50 Things I’ve Learned in the First 90 Days of Running a Company

Reflections on my first three months as a CEO

Photo by Proxyclick Visitor Management System on Unsplash

Time flies. This past Friday I completed my first 90 days at Metasys. Thus far the journey has been gratifying, challenging, intense and eye opening. One of the exercises I promised myself I would do at the outset of this journey is place a deep importance on self reflection.

To that end, here are 50 things I’ve learned in the first 90 days:

  1. Create an identity for your company: It’s so easy to get enamored by shiny objects and the latest new ‘hot strategy’. The best thing you can do for yourself early on is create an identity for your company. Identify the value in your industry and decide strategically where you want to go. There’s a lot of ways to drive impact, but you can’t do all of them at the same time. Focus is key.
  2. When in doubt, just ask “Why?”: Just like it’s easy to get enamored by shiny objects, it’s easier to get enamored by our inherent biases. Whenever I want to push deeply in a problem solving session, I’ve found the easiest tactic is to simply ask “Why?” Asking why either gets us to ground truth or it highlights a gap in our thinking. If we can’t come up with a good answer, then I know we haven’t yet cracked the nut.
  3. Allow things to sort themselves out: Fighting the urge to always jump on something at first blush is not only good for productivity, but also good for team dynamics. For non-urgent items, sitting on it for a little bit pretty much always produces a better outcome. I’ve noticed one of three outcomes most frequently: (a) the situation sorts itself out, (b) someone else on the team comes in with a different (and often better) perspective, (c) if I need to provide perspective, I’ve had time to reflect and respond with something more meaningful.
  4. Be true to yourself: You will be faced with imperfect information way more often than you like. You have to adopt your own style and have the confidence and courage to pursue it. This is the only way to develop instincts and not be paralyzed by decision making. In one of my upcoming podcast episodes with Mike Knoop, Chief Product Officer at Zapier, we discussed decision making fatigue at length — solving this is one of the most critical things you can do for yourself as a leader.
  5. Listen to yourself: If you get advice from enough people, the advice will cancel out; that is, you can likely find 2 smart people to take opposite sides of the argument on virtually every topic. Trust your intuition and instincts.
  6. You don’t have to rely on yourself to develop instincts: Morgan Housel, Partner at Collaborative Fund and one of my favorite business writers today talks about this a lot: “Your personal experiences make up maybe 0.00000001% of what’s happened in the world but maybe 80% of how you think the world works.” I’ve found that the only way to close this gap is to adopt a continuous learning mindset. I’m a voracious reader. If there is a good idea from another company, I try to learn about it and see if it fits my company’s context. If so, I copy it — it’s outsourced R&D :)
  7. You also don’t have to rely on the business world to develop instincts: This has been one of the more interesting things I’ve learned — the more senior leaders I talk to, the more I hear about the importance of learning about non-business topics. Horizontal learning builds depth into your mental models.
  8. Always have a perspective: Having a perspective always pushes the ball forward. No matter the situation, you should always know enough to ask the right questions.
  9. It’s okay not to know the answer. It’s not okay not to have a path forward: Always having a perspective is not to be conflated with having the right answer. More often than not you will not have the right answer. What’s important in that instance is to supply a framework and a hypothesis. If you don’t, you paralyze your team.
  10. Sweat the details: The details are where impact lives. There is so much work at the company that is incontrovertibly messy. This is by definition where most people do not like to dive in. But if you let each of these details go, you slowly chip away at the core of your company. Doing 2% less over the course of 10,000 action items has an outsized negative impact on your business. Imagine trying to put together a huge puzzle with a lot of slightly chipped pieces. Disaster.
  11. Letting go is important for everyone’s sanity: Details matter, but learning to let go is just as important. Everyone does things in their own way. It’s your job to provide a box/foundation for guideposts and structure, but one that is malleable and large enough to give flexibility to operate.
  12. Use a decision matrix and say ‘no’ often: Before engaging on a topic, I consider whether or not I should be involved. If I’m personally involved in too many things, I turn into a bottleneck for the organization. I also turn into a crutch for my colleagues using their own judgement. I’ve adopted Shane Parrish’s decision matrix to minimize my involvement in most things.
  13. At a systematic level, follow the ‘mission to metrics’ framework: SpaceX is known for their ‘mission to metrics’ framework. Everybody in the organization knows the North Star Mission and it boils down to individual metrics that contribute to the North Star. This is something we are actively working on and rolling out over the next quarter. It’s really powerful when you know how your specific goals contribute to the broader company’s success.
  14. Simplicity is beautiful: But don’t overcomplicate the ‘mission to metrics’ exercise. This can get unwieldy quickly. Lists of three and broken down goals that roll up and aggregate is the best way to orient the team.
  15. Be extremely transparent and clear with others on how you like to work: I received great feedback from my team on ‘A Guide to Working with Romeen.’ I’ve encouraged everybody on my team to write their own Guides — you can only work well together if you know each other well.
  16. Encourage anti-perfection: If everything is perfect, it means you aren’t taking enough risk. I don’t think failure should be celebrated, but it’s critical to have an environment in which failure is acceptable.
  17. Only encourage anti-perfection after you have defined standards: Risk taking and standards should not be conflated — you should always have a gauge for taking risk and a separate threshold for performance. Everyone in the company should know what this bar is and you should always strive to keep the company above it.
  18. Curiosity is the best predictor of performance: I have noticed a direct correlation between my colleagues that are highly curious and are high performers. Curiosity pushes you to continually evaluate how you are performing and what the mechanics that can be leveraged for improvement are.
  19. Work ethic can’t be taught: It’s not your job to teach work ethic. It’s your job to find people that have work ethic and create an environment where they want to contribute it.
  20. The best team has Rogers and Tigers: I have an article coming out on this soon, but it’s critically important to have a team of Rogers and Tigers. Tiger Woods is a poster child for specialization (walking by 6 months, golf club by 10 months). Roger Federer is a poster child for being a generalist (his mom was a tennis coach and she actively discouraged him from picking up a racket until his teens). Specialists + generalists by definition have different muscles. Together the best of them make magic.
  21. Use non-obvious metrics as heuristics for culture: Define your own gauge to judge your company’s culture. This is a highly personal and specific exercise. I judge our culture by continuously asking myself, “How much pride would colleague X feel if somebody asked them, “how’s work?” at a social event?”
  22. Celebrate the small wins: It’s too easy to keep pushing the baseline up. Small wins are critical to get you to where you want to go.
  23. Keep small wins in perspective: Celebrating small wins is critical; confusing and conflating the larger company goals with small wins is dangerous. Be transparent about overall challenges and show how the wins, while critical, are one step to larger goals.
  24. Don’t get too high or too low. Stay on an even keel: Running a business is a roller coaster. Things are never as great as they seem and they surely aren’t as bad as they seem.
  25. Always lead with a strong face: This is something I have had to learn. Body posture, verbal cues and excitement start with me. It’s mandatory to bring high energy every day for your team.
  26. Do what makes sense for your scale: This goes back to #1 on the list of defining your identity. Implement practices that make sense for your size; there is a balance in being agile versus being process oriented. At every stage it’s a different formula. Execute based on what makes sense for where you are.
  27. Start with imagination, end with logic: Painting a vision of the world you believe in is critical. Rooting that vision in tactical plans is how you differentiate between being a dreamer and a builder.
  28. Push your team to think exponentially: It is really counter-intuitive to think exponentially (cue: why compound interest is a favorite topic amongst finance gurus). But it’s so possible to be a company that drives exponential returns. Exponential thinking starts with you; if you don’t do it, nobody on the team will.
  29. Push your team to put things on paper: Brainstorming is awesome. It’s also incredibly susceptible to glossing over specifics. Push your team to get in the habit of putting the conversation down on paper and ironing out the kinks. This builds execution muscle.
  30. Business is a mind game — you have to believe you’re great to have a shot at being great: Draymond Green said it best. https://www.youtube.com/watch?v=chnCF3D8Qs0
  31. Underweight position and overweight momentum: Position is a static point in time and is highly visible from the outside in. Momentum is literally impossible to diagnose from the outside in. Ten companies that are doing $X in revenue today all look the same more or less, from a position perspective. However they are likely wildly divergent from a momentum perspective. Learn to appreciate momentum.
  32. The days are long, but the months are short: You never see impact in one day. If you get discouraged by lack of movement on a day-to-day basis you will lose. You have to consistently drive the right work to see impact over protracted periods of time.
  33. Inputs drive output 98% of the time: It’s really important to separate inputs (process) from output (outcomes). Every so often you will have a great outcome that seemingly comes out of nowhere — this is luck. Do not get seduced by it, because it is not repeatable. You can control your process and by and large, process drives outcome.
  34. Think of process as a function of misalignment: It prevents you from driving the wrong level of process for your organization. It’s your job to use process as an accelerator, not detractor.
  35. Everyone hears you differently: Being a steward of alternative communication styles is not only powerful, it’s necessary. We did an exercise with a few members of our sales team the other day and came away with a deep insight: belief that we could do 2x what we had originally set out to do this year. It was especially incredible because it took an alternative communication style (a detailed Excel model of all things!) that caused ourselves to take pause and look at the problem differently.
  36. Say the same thing at least 10 times if you want it to stick: If something is important, you need to say it at least 10 times for it to stick. Once you realize that everyone has 20+ things they are consumed by on a daily basis, you understand how important it is to consistently repeat your message.
  37. Distinguish ‘the snack’ from ‘the full meal’: Information digestion is a function of form and forum. This goes back to #13 and the beauty of simplicity. Know when to give the highlights and when to go deep. There are appropriate times for both.
  38. Quickly learn what you are good at and double down on it: I had a firm belief before I started running Metasys, that amplifying your strengths (versus being an all rounder) aligns with outsized impact. Now I can’t imagine thinking differently. Double down on what you are good at, make room to be the leader of those things for your organization and hire people that have that same spike in areas you are not as good at.
  39. Self-awareness is an underrated mentality: Encourage everyone on your team to consistently take inventory of their strengths and weaknesses.
  40. Writing is an underrated skill: Narrative and text based communication is an extremely high leverage activity. If there was one superpower I could instil overnight into everyone in our company it would be 10x’ing writing ability. This is a skill I will invest in deeply for all of our colleagues regardless of function.
  41. Pulse checks are an underrated company practice: Think of your company like a balance sheet, not an income statement. Consistently push for pulse checks to get a feel of how things are going; don’t wait until the end of the quarter to ask.
  42. Manage your personal energy: Leading a company is a marathon, not a sprint. If you treat it like a sprint, you will burn out.
  43. Take a step back and consistently reflect: You need to slow down to speed up. Extremely easy to say intellectually; incredibly difficult to appreciate in practice.
  44. Adopt an “it’s my fault” attitude: The more quickly you do this, the more quickly you orient your mind around problem solving, as opposed to being resentful. Encourage everyone on your team to always think this way.
  45. Everything is quite literally not your (or your team’s) fault: Be sure to distinguish these occurrences and make this clear to your team.
  46. Giving (deserved) praise is a LOT of fun and you can never do too much of it: Taking pride in company accomplishment is great; recognizing everyone who contributed to the accomplishment is 100x more gratifying. In the last 90 days, I’ve been most energized by recognizing and praising great work.
  47. Humans all want the same fundamental things: At the end of the day, everyone in the company wants the same thing: to feel fulfilled, have a sense of pride and enjoy what they are doing. Remember that, apply it to every interaction you have and you can get through the toughest of conversations.
  48. Genuine relationships move mountains: You will inevitably go through highs and lows as a team. Even if you have kept your personal perspective in check (#23), there’s nothing quite like genuine relationships in the face of adversity.
  49. Create a support ecosystem for yourself: I’m lucky to have a great spouse and family as my support ecosystem. It always helps to have someone to talk to and provide an outside-in perspective when the day has been tough; it’s equally as enjoyable to have someone to share news with when the day has been great.
  50. Don’t make lists of 50 because you’ll always fall one short :)