Good morning, dear reader,
Welcome to the first edition of Small Truths.
Over the last few weeks, I spoke with a dozen professionals—startup founders, investors, and not-for-profit leaders—about the relationship between truth-telling and trust. They all agreed on two things: it's extremely important, and no one is talking about it.
Why? Because honesty feels traditional, boring, even clichéd.
But when I asked them how to actually do it—how to tell hard truths at the right time, in the right way—I found some answers and a more burning question:
What separates leaders who earn trust from those who lose it?
After observing nearly 200 companies, Pradeep K Jaisingh has identified a pattern.
“I don’t claim to know which founder will be successful, but there is a pattern I have observed that stands out,” said Jaisingh, who is a founder, coach and angel investor with investments in nearly 200 companies. He is also a fellow at the Distinguished Careers Institute at Stanford University and the founder and chairman of Healthstart, a healthcare incubator.
“Roughly 30% of founders share clear updates, including good news, bad news, and even the ugly details. Another 60% may have the intent to do the right thing, but they are reluctant to share the bad news. This pattern of avoiding the truth also shows up in seemingly inconsequential communication systems within the team,” Jaisingh believes.
The remaining 10%? They're deliberately fraudulent.
The 30-60-10 rule
It is the little things that first-time founders overlook that, within a few years, become key differentiators. The successful entrepreneurs create a structure of feedback across the company. They bring people early on who establish checks and balances, and they want to be shown the mirror with sharp objectivity. This kind of culture means they are able to walk the talk consistently.
The second kind of founder is more secretive, restricting communication outside the founder group, and will not prioritise transparency. At some point, sooner or later, things will start to unravel. There will be a negative spiral that will become harder to control.
Jaisingh is sure that while some founders may have ill intent, most know the value of truth but don't know how and when to share what and with whom. They miss the subtle indicators of diminishing accountability in the team culture until the challenges become too big to fix.
Some walk the straight and narrow. Others fall for the greatest lie: that building trust takes time and that teams, investors, customers, and the world in general will be patient with them.
Truth-telling compounds faster than you think
But those who master truth-telling—even when it's uncomfortable—unlock exponential returns. Take Deepak Goel, an investor, mentor, and serial entrepreneur who has judged business plan competitions at the University of Chicago Booth School of Business and Haas School of Business at UC Berkeley.
"A client wanted us to do a project for $25,000. I told them to spend $3,000 and decide later if they wanted to spend the remaining $22,000. They didn't need to spend any more on that project. But two years later, they referred another client to us who brought business worth more than $50,000.”
Goel has even founded a product on this principle. POOLit is a trust-based professional network built on the premise that in high-trust environments, everyone wins. But when distrust is high, the market wins.
In Goel's experience managing ProductStudio, a software development services company, the quality of the transaction or money exchanged trumps trust when there is general distrust against the leader, system, and seller. It's why users are more likely to leave negative reviews than positive ones.
Trust-building is a constant journey against the current. Even after it's built with users, team members, and investors, it's never stable. Left alone, it deteriorates over time.
In his own leadership, Goel practices specific rituals. These include always answering the 'why' behind every decision, like changing the compensation structure.
"As a leader, constantly explain the rationale of organisational moves, encourage critical questioning in all-hands meetings, nurture psychological safety by conducting anonymous surveys, and keep a check on the pulse of the company," he said.
The same principles apply in the not-for-profit world
These same dynamics play out wherever funding depends on trust. In the not-for-profit sector, the stakes for communication are equally high.
Svetha Venkatram, a public policy professional, has had previous experience supporting non-profit applications looking to build pilot programs.
“I observed that many applicants who may have been doing good work in their respective fields were often not able to communicate their ideas in a way that is easy to understand. Stand-out non-profits were those who paid careful attention to how they communicated their ideas – either the founder’s personal journey, or organising a meet-and-greet with intended beneficiaries,” she said. “Clarity of their ideas mattered just as much as the substance of the work. Work done by the Wheelchair Basketball Foundation of India (WBFI) and the Government of Telangana’s WE-Hub are some success stories that come to mind,” she added.
Both WBFI and WE-Hub, a state-led incubator that fosters and promotes women entrepreneurship, showcase that the same pattern of sharing their story clearly and consistently has earned them support from various stakeholders.
Some kind of a pattern emerged. Truth presented clearly, at the right time, in the right format, earned trust and opened doors.
What I am reading
How to Do Great Work by Paul Graham
The core of being earnest is being intellectually honest. We're taught as children to be honest as an unselfish virtue — as a kind of sacrifice. But in fact, it's a source of power too. To see new ideas, you need an exceptionally sharp eye for the truth. You're trying to see more truth than others have seen so far. And how can you have a sharp eye for the truth if you're intellectually dishonest?
One way to avoid intellectual dishonesty is to maintain a slight positive pressure in the opposite direction. Be aggressively willing to admit that you're mistaken. Once you've admitted you were mistaken about something, you're free. Till then, you have to carry it.
If you don’t want to read it, you can listen to the summary on YouTube here.
I conduct bespoke coaching programs for ambitious, purpose-led professionals and teams who want to craft authentic, trustworthy narratives. If you want to secure a spot, please apply here.
What did you think of this first edition? I'd love to hear your feedback—just hit reply and let me know what resonated (or what didn't).
See you next week for Small Truths #2.
Yours,
Ruhi