When how you operate in your personal life bleeds into your professional life, it’s often hard to know what boundaries are needed and where to apply them. With decision-making, that boundary is speed — knowing when fast is right, and when it isn’t.
With everyone using Google searches, smartphones, laptops, and now AI, we’ve trained ourselves not to deep-dive when we need to. Devices and increasingly complex software give us quick answers, and we’ve stopped questioning whether a quick answer is actually enough.
While CEO of my former company DragonDev, a major telecom client asked to renegotiate my existing contract after a recent merger of theirs — a deal potentially worth roughly $175K a year to my SMB.
Both sides decided to use the existing contract as a starting point for terms, which is normal in any renegotiation. The previous agreement included a termination clause allowing either party to exit with 30 days’ notice. As part of the renegotiation process, terms were added, terms fell out, round after round, across seven versions. But by round 5, I was in TL;DR (too long; didn’t read) mode. Each new version came back “approved,” and I moved fast — trusting that approval meant the whole document still held, rather than slowing down to check it against the deal-breakers that mattered most to me.
It was on me to catch it, and in rounds 5 and 6, I didn’t.
In the 11th hour, I discovered my client had changed language that voided certain non-negotiables for me in round 5, a change I had missed twice more. Going back two steps at that point meant blowing the hard deadline my client needed to close the deal. When I raised the issue of the language impacting my deal-breakers, my client exercised the 30-day termination clause and walked away. A mistake I have not repeated since.
Reflecting back, I realize I lost that deal because I was moving too fast when it mattered most — I trusted the approvals and the process instead of slowing down to verify the details that actually changed.
I never had an upfront contract with myself about tracking the deal-breakers across rounds. There was no explicit checkpoint, no: “before I approve this version, I re-verify it against my non-negotiables.” I was relying on my reflex, which was TL;DR, and I let that reflex become the norm in my life, even when the negotiation demanded something deeper.
I wasn’t self-aware enough in the moment to notice I’d slipped into that mode. Self-awareness isn’t just knowing your tendencies in general — it’s catching yourself defaulting to one in real time, before it costs you something.
That’s the real cost for SMB leaders. Poor decisions don’t usually come from a single bad call — they come from things that never got properly vetted in the first place, because we all feel the pressure to turn things around quickly. My contract renegotiation is one example of that. Every leader has their own.
Moving fast and slowing down are both great skills. Knowing when to use one or the other is what matters most. Moving fast doesn’t mean your decisions are getting worse. It just means you might have missed something that requires more work down the road.
On the other hand, sometimes moving fast feels like the right thing to do, but isn’t in your best interest. A leader’s job might be to coach the other side — a client, an employee — to slow down, so it doesn’t create unintended outcomes or rework.
I learned this early on as a new leader. I would often do what I call “word vomit” on my employees — what we now refer to as vibing out loud, usually because I was excited about something I’d just learned, a new client, a potential new vertical, etc. But my vibing out loud often had the unintended consequence of pushing my employees to redirect or speed up what they were working on. What I learned was that I needed to slow down and strategically plan when I introduced something new, so my team could stay focused. And even when I felt the need to share the vibe output, I learned it was better to coach the other side to slow down to prevent unintended outcomes or duplicative work.
I also learned there were more appropriate venues for that vibe output in the first place. External peer groups, and coaches gave me a place to think out loud, stress-test an idea, and get it out of my system — before it ever reached my team. By the time something made it to my employees, it had already been through a filter. That’s a different kind of self-awareness: knowing not just when to slow down, but who the right audience is for your unfiltered thinking in the first place.
Modern tools like smartphones and laptops give us instant answers that train our brains to default to TL;DR, even for things that require more depth. The cost isn’t that we make poor decisions — it’s the avoidable rework and unintended outcomes that come from a rushed pass.
The clear takeaway for SMB leaders: recognize when you need to slow yourself down, and recognize when someone else needs coaching from you to slow down.
But here’s the part leaders often miss: it’s not just you. If TL;DR is your reflex, it’s likely your team’s reflex too. The report that skipped a step. The decision made on a partial read. The corner cut because “good enough” quietly became the standard nobody questioned. Individually, each one looks small. Add them up across a team, a quarter, a year, and the cost compounds in ways that are easy to miss until you’re the one standing at the 11th hour wondering how you got there.
Noticing your own reflex is step one. Noticing it in your team requires that same self-awareness turned outward — asking yourself, “am I modeling depth, or am I modeling speed?” Teams tend to mirror what they watch, not what they’re told.
This is where leadership actually shows up — not in doing the deep-dive yourself every time, but in building a team that knows when depth is required and feels safe enough to slow down and ask for it. That might mean normalizing the question “did we actually verify this, or are we assuming it?” in a status meeting. It might mean rewarding the person who flags a gap instead of quietly praising whoever turned something around fastest. Either way, it’s a cultural shift, not just a personal one — and it starts with the leader modeling it first.
AI can help leaders find that happy medium. Configured correctly, you can ask AI to synthesize and summarize as a check and balance. But here’s what AI doesn’t do: it doesn’t retrain your reflexes. In fact, it often does the opposite — it can give you the false impression that you’ve gone deep, when you’ve really just consumed enough to feel confident. Confidence isn’t the same as understanding.
Slowing down isn’t just about taking more time — it’s about what you do with that time. If you slow down but only ask questions that confirm what you already believe, you haven’t actually gone deep. You’ve just built a slower echo chamber.
Real curiosity means asking the questions that could prove you wrong, not just the ones that confirm you’re right — and that starts with turning that question on yourself first: am I actually asking to learn something, or just moving through the motions of asking? In my contract negotiation, that would have meant re-reading each version against my original deal-breakers — not just checking whether the round’s specific ask had been addressed. In the vibing example, it meant getting curious about how my excitement landed on my team, not just assuming they’d catch up.
So the real move isn’t “slow down.” It’s slow down and stay curious in a way that challenges your own assumptions — otherwise you’re just slower, and not necessarily wiser.
Keith Dragon is an executive coach, consultant, and former SMB CEO. He works with business owners, founders, and emerging leaders to help them adjust their cadence to achieve their highest potential. Connect with Keith on LinkedIn or visit SolutionDragon.com.
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