A common mistake for new managers is to do their reps' jobs for them, especially in tough deals. This approach, born from insecurity or a desire to prove worth, prevents the team from developing self-sufficiency and ultimately fails to scale. The manager's true job is to build skills and muscle in their reps.

Promoting top individual contributors into management often backfires. Their competitive nature, which drove individual success, makes it hard to share tips, empathize with struggling team members, or handle interpersonal issues, turning a perceived win-win into a lose-lose situation.

Tommy Mello realized his scrappy, "do-it-all" hustler mentality, which built the business, was preventing it from scaling. He had to consciously shift to a systems-oriented leader, focusing on processes and delegation to enable massive growth, stating "the hustler had to die for the leader to be born."

Amplitude's CEO describes the painful transition from founder (running to the hardest problem) to large-company executive. The latter role requires embracing hierarchy, saying "no" to most things, and managing through leverage rather than direct contribution—a skill set many founders resist and fail to learn.

To transition from working 'in the business' to 'on the business,' Snowflake's CRO was told his hands-on, 'deal hound' approach wouldn't work at scale. The solution was to hire other capable 'drivers,' trust them to do their jobs, and hold them accountable. If a leader has to do their team's job, it's a problem with the team member.

Snowflake's CRO, Chris Degnan, kept his job through multiple growth stages where he could have been replaced. His longevity wasn't due to a pre-existing "scale" playbook, but his intense coachability and ability to "morph" and adapt his strategies based on direct feedback from the board and new leadership.

First-time managers, often former top performers, default to doing the work for their reps. This creates dependency and prevents the team from developing self-sufficiency, which is crucial for scaling. A manager's true role is to build the team's skills, even if it's slower in the short term.

Founder-led selling is essential for the first 6-12 months but becomes a critical growth bottleneck if it continues. Founders who can't let go create a self-fulfilling prophecy where the business can't scale beyond them. They must be coached to transition from being the primary seller to an enabler of the sales team.

The very traits that help a founder succeed initially—doing everything themselves, obsessing over details—become bottlenecks to growth. To scale, founders must abandon the tools that got them started and adopt new ones like delegation and trust.