I am currently involved in three peer advisory groups for business owners and C-suite professionals.
Even before those formal alliances, I always benefited the most from conferences by meeting with similar growth-oriented entrepreneurs after the official sessions.
From those interactions, I’ve identified at least four things that successful entrepreneurs do differently
1. They invest in themselves.
Successful entrepreneurs make learning a priority. How you learn is less important than making it a habit, and those habits might change. Prepandemic, I was a voracious reader, but that was because I took more relaxing vacations with lots of downtime. My vacation habits have changed: I now consume more audiobooks and podcasts daily and am involved in mastermind groups.
Afterward, I ask myself, “What will I try in my business because of what I learned?” Successful entrepreneurs do not wait for problems to start learning something new; they set aside time and money for learning.
2. They treat employees as assets, not expenses.
Payroll is a major line item on the P&L, so it is easy to see people as a cost. Successful entrepreneurs avoid this mindset and recognize the value of human capital.
They know the real value of the company walks out the door every night. Employees’ skills, judgment, relationships and attitude are what keep customers coming back.
This does not mean leaders should accept poor performance. In fact, owners who value their employees often deal with a bad fit (i.e., fire the problem) more quickly. Why? Because if one person who does not do the job, shares values, or treats others well, they can drive away valuable employees.
I lead a value-builder process for a Williamstown-based food services company. The owners and the owners’ children were part of the process. When we addressed talent development and recruiting, the patriarch scoffed, “They don’t need training; they get a check. They should do their job.”
It shouldn’t surprise you that employee turnover was high and employee engagement and customer experience were low by industry standards. Also, recruitment was a priority for them, but they were losing out on hiring quality candidates without a worker-first culture.
Unfortunately, their view had been that there were no good candidates out there, but the reality was that their treatment of employees as an expense kept potential employees at bay.
We turned that around by defining employee responsibilities and goals to foster engagement and a sense of purpose. Management gave direct feedback, offered workers support through certification, and allocated funds to pay for higher education.
3. They welcome problems.
As companies grow, owners cannot and should not try to control every detail. Good leaders delegate and let others make decisions. A company cannot scale if the owner remains the bottleneck.
However, delegation brings a new risk: the owner can become out of touch with what is really happening. Employees might stop sharing problems because they do not want to seem negative or think the boss is too busy. Successful entrepreneurs want to hear about problems because that is where the next improvements are found.
A growing company will always have problems. If there are none to speak of, it might mean the business is not pushing itself, employees are hiding issues, or leaders are not paying attention.
New customers bring capacity problems. New products bring process problems. New managers bring communication problems. Problems are a feature of a growing business, not a bug.
The key is to set up a way to bring problems to light. In leadership meetings, ask three questions: What is stuck? What is costing us time, money or trust? What decision do you need from me? Encourage employees to reframe what might feel like an unwanted complaint into a spark that ignites solutions and impact.
The owner should not jump in to fix everything. Doing so only teaches the team to wait for help. A better way is to coach by asking, “What have you tried? Who else should be involved? What would you do if I were not here?” This helps people grow stronger and gives the owner better information.
4. They are goal-driven and willing to take chances.
Successful entrepreneurs are usually competitive, even if they do not always show it. They want to win customers, improve profits, enter new markets, keep great employees and build something that lasts.
That drive requires structure. Successful owners connect vision and goals, and goals with tactics. They tell the company where it is headed, define what success looks like this quarter or year, assign responsibility, and check progress often so they can move the execution along when things get stuck.
They also take calculated risks. For example, Buzz, the owner of a lawn and garden distributor in Adams, was thinking about a new product line and gave his team 60 days to test it with 20 current customers before making a big investment.
He learned which customers were interested, what price would work, and what problems might come up. Buz gathered enough information to make a calculated decision with a large investment.
The list of things that separate the winners from the also-rans is longer, and investing in yourself will unlock those trends.


