Level Up Your Startup: Seven Hard-Earned Lessons in Talent and Strategy
Originally a thread on X/Twitter:
1/19: One of my favorite things about the #startup ecosystem is that best Founders are hungry to grow their own skills as quickly as they can. I’ve shared some hard-earned insights in past threads and thought it was time to share 7 more nuggets.
2/19: Nugget 1: Always find someone on the team to take the opposite position on an important decision. Doing this religiously trains the team to challenge each other and debate decisions in a professional manner.
3/19: By setting the expectation that all decisions will be challenged it shifts the group’s focus from an unhealthy mindset (i.e. – Is this a personal attack? Don’t they trust me?) to a healthy mindset (i.e. – This is how we bullet proof our decisions as a team.)
4/19: Nugget 2: Once a startup has grown beyond about a dozen people, a Founder should set the expectation that hiring and nurturing talent is at the top of everyone’s priority list. Under-emphasizing the importance of talent is the easiest way to limit a startup’s potential.
5/19: If a team spends 25% of its time recruiting, it will spend 10% of its time managing minor mistakes. The alternative is for a team to spend 10% of its time recruiting and 50% of its time undoing significant damage caused by problematic hires.
6/19: The costs of setting your hiring bar too low compound over time. It’s critical to focus on making sure the junior talent you’re hiring has the potential to outperform the senior team you’ve already hired. Don’t let insecurity get in the way of talent acquisition.
7/19: Startups eventually stall out when the most talented people uniformly sit in the top layer of the organization. They struggle to scale, execution level mistakes are made that hurt the business, and they’re always limited in how many “big things” they can take on.
8/19: A startup isn’t taking enough risk if the inner circle isn’t nervous about giving critical responsibilities to junior and mid-level team members. Talent needs experience to grow and the best way to do this is to throw your best swimmers into the deep end.
9/19: Nugget 3: It’s not OK to forgive sloppy thinking. Full stop. Sloppy execution can hurt but it can also be fixed over time if an organization focuses on process, tracking and delivery. But sloppy thinking can’t be undone.
10/19: Strategic clarity sets the foundation for building a business. Focusing on tomorrow’s initiatives is important but knowing what success looks like is more important. And knowing how your successes will compound to build a durable business is everything.
11/19: Nugget 4: Spend as much time where you’re winning as you do where you’re struggling. The natural tendency is to throw talent at broken pieces of a business. But it’s much easier to grow a small, hot fire into a blaze than it is to put out a forest fire.
12/19: Success can compound quickly so always prioritizing the problem du jour is rarely the right answer. I know this is difficult to do when you’re in the middle of a crisis but allocation of resources to generate maximum return is one of the most important jobs of a leader.
13/19: Nugget 5: Organize around a very tight learning agenda. Set out to crush no more than 3-5 goals at any given time. You solve what you organize around and a typical organization can’t deliver against more than a few big goals at any time.
14/19: Doing one thing isn’t enough – Don’t suffer from the “Tyranny of the Or”. But doing more than a handful of things will spread your talent like peanut butter and significantly reduce your chances of success.
15/19: Nugget 6: Learning everything you can about your teammates and direct reports has more leverage than most novice Leaders appreciate. It’s not only about relating to each other in a “human” way. It’s also about driving results through alignment.
16/19: The more you know about a person’s personal life the easier it is to make sure that their responsibilities match the cadence of their life. And if you know about a person’s professional goals you can structure what they’re working on to increase their long-term happiness.
17/19: Nugget 7: Startups have very few advantages over at-scale incumbents and speed is a competitive weapon that needs to be on every startup’s arsenal. What’s missed by many first-time Founders is that speed is a function of process.
18/19: Speed starts by framing WHO can make WHICH decisions. Acceleration happens when the AMOUNT OF PROOF needed to make a decision matches the IMPACT of the decision. Max speed comes when there’s NO LAG between a decision being SURFACED and decision being MADE.
19/19: Hopefully a few of these nuggets are helpful. Growing one’s skill set starts with awareness of gaps and a receptivity towards ingesting new frameworks. But real growth only comes with practice and practice can be uncomfortable. But you’ll never grow if you don’t try!