The Six Questions Every Operator Must Ask to Build a Talent Strategy

What Operators Get Wrong About People Strategy

At early stages of growth, most companies build their teams reactively. They make hires to relieve pain, fill seats, or chase scale based on shiny promises from exciting strangers. But at a certain point, patchwork hiring strategies start to show cracks—especially when the business is scaling, fundraising, restructuring, acquiring, or heading toward an exit.

The mistake isn’t always the hire. It’s the lack of an underlying hypothesis guiding how that hire fits into the system. Founders wouldn’t run product or revenue without a clear strategy. Yet people decisions—the ones with the highest stakes—often rely on gut feel rather than structured frameworks.

At Talent to Team, we work with companies at critical inflection points—moments when the business is changing faster than the people systems that support it. The moments where we realize ourselves and/or our founding team members are plugging holes in gaps with their fingers, and they’re about to run out of digits. These transition periods expose underlying strategy gaps and make it clear that reactive hiring or informal org design won’t scale. That’s when the real work begins: helping founders design a talent strategy that matches their stage, pace, and growth goals. 

If you’re building a team designed to go the distance, these questions are where to start.

1. Where are you now? Where are you going? 

Hiring decisions should be grounded in the current state of the business, not just its future potential. Too often, founders build for the company they hope to be, rather than the one they’re actually leading. That disconnect leads to bloated teams, unsupported leaders, and systems that can’t support the pace of growth.

Each stage of business maturity brings specific organizational needs designed to fit specific types of talent. Early-stage companies benefit from generalists and flexibility who love to leave their mark on the culture and get to take on as much as they can handle. Mid-stage teams need repeatable systems and processes, specialists, structure, and clear swim lanes. Mature companies must be built around layered leadership, checks and balances, and systems that operate independently of the founder.

Before hiring another role—or misdiagnosing problems—founders need to objectively evaluate where are we now, where are we going, and what’s it going to take to get there? 

2. How fast do you need to get there?

Most companies underestimate the impact that pace has on their people systems and we forget to re-evaluate. Business speed is not just a culture trait; it’s a strategic decision that should influence everything from role design to comp models to retention strategy. When we started our companies we put our all into it. Our first team members did too. Now we are 5 years in and we still haven’t had a vacation. 

At Talent to Team, we categorize organizational pacing into three modes: marathon, sprint, and tough mudder. Each has real implications for how roles are scoped, how performance is measured, how compensation and benefits are designed, and how sustainable the current strategy will be by role over time. A marathon company needs consistency and depth. A sprinting team needs urgent focus with built-in rest cycles. A tough mudder environment may be temporarily necessary—but it comes at a cost.

Without clarity about the intended pace of business, teams begin to default to overwork, misalignment, or burnout. Worse, the expectations of founders and leadership often diverge, creating friction that no amount of performance management can solve.

Being explicit about pace—and aligning the people strategy to match—is one of the most overlooked levers in organizational design.

3. Who do we think can get us there? Or what resources do we need to add for our current team to get us there?

Headcount is not always the answer. Founders need a way to evaluate whether a role should be hired internally, outsourced, automated, supplemented, or delayed. We use the Build–Borrow–Buy–Bot model to help companies make that call.

• Build: Invest in developing internal team members who can grow into the role. This is long-term talent development—and it requires coaching, structure, and time. But no one brings enthusiasm and care like a ‘build’ team member.

• Borrow: Bring in fractional support, particularly when the business needs senior expertise that it can’t afford, doesn’t need full-time, or who specializes in a specific stage or type of growth, and you only need them for a period of time. Fun fact, you can borrow ‘buy’ or ‘build’ talent. Just make sure which one you are getting and that they are priced accordingly.

• Buy: Hire someone with deep expertise and a proven track record. These team members are often expensive, strategic hires that move the business forward immediately because they’ve been there and done that.

• Bot: Automate or outsource part or all of the work entirely. In some cases, the job doesn’t need a person at all—it needs a system, a workflow, or a piece of AI/software. 

When you are scaling a company fast, your career ladder looks a lot more like ‘Chutes and Ladders’ than a linear progression. If we keep our hiring strategy fluid and targeted, we spend a lot less time worrying about hurting relationships and a lot more time driving towards goals. This model prevents overhiring, clarifies expectations, and creates space for founders to design teams that are lean, fluid, capable, and ready to scale.

4. What do I need to pay for this role to attract and retain the right person? 

Compensation models often evolve without intention. They reflect legacy decisions, urgent offers, or individual negotiations. But compensation, especially at growth stages, is one of the clearest signals a company sends about what it values, who it values, and how it operates.

A thoughtful compensation philosophy should be tied to more than just competitor website market benchmarks. It should consider pace, performance expectations, tenure, special skills,  and fit into a compelling culture and opportunity for the right person. This includes short-term incentives for sprint-based businesses and long-term structures (such as equity (true or shadow) or profit-sharing) for companies that require loyalty and endurance.

Unexamined comp practices eventually lead to confusion, resentment, or unintentional inequity. Founders and leadership teams need to decide: Are we paying for potential, experience, tenure, or results—and do our systems reflect that decision?

5. Ok, we have a plan. How do we know if the strategy is working?

Set realistic targets and analyze your data. The best people strategies are built with feedback loops. Measure meaningful data on whether your hypothesis structure, roles, and systems are doing what they were designed to do.

Founders should look at performance signals across the organization: manager capacity, turnover by function (or manager), employee and customer engagement trends, time-to-productivity for new hires, and alignment between team performance and business goals. Tools like T2T’s HR Diagnostic help companies benchmark these areas and identify where gaps exist.

Netflix offers a strong example of how this can be done in practice. Its people strategy—centered on “freedom and responsibility”—is clearly defined, publicly shared, and reinforced through every system, from hiring to feedback. What stands out isn’t just the culture itself, but the company’s discipline in measuring and evolving it over time. That kind of intentional feedback loop is what most scaling companies lack—and without it, decisions quickly default to personality or untested narratives: performance reviews either don’t exist, or lack consistency and rigor. ole changes feel arbitrary, (maybe you are accused of hiring the next “shiny person” and alignment breaks down.

Designing a strategy is only the first step. Testing it—and revising based on what the data shows—is where the magic comes in. 

6. Are we solving for the person or the system?

When a team isn’t delivering, founders often assume they have the wrong people. But in our work with scaling companies, we consistently find that what looks like a performance issue is more often a structural one: a role with no clarity, unclear expectations,  undefined or undefined company goals, a system with no ownership, or a top-heavy org chart designed for a different pace of business.

Restructuring before you re-evaluate the system is like replacing the pilot without checking the flight plan. Founders need to start with the destination, build the hypothesis on how we get there and with whom, and then assess whether the people in place are being set up to succeed or destined to fail.

Addressing people-level issues first isn’t about avoiding hard conversations. It’s about making sure those conversations happen in the right context, with the right diagnosis, and the right next step.

Take the Next Step: Align People Strategy to Business Strategy

Operators and founders don't need generic HR advice. They need strategic frameworks built by people who know how to match the complexity of scaling a business through each stage of growth. They need tools that turn personal decisions into business decisions.  And they need support that sees talent as a driver of growth—not a cost center to manage.

If your business is scaling, raising, acquiring, or preparing for an exit, this is the moment to build your people strategy to hit and exceed your growth goals.

Join Talent to Team founder Amy Giggey-Burns for a live webinar: How to Build a Talent Strategy That Matches Your Stage and Pace. This webinar will take place via Zoom on Thursday, November 6, at 12 PM MST.

You’ll walk away with a framework, methodology, and language you can use immediately to uplevel your team and your business—plus KPIs to help you measure whether your current strategy supports your next stage of growth. 

Register here

The strongest teams aren’t built by accident—they’re designed through strategy, structure, and decisions based on experience. These frameworks and questions give operators & founders a methodical and reason-based way to align people and performance with business goals. Now is the time to move from instinct to intention.