Building a Winning “Team” as a Solopreneur

As a solopreneur, we don’t have a team; we have a network. We will thrive or barely survive based on that network. Here’s how the principles in Roy Dekel’s “How to Build a Team That Doesn’t Just Work—It Wins” translate into opportunities, challenges, and strategic moves for solopreneurs. (Inc.com)

Summary of Dekel’s Six Team-Building Principles

Dekel argues that most teams are built to function, not to dominate—but in today’s environment, “functional” is a death sentence. (Inc.com) He gives six prescriptions:

1. Hire for attitude, not just skills

2. Make mentorship mandatory

3. Kill drama (eradicate toxicity)

4. Demand radical ownership

5. Encourage big, bold mistakes

6. Hold ethics as strictly as profits (Inc.com)

What These Teachings Mean for Solopreneurs

As a solopreneur, you may not (yet) lead a full team, but many of these principles still apply—especially as you scale, partner, subcontract, or build a “team” of collaborators, freelancers, or virtual assistants. Below is a breakdown of how each principle shifts when you are the one-woman show or building a very small network. Breakdowns include:

• Principle, the idea

• Impact / Challenge for Solopreneurs

• Strategic Adaptation

“Hire for attitude, not just skills”

• Solopreneurs often outsource or contract rather than hire. If you bring in collaborators (VAs, designers, copywriters), focusing only on “can they do the task” is short-sighted. You risk bringing people who are technically competent but disengaged or unreliable.

• In vetting collaborators, emphasize things like grit, alignment with your mission, communication habits, and growth mindsets. Use small tests or trial projects to gauge attitude first.

“Make mentorship mandatory”

• You don’t have layers of organization, but you can embed mentorship or learning pathways into your relationships. If you rely on freelancers, treat the collaboration as a mutual investment, not just one-off gigs.

• Offer feedback loops, pair newer collaborators with more experienced ones (if you have a small network), or invest in coaching/learning sessions with your team. Structure “how we do things” documentation that mentors future contributors.

“Kill drama”

• As a solopreneur, drama may manifest via miscommunications, inconsistent expectations, scope creep, or contractor conflicts. Letting “drama” persist is especially costly when you’re lean.

• Be explicit about communication norms, conflict resolution channels, deadlines, and how feedback is given. Address friction early—don’t let misunderstandings fester.

“Demand radical ownership”

• When you subcontract or delegate, many contributors treat tasks as “rentals”—they do what’s assigned, no more. But when ownership is lacking, quality and innovation suffer.

• Frame roles as “missions,” not tasks. Give collaborators room to propose improvements or take initiative instead of micromanaging every detail. Let them “own” parts of the project.

“Encourage big, bold mistakes”

• Without tolerance for failure, collaborators will play it safe, and you’ll lose out on creativity. But errors by contractors can also hit you hard (in time, cost, reputation).

• Define safeguardrails. Celebrate experiments even when they fail. Use small-scale pilots or prototypes before committing heavily. Make clear: mistakes are feedback, not punishment.

“Demand ethics like you demand profits”

• Integrity is non-negotiable. If someone you partner with behaves unethically, it can reflect on you. As a solo brand, your reputation is fragile.

• Be selective about whom you collaborate with. Set ethical standards (e.g., around deadlines, transparency, communication). Don’t compromise on values for short-term gain.

Deeper Impacts & Strategic Leverage

1. Quality over quantity in team scale
   Dekel’s principles imply that “right people” matter more than scale. As a solopreneur, this gives you permission to stay lean and cultivate “talent density” rather than expanding a large, mediocre team. Investing in a few high-alignment collaborators can outpace having many disengaged ones.

2. Your internal “team” starts with you
   Many of these ideals—ownership, ethics, mentorship, attitude—must first pertain to you before extending outward. If you don’t internalize radical ownership or tolerate mistakes within your own work, you’ll struggle to demand it of others.

3. Scaling mindset earlier
   Even before you have a big team, thinking in team terms helps you scale more gracefully. For example, writing “how-to” playbooks, onboarding protocols, communication standards, and feedback loops from day one will save you from chaos when you do bring on others.

4. Culture from the ground up
   The typical dynamic is “culture emerges when teams grow,” but in your case, you’re building the culture out of the founder’s values. If you bake in norms like “no-drama feedback,” “shared ownership,” and “ethical rigor” early, they’re harder to erode later.

5. Reputation and brand differentiation
   When you partner, subcontract, or outsource, the people you bring in become part of your brand narrative. If they “win” alongside you, it strengthens your reputation as someone who builds excellence rather than just “gets stuff done.”

About Charissa

Charissa Gant, Change Strategist with over 30 years of experience driving change for Fortune 500 companies. Most recently, a Principal Director at one of the largest consulting firms. Leading change with empathy. Unlocking leadership potential. Owner and Founder of BoldLEAP Collective, a community for courageous solopreneurs. Charissa@boldleapcollective.com