Strategy, Legal & Operations

Scariest business decisions: Experts share their tips and advice for the post-COVID future

“There are millions of small business owners who can share their scariest business decisions from 2020 thanks to COVID-19. No one could have expected or planned for the year we are having now.” – Brian Moran @brianmoran

Running or starting your own business can be scary at any time.  But, as Brian Moran stated, 2020 presented small business owners with unique challenges that no one could have predicted. During our recent #SageInspire Twitter Chat we asked our business experts to share their scariest business decisions, tips for overcoming fear, and advice for the post-COVID future. Here is what they said:

What are the scariest business decisions you’ve had to make?

“Leaving the security of a regional CPA firm [where I was a partner] and focusing on consulting and technology related services. The firm [I left] was focused on compliance and [the] leadership did not have a shared vision.  I was not concerned about myself as much as I was about the employees who trusted and bought into our vision and strategy.” – L. Gary Boomer @lgboomer

“Starting our own business in the first place! I’d never envisioned doing this, but after the great recession hit, I became an accidental entrepreneur.” – Laure McCabe @lauriemccabe

“Leaving a full-time position (with great pay and benefits to go to work for a small startup.” – Alyx @ColfaxInsurance

“Jumping in and purchasing my own insurance agency.” – Charlie @ColfaxInsurance

“I know it sounds strange, but increasing my rates scares me.” – Monica Davis @elitetaxnj

“Quitting a very good corporate job to go full-time in my company. I was going to lose a steady paycheck and good health benefits, but I knew that I could make it work.  It’s been 6 years now and I haven’t looked back.” – Nicole Davis @wifemomcpa100

What is your strategy and process for smart decision making?

“All small business owners should have a team they can rely on. This could be other SMBs. It should include your accountant. A mentor is especially helpful. Need one? Head to @SCOREMentors.” – Rieva Lesonsky @Rieva

“For sure. @SCOREMentors is a good place. I’d add a financial advisor to the team.” – Carol Stephen @Carol_Stephen

“My sounding board is my biz partner and significant other too.” – Nicole Davis @wifemomcpa100

“We start with ‘why – purpose’ and think of strategy as a process, not an episodic every five-year thing. Each year we update our strategic plan based on looking back at the prior year, forward at future trends, and developing insights to inform our strategy for action. Then we set goals and are prepared to adjust as we go forward.” – Tom Hood @tomhood

“Consider the who, what, and why. Why are you doing this? What outcomes do you want? And, what resources do you need to get it done?” – Laurie McCabe @lauriemccabe

How do you recognize when a business decision is wrong and what do you do next?

“Fix it as best you can, learn from your mistakes, and move on! Don’t beat yourself up, we all make mistakes.” – Laurie McCabe @lauriemccabe

“We believe in ‘fail forward’ and learn…Failure is identifying one more thing that does not work. We always capture our learning and insights along the way.” – Tom Hood @tomhood

“Fail fast. Failure is part of the education system. Manage your costs by owning your failures. They are expected in the entrepreneurial world.” – L. Gary Boomer @lgboomer

“I decide how and when to pull the plug by preparing for it before it happens. I measure concrete things that can help me decide if, and when, the project is failing. I trust my gut.” – Tripp Braden @TrippBraden

“I know a business decision is wrong when I start to veer off the path I put together based on the opportunity. When milestones and deadlines are missed, it’s time to seriously consider pulling the plug. Don’t waste precious time and resources on a bad idea!” – Brian Moran @brianmoran

“Missed deadlines and milestones are good leading indicators to a bad or not well thought out decision.” – Nicole Davis @wifemomcpa100

How can a small business owner leverage technology to make smarter decisions?

“Technology can help leaders keep track of progress on any aspect of business.  Defining the critical success factors and then measuring against them allow for any business to make better decisions faster and be aligned closely with their business goals.” – Tripp Braden @TrippBraden

“Let’s not forget that technology isn’t just computers and apps. Technology is finding ways to do things (anything) better. It’s the application of knowledge.” – Nicole Davis @wifemomecpa100

“You don’t have to know how to build the watch, but you do need to be able to tell time. You have access to peers, expertise, and resources that entrepreneurs in the past didn’t.” – L. Gary Boomer @lgboomer

“There are many ways to leverage tech to help in making better decisions. 1) Use AI to automate daily tasks to give you ‘more time’ to make important decisions. 2) Use analytic tools to measure your KPIs so you know what works and what doesn’t.” – Brian Moran @brianmoran

“It’s always a smart plan to have [the] necessary technology available to you, so you can actually do your job. It’s really up to each individual business and its owner to figure out how technology can help advise smart decisions in the future.” – Charlie @ColfaxInsurance

“Remember – It’s not about the technology. It’s about the business strategy – doing digital vs being digital. It needs to be in your DNA.” – Tom Hood @tomhood

“Automate as many back-office tasks as possible to save time. Utilize online forms to gain quick customer feedback to assist in future business planning.” – Lara Livingstone @divasdelite

Are there any past business decisions that still “haunt” you today?

“No, get over it! There isn’t anything you can do about it other than gain motivation and wisdom.” – L. Gary Boomer @lgboomer

“Yes, I made a decision on how I was compensated by a client. Took cash, should have taken partial payment in stock.” – Tripp Braden @TrippBraden

“Oh boy, where do I begin? Bad stock purchase, spending good money on bad products, hiring the wrong person, not firing people soon enough. Moving on and being optimistic is critical, though.” – Carol Stephen @Carol_Stephen

“Business owners should never let past mistakes weigh them down. You fall down, pick yourself up, and move on. Learn from it, and don’t make the same mistake twice (or try not to). You will make more in the future. That’s what it means to be an entrepreneur.” – Brian Moran @brianmoran

“Getting over it is easier said than done. Maybe “haunt” is the wrong word, but it is a periodic reminder to not do it again.” – Nicole Davis @wifemomcpa100

What decisions should businesses be making now to prepare them for the post-COVID future?

“First, we have to deal with today’s reality which says COVID-19 isn’t going away anytime soon. We need to plan to deal with that before we can even know what a post-COVID world looks like.” – Rieva Lesonsky @Rieva

“We’ll probably have a hybrid situation, depending upon where in the world you are.  Be prepared for many pivots. Flexibility will be key.” – Carol Stephen @Carol_Stephen

“Get your books in order.  Many business owners were panicking this past spring to get COVID relief because their financials weren’t a priority until they needed to be. Be prepared for the next wave of relief to ensure your business weathers the COVID storm.” – Nicole Davis @wifemomcpa100

“They should look for ways to take advantage of new business opportunities in their industry. Several of my clients are making critical business acquisitions to add critical capabilities moving forward.” – Tripp Braden @TrippBraden

“Businesses should be accelerating all of their digital transformation projects around cloud, e-commerce, customer experience, and even staff experience. COVID-19 has accelerated all of the trends happening by an average of 5 years – 2020 is the new 2025, don’t get left behind!” – Tom Hood @tomhood

Additional Resources

Thank you to everyone who participated in this Twitter chat. Visit our Twitter moment to read the full conversation.

Below is a list of additional resources to help your business manage uncertainty and plan for the future:

Article: Seven characteristics of an effective mentor

Article: How business intelligence tools can transform your small business

Article: 5 reasons you should be using a receipt app

Download: Small business survival toolkit

Download: Business plan template

Download: Cash flow forecast template

Download: How to choose an accountant eBook