Five Things Entrepreneurs Need to Know About Problem-Solving

As an entrepreneur, you fulfilled a missing need for either you or your customers. But that was just the tip of the iceberg.
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Five Things Entrepreneurs Need to Know About Problem-Solving


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By Dean Kaplan, CEO and President, The Kaplan Group

About 20 years ago, after owning and operating a variety of businesses, I took over my family business. Today I run a commercial collection agency. I work with many different kinds of companies and many entrepreneurs. This has given me a birds-eye view into the problem-solving techniques entrepreneurs need to know. 

These are the five rules I find most important. 

Solve for your industry
When I owned AMI, a fiberglass manufacturer with clients as big as Disney, Warner Brothers and Macy’s, we followed the simple builder’s rule “Measure twice, cut once.” So, it was a bit of a surprise to me when I moved into online businesses to find out that the rule there was “cut, test, cut again.” Too often, entrepreneurs will take solutions that worked in one field and try and apply them to a new field.

If you’re lucky (and smart) and have experienced mentors, you’ll need to view their advice through this rule as well. A few weeks ago, I had a conversation with an intern. He said that his father thought he wasn’t looking for a job because he wasn’t printing out resumes and mailing them to various companies. The core message of his father’s advice, “you have to keep looking and working to find a job” is valid. The method, printing and mailing resumes, was outdated. As an entrepreneur trying to solve a problem, you need to listen to the advice of others but take only what’s valid for you and your business.

Seek help
Speaking of the advice of others. As smart as you are, you can’t solve all your problems alone. I have seen many promising companies go under because the owner didn’t know how to solve the problem of customers not paying their invoices. If the customer had consulted with a collection agency sooner, the company might have been saved. Entrepreneurs tend to be independent, but independence doesn’t mean you do everything alone. If you’re facing a thorny problem, ask for clarification and information. Ask for help.

Solve for the future, but not too far ahead
When negotiating a salary for a new hire, it’s a good idea to think not only of the person sitting in front of you but of other employees you plan to hire in the future. You don’t want to spend your entire budget on one new employee. What to pay someone is the type of problem you want to solve, not just for now, but also for the future. 

On the other hand, you need to be careful in setting precedents. I once worked with an entrepreneur who had grown her company to five employees. One of her employees was pregnant. Together, they tried to work out a maternity leave plan. The employee wanted to take three months off, then work from home for three months.

The owner was fine with this plan. She had done something similar herself. But, she worried about setting a precedent. What if one day they had a pregnant employee whose job didn’t allow for working from home? What would she do then? It’s natural to want a scalable solution to any problem. However, you don’t want to risk losing your current, valuable employee because you are worried about future employees. 

Don’t let perfect be the enemy of good
In 1770 the writer Voltaire first declared, “perfect is the enemy of good.” Voltaire was not an entrepreneur, but he knew what he was talking about. 

Whatever problem you’re facing, there is unlikely to be a perfect solution to it. If you let your problem-solving get bogged down in finding the ideal solution, you will be unable to find any solution. Working with Software as Sales (SaaS) companies has helped me see value in moving ahead before things are perfect. The SaaS model allows companies to learn from their users and improve their products in real time. You should never go to market with a product that doesn’t work or doesn’t fulfill its promise, but it’s OK to have a second or third iteration. 

If you’re unsure of a solution, consider what Key Performance Indicators (KPIs) or measurements will help you decide if the solution is working. Identify a reasonable time, evaluate and then either change the solution or continue with it.

Solutions change
Hopefully, your business has a long life ahead of it. That means that the problems you solve today will come up again. As technology, work expectations and the size of your company changes, so will the answer to your problems. No matter how good a solution is, don’t get so tied to tradition that you can’t improve on it later on.

You started a business to solve a problem. To have a successful business, you’ll need to keep your problem-solving energy strong.

Dean Kaplan is president of The Kaplan Group, a commercial collection agency specializing in large claims and international transactions. He has 35 years of manufacturing, international business leadership and customer service experience. Today, he provides business planning, training and consultation to a variety of global companies.


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