Women in Business – Surviving the First Two Years: “Take other people’s advice with a grain of salt.” Interview with Carrie Collins

Interview with Carrie Collins, founder of H.O.W. Highly Organized Woman, on her experiences being a woman entrepreneur.

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Please tell us a bit about yourself, and describe your company.

Carrie Collins, JD, PhD:  I craft order from chaos and create inspired and inventive ways to find time.  A consummate connector, I have a keen ability to facilitate conversations and establish and foster mutually beneficial partnerships.  I’ve served as one of the most senior executives at two institutions of higher education and participate in the management of virtually every aspect of the business of academia.  As strategic opportunities arise, I play a critical role in quickly and decisively analyzing new prospects for growth.  I lead strategic planning at an institution with multiple locations in 2 states, as well as oversee and fundraising and alumni engagement.  In 2020, my team concluded the most successful fundraising year in the institution’s 120+ year history.

In January 2020, I founded H.O.W. Highly Organized Woman to teach people how to find time by thinking strategically about productivity, performance, and leadership progression.  Offering team training, 1:1 sessions, virtual retreats, and consulting engagements, H.O.W. shares practical and accessible strategies to amplify any tool, system, or process to find the time.  If you want to learn innovative approaches that shift thinking, spur action, and create results, H.O.W. helps you show busy who’s boss.

In my spare time, I am an executive producer for several British short films and love riding my Peloton with Cody Rigsby.  

What has been the most challenging thing you have faced in the first two years of operating your business? How did you overcome it?

As a solopreneur, the greatest challenge for me is finding ways to raise brand awareness, i.e., how do I get people to learn about my business and the value that it brings to organizations and their teams?  It’s easy to get swept up into participating in opportunities that have little to no ROI because that’s what you see other companies doing.  It’s so tempting to believe, for example, that paid social media will send people flocking to your doorstep.  (I don’t even want to admit how much I spent on ill-fated Facebook ads.)  An added layer of that challenge is striking a balance between giving your services for free to raise awareness while getting other prospects to convert into paid clients.  

Through guidance from a more seasoned small business owner, I finally paused and took a step back from several awareness activities that did drive traffic to the H.O.W. website, but resulted in zero business.  I spent the month of December refining brand positioning, messaging, and the overall approach, moving from a B2C model to a B2B model.  I also realized that I needed to strengthen and expand my network to create personal relationships with key decision-makers who had the ability to hire H.O.W., rather than relying on tactics that work for much larger enterprises.  In the month of January 2021, I closed more new clients than I did in the last 6 months of 2020.

What are some of the biggest digital marketing challenges you have faced to date?  How have you overcome them?

Gaining followers on social media was a primary driver when I first launched my business, and I had an aggressive posting schedule for Facebook, Instagram, and LinkedIn.  This led to some less-than-stellar content and content that didn’t exactly mesh well with the overall brand.  I began to scale back the frequency of posts on certain channels and look for ways to optimize the presence on others.  Today, I post once a week on Instagram with content that’s designed to be fun, creative, and informative.  I’ve established a partnership with a major brand and have had the opportunity to do Instagram Live Takeovers of their account resulting in over 30,000 views of those videos on IGTV.  I now post twice a week on LinkedIn: one post that demonstrates thought leadership and/or summarizes strategies to find time and another that highlights a company, team, or other partnership that I’ve established.  Not only am I promoting my business and expertise, but theirs as well. I still don’t have legions of followers, but the content and strategy are solid.

Please tell us what led you to the path of entrepreneurship. 

Professionally, I’ve been somewhat risk averse and never pictured myself as an entrepreneur.  But I joined an amazing women’s networking group based in New York City called Chief and was blown away by the number of women who had forged their own paths—and done so with incredible success.  In November 2019, Chief hosted a dinner party that I attended, and the guest of honor was a well-known serial entrepreneur.  She made an offhand comment that there must be a business in “productivity hacks,” particularly for women, and I started furiously writing notes.  After returning home, I thought about this obsessively until one evening it hit me.  People were always asking me, “How do you do it all?”  My response would now be that I am a Highly Organized Woman, that’s H.O.W.  Thus a business was born.

What are the three most important things every woman entrepreneur should do, when first thinking about starting a business?

Scope out the competition.  It’s incredible how many products, services, niche practices, and ideas are floating around out there.  Before you invest a significant amount of time, energy, and effort into creating a business, make certain you know your competition and are prepared to articulate how you are different.

Recognize that you’re not going to get it right the first time, but there does need to be a first time.  In other words, don’t let perfection be the enemy of progress (thank you, Winston Churchill).  It shouldn’t be sloppy or have obvious mistakes, but put your business out there and see how people react.  Within 2 days after launching my business, I had 2 people ask me if men could attend my sessions.  What I had thought would be appealing to only women clearly had broader appeal.

Take other people’s advice with a grain of salt.  People are likely to be incredibly supportive of your new venture and offer a plethora of unsolicited advice about how you should bring it life.  Certain opinions should carry more weight than others, but it’s important to remember to nod and say, “Thank you.  I’ll consider that”—even if you have no intention of doing so.

Are there actionable steps a woman in business should take to ensure that her company is successful in two years?

Get organized.  From legal to finance to business development to marketing, it’s simply too hard to run an effective business if you aren’t organized.  To-do lists, calendar management, and strategies for emails can save you valuable time looking for and remembering to do critical activities.  

Determine what tasks you can do and which ones you can outsource.  What systems and technologies can make your business run more smoothly?  Don’t try to do everything yourself when there are excellent and affordable tools for everything from invoicing to social media planning.

Invest in a Customer Relationship Management (CRM) system.  If you hope to grow your business at all, you will need a system for keeping track of what you said to whom, with whom you need to follow up and when.  A spreadsheet may work for a few weeks or months, but it’s quickly going to become burdensome to manage.  The CRM that I use is $10 a month and is absolutely invaluable to keeping my client development work organized and on track.

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