15 Entrepreneurs Explain How They Make Bold Decisions

Entrepreneurship and decision making go hand-in-hand. Some decisions like firing employees require boldness which is not always a walk in the park. The decisions you make can make or break the future of a business hence due diligence is necessary before making bold decisions.  We asked entrepreneurs and business owners how they make bold decisions and here are the responses.

#1- Not allowing indecisiveness due to fear

Photo Credit: Dave Ramsey

We are afraid sometimes, but we make the call anyway and don't let fear be the driving force of the decision. Sometimes good decision making can mean deciding to be passively active (deciding not to decide right now. – that is a decision. We have, as an organization, decided many times to simply not act on something today. That's different from being paralyzed by fear.

Thanks to Dave Ramsey, EntreLeaders!

#2- Being upfront with employees and getting a second opinion

Photo Credit: Jacob Dayan

Making a big decision in your company is never easy, especially when you have employees who count on you. To make a large decision confidently, you need to first and foremost have confidence in yourself and your ability to carry out the large decision at hand. In order to confidently make this decision, you should consider as many known/unknown and internal/external constraints that could affect this decisions outcome. Thereby limiting the chances of failure. I like to get as many opinions as I can before jumping into any major decision as I believe a second opinion is always a good thing. I also like to be upfront to my employees before making the decision (depending on the decision) and let them know of my decision and will then do my best to address any concerns. Employees tend to appreciate being notified in advance of large decisions, especially if it will directly impact them. The bottom line is you will make mistakes from time to time. However, you will learn and become stronger from them. It is important to remind yourself that failure is only determined by where you quit. You will never know the outcome if you never try.

Thanks to Jacob Dayan, Finance Pal!

#3- Asking a simple question

Photo Credit: Chris Williams

When it comes to big decisions in my business I ask myself one question, Can I gain something from this? If the answer is yes, I do it, simple as that. The best and worst part of owning your own business, especially when you run a business alone, is that you're alone. Every decision impacts me, and me only. Worse case scenario, I experience a set back. Best case scenario, I benefit from the decision. I find that when you are an entrepreneur or you own your own business there is no room for doubt. When it's all said and done your success is equal to the number of opportunities you CHOOSE to capitalize on.

Thanks to Chris Williams, Clock In Marketing!

#4- Relying on experienced advisors

Photo Credit: Matthew Wollack

Decision making really comes down to a calculated risk. Every decision I make for my business is an investment, both short and long-term plays. Like any investment, I work to understand the variables and consequences, negative and positive. I often rely on experienced advisors, not just one but many of them, and surround myself with experts in industries aside from my own. The worst decision is never making a decision.

Thanks to Matthew Wollack, Noble Child!

#5- Writing down situations

Photo Credit: Giancarlo Girardi

I’ve learnt from experience and through the great Ray Dalio’s Principles that important decisions have to be taken leaving out harmful emotions and taking enough time to learn (and synthesize) the situation before deciding. If you look carefully, after some time, you will notice that the situations you face keep repeating. It’s a great practice to write down situations (even those who look especially bold) and the decisions taken to speed up the decision process and be more consistent. For product strategy decisions, trying out things (for example as part of design sprints) is a great method to make sure that things are feasible and attractive to customers before investing too much into analysis and development.

Thanks to Giancarlo Girardi, Teamprove GmbH!

#6-Not being afraid to make mistakes

Image Credit: Zondra Wilson

Fear of making mistakes is what paralyzes many of us from making decisions. Don’t forget that even a bad choice is better than no choice at all. We live and hopefully we learn. Don’t underestimate the power of bad choices. My mistakes have helped me make bold decisions. Even the most successful people have made really bad decisions. They didn’t let that stop them from making a bold and eventually the right decision that led to their success.

Thanks to Zondra Wilson, Blu Skin Care, LLC!

#7- Considering a number of things

Photo Credit: Ray Li

Business (and life in general) is very similar to poker. You are making decisions based on limited information and there's luck at play. The problem with a lot of business owners, even really successful ones, is that the decision is much more emotional than they realize. You really have to assess the situation, understand the odds, and then make a bet. And then realize that a great decision doesn't always equal a great outcome, and a bad decision doesn't always equal a great outcome. Learn what you can and continue to optimize.

Thanks to Ray Li, Sene!

#8- Do two to three background interviews first

Photo Credit: Wendy Toth

Background interviews are a secret weapon I learned to use in my nearly 15 years as a journalist. This is a no-strings-attached conversation that you have to gather information and—in this case, confidence—quickly. Seek out professional contacts, or even friends, that have made similar decisions in scope and size. The industry or situation is of less importance in this case. The goal here is to find out from them: all the steps that led to their big decision; how they made it; and what happened afterwards. This narrative will make your big decision seem much more achievable. It will enable you to clearly picture yourself doing what needs to be done. And it will give you the courage and support to do it.

Thanks to Wendy Toth, PowerSuiting!

#9- Four steps

Photo Credit: Jonathan Prichard

I ask my employees, accountant, spouse, and friends for their opinion on the decision. Specifically, how it might affect the company positively and negatively. 2) I post in one or more topically focused business Facebook groups that I belong to and get advice from other entrepreneurs who have been faced with similar decisions. 3) I identify how much financially the company is expected to lose/gain from the decision. 4) I create my own pro/con list, add the information I received from the first 3 steps, and make a final decision from there.

Thanks to Jonathan Prichard,!

#10- Being confident

Photo Credit: Tom Corson-Knowles

Boldness comes from the confidence you have in yourself. If you aren't confident in what you do and what you offer as a business owner, how will your company survive? I try and remember this on a daily basis, as I sometimes have to make decisions that may not be the most popular of choices with my employees. It's a matter of being confident in that decision and knowing it is best for the company.

Thanks to Tom Corson-Knowles, TCK Publishing!

#11-Making decisions based on data

Photo Credit: Matt Cooper

Data is always one of the first things I take into account as a starting point for making big decisions, but I don’t only relay on the quantitative to guide me. Surrounding myself with a strong executive team who can help provide guidance, especially when it comes to identify pattern recognition from previous their companies, has been invaluable. It’s also easy to get tunnel vision when you are too close to a challenge or project, so I often gut check with others outside of my company who can offer valuable insight. This could be a board member, advisors, friends of friends — don’t be afraid to tap your network.

Thanks to Matt Cooper, Skillshare!

#12- Having information first

Photo Credit: Gennady Litvin

When you go to make bold decisions that will have a big impact on your business especially in the long run, you first want to have as much information pertaining to that decision and its outcome on your business as possible. You NEVER want to make a blind decision. Always have your facts, stats, information, calculations, etc, on hand so you can make the BEST decisions for your business and everyone in it. It’s also wise to consult the people in your organization, hear what they have to say, factor in their answers and then ultimately make your decision. You should look at every decision you make through the “lens” of your business goals. This means that the decisions you make should correlate highly with the goals of your business. If they don’t or you’re not sure if they do then I would advise you to hold off on making that decision until you can come to some sort of resolution to whether or not this decision will either hurt or help the business. There’s this false idea that says entrepreneurs are the biggest risk takers, that’s actually false because there is a difference between taking a “calculated risk” versus a dumb one.

Thanks to Gennady Litvin, Moshes Law!

#13- Less separation between thinking and acting

Photo Credit:Tim Brown

After simmering on the need in our company for bigger retainers, I finally had a a-ha moment in the shower 2 weeks ago – I told the team about it when I got to work that day, and in 2 weeks have 3 of them sold to existing customers. This – because I didn't over think it, I sold marketing retainers 3x what we normally charge, because I knew what we were offering had value, and didn't stop myself, even though I didn't exactly know how we'd deliver on promises. Because I trust myself and our staff to figure it out, it doesn't worry me in the slightest that I didn't sit their deliberating for 6 months before writing a crazy detailed description of the service. By the time we did that – a competitor would have likely implemented similar, but as it stands there's not one person offering this in our market that I know of. Ahead of the curve – requires bold action.

Thanks to Tim Brown, Hook Agency!

#14- Use my intuition by being in my peak state.

Photo Credit: Georgi Todorov

To be able to make big decisions in the best way possible, it's essential to use my intuition and for that I need to be in my peak state. It's kind of being naturally high. And for me it requires to be in the nature, to travel, being in the company of my family or close friends, creating new things and doing good for the word. In those moments I’m more connected with my inner self and with a clear view of which action I should take.

Thanks to Georgi Todorov, Digital Novas!

#15- Considering a few things

Photo Credit: Ben Creamer

In any big decision, it's important to get opinions from your entire leadership team. For example, we recently acquired new corner office space in downtown Chicago. A large financial decision such as this has long-term implications and must be weighed carefully while considering all of the input (both positive and negative) from your trusted leadership team. Perhaps more importantly, the decision-making process cannot start when an opportunity presents itself. It takes years of prudent financial management to grow a strong, healthy business that can capitalize on big opportunities and make bold decisions without jeopardizing the viability of the business. Finally, it's important to understand the long-term prospects for your company and belief in your team to deliver results. Fortunately, we have an amazing team and feel very confident investing in them for the long term.

Thanks to Ben Creamer, Downtown Apartment Company!

How do you make bold decisions in business? Tell us in the comments below. Don’t forget to join our #IamCEO Community.

Mercy - CBNation

This is a post from a CBNation writer. CBNation is a Business to Business (B2B) Brand focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts ( and videos ( CBNation is proudly powered by Blue 16 Media.

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