Every Black entrepreneur I know has faced the struggle of “finding good help”—and in 2025, this challenge remains as real as ever. The problem often starts with last-minute hiring decisions, which rarely lead to the best outcomes. I’ve been there: rushing to find the right person, investing time training them, only to see them fall through and end up doing the work myself. That frustration can make you swear off hiring altogether. But is doing everything solo really the answer? I surveyed Black entrepreneurs and added my own insights to help make this process smarter and less painful. Got something to add? Drop a comment.
Looking in the Wrong Places
Too often, Black entrepreneurs lean heavily on friends, fellow entrepreneurs, or social networks to find help. That’s a trap. These circles tend to be saturated with people who “need a job” more than they “need to get the job done.” Loyalty in these networks usually runs toward family and friends, not your business. This dynamic wastes your time and can strain relationships when the work isn’t up to par.
In 2025, with AI-powered hiring platforms and niche talent marketplaces, it’s easier than ever to widen your search beyond your immediate network. Use these tools to find candidates who are motivated by the work, not just the paycheck or a favor. Keep emotions out of hiring decisions and be ready to enforce standards without guilt—your business depends on it.
Hiring the Wrong People
One mistake I made was hiring people with big social media followings, hoping to get brand exposure while they worked. The reality? They were more focused on building their own brand than yours. In today’s creator economy, this is even more common. If you’re paying for a service, the focus must be on your brand’s success—not theirs.
Instead, look for candidates with solid industry relationships and a genuine commitment to your goals, even if their social media presence is modest. Relationships still matter most, but they take time to build. Watch for red flags like candidates who say “we” when referring to your business—they might see themselves as partners rather than contractors.
You’re Too Available
In 2025, with AI tools handling much of the initial communication, entrepreneurs can protect their time better than ever. Don’t be the open door that invites constant requests and distractions. Use email or automated scheduling apps to control when and how candidates contact you. This distance helps maintain professional boundaries—remember, you’re the boss, not a social worker or bank.
You’re Too Soft
Being friendly during interviews is good, but don’t mistake friendliness for weakness. Candidates will test your boundaries if you’re too soft. Especially when hiring friends or acquaintances, it’s easy to let standards slide. As TD Jakes said, if you work for him and don’t know him, you might think he’s harsh—but there’s a job to be done, and it must get done.
Job Not Clearly Defined
Clear, written job descriptions are non-negotiable. In 2025, use digital contracts and e-signatures to formalize expectations upfront. Spell out deliverables, deadlines, and payment terms. This upfront clarity saves headaches and protects your business.
Playing the Money Tree
Many Black entrepreneurs know what it’s like to be strapped for cash, but mixing sympathy with business can be costly. Paying early or bending payment terms often leads to subpar work because the focus shifts to money, not quality. Set firm pay dates—say, the 1st and 15th—and stick to them. If someone pushes for early payment, offer a steep discount and see how they respond. Pay on time, get better results; pay early, get sloppy work.
Unplanned Searches
Waiting until the last minute to hire is a recipe for disaster. Avoid the stress by planning your hiring needs ahead of time. Invest at least an hour to write down exactly what you want and expect. This preparation makes your search more strategic and less reactive.
Too Loyal
Loyalty is admirable but misplaced loyalty can sink your business. Don’t keep underperforming workers out of sympathy. Your business is your legacy—hire people who elevate it. If you want to help others, find charitable avenues, but keep your business standards high.
Not Checking References
Resumes are just the start. In 2025, use online tools to vet candidates thoroughly—Google their names, check social media, and verify references. Spending an hour researching upfront can save you 10 hours of training and fixing mistakes later. This is an investment in your business’s future.
Looking for a One-Stop Shop
Don’t expect new hires to read your mind or run your business like you do. The best way to save time is to invest time upfront in training and testing. Occasionally, you’ll find a gem who can handle more responsibilities—but that’s the exception, not the rule. Keep an eye on who excels and consider expanding their role gradually.
Not Understanding the Job Market
Millennials and Gen Z workers crave instant gratification and personal branding. Many want to build their own brand—even if it means piggybacking on your hard work. In 2025, with AI tools and automation reshaping jobs, be clear about what you expect and what’s off-limits. Protect your brand and intellectual property fiercely.<
Kevin "KevRoss" Ross is a music and radio industry expert. He is a 20 -plus year entrepreneur with the leading most successful industry trade publication and site Radio Facts (www.radiofacts.com). He has also published various books, magazines, performed marketing and promotions for major corporations and recording artists and he is on the advisory board of several industry organizations. This year Ross introduced his non profit organization LOMARI (Leaders of the Music and Recording Industry) to help teach young minority students how to market and manage their music and products.
