Jake Butler on LinkedIn: I once witnessed leadership so bad... I use this example to show other… (2024)

Most companies die in between product market fit and scale.As hiring ramps and goals get more aggressive, teams will break without proper infrastructure.Organizational design becomes critical.I was fortunate enough to see successful (and unsuccessful) org designs while growing DoorDash from $20m to $8b+ revenue.Here’s the process I’d follow to reorganize a team/company for scale:(1) Always get thorough alignment on North Star objectives. If one thing needs to be true, what is it? Layer in subsequent priorities. Your decisions will be anchored on their impact on these priorities.(2) Ideate on at least 3 options, carefully weighing key considerations against those, including all benefits and risks. This will lead you to a calculated decision quickly.(3) Consider key players/teams and their role in the changes. Who will you bet on to take the business to this next level? Do you have these leaders internally, or do you need to hire someone who has “been there, done that”?(4) Don’t forget about those who might not be benefitting from the changes. How will you mitigate any risks associated with those teams?(5) Write the communication and change management plan. First, consider if this can be tested before full implementation (assuming it’s not too sensitive). Second, detail exactly how you will communicate and ensure you have plans in place for all system changes.(6) Implement quickly. Don’t wait to implement your plans for long because you don’t want the word to leak. Rumors can be detrimental.Solid organizational design and implementation can dramatically improve a team’s performance. We led an organizational redesign at DoorDash that improved sales productivity by 39% QoQ.Failure, on the other hand, can push teams in the opposite direction, crushing productivity and causing key players to leave.

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I learned this the tough way.I was a young, eager manager who thought they could teach anyone how to be a great salesperson.I was dead wrong.If you think you can hire anyone and teach them your ways, you’re in for some tough learnings.There is no substitute for great people, and hiring is the most important part of building a team or business.So here are three tips that help me hire A-players:→ You are always recruiting. It doesn’t matter if you’re actively hiring. Always network to keep your pipeline healthy.→ You need to know exactly what you’re looking for and hire someone who is world-class at that specific thing. Hiring someone who checks every box doesn’t make sense if they’re not the best at solving the problem you need to solve.→ Know when to take slope bets and when to hire on axis. Slope bets have raw talent and insane ambition but don’t have all the answers. You hire them because they have unlimited potential to grow (great for startups). Axis hires have proven themselves and have the right experience, but they may be closer to their ceiling. You hire them to do a specific job (generally a safer bet).But most importantly, don't expect that you can teach anyone how to be you. It won't work.

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One of the highest returning learnings in my career is about positivity.But it’s not actually about being positive.Quite the opposite: being positive about everything is disastrous.Most people know when things aren’t going well. If you, as their leader, spread the message that everything is going well, you will:→ Create trust issues→ Lose credibility→ Enable a culture of ignoring problemsYou can’t solve a problem if you pretend it doesn’t exist. And people don’t get better when they think they’re doing great.Be real, especially when things aren’t going to plan. Your team will respect you for it and work hard to improve the situation.

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The speed of the leader determines the speed of the pack.That’s why so many of the world's best founders are maniacal about speed.Look at Elon Musk. He is maniacal by all standards. When Tesla was behind production targets, he would sleep on the floor of the manufacturing plant.I’m not saying everyone should operate that way.But if you want to build a billion-dollar company (or, in Elon’s case, several), you need to set an exceptional pace for the rest of your pack.

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I’m thankful to have had some incredible managers in my career.Here’s a list of the great things they do:1. Praise in public, criticize in private2. Invest in their team’s development3. Give autonomy to people they trust4. Lead cultures where people deliver results and have fun5. Ask challenging questions that make you think differently6. Admit when they make mistakes7. Lead by example8. Give their team opportunities to try new things9. Give clear direction10. Care about you as a human outside of work

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People like this give me energy.Nobody wants to spend time with people who zap excitement away from your accomplishments.You should show love and support for people who are doing great things.Shoutout to Connor Rodriguez, who lives this mentality better than anyone else I know.

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The most admirable thing about high-caliber operators is their ability to fly at 30,000 feet AND get into the lowest level of detail.It’s easy to get stuck in strategy land. It’s fun, and honestly, once you have the skillsets, it’s easier than getting into the weeds.But getting into the weeds regularly will 10x your strategy.Doing the work of front-line employees will keep you close to the most important thing: your customer.

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I’ve seen a strange paradigm amongst people who gain rank within their company.They suddenly think their title gives them additional entitlement.These people think they can now strong-arm their decisions with authority. This will get you nowhere. You'll get frustrated cross-functional partners who want to half-a** anything they do for you.Organizational leaders need to:→ Debate for the right decisions and be willing to be wrong. In some cases, disagree and commit.→ Approach cross-functional decision-making from a place of curiosity.→ Be respectful in their resolute.→ Recognize the importance of compromise.You either increase or decrease relationship equity with your cross-functional partners when you interact with them.If you’re unreasonable or demanding, you will quickly deplete that equity and lose them as true partners.There will be occasions when you need to battle for your team. Make sure you build up equity for those occasions, or you’ll have none when you need it most.

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There's one characteristic that gets overlooked in recruiting too frequently.The sharpest leaders I've ever worked with exemplify this in every meeting.They're curious.They ask "why" and "how" over and over again.Here’s why curiosity is such a powerful trait:→ When you ask “why” you force first principles thinking, which leads to innovation.→ When you ask “how” you identify repeatable themes or systems, which is key for scale.→ The desire to learn from within is a sign of intrinsic motivation.→ Curiosity creates an intellectual gain loop. The more you know, the smarter you are and the more curious you become. And so on.I love learning. It feels like a win every time I learn something new.The more I learn, the more I can achieve.

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