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A conversation with the CEO of Meetup reveals perspectives and processes that help make challenging decisions.

BY ROBERT CHEN

No matter what role you’re in, you’re constantly making decisions. As you continue to move up in your career, those decisions become more consequential. When the stakes rise, it’s easy to feel paralyzed for fear of making the wrong decision.

David Siegel, CEO of Meetup and author of Decide & Conquer: 44 Decisions that Make or Break All Leaders, knows what it means to make impactful decisions under pressure. In his first 18 months as CEO, the COVID-19 pandemic disrupted Meetups that were all in-person experiences across more than 190 countries. He led the charge to enable more than 300,000 Meetup groups to continue building their communities virtually for over 5 million online events. It paid off. He brought Meetup to its most profitable state in the company’s 18-year history with a $21.5 million swing from the lows during the pandemic.

In my conversation with Siegel, he shared his top 10 decision principles to help you make the tough calls when the stakes are high.  

INCREASE OPTIONALITY

Choose the path that creates more options for you. Siegel contrasts choosing a career in trading versus investment banking in financial services. Traders, typically, have fewer options than investment bankers a few years into their careers because of the skill set they are building. The more options you have, the more opportunities you have for serendipity. Essentially, you’re creating luck for yourself. 

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BE KIND

It’s important to be able to attract talent, and it’s harder to do that if you’re hard to work for or with. Research reveals that there is a big difference between being kind and being nice. Firing someone is not nice, but it can be kind if they are freed up to pursue a role that’s a better fit for them. Letting a low performer go is also being kind to the rest of the team who had to work with the low performer. This principle is also a good reminder to be kind to yourself. 

DISAGREE

Siegel looks to create healthy tension and quotes management guru, Peter Drucker: “The first rule of decision-making is that one does not make a decision unless there is disagreement.” One way he ensures that extroverts are not crowding out the opinion of others is to have a shared document where an idea is posited and people can share their thoughts and disagree asynchronously. Surround yourself with people who can and will disagree with you. 

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BE BOLD

Notice when fear becomes one of the default guides for your decision-making. Sometimes, it’s warranted, but other times, you might be making a more risk-averse choice that may not serve you or your organization. Of course, there are some people who may be too bold, so if that’s you, you may want to skip this principle and move to the next. Another option is to surround yourself with people who may have a different level of risk tolerance than you to give you additional perspectives to consider. 

BE SPEEDY

Siegel believes in getting a Minimal Viable Decision (MVD) out there so you can learn and iterate. He sums this up well with a quote from former U.S. President Theodore Roosevelt: 

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“In any moment of decision, the best thing you can do is the right thing, the next best thing is the wrong thing, and the worst thing you can do is nothing.” 

BALANCE SHORT AND LONG TERM

If you are a high performer, you’re likely skilled at subordinating short-term pleasures for long-term results. Keep in mind that we often have a much better sense of what we want and care about in the short term than in the long term. By slightly optimizing for the short term in your decisions, you increase your chances of being correct about the positive feelings you’ll experience, especially in the moment. You can still create space to build for the long term. Just note that whatever you’re building may or may not satisfy you when you actually get there. Also, if you’re in a joyful mood, that will positively impact your current interactions and work, which may have long-term gains. 

BE HONEST

Everything comes back to you, so it’s important to have integrity and to protect your reputation. Siegel recounts an interaction with a potential buyer when he was looking to sell Meetup. The buyer mentioned that his key deciding factor for the deal was his comfort level with the CEO. As part of the due diligence, the buyer found that a good number of people loved working with Siegel, but a few people really hated him as well. Due to this binary opinion, the buyer decided to pass on the deal despite some of these experiences being decades old. 

DO WHAT IS RIGHT FOR THE BUSINESS

Whether you lead an organization, team, or project, the decisions you make should be about the goal that the group is looking to accomplish, not your own personal goals. Of course, the right incentives should be in place so what’s right and good for the business should be good for you as well. Resist any temptation to put your own needs above the organization. 

AVOID DECISION SURPRISES

Most people, professionally or personally, don’t like being surprised by decisions that impact them. Siegel has realized that, in most cases, everyone knows everything, so it’s better for you to communicate decisions across the organization whenever you’re not bound by confidentiality clauses. 

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UNDERSTAND YOUR BIASES

Our decisions are impacted by our natural biases. You’ll want to learn how common biases impact the decisions you make (and how to outsmart them). Siegel highlights the recency, confirmation, status quo, and sunk-cost-fallacy biases as the ones that come up for him the most. There are numerous others

As we wrapped up our conversation, Siegel shared an excellent exercise to help anyone become more attuned to their decision-making tendencies. Since we learn more from our failures than our successes, he suggests: 

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  • List out the five business or life mistakes you’ve made 
  • Note what happened and the specific issues or behaviors that were present in each mistake 
  • Reflect on any patterns or common derailers 

Robert Chen is a partner at Exec|Comm, a global business development and communication skills training company. He is the author of Selling Your Expertise: The Mindset, Strategies, and Tactics of Successful Rainmakers.


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