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Three of the Most Empowering Words a Boss Can Say

Todd Gibby
Nov 4 · 5 min read

It was 2001; and my boss was impressive — some would say intimidating. A whiz-kid founder and CEO of a fast-growing start-up that had raised capital at lofty valuations, he was precociously business-savvy and had a seemingly unshakable self-confidence. All of which made it that much more remarkable when he put his hands up and uttered those unforgettable words: “You convinced me.”

The truth is that we had very different leadership styles; and I often found myself filing the minority report when it came to debates among our company’s leadership team. But on this day, (and many times thereafter), I was grateful to be offered the opportunity to successfully make my case. I remember being surprised that day about the outcome itself, and about the impact it had on me — I’ll never forget that feeling of having a real voice in the business. Fast forward twenty years: I participate in many similar business debates, but now I often find myself in the senior role. I’ve learned that those same three words have enormous power, not only to make someone’s day…but to profoundly influence how businesses tackle challenges. I try to keep them top of mind and use them whenever possible. Below are some thoughts on why this practice works so well and some safety precautions when wielding this powerful tool.

At a primal level, it’s obvious why this can be such a potent approach — it is a succinct and unambiguous way for leaders to share decision-making authority with less senior folks. Beyond that, though, some subtle nuances make it consistently effective in small-scale growth companies:

· Growth Posture: Companies that are stagnant can operate in a command-and-control way, with rigidly unchanging roles and responsibilities. That is wholly untrue in fast-growing businesses. The only way to scale is with agility and delegated decision-making. Otherwise, leadership inevitably becomes the bottleneck. Takeaway: This approach clearly signals that everyone is expected to meaningfully think and contribute, not just follow orders.

· Meritocracy of Ideas: Although many tech companies aspire to offer meritocratic environments, the reality is far more complex. But this simple act of leaders being “convincible,” creates an isolated instance where the best ideas truly win. In terms of getting to a good answer, this is an incredibly powerful step. Takeaway: This small act won’t change the world…but it almost certainly will create a better environment for navigating a particular issue at any moment in time.

· Open Mind: Let’s face it, company leaders tend to be a pretty smart lot; and they often have access to far more information than others in the organization. This combination can create a myopic sense among leaders that they are best positioned to make all decisions. But when one is available to be convinced, they are quite literally opening themselves to a whole world of new and valuable perspectives. Takeaway: Being convincible turns the passive concept of open-mindedness into something readily actionable and based in trust.

· Underrated Humility: Countless studies of leadership point out the efficacy of leaders demonstrating humility and practicing vulnerability (two of my favorites are Jim Collins’ “Good to Great” and Daniel Coyle’s “The Culture Code”). What better way for a leader to genuinely embody intellectual humility than to verbally acknowledge to others that his / her position has been revised by their input. Takeaway: In a world where it can be a real challenge for many leaders, this is an easy way to credibly embrace the highly effective trait of vulnerability.

Like any powerful instrument, though, using this approach comes with related dangers. Below are a few cautionary thoughts for the safe operation of this tool.

· Clarify What Worked: It’s not enough for leaders simply to communicate that their opinions were swayed; rather, it’s important to explain what did the trick. If logic, reason, risk, results, and data were the central pillars of the winning argument, be sure to articulate that. Doing so will ensure similarly constructed arguments from others in the future. But be careful — if leaders simply reward the squeakiest wheel in a debate, they should be prepared to acknowledge that and to deal with the consequences. As Walker White says: “You get what you tolerate.”

· Don’t Manufacture Opportunities: People are smart, and they can smell insincerity a mile away. Don’t take an artificial position, for the express purpose of later making a public show of changing it. That is a great way for leaders to predictably erode their own credibility. Like letting your kids win in board games — they know you’re doing it…and they don’t like it. Make them earn it; it’s better for everyone.

· Don’t Say it If You Don’t Mean It: If the business case hasn’t been convincing, don’t falsely claim that it has. This can be tempting for leaders, particularly when dealing with the previously mentioned squeaky wheel. But don’t succumb to this near-term temptation; it only creates problems downstream. Which, in turn, can lead to…

· Don’t Re-trade: Re-trading (agreeing in a meeting to a given position, only to question or lobby to reverse that decision later) is a toxic behavior that poisons many organizations. It’s bad enough when individual contributors do this…don’t EVER be the leader who re-trades. Deceptively claiming to have been convinced is a dangerous first step that can put leaders on the slippery slope toward toxic re-trading downstream. Just…don’t.

Looking back, I realize how much I learned from that boss back in the early 00’s; and no lesson was more valuable than this one. Having a legitimate forum to change our CEO’s thinking offered a feeling of empowerment that I still haven’t forgotten. And, I was a member of the senior leadership team…which further highlights just how impactful it can be when leaders create this type of environment all throughout their organizations. A big step in this direction can be taken with three simple words: “You convinced me.”

Made Not Found

In SaaS businesses, operating results are earned every…

Todd Gibby

Written by

SaaS operator-turned-investor | Founder of Lock 8 Partners | Sharing observations, thoughts, and lessons learned from the ever-educational journey.

Made Not Found

In SaaS businesses, operating results are earned every single day; and good businesses are made, not found. Writing here about building organizations, learning from the experience, and appreciating the ride.

Todd Gibby

Written by

SaaS operator-turned-investor | Founder of Lock 8 Partners | Sharing observations, thoughts, and lessons learned from the ever-educational journey.

Made Not Found

In SaaS businesses, operating results are earned every single day; and good businesses are made, not found. Writing here about building organizations, learning from the experience, and appreciating the ride.

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