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How entrepreneurs manage uncertainty with planning & capital strategy

Planning for possible scenarios and outcomes can improve your company’s ability to weather surprises, business leaders say.


In brief
  • Managing your business securely amid uncertainty requires mindfulness around possible risks.
  • While modeling scenarios, factor in the risk aversion level of your investors, your board — and yourself.
  • The decision around where to put capital to work is a continual balancing act.

Entrepreneurs are often told to embrace uncertainty, but what does that really mean? And with ongoing geopolitical issues and technological changes, is uncertainty actually a certainty? At the 2025 Strategic Growth Forum®, three seasoned executives shared what embracing uncertainty means when you’re making real financial decisions. The conversation touched on three key areas:

  1. Uncertainty. Count on it, plan for it.
  2. Scenario planning. Start with your North Star.
  3. Capital allocation. Run it out like a playbook.

Planning for uncertainty in a changing business environment

When the future is uncertain, preparation is key. “Embracing uncertainty doesn’t mean abandoning rigor,” said Tricia Trester, Head of Client Solutions for real estate firm Cresa. Every industry and sector has some level of uncertainty, and there are many different types. Some are unpredictable “black swan” events, such as a pandemic; others are less-eventful business occurrences, like supply chain challenges.

 

Because uncertainty introduces new risks, managing your business securely requires the ability to manage around the challenges of uncertainty. “It needs to be something that you’re thinking about all the time,” said Larry Dominique of LD Management Consulting, LLC. “I don’t know many entrepreneurs who believe that there’s just stable life around them.”

 

How you plan will determine how well your business weathers surprises. Leaders should look at every strategic plan as a living plan, Trester said, “something that constantly evolves, that you are constantly moving around.”

Scenario planning toward your North Star

Businesses should be prepared for more than one plausible future when the environment is unpredictable. “Developing a scenario plan that looks at those different realities is a really important part of the process,” Dominique said.

However, many entrepreneurs overlook the importance of having a North Star to clarify the company’s overarching goals. Having a shared understanding — including with your investors and your board — helps you make difficult choices and adds confidence to the mix.

In chaotic times, business leaders may make less-deliberative decisions. Having a long-term plan grounded in your company’s North Star serves as a solid guardrail. Like an athlete, business leaders can build out their own playbook to get an idea of what each scenario would look like. Trester advised considering many different scenarios the same way you would prepare for a presentation to a client.

While modeling scenarios, also factor in your level of risk aversion. Consider not just your sensitivities but those of your investors and your board. Communicating these scenarios to address different outcomes without seeming indecisive can be a challenge. A prudent approach might be: the best, the worst and what Trester described as “something interesting.” The latter might be appropriate if you’re planning how to scale, innovate and disrupt the market. However, it’s always important to first think about your core business and how you’re going to balance your investments and your revenue.

Be prepared to clearly lay out all the basics that investors and board members are looking for, Trester said, for instance: “This is what scenario one means for revenue, pipeline, headcount.” Have a plan and a scaling option ready, and be prepared to answer questions.

Raj Malik, Founder and CEO of Bioworld Merchandising, Inc., added that even entrepreneurs with the most thorough scenario planning can be caught short: “It’s important to have a mix of talent and team that can really think on their feet and come up with on-the-fly plans.” Yes, it’s about good planning, he said, but you need the right teams, with the right people, to make it work.

Capital decisions to fit business priorities

Decisions of how and where to put capital to work become even more fraught in times of uncertainty. “As an entrepreneur, you’ll know at every stage what your biggest need is,” Malik said, calling it a continual balancing act. Mainly, his goal has been to invest back responsibly for the key initiatives that will drive growth the next year.

Everybody, regardless of the size of the company, has capital discussions and capital decisions to make, Dominique said. Priorities become different, he added, if you’re investing in long-term initiatives, which affects cash flow — and impacts value. He reiterated the importance of scenario planning. Knowing your strategy and scenario will help to guide you in capital decisions, he said.

Milestones can help entrepreneurs make capital decisions, Trester said. For example, reaching a certain milestone may enable a purchase; a dip in business may require pulling back on staffing.

Capital decisions can also benefit from incentive opportunities, Dominique said. He recalled that when he was deciding on a company headquarters location, five cities were vying for the business. “The real estate company we’re working with was able to identify for us some state-based incentive opportunities,” he said.

Incentives aren’t only for big companies, Trester said. “People think you have to be Microsoft or something to qualify for an incentive,” she added. “Not at all true. And there are different types of incentives also in some of these municipalities that would surprise you.”

Summary 

As entrepreneurs chart a course through uncertain terrain, mastering scenario planning, making strategic capital decisions and leveraging incentives become vital tools for success. By preparing for a range of business outcomes, leaders can build resilience and position their ventures for sustainable growth. With disciplined planning, entrepreneurs can turn challenges into meaningful growth.

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