How to Build a Strategic Hiring Plan as a Founder

"We need to hire fast!" is hurting your startup. I work with founders and hiring leaders scaling their teams. I keep seeing the same pattern: The pressure to fill a role quickly leading to surface-level hiring. → A few quick interviews. → A gut decision. → A rushed offer. Speed matters. But speed without strategy is expensive. And here’s what happens next: → 6-12 months of wasted runway You hire someone who looks great on paper but doesn’t deliver. → Team morale declines Your best people pick up the slack—until they burn out or leave. → Market momentum slows Mis-hires don’t drive results, and now you're playing catch-up. → Customer trust fades Inconsistent execution leads to missed deadlines and dropped deals. Then reality hits: You spend 3X more time and money fixing the mistake than you would have spent hiring the right way. Here’s what to do instead: 1. Define the win before opening the role.      What must this hire achieve in 6 months?      If you can’t answer that, you’re not ready to hire. 2. Cut through the fluff.      Structured interviews > generic Q&A. 3. Assess real-world ability.      Forget the “culture fit” trap.      Can they actually do the work at the level you need? 4. Get buy-in early.      Alignment upfront means fewer roadblocks later. 5. Move fast—but never reactively.      Hiring with urgency is smart.      Hiring out of panic is expensive.      Hiring with a STRATEGY makes the magic happen. When the right person is in the right seat, everything moves faster and smoother. Your business THRIVES. What strategy do you implement to hire quickly the right way?

Founders are often advised to “hire the best people,” which sounds good in theory but isn’t realistic for most. Here’s why this advice misses the mark: Early on with Chezie, I posted an engineering role with a $120K salary. A Silicon Valley leader straight-up told me, “That’s pretty low; you’ll have trouble recruiting.” And she was right. Most applicants were junior devs, not the “rockstar” hires investors envision. And as I saw other founders making high-profile hires, I noticed a pattern: nearly all of them had raised millions in funding. When investors tell you to “hire the best,” they’re often picturing someone with a resume from Stanford or Google—a “best” that’s incredibly costly and exclusive. This advice overlooks talent from less traditional backgrounds and ignores the financial reality for most founders, especially those who are bootstrapping or underfunded. Here’s what worked for us instead: 1. Redefine “best” - The “best” hire isn’t just someone with a prestigious resume; it’s someone who believes in your mission, fits your budget, and has the skills to grow with you. 2. Hire strategically, not full-time - Before making a full-time hire, exhaust software solutions and part-time contractors. Scale up only when absolutely necessary. 3. Be transparent about compensation—Listing salaries and equity openly filters out mismatches and helps you attract the right candidates who are on board with your mission. My advice to founders? Hire the best YOU CAN AFFORD. Focus on making every hire count without breaking the bank. Want to learn more about building a world-class team on a startup budget? Subscribe to my newsletter, Equity Shift: https://lnkd.in/eJjCSSCe

Hiring never seems to get easier as a founder. I’ve managed to fuck it up left, right, and sideways. So I took each of these fuckups and turned them into a list of questions I must answer before giving an offer. I call it my “Don’t fuck this up again you silly little man” checklist. 1) Is the job crystal clear (in terms of the 3-5 core responsibilities)? 2) Are the skills crystal clear (in terms of the 3-5 qualifications needed to do the job well)? 3) Are the deficiencies of the candidate clear? 4) Are the deficiencies a dealbreaker or is there a clear path to mitigate them? 5) Has this candidate been compared against another high quality candidate (such that the decision isn’t driven by feeling rushed or by emotion)? 6) Has this candidate demonstrated substance and not just salesmanship? 7) Does their comp make sense financially for the business? 8) If you have to fire this person in 6 months, what would the reason be? 9) How can you avoid that scenario happening?