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Scaling Your Shadow: How Your Small Business Can Overcome Imposter-Syndrome

Scaling Your Shadow: How Your Small Business Can Overcome Imposter-Syndrome

The truth is, every business has the ability to succeed — if it can scale its own shadow. Here are seven ways small businesses can navigate imposter syndrome.

Every small business struggles as it balances certainty with growth. As small business leaders and owners, we’re always trying to secure our runway and longevity, so it’s on us to test the market and grow as quickly as possible. But growth is hard and scary. Every new dilemma challenges our confidence in what we’ve already accomplished.

Imposter Syndrome is defined as “the persistent inability to believe that one’s success is deserved or has been legitimately achieved as a result of one’s own efforts or skills”. Though this is often discussed in terms of the individual, it can also manifest itself at the organizational level. Which type of business is more likely to feel imposter syndrome the most? Yep — small businesses.

The truth is, every business has the ability to succeed — if it can scale its own shadow.

Where the fear is rooted

To overcome fear, we must first identify it. Here are four fears that small businesses commonly develop when they start to doubt themselves. Which of these resonate with your small business?

1. Inexperience

Every day, it feels like there’s something new to conquer. Sometimes our inexperience can make use second-guess our key assumptions and potential.

2. Insufficient

Every business, regardless of size, is strapped for resources making it seems like we can’t accomplish the things that need to be done in time.

3. Incomplete

Our business is a work-in-progress, but customers are here today with expectations and priorities of their own. We’re constantly worried they won’t be satisfied and that we’re not “done” yet.

4. Impossible

Some demands just seem too big for us to even comprehend. It’s bewildering when we can’t see the immediate path forward.

Scaling the shadows

Instead of being led by fears, we can scale them. Pause to reexamine what we fear gives us the chance to flex our creative muscles to find new solutions to the seemingly impossible challenges we face. While this isn’t an exhaustive list, consider it a thought starter. Here are seven ways small businesses can navigate imposter syndrome.

1. Seek mentors

Great mentors can help you hone skills and provide on-demand experience for any business problem. Create opportunities to meet others who can mentor you and be clear and concise about how a helpful hand may help you — you’ll be surprised how many rise to the occasion. Also, consider mentors that overdeliver may make for great additions to your core team.

2. Educate your customers

Customers don’t know everything we know about our product or service. Sometimes, we must take it upon ourselves to give them a full look at how things work and, most importantly, why they work the way they do and the assumptions we’ve made along the way. If you find yourself unable to make a solution work, you may need to go back to the drawing board and get more input from customers.

3. Own the workaround

Customers will accept workarounds, at least for some time, if they love what you’re doing and where you’re going. When a customer gives you a request you can’t directly service, make sure you exhaust options and give them as many alternative ways to solve their problem while you work on a lasting solution.

4. Build a roadmap

Customers love vision and passion, especially from small businesses. A well-defined, articulated roadmap helps them understand what you’re prioritizing and where you’re going. It also gives them an opportunity to forgive any short-term inadequacies with confidence that those challenges will be solved.

5. Say it with fidelity

Eliminate any roadmap doubt by progressively adding more and more fidelity to your ideas so new concepts come to life for customers to experience and interact with.

6. Find partners

Nothing’s impossible — with help. When things seem impossible to imagine, partnering with an expert is the solution. Great partners allow you to expand your footprint without growing fixed costs. Partners offer not just bandwidth, but also insights into how to make new ideas come to life. They get double points when they can also bring their customers into the fold.

7. Build champions

Not all experts are outside of the house — sometimes they’re customers. Every customer is a domain expert in their own right. When someone has a big ask, it’s entirely possible they also already know a solution. Partnering with your best customers, your champions, gives you an inside edge and a built-in customer base.


Small businesses, remember that you have innate abilities that many big businesses don’t have — ingenuity, agility, and resourcefulness. When we lose track of these critical tools or start to undermine them, our fears can quickly take over our thinking and limit our opportunities. Fortunately, everyone who’s scaled an idea into a business is already too brave to let their fears get in the way of their determination.

Salesforce Essentials helps you find more customers, win their business, and keep them happy so you can grow faster than ever. Learn more about our small business CRM solutions by following us on TwitterLinkedIn, and Instagram.


Gregarious Narain

Gregarious Narain is a serial entrepreneur and founder, having founded more than a dozen companies over the past 25 years.  His most recent company, Chute (YC W12), raised $16MM, grew to millions in revenue with 50+ employees spanning 6 cities, before being acquired in 2018. Prior to Chute, Greg was the first employee and VP Product at Klout. Connect with him on LinkedIn.

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