutely must do it.
  51. We condensed the traits we look for in our hires into one sentence: “at Slush, we look for people who exhibit clarity of thought, limitless potential, and people who resonate positive energy.” This turned out to be a useful tool when we ramped our hiring.
  52. After every week, ask yourself what you really accomplished. It’s easy to fall into a trap where you fill your calendar with seemingly important work (email, meetings, scheduling meetings, etc.) Avoid this by planning your week properly, identifying one top goal (One Big Thing), dedicating time for it on Monday and Tuesday (I find that they define the rest of your week), and reflecting on it when you get to the end.
  53. Full autonomy is not necessarily the most optimal leadership style. People seem to enjoy a small amount of micromanagement. If done well, it shows that you care about the quality and details of their work.
  54. Having a communication channel only dedicated to spreading positive news is a great method to build a culture of appreciation and encourage people to celebrate small wins. For us, it was a Slack channel called #posiposiposi.
  55. In decision-making, it's very valuable to think about both sides of the decision. Even when you believe something strongly, it's helpful for others if you argue why it might be flawed. All decision-making should seek the truth.
  56. Help others by dedicating time to coach their short-term execution plan. For example, ask them to write down their plan on paper and then present it to you. One of my team members did a GANT chart of all things his team should do before the summer. This exercise alone brought a lot of clarity for him and was effective as I kept him accountable.
  57. You can assign hidden cultural responsibilities to your team members. These can include overall efficiency, high-quality standards, or something very practical like ensuring that all meetings end in clear follow-up actions. These people then put extra emphasis in signaling these cultural elements across the organization.
  58. As a CEO, it's crucial to point your leadership team in the same direction. This helps the whole company to better align its focus.
  59. Every now and then highlight your company-level focus in an all-hands meeting. For example like this: "For August and September, our company-level focus will be sales and reaching X revenue threshold.” Ideally, this should be visible in your weekly deck, at your office, in your internal Notion, etc.
  60. When writing a job description, it's good to check whether the language and choice of words might affect who would consider themselves eligible to apply. Avoid words that are leaning toward masculinity or unnecessary use of superlatives.
  61. Make your values action-oriented. Values are traits and patterns of behavior that your company values in its team members. They are the foundation on top of which your company culture is built. An example of Slush's core value: “curiosity – a strong desire to know or learn something new. We ask questions emphatically, give candid feedback often to help each other grow, and enthusiastically share what we've read and learned. We love people who are insanely passionate or obsessed about something.”
  62. Writing down your operating principles is a useful tool to scale your culture and habits. For Slush, operating principles were the Modus Operandi: traits, actions, or characteristics to define how the Slush team operates. An example of Slush’s operating principle: “for us, results matter more than how much time you spend at the office”.
  63. Create a standard deck for your all-hands meeting that includes at least: mission, key updates, recent hires, and 1–3 selected topics that you pick each week. You can also include one slide to respond to the question "what is important right now".
  64. You need to talk about your mission, vision, story, values, operating principles, strategy, and targets more often than you think. The best way for the new team members to learn to talk about your company is to hear it first from someone else a couple of times.
  65. Celebrate and highlight actions that you wish to enforce in your culture e.g. a brilliant email, an effective meeting, being on time, a clear financial model, a well-communicated decision, or an action that deeply reflected your values.
  66. Be rational about risk: what's in your control and what's not. Use this to communicate and be transparent. Force your team to focus on what's in your control.
  67. Define beforehand if the purpose of a meeting is to inform, decide or align.
  68. When time is scarce, allocate it to something that has a multiplier effect on the organization e.g. decision that helps multiple people or teams move forward.
  69. We defined a mission statement for each team. For the leadership team, it was “to provide direction, define success and ensure happiness.”
  70. Your team is like a sports team, not a family. With your family, you tolerate certain behavior because you love them from the bottom of your heart. In sports teams, the best teams are formed when you have to fight for your spot in the light and everyone plays a critical role in the team. With that being said, the best teams care deeply about each other.

Slush was a life-changing experience for me. Thanks for the ride.