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So much of life comes down to decision making. Deciding who to work with. Deciding what to work on. Deciding how to scale your product. Etc.
There aren’t many great guides to help you improve your decision making, and so I got in touch with Casey Rosengren, a founder and executive coach based in New York, who has lots of experience helping founders and teams make better decisions.
I asked him to write the most useful possible guide he could to helping people with decision making, and below was what he put together. I think it’ll be helpful to you!
Whether you’re building a startup, managing a team, or choosing a career path—decision velocity determines your trajectory. If you can increase decision speed without sacrificing quality, the benefits compound over time.
Consider this: If it takes four attempts to hire a great head of sales, and you take nine months to replace each failed hire, you’ve burned three years. Cut that to six months per decision, and you save a year. That could be the difference between capturing the market or running out of cash.
Yet, I often see founders drag their feet on key decisions, like:
Firing a senior executive who isn’t working out
Hiring for a role they’ve never hired before
Making a significant shift in strategic direction
Scaling back the business to extend runway
Investing in an area of the business where they have less expertise (sales, marketing, etc.)
These are strong founders, often with 7-8 figures in revenue—and yet, it still happens. In fact, I’d say a consistent part of my work with clients is helping them notice when they’re avoiding a decision that they really should be acting on.
Why does this happen? And how can you overcome this to make decisions faster?
In the 1960s, NASCAR teams discovered that raw horsepower wasn’t enough. To win races, they had to reduce aerodynamic drag. Thus entered the “aero wars”—a period that revolutionized racing. Suddenly, the shape of the car mattered as much as the engine.
Startups have similar physics. You can add horsepower—work harder, hire more people, raise more capital. But if decision-making drag slows you down, that extra power gets wasted fighting resistance instead of creating forward motion.
Two primary forces create this drag:
Experiential avoidance (avoiding emotional discomfort)
Time discounting (overweighting short-term pain)
Understanding these forces—andhow to reduce them—is key to accelerating your decision velocity.
When you avoid a decision, it’s often not the decision itself that you’re avoiding, but the uncomfortable thoughts and feelings that surface when you approach it.
For example, I worked with a venture capitalist who spent years thinking about leaving to start a company. Every time he neared the decision point, a cascade of difficult thoughts emerged:
“Is this the right idea?”
“Am I really the type of person who starts a business?”
“Am I throwing away a perfectly good career in VC?”
“What will my colleagues think if I fail?”
These thoughts triggered waves of doubt and fear. The closer he got to deciding, the more intense they became. As a result, he stayed in venture capital years longer than he’d intended.
Behavioral psychologists call this “experiential avoidance”—the drive to escape unpleasant internal experiences. It’s a powerful force because startup decisions involve uncertainty, which is psychologically uncomfortable. Moreover, every decision requires letting go of alternatives—what psychologist Irv Yalom describes as a “mini-death.”
But not deciding is itself a decision—and inaction is often more costly than a suboptimal decision made quickly.
To overcome experiential avoidance, ask yourself:
What discomfort am I avoiding?
What could make that discomfort worth facing?
Most of the time, the pain associated with tough decisions is unavoidable. But you can choose how to respond to it. Clarifying what you’re fighting for provides the fuel to push through the resistance.
Humans systematically overweight immediate consequences and underweight future ones—a bias that likely helped our ancestors survive immediate threats, but can sabotage modern decision-making.
Behavioral psychologists call this “time discounting.”
For example, a bootstrapped founder I advised was facing a major cash crunch. After a growth period where she’d made new hires, her sales pipeline had suddenly dried up, leaving only three months of runway. She knew the logical move was to right-size the company, but she felt guilty about letting go of talented hires who had done nothing wrong.
Her plan was to wait 1-2 months, hoping sales would rebound before taking drastic action. I invited her to visualize two scenarios: what the company’s cash position would look like in two months if sales hadn’t recovered, versus what her runway would be if she acted immediately.
The stark contrast made the decision obvious. She made the cuts that week, doubling her runway and giving the company enough breathing room to fix sales before rebuilding the team.
Reducing This Drag:
To overcome time discounting, ask yourself: “What’s the real cost of delaying this decision?”
When clients struggle with this, I have them visualize living with the status quo for three, six, or twelve months. It’s easy to postpone firing someone for another day. But imagining working with that person for another year often clarifies the situation’s unworkability.
Sometimes, this question alone is enough to spark action. Other times, it can help clarify how long you’re willing to put up with a situation before it becomes untenable. Either way, you’ve reduced the drag this force exerts on your decision-making.
Now, it’s important to note that sometimes, deliberating on a decision pays off. In particular, one-way doors—selling your company, major pivots, shutting down a product line—deserve careful consideration.
However, I often see founders delay decisions that are 100% reversible. For example, a serial founder I worked with once spent weeks deciding whether to bring on a potential cofounder for a new project, despite the fact that:
They could easily part ways if it didn’t work out
The only way to truly evaluate fit was to try working together
With a little encouragement, he decided to bring the person on, and it turned out his misgivings were right! The person didn’t work out as a cofounder, which meant he could move on to meeting and vetting new people instead of being stuck in analysis paralysis.
When stuck on a decision, rather than endless deliberation, try to find a way to prototype the decision as quickly as possible in a way that’s “safe enough to try, small enough to fail.”
If you’re thinking of selling your company, talk to former execs who have left the acquirer about what it’s really like to work there. Have conversations with other exited founders about their experience. Take a few days fully offline and see what it’s like to step away from the business.
While reflection is an important part of the decision-making process, it’s only as effective as the data you have to go on. And taking action in the world is how you get more data.
One tactical way to maintain high decision velocity is to implement a weekly decision audit. Each week, ask yourself:
What decision am I potentially avoiding?
What is it about this decision that I feel pulled to avoid?
What’s the real cost of delay?
For example, I once worked with a founder who had early signs of traction, but was dragging his feet on ramping up the team. He wanted faster execution, but he wasn’t sure if hiring would help or just add complexity. So he sat on the decision for weeks, hoping for additional clarity.
When we introduced the weekly decision audit, he realized this question had been weighing on him for far too long. He couldn’t think his way to the “right” answer—the only way forward was to act, get data, and reevaluate. He decided to hire aggressively, knowing he could always scale back later if needed.
This simple practice shines the light on slow decision-making before it compounds into major delays, allowing you to build momentum instead.
In startups and in life, velocity often beats perfection. A good decision made quickly often outperforms a perfect decision made slowly, because speed enables iteration and learning.
Every delayed decision creates a cascade of downstream delays. A quick decision made well creates momentum and gives you data for future decisions. Sometimes, increasing your decision velocity is all it takes for a project to take off.
Ultimately, no one gets through life without making significant decisions. And it’s the choices we make that define the companies we build and the lives we ultimately lead.
So I’ll leave you with one question:
What one decision have you been avoiding that you could face today?
The clock is ticking. Make the most of it.
Casey Rosengren is a founder and executive coach based in New York.
If you’re a founder or operator stuck on a key decision—about your team, product, or career—he offers a free 30-minute triage call to help you get clear and move forward. Or follow him on Substack: Human Missives.