How to support, develop, and lead your team effectively

Executive overview

Most managers follow up on tasks instead of supporting the person doing them. The result is teams that feel managed, not grown.

Flip the model: use one-on-ones for human check-ins, use your project tool to identify what's yellow or red, and make delegation the default rather than the exception.

Your job as a leader is to grow people's skills, confidence, and connections until they no longer need you day-to-day.

One-on-ones: support over status

• Never use one-on-ones to follow up on tasks — that's what your project management tool is for
• Only discuss projects or metrics that are yellow or red; green means they have it
• When something is off-track, ask "what do you need from me?" not "why aren't you on track?"
• Check in on the person first — grief, stress, and life events make task updates pointless
• Batch your Slack/email questions into the one-on-one instead of pinging people during the week

Humanising remote communication

• Replace text replies with 30-second Loom videos to restore tone and expression
• Use Marco Polo (video voice notes) for async human connection
• Virtual coffee chats — working on video together — reduce isolation without requiring a planned agenda
• Jam Group runs online social events (~$25/person) for remote team connection
• Airbnb working days: rent a space with a pool, bring laptops, skip the agenda

Delegation as a leadership multiplier

• Your job is to make sure work gets done, not to do it yourself
• Test: divide your hourly rate by four — delegate anything below that threshold
• Show people what "finished" looks like; ask how they'd approach it rather than dictating the path
• Specify the destination and parameters (deadline, quality level, constraints) — not the route
• Parkinson's Law applies: define how little time and money to spend, not just the outcome
• As people grow, reduce oversight; move from parent to coach to peer

Building a culture of trust through core values

• Trust is not earned from zero — it's assumed until broken
• Live core values visibly; call others on violations anchored to the values, not personal criticism
• Celebrate core values publicly: shout-outs in meetings, a dedicated Slack channel, weekly praise rounds
• Catch people doing things right, not just wrong — this is the one-minute manager principle
• The skill follows a learning curve: awkward at first, then automatic, like riding a bike

Leading up: aligning with the management team

• Your direct reports won't respect leadership you don't respect — alignment starts with you
• Call out core value violations upward, calmly and by name; frame it as "you're breaking your own values"
• If the culture above you genuinely won't change, that's information — it may be the wrong company
• Your primary team is always the leadership team, not your functional area

Scaling dynamics: what changes at each growth stage

• 10–30 employees / $3M–$10M: first-time leaders, decisions made in a vacuum, minimal politics
• 30–100 employees / $10M–$30M: politics emerge, cross-functional buy-in becomes required
• 100–300 employees / $30M–$100M: seasoned leaders, P&L autonomy, command-and-control shifts to direction and culture
• 300+ employees: you won't know everyone's name or department — skip-level meetings become essential for cultural connection

Running a learning culture

• Pay for any conference, coach, or course an employee wants — no approval required
• The only ask: teach one thing you learned to the rest of the team when you return
• Put multiple leaders through training simultaneously; run short weekly book reports between modules
• Rewatch and re-read content quarterly for a full year — comprehension compounds with practice