Peter Doyle, Founder & Chairman @ Consult Group Worldwide.
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Over three decades of advising founders and boards on governance and ownership questions, I have read more term sheets and shareholder agreements than I can count, and one pattern never stops surprising newer operators.
The same founder who will agonize for a month over which project management tool to adopt will initial a vendor’s boilerplate terms or a routine lease renewal inside 20 minutes, because those decisions arrived wrapped in the language of routine rather than announced as decisions in their own right.
Nobody plans it that way. It happens because most people size a decision by how urgent it feels in the moment rather than by what it actually costs to undo.
Size: Not The Right Measurement
The instinct is to treat “important” as a function of dollar value or visibility. A hiring decision for a senior role feels weighty because a person’s livelihood is attached to it. A pricing change feels trivial because it can be adjusted with an email. But cost and consequence are two different axes, and conflating them is where a lot of founders lose their footing.
The pricing change might genuinely be reversible within a billing cycle. The hiring decision, if it goes wrong, might also be reversible within a quarter, with real but bounded cost. Neither compares to a decision that quietly reallocates who has the final say when it matters most, what precedent gets set with your first institutional investor, or what a contract clause commits you to five years out with no exit ramp.
Those decisions do not announce themselves as the big ones. They often arrive dressed as paperwork.
What Can Get Missed Because It Looks Like A Formality
The clearest public illustration of this I have seen sits inside WeWork’s 2019 IPO filing.
When WeWork filed to go public in 2019, its IPO paperwork laid out a share structure that gave founder Adam Neumann much more voting power than other shareholders. Class A shares came with one vote each, while Class B and Class C shares carried 20 votes per share. Neumann owned or controlled nearly all of the Class B and Class C shares, giving him majority control over shareholder votes even after the company went public.
The filing also said Neumann would control more than half of the company’s total voting power after the IPO, making WeWork a “controlled company” that could bypass certain corporate governance requirements for publicly traded companies.
WeWork’s planned IPO fell apart in 2019 amid investor concerns over the company’s losses and potential conflicts of interest involving Neumann, who stepped down as CEO that year. The company eventually went public in 2021, but its financial troubles continued. By November 2023, WeWork’s stock had lost more than 99% of its value, and the company, once valued at $47 billion, filed for Chapter 11 bankruptcy protection.
The Discipline Most Businesses Never Build
This is not a rare failure of judgment. A 2026 Deloitte survey found that 57% of organizations operate at a low level of decision-making maturity, with minimal training or structure around how decisions get made in the first place.
Most companies do not have a broken decision-making process. They have no process at all, just a single default setting applied uniformly, whether the choice is which vendor to use this month or which investor gets a board seat for the next decade.
Founders who run lean operations often take pride in moving fast on everything, and speed is a genuine advantage on the reversible decisions. Applied to the irreversible ones, it is closer to negligence wearing the costume of decisiveness.
Sorting Before Deciding
In my experience, what separates operators who make running a business look almost easy from the ones who are permanently exhausted by it is not raw judgment. It is a habit of sorting before deciding.
Before any meaningful choice, they ask a narrower question than “is this important”: What does it cost, in time and options, to reverse this if it turns out to be wrong?
A decision that is cheap to reverse earns speed and a light process, even if it looks consequential on the surface. A decision that is expensive or impossible to reverse earns friction on purpose, even if it arrives looking like routine paperwork, a standard clause or a customary structure nobody thinks to renegotiate.
That second category is usually smaller than people assume, which is precisely why it deserves outsized attention when it appears. Spreading scrutiny evenly across every decision does not produce careful businesses. It produces tired founders who have used up their diligence on the decisions that never needed it, and have none left when the one that mattered walked in disguised as a formality.
The businesses that get easier to run over time are rarely led by the most decisive people in the room. They are more often led by the ones who decided early which decisions were allowed to be hard.
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