• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
CommentaryLeadership

Here’s the ‘Right’ Way for Every CEO to Fail

By
Russell Fleischer
Down Arrow Button Icon
By
Russell Fleischer
Down Arrow Button Icon
July 23, 2016, 10:00 AM ET
Stressful day at the office
Photograph by PeopleImages.com — Getty Images

Russell Fleischer is a three-time software CEO and currently a general partner at Battery Ventures, a global investment firm, where he focuses on investments in enterprise software.

Building a business is challenging, and mistakes are inevitable. Sometimes those mistakes are catastrophic, and your entire business model gets scrapped. This is politely termed a ‘pivot,’ and many successful CEOs have pulled off one (or several). But these days, in a volatile stock market, investors are scrambling for safety, and a CEO courting big-time “failure” in any industry inspires less confidence. Bouncing back from a substantial failure just may not be possible.

So how do you avoid catastrophic failure? Somewhat counter-intuitively, I think it’s through a series of smaller failures. As a software-company CEO who navigated up and down markets, I always urged my teams to “fail fast,” but small. In other words, don’t deliberate excessively—be thoughtful, but make key decisions and move on, knowing you can fix some mistakes later. Now that I invest in software companies, instead of managing them directly, I still like this approach. I don’t believe it’s very tough to implement—as long as you can focus on it and block out external distractions.

At a high level, creating an environment that encourages decision making without the fear of failure frees up an entire organization to execute against its objectives and, most important, take care of customers. But most operations I’ve seen are surprisingly reluctant to experiment in big and small ways—let alone make quick decisions.

I saw this constantly when I ran my businesses. Many of my teammates felt they needed to conduct an exhaustive study on the smallest of decisions before bringing an answer back to the broader team. Pricing a new product, for example, was always a source of consternation. My marketing teams would want to scour the landscape, find every possible competitive example, enlist consultants, spend time with industry analysts and create complex algorithms before making a pricing decision. You get the idea.

I’d reorient them by reminding them we weren’t dealing with a heart transplant patient on the table. I told them that if we make a mistake, we can fix it — so let’s run a few test cases, find real-world situations where we can work with live prospects and test pricing that way. After a couple of sales cycles we’d have it right and could go to market more broadly. That iterative approach served us well and helped us get the details right for a broader audience.

Another thing I liked to encourage my team to do was “act,” instead of “meet.” We were so incredibly busy, we didn’t realize how many minor decisions we tabled through endless discussions — or how those everyday delays gummed up the works.

Now, as an investor in mid-sized software companies, I see this same scenario play out all the time. When you’re leading a business in growth mode, every decision feels enormous. It’s easy to become paralyzed. But you shouldn’t —and, instead, should opt to Think. Decide. Act. Here’s how my motto works in more detail, and how it allowed the companies I ran to move forward more efficiently, try more new ideas, and make real progress toward goals.

Think.

For every 10 decisions you make, get seven right and fix the other three later. I’m not encouraging you to make rash decision, but you can’t spend too much time on the thinking stage. Discussion and deliberation all matter. However, the key is to move through this phase quickly — go over the evidence, discuss pros and cons, determine exactly what’s holding you back from making a decision, and whether that’s important. Schedule the moment of decision in your calendar, and set a timer for discussions if you have to. Keep the thinking stage active, concentrated, and time-delimited.

Decide.

If you let the pressure of running a project or a company get to you, you’ll keep putting off the decision. That delay can be fatal. Once you’ve processed the evidence in favor of each potential option, just choose. Remember, we’re aiming to make 10 decisions and get seven of them right. That’s a 70% success rate. That’s a C on a multiple choice test. Decide and move on.

Act.

Once you’ve decided, put that decision into action immediately. Come up with a plan, calendar it out, and get moving. I’ll take a good answer today versus a perfect answer in a month. You can’t fix your three mistakes until you’ve made them. Take action fast. If it looks like your plan isn’t working, go back to step one, think some more, and repeat.

The only way to realize your company’s full potential is to keep making the small decisions that move you forward incrementally every day. So Think. Decide. Act. It’s that simple.

About the Author
By Russell Fleischer
See full bioRight Arrow Button Icon

Latest in Commentary

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map

© 2025 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.


Most Popular

placeholder alt text
Economy
The $38 trillion national debt is to blame for over $1 trillion in annual interest payments from here on out, CRFB says
By Nick LichtenbergDecember 17, 2025
2 days ago
placeholder alt text
AI
'Robots are going to be amongst us': Qualcomm exec says buckle up for the next 5 years. Your car is going to be the first shoe to drop
By Nino PaoliDecember 17, 2025
2 days ago
placeholder alt text
C-Suite
Red Lobster CEO Damola Adamolekun says the key to being a better leader is being a better person: ‘Leadership is self-improvement’
By Sydney LakeDecember 17, 2025
2 days ago
placeholder alt text
Success
As millions of Gen Zers face unemployment, McDonald's CEO dishes out some tough love career advice for navigating the market: ‘You've got to make things happen for yourself’
By Preston ForeDecember 16, 2025
3 days ago
placeholder alt text
Success
Britain’s defense chief calls on Gen Z grads leaving university to skip corporate jobs and join the military as war with Russia becomes a growing risk
By Emma BurleighDecember 17, 2025
2 days ago
placeholder alt text
Future of Work
LinkedIn CEO says it's 'outdated' to have a five-year career plan: It's a 'little bit foolish' considering the pace AI is changing the workplace
By Sydney LakeDecember 18, 2025
15 hours ago

Latest in Commentary

unemployed
CommentaryLayoffs
The AI efficiency illusion: why cutting 1.1 million jobs will stifle, not scale, your strategy
By Katica RoyDecember 18, 2025
12 hours ago
Muddu
CommentaryIT
IT service is reaching its breaking point. At Salesforce, we see 3 tipping points
By Muddu SudhakarDecember 18, 2025
16 hours ago
small business
CommentaryLayoffs
Our data shows that companies of 500 and fewer workers mostly avoided the AI layoffs. They’re making AI work for them
By Gabby BurlacuDecember 18, 2025
16 hours ago
Sophia Romee is the General Manager of the GenAI Studio at the College Board
CommentaryEducation
Gen Z is on the fence about AI in the classroom. That’s a good thing
By Sophia RomeeDecember 18, 2025
16 hours ago
Tim Parker
CommentaryAutos
How Bentley’s brand is creating business advantage in disruptive times 
By Tim ParkerDecember 18, 2025
19 hours ago
layoffs
CommentaryLayoffs
The AI layoff wave is just beginning — and it’s by design
By Kevin OakesDecember 17, 2025
2 days ago