Strategic Questions Every Leader Must Answer

Why You Have to Answer These at All

What got you here won’t get you there. As companies grow and hit inflection points, new and unknown challenges arise. What seemingly worked smoothly yesterday is broken today. New challenges demand upgraded skills, talents and approaches.

As your business increases in velocity, the need for clarity and alignment grows with it. Your ability to impose your will on the business decreases. Your pulse on the business wanes. Clear leadership structures and decisions become imperative to your continued success.

This is why you must regularly review and plan your business. Planning should happen every ninety days to drive discipline and focus for the new execution cycle, while maintaining a three-year longer-term focus for the context of those decisions. The planning process should generate conviction on the bets you make as a company. You should leave convinced on the roadmap. With that convicted clarity, the noise of shiny objects dissipates.

Two critical components to succeeding:

1. Focus comes from writing the plan so it can be universally understood.
2. Discipline comes from regularly meeting to review the progress, metrics and KPIs.

Now, the questions.

Vision: Your North Star

What you do plus why you do it. Contribution plus impact. If your people can’t recite this, they can’t aim at it.

Values: The Operating System

Values outline the standards of behavior. Most companies stop at a poster on the wall. Go deeper. Patrick Lencioni’s four-category values model is the sharpest sort we’ve found, and here’s how we run it:

• Core values. Your unique operating system. The behaviors that make your company yours.
• Inherited values. Accepted due to a vacuum and left unaddressed. You never chose these; they moved in while nobody was watching.
• Aspirational values. You’re not doing these yet, but you want to. Be honest about the gap.
• Basic values. Honesty, integrity… also breathing? These are table stakes, not differentiators. Don’t confuse them with core values.

Talent Management Strategy

Answer, in writing:

• Hiring strategy, overall and by department
• Compensation strategy, including benefits
• Perks
• Onboarding process
• Leadership development
• Personal development
• Org chart structure (matrix, functional, hierarchical, product, etc.)
• Remote vs in-person

Culture Strategy

Culture is not perks and benefits. It is the ethos of the company. Your culture strategy should be closely aligned with your vision, values and talent management. If those three point one way and the lived culture points another, the lived culture wins.

What Important Problem Do You Solve?

• What is the important and painful problem you solve?
• Who do you solve it for, SPECIFICALLY? Yes, you can have different ICPs.
• Where do those people hang out?

Vague answers here ripple through everything downstream: marketing, sales, product, hiring.

Value Discipline: Where Do Resources Go?

From The Discipline of Market Leaders, pick your lane and allocate resources accordingly:

• Product leadership. Best product. Think Apple.
• Operational excellence. Best total value. Think Walmart.
• Customer intimacy. Best long-term solution. Think Ritz Carlton.

You can’t be all three. Choosing tells your whole company how to make trade-offs without asking you.

Revenue Strategy

What is the key driver of revenue?

• Marketing led or sales led?
• What is a “good” customer?
• What is a “good” order?
• Distribution strategy: who has access to your product or service? How do customers get access to it?

Financial Model

• Pricing strategy, and who owns pricing: marketing, sales, or product?
• Revenue growth target
• Gross profit
• OpEx
• CapEx
• Profit margin
• Key drivers of enterprise value: why would someone buy you?

Meeting Strategy

Driven by the size of your company, decide your cadence across:

• 1:1s
• Team meetings
• Departmental meetings
• All-hands company meetings
• Ad hoc

Go To Market

How will you build awareness of your product or service? Choose deliberately among:

• Inbound
• Outbound
• Partner
• Community
• Product
• Event

Planning Strategy: Live in the Future, Not the Past or Present

• Decide: bottom-up or top-down
• Weekly executive leadership
• Monthly executive review
• Quarterly planning process
• Three-years-out planning

Who Does What by When

The last question turns strategy into execution: a customer journey process map by department.

• Determine standards and priorities
• Set core accountability by person, with expectations
• Generate metrics and KPIs: how do we know it’s working?

For each department, put it on one page: the department, its leader, the key result, the standards and priorities, and a table of core accountabilities matched to a person and clear expectations. Then build the scoreboard: each item defined, with an expectation, a source, and the why behind it. If you can’t fill in the scoreboard, you don’t have a plan; you have a wish.

The Standard

Every one of these answers should be written and published so anyone in the organization can find them. Unwritten strategy isn’t strategy; it’s a rumor. When the answers are written, understood, and reviewed every ninety days, your people stop waiting on you for decisions, and the business moves faster than you can.