12 Answers to Common Leadership Questions from Cameron Herold

Executive overview

Cameron Herold answers 12 frequently asked leadership questions covering delegation, conflict resolution, time management, coaching, daily huddles, hiring, and financial literacy. The throughline is that a manager's primary job is not to do work but to grow people's skills, confidence, and connections. Practical frameworks — situational leadership, conflict models, time audits, Parkinson's Law — are applied to real workplace scenarios. The best leaders do less work themselves and invest that time growing their people.

The leader's core job: grow people, not do work

• Every manager's to-do list belongs to the team — delegate everything and use the freed time to develop others
• Ask "what do you think?" instead of answering questions; send people away to think, then act on their own answer
• Example: teaching a 15-year-old to fry an egg — the next day he's making an omelette from a YouTube tutorial without being asked
• Growing people means growing skills, confidence, and external connections (mentors, networks, courses)
• If you manage an IT head but aren't technical, source them an external IT mentor rather than trying to coach the content yourself

Situational leadership and authentic feedback

• Situational leadership requires adapting style (S1–S4) person-by-person and project-by-project
• Frame style assessment conversations as "I assessed you one way — let's compare how you assess yourself" so it feels collaborative, not critical
• Employees respond well when the leader frames the conversation as wanting to lead them in the best possible way

Conflict management model

• Use a structured conflict model so both parties feel safe — the issue stays about the situation, not the person
• Train everyone in the model so "I want to run through the conflict model with you" signals a safe, structured conversation
• Establish a shared de-escalation trigger word (the "meatballs" concept) to pause and revisit later
• For managing up: same model applies — frame feedback with specific behaviours, impact, and a clear request for change

Time audits and activity inventory

• Every employee should do a time audit every 3–6 months; leaders review it together to optimise ROI on people, time, and money
• Cap the audit at one hour — invoking Parkinson's Law: work expands to fill the time given, so set a tight container
• Weekly one-on-ones balance three things: direction (right work), development (skills and confidence), support (removing obstacles)
• Follow-up during the week is not nagging — it's asking "what do you need from me to deliver on your promises?"

Maintaining standards through hard times

• Personal hardship does not excuse breaking core values (e.g., showing up late, being unprepared)
• Separate personal support (budget, time, coaching) from professional accountability (core values, basic commitments)
• Have the "come to Jesus" meeting clearly: "Can you deliver on the basic core things, or do I need to find someone who can?"
• Gen Y managers often struggle with this directness due to participation-trophy upbringing — the skill must be deliberately developed
• Model: firm but fair, the same as effective parenting

Daily huddles

• Keep huddles to a maximum of seven minutes, run at an energy dip (11 am or 2 pm)
• Stand up even on video — changes energy and focus noticeably
• Rotate departmental updates across the week (e.g., marketing Monday, finance Tuesday) rather than forcing everyone to speak daily
• Expect awkwardness for the first 4–6 weeks; own it and push through — 1-800-GOT-JUNK ran daily huddles for 23 years without missing a day
• For large teams (20+), department-level updates are the only practical format within seven minutes

Coaching is continuous, not scheduled

• Coaching = praise + situational leadership + showing how + delegating cleanly — not just corrective feedback
• Catching someone doing something right is as much coaching as correcting them
• In group settings, lead heavily with praise before any constructive criticism; public criticism destroys confidence
• Praising someone publicly for having the courage to flag their own gaps builds trust and models the right behaviour

Delegation done properly

• Tell the delegate: what you want back, how little time to spend, how little money to spend, and what "complete" looks like
• Assess their project-management capability — if weak, help build the plan and block calendar time with them
• Check in mid-project with "what do you need from me?" not "is it done yet?"

Hiring decisions and headcount discipline

• Managers default to "add more people" when they lack P&L understanding or skills to get results through others
• Before hiring, ask: can we automate, offshore, or say no to the work entirely?
• Spend as much time on a $100k hiring decision as on a $100k marketing campaign — typically far less time is spent on hiring
• Lock budget, staffing plan, and core projects for the full year by end of November so January starts clean

COO compensation and value argument

• Show the company how you generate 3–4x your cost in gross margin (e.g., $300k salary requires ~$1m gross margin or ~$2.5m revenue at 40% margin)
• Title and comp should reflect: strategic insight, autonomy level, P&L responsibility, people you bring in, and true scope of role
• A "COO" title at a small company may actually be director-level scope — comp follows scope, not title

Remote COO effectiveness

• Strong video presence and communication skills matter more than in-person frequency
• Prioritise physical health on the road: gym, running, healthy food — burnout disqualifies you from inspiring others
• A healthy mind and body is a professional performance requirement, not a personal preference

Financial literacy for leaders

• Watch ten 3-minute YouTube videos on reading a P&L; 30 minutes creates meaningful competence
• Share the full P&L monthly with all employees, reviewed line by line — 1-800-GOT-JUNK did this company-wide
• Review every expense in the general ledger quarterly with the full leadership team; waste surfaces immediately
• Show employees a personal home P&L/budget — the most accessible way to teach financial thinking
• Use a vivid vision review process: highlight completed items green, in-progress yellow, and discuss what was missed and why before extending three more years out