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15 Common Strategies for Navigating Entrepreneurial Challenges

Coaching entrepreneurs can present unique challenges. Often creative, high-energy and intently focused, entrepreneurs have a wide pool of strengths. Yet there are other traits that professional coaches see over and over in entrepreneurs that may lead to mistakes or misapprehensions and hinder their success and happiness.

Below, highly experienced entrepreneur coaches from Forbes Coaches Council share 15 common strategies for navigating entrepreneurial challenges including the missteps (they often see their entrepreneurial clients making), and some go-to guidance to get through the situation.

Scroll down to #8 to ready my contribution.

Members of Forbes Coaches Council share the most common pitfalls they see their entrepreneurial clients facing and their go-to guidance to get entrepreneurs through it.PHOTOS COURTESY OF THE INDIVIDUAL MEMBERS.


  1. Wearing Too Many Hats

An entrepreneur must learn and do many different functions, but no one can do everything at an optimal level without eventually burning out. Two of the most important things for an entrepreneur to understand are what they don’t do well and the value of each task they are performing, in order to strategically invest in additional resources such as employees, systems, services, advisers and a coach. – Andrea MacKenzie, Lead With Harmony

  1. Expecting Immediate Results

Some clients publish content for three weeks and wonder why they do not get heaps of engagement, comments and likes. I remind them of the fact that a thought leadership personal brand isn’t built in a month, as well as how social media works and how long people who are called “geniuses” today needed to reach their level of greatness. I also encourage my clients to celebrate milestones (e.g., their 20th video). – Dr. Natalia Wiechowski, Think Natalia

  1. Overlooking Culture-Building

Many entrepreneurs are singularly focused on getting to their goals. In the early stages of building their business, they frequently overlook the importance of building a sustainable internal culture, believing instead that the culture will build itself. When they reach external viability, they come to a moment of truth—continued success is contingent on engaged and dedicated staff. – Karyn Gallant, Gallant Consulting Group

  1. Missing Nonverbal Cues

They don’t read the nonverbal signs of others—whether it is possible investors or when attaining new clients. Actively paying attention to the nonverbal signals can inform you of how to proceed next. It is a unique form of listening. Like a good poker player, you need to know when to fold and when to stay in the game. Showing sensitivity to the other person will gain more trust. – Melinda Fouts, Ph.D., Success Starts With You

  1. Being Unwilling To Learn

The most common pitfall entrepreneurs face is an unwillingness to learn. Making assumptions that your ideal clients/staff are just like you gives us double the problems we faced alone. Deeply listening to our market and hiring those with complementary talents provides us with better outcomes. Practicing humility by investing in a coach or mentor will help us become more impactful visionaries. – Nina Segura, Metaspire LLC

  1. Not Asking For Help

Often entrepreneurs face a malady akin to the days before GPS, when people would wander around looking for a destination instead of stopping at a gas station to ask for help. As dreamers and doers, entrepreneurs can travel great distances before they realize they need to hit the brakes and reach out for guidance. Humility and a learning mindset are key! – Joseph Michelli, The Michelli Experience

  1. Developing Tunnel Vision

It’s common for entrepreneurs to get so caught up in their business that they develop tunnel vision. I would recommend having support from an objective third party who can guide them through ensuring that they haven’t drifted from their vision, examining the productivity and performance of their projects to ensure maximum growth, and encouraging them to leverage their network and opportunities. – Carolina Caro

  1. Not Focusing On What’s Important

Marketing, sales and leadership are the engines of an entrepreneurial organization. By focusing on the right things, having confidence in your mission and the courage to move forward with conviction, and not allowing yourself to get distracted, you will gain the momentum and traction required to create the most success with the least amount of struggle. – Michela Quilici, MQ Consulting and Business Training, Inc.

  1. Lacking A Clear Plan

Many entrepreneurs lack a clear plan. In the beginning, they are chasing many ideas, few of which end up working out. It is imperative that they sit down with a coach and work on a precise plan for their business. They need to answer several questions, such as: “What does success look like? When will I know an idea is failing?” A clear plan is important for clarity and accountability. – Amy Modglin, Modglin Leadership Solutions

  1. Having Low Self-Esteem

I find many entrepreneurs struggle with low self-esteem. It’s a quiet stumbling block. We assume brilliant people who are creating new companies and products we embrace will not look in the mirror and question themselves. Having clear expectations of yourself, your team and your support network helps tackle low self-esteem, as does the realization that the stigma around this challenge is perceived, not real. – Leila Bulling Towne, The Bulling Towne Group, LLC

  1. Living In Your Own Head

A lot of clients have the inclination to only follow their gut and ego when making decisions. They see only their perspective from their point of view. It’s not bad by itself, and it’s what’s gotten them where they are, but they are missing out on the views of talented people who work for them. My goal is to show them the benefits of other sides and make them more open-minded to the “collective” genius. – Alex Fedotoff, Alexandr Fedotoff Consulting

  1. Overpromising And Underdelivering

Overpromising usually happens when an entrepreneur suffers from the illusion that they have more time, energy and resources than they actually have. Entrepreneurs are typically energetic, but you are better off to underpromise and overdeliver. Disappointed customers don’t recommend you. Breaking trust damages your credibility and your self-confidence. Keep your feet on the ground to grow. – Erin Urban, UPPSolutions, LLC

  1. Resisting What You Don’t Like Doing

Someone once said to me that when you become an entrepreneur, whatever it is you love to do you’ll be lucky to do 30% of the time. Choose to fall in love even with the stuff you think you don’t like, including sales, financials, IT, hiring/firing and customer service. Ultimately, you must be aware of all aspects of the business. Rather than resist, ask, “How much fun can I have with this?” – April Armstrong, AHA Insight

  1. Not Charging What You’re Worth

As a six-figure-plus entrepreneurial consultant, I see many businesses tank because they make assumptions of what clients can pay and adjust rates to charge less. While they close the sale, it requires them to scramble to land more clients, work for less and struggle to make ends meet. Market analysis and learning to close should be the backbone to pricing, not beliefs that are not reality-based. – Laura DeCarlo, Career Directors International

  1. Succumbing To Shiny Object Syndrome

The entrepreneurs as well as the executives and leaders I support struggle mightily to fight off distractions and avoid shiny object syndrome. All carry unlimited work expectations and limited time to do it all. Add today’s culture of busyness as a badge and it’s easy to see how focus can be so elusive. I support my clients in choosing to 1) do less, 2) say “no,” 3) be positive and 4) not just do it, review it! – Ann Farrell, Quantum Endeavors, Inc.

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About Michela Quilici

International Business Growth Coach, Award-winning Marketing Strategist, Best-Selling Author, Speaker and Forbes Coaches Council. Known as a Business Navigator, Michela works with growth-minded business owners, service professionals and CEOs who want to ignite their businesses and accelerate growth, while building a business aligned to who they are.

She is passionate about creating roadmaps that ignite leaders to take inspired action to navigate their growth on purpose using strategy, systems and self-leadership, so they can get noticed, get clients and get profitable.