Making Business Decisions Under Pressure: Are you Carefree, Careful, or Careless?

Steve Schloss
7 min readJun 2, 2022


Photo credit: Andres Ayrton

“Wherever you see a successful business, someone once made a courageous decision.” Peter Drucker

I stood in front of a room of high-performing, high-growth company CEOs last week and asked a simple question: what’s keeping you up at night? Several hands immediately shot up, starting with one CEO who openly spoke about retaining top engineering talent even as a globally remote-first company. Others spoke of burn rate, lower valuations, organizational transparency, recruiting, and the changing dynamic of the modern workplace. Like many CEOs, they are facing new opportunities and challenging decisions against the backdrop of market disruption and economic headwinds.

Later that day, one CEO came up to me and mentioned an additional challenge of managing the stress, demand, and volume of decisions especially under pressure. We talked about his approach, the quality of his leadership team, to whom he looks for counsel, and what habits or behavioral changes he might consider making to help alleviate some of what he described.

I also chose to share a personal story with him from just two weeks prior.

The Fearful Decision Maker

I mentioned that I was faced with an important business decision for which I considered conferring with a trusted colleague, my wife, or just going with my gut. On this day, I actually chose another route, slowing things down a little and shutting down the laptop, electing to book a tee time to engage in my lifelong obsession: a round of golf.

I opted to play a public course just down the road. Playing as a single golfer, I joined three strangers there on the first tee. A wonderful part of the game is that over four hours these “strangers” could become fast friends, armchair philosophers, silent partners, or for a few dollars, willing competitors.

Our group included a husband-and-wife tandem of small business owners and a former law enforcement leader, I will call George. Like me, George enjoyed walking and carrying his golf bag. He was a passionate golfer who started seventeen years ago … at the ripe old age of 67.

Yes, George, at 84, was really a kid in a proverbial candy store on the golf course. He and I talked about many things while playing and found common ground in an aligned perspective for the game’s ethos. We also talked about his begrudging decision process to retire … just over the course of the past year.

Decision-wise, however, George had a far more pressing issue. Some golfers have a rather difficult time starting their golf swings and George was among this group. Like the kid who never swings her or his bat in Little League for fear of striking out, or concern for the speed of the ball hurdling at them, there is a “go” / “no-go” moment in golf that — for some — gets visited and re-visited in a mere matter of seconds.

In George’s case, this moment coincided with him standing over the ball at address and entailed the constant gripping and regripping of the club and some very specific leg, arm, and hip movements intended to make him feel comfortable and confident.

Over 18 holes, each shot required about thirty seconds of gesticulation while George cycled through the full battery of these habits. (In all honesty, it was a rather painful decision process to watch as we all waited to hit our own shots).

But it was even more painful for George.

See, most golfers know offering advice in the middle of a round, especially among strangers, is sort of frowned upon. In this particular case, being an executive coach and advisor, I wanted to help George in some small way. So, I politely asked why he was so frozen in his swing decision-making? I simply wondered if there might be some way to evolve his outlook, behavior, or form a new habit.

George looked at me and shared an honest answer: he truly didn’t know why he did what he did, nor did he know what to do differently. But he did share with me that since he started playing the game later in life, he felt a certain sense of pressure to perform around other golfers who had started at a much younger “and more confident” (his words, not mine) age.

George, in essence, was a fearful decision maker.

Before the round ended, I had offered him a few pointers and helped him consider how he might approach the swing decision process with a little less self-induced pressure and perhaps a greater sense of possibility versus fear.

Regardless of playing level, the game of golf is fun, even while being difficult. Golf is truly a deeply mental game which causes the most accomplished and successful people to do strange things counter to the person who others may experience in the board room or around the leadership table.

Or maybe not.

The Pressure to Perform

While my son was still in the throes of high school, I used to tell him making a bad decision was easy. It required no thinking or recognition of the implications of his choice. In the moment of impulse or reaction, the ability to stop, consider, and pivot might seem wholly inconvenient and uncool, but for a high school kid, it’s an important aspect of self-awareness oriented to ultimately serve one well in life.

Brought forward, leading any organization today features a continuous series of decisions with an assortment of implications: financial and operational, talent and cultural, internal and external, strategic and tactical, individual and team, short- and long-term. The best and worst executive-level decision makers learn, adapt, or struggle to prioritize, tradeoff, delegate, collaborate, analyze, gut-out, pivot, and communicate. And most subject themselves to frequent questioning by key stakeholders once their decision is eventually made.

Like George (and the high-performing, high growth company CEO), the pressure to perform is constant and unending.

Regardless of the decision, executive leaders apply their own filters and approaches to help themselves “cope” under pressure. Some remain steadfast in their decision regardless of input and feedback, others waffle and defer, some pivot based on stakeholder sentiment, and some choose to “grant” accountability to front line leaders and their respective teams.

Among senior executives with whom I have worked, individual decision-making processes often speak to values, character, and integrity, more so than mere competence and credibility. How one makes decisions also speaks to the importance of knowing what one DOES NOT know (as we learned through the pandemic), the power of seeking advice, and recognizing that the organization you lead is part of a connected system of external stakeholders you serve, and who can also serve you.

Still, there are many real-life C-suite leader archetypes with whom I have engaged who are their own worst enemies:

· The process leader who could not decide without poring through reams and reams of data (often with their entire team present) just to be extra sure that saying yes or no was considering every viable angle. Then, after that litany, they often change their mind after the fact.

· The self-important leader driven by vanity, reputation, and personal brand, followed by fear-based check-ins when others did not show support for, or interest in, following through on their decision.

· The visionary leader who trended toward compulsive, emotional, and “shiny object” decision making, resulting in a lack of clarity and continuous workplace disruption. This leader also seemed to derive a personal “rise” from spurring instability.

· The consensus leader who down spiraled to indecision in areas that required greater personal ownership and directness. Upon moving forward, this leader often undercut themself by showing a lack of confidence in trusting their own decisions.

· The directive leader who saw every decision as a top-down process with anticipated swift follow-through and action. This leader often asked for feedback from the executive team before making the final choice, but only to placate them and other senior leaders who were invited to weigh-in.

When offered feedback or suggestions, each executive responded with varying levels of interest, defensiveness, minimization, or a simple recognition that they could be more situationally effective under pressure, acknowledging that old habits are hard to break.

The challenge of making decisions in today’s climate continue to test all of us.

In the end, while George struggled with his golf swing decision making, I considered my own decision-making strengths and weaknesses. Consider the same questions for yourself or others:

1. How would you rate your decision-making ability under pressure?

2. What examples can you think about that suggest strengths and weaknesses?

3. In what ways are your approaches the same or different under different scenarios?

4. What would your leaders or peers say about your decision making under pressure? Your team?

5. Where do you seek counsel? Maybe more importantly, how do you factor or consider the counsel you seek?

6. What practices or behaviors have you learned to be a more effective decision maker in those pressure moments?

7. Finally, are you like George and the CEO I referenced: open to listen and learn, from those you also partner and serve?



Steve Schloss

Coach and advisor to CEOs, executive leaders and teams. Sharing thoughts, observations, and ideas around leadership and culture. Trying to break 80 more often.