The 7 Staffing Challenges Every Entrepreneur Faces

Done right, staffing your growing business amplifies everyone's contribution, pushing it past milestones. Here's what to focus on.

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By Anna Johansson


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Building a successful business begins with building a successful team; no matter how impressive or unique your idea is in theory, it takes a team of people working together to bring that idea into reality. You may be the visionary and decision maker, but unless you've got a one-in-a-million idea that can feasibly be independently produced, there's no way you can do everything yourself.

This presents an obstacle, as finding and keeping good employees is one of the most difficult elements of entrepreneurship. These seven problems are some of the most significant challenges you'll need to overcome:

1. Determining your needs.

Your first step is determining who actually needs to be on your team. You might look at a competitor's model, or copy some other existing framework, but it's hard to tell exactly how many man-hours each of your departments or processes are going to require until you get up and running. Try to estimate these figures the best you can based on your industry knowledge, the experience of your mentors and advisors, and any personal research you can do (such as surveying existing companies). But be sure to factor in a degree of uncertainty as well.

2. Finding the right culture fits.

As you're undoubtedly aware, company culture is a big deal -- especially in a startup. It's going to affect your employee morale, the quality of your work, the enjoyment of your entrepreneurship, and even the characteristics of your brand. Don't take this lightly; seek out employees you can envision fitting in with the expectations you've set for your environment. Avoid compromising on your priority traits, such as work ethic, demeanor, or cooperativeness.

Related: 3 Ways to Create the Company Culture You Want

3. Balancing experience and cost.

In a startup setting, funds are tight. You can't afford to hire the best of the best, but at the same time, you need people who know what they're doing. Achieving a balance between experience and cost is essential if you want your company to survive its early stages. As an alternative here, seek out talent rather than experience. Instead of counting up years of experience, take a qualitative look at your candidates' portfolios, and look at work achieved rather than time spent.

4. Timing initial hires.

Your initial hires are going to be the hardest ones you make. Why? Because your company is in its most volatile position. You haven't tested the waters of working jointly with a team yet, your processes are still in flux, and your revenue streams aren't up and running yet. At the same time, you need to fill your initial positions quickly, or else you won't get to start working toward those revenue streams. Don't rush this process, as filling positions thoughtlessly can do more harm than good at this juncture. Take as much time as you can.

Related: What to Look for in Your First 5 Hires

5. Achieving flexibility.

Your startup is going to evolve over the course of your first several months (and years), probably in ways you aren't expecting or can't currently account for. Accordingly, you need people who are willing to be flexible in their roles; that might mean finding workers who aren't afraid of taking on responsibilities outside their realms of expertise, or hiring part-timers and independent contractors to help you fill in the gaps. As a general rule, strive to hire flexible employees who are willing to compromise and work with you when you need to adapt.

6. Growing manageably.

Most entrepreneurs are excited to achieve substantial business growth, but managing the pace of that growth can be tricky. If you hire too many people too soon, you may end up spending too much money or suffering from immature processes and hierarchies. If you hire too few people too slowly, you may end up with an overextended staff or an unsatisfied customer base. There's no easy solution to this, other than to monitor your growth closely and hire one new candidate at a time.

Related: How to Avoid the Premature Scaling Death Trap

7. Retaining talent.

Unfortunately, the volatility of startups makes it occasionally difficult to retain staff members, especially those you've hired at the top of the talent pool, or at below market price. A competitive offer from a more established company could threaten to remove them; be proactive here by making up for your financial or logistical limitations with company culture and flexibility.

If you can overcome these seven major challenges in entrepreneurial staffing, you'll be further ahead than most. There's no such thing as the "perfect" team, or even the "perfect" employee, but working toward long-term fits and simultaneously addressing your most urgent concerns should leave you with a solid enough foundation to start working toward your ultimate goals. Take solace in knowing that staffing is a challenge for everyone, and try not to stress about it.
Anna Johansson

Entrepreneur Leadership Network Contributor

Freelance writer

Anna Johansson is a freelance writer who specializes in social media and business development.

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