Still in the Room: What Kevin Armstrong Taught Me About Winning Right Now

There are some conversations that end and you immediately know you need to just sit with them for a minute. My recent Coffey Talk with Kevin Armstrong was one of those. I don’t usually write summaries from my blogs, but more what my takeaways were…the thing is…my takeaways are a summary of the podcast. So…here ya go. 

Kevin has been in the technology space for over 30 years. He has navigated the early internet, Y2K, 9/11, the 2008 economic collapse, the cloud boom, and now the AI era. When I asked him what word comes up when he looks back at all of it, he didn't hesitate. Grateful.

Not triumphant. Not exhausted. Grateful.

That word set the tone for everything that followed. And what followed was one of the more honest, grounded conversations I've had on this show about what it takes to build a career that lasts, and what it looks like to keep winning when the rules keep changing.

Kevin shared five principles he keeps coming back to. They're his, and I want to honor them as such, because I think they're worth sitting with whether you're in sales, in leadership, or just trying to figure out your next move.

Be Curious

Kevin leads with this one and there's a reason. He said people get stale, and I think he's right. When stress hits and uncertainty creeps in, it's easy to turn inward. To stop asking questions. To wait for someone to hand you the answer. But curiosity is what keeps you relevant. It's what keeps you in the conversation.

He talked about using multiple AI platforms every single day, not because he has to, but because he wants to know what they each do differently. That's not a technology habit. That's a mindset. He is genuinely interested in the world, and it shows up in every room he walks into.

I've been called contagiously curious more than once in my life and I've always taken it as a compliment. This conversation reminded me why I should keep it that way.

Be Prepared

Kevin called it the practice-to-performance ratio. In sports, preparation is everything. In sales and business, we have a habit of throwing people into performance without nearly enough practice. We wonder why deals fall apart and careers plateau.

He was direct about this: if you're not doing the work before you get in the room, you're the problem. Not the market, not the buyer, not the timing.

One of our culture fundamentals at my company is to be more prepared than anybody else in the room. I've lived by that principle, and I can tell you it opens doors. Kevin put language around something I've felt for years. Preparation isn't just about knowing your stuff. It's about being ready to add value the moment the conversation starts, even if it goes in a direction you didn't expect.

Have a Perspective

This one came with a line I won't forget: tell them something they don't already know.

Not your features. Not your pricing. Something that makes the other person in the room think differently about their own situation. That's perspective. And you build it by doing the work, studying the industry, understanding the outcomes your buyers are actually chasing, and caring enough to have a real point of view before you ever open your mouth.

Kevin said buyers don't care about your product. They care about going to sleep at night knowing their problems are handled. If you can speak to that, you're already ahead of most of the people in the room.

Understand Your Value Equation

Know thyself. Kevin said it plainly and called it a cheat code, and I think he's right.

He told a story about a guy named Paul Alley who walked into a new industry knowing nothing about the products, nothing about the ecosystem, but being one of the most likable, curious, and responsive people Kevin had ever worked with. Paul went from zero to club trip in year one. Not because he was the most technical. Because he knew exactly what he brought to the table and he showed up with that every single day.

That story stuck with me because I've seen it play out in my own career. I'm not the most technical person in most rooms I'm in. But I care, I follow through, and I show up prepared. That's my value equation. Knowing that, owning it, and not apologizing for it has served me well.

Kevin also said something important for anyone who's navigating a job loss or a career transition right now: lower your stress first. You cannot assess your value equation clearly when you're running on adrenaline and anxiety. Step back. Breathe. Then build the plan.

Be Responsive

Time kills all deals. Kevin said it and I felt it immediately, because it goes so far beyond sales.

He put it simply: more deals are lost to no decision than to competition. And the way you fight a no-decision is by removing every reason for delay that's on your side of the table. Get the email out. Send the follow-up. Deliver what you said you would. Don't make the other person work to keep the conversation alive.

Our intern said something to me early on that I loved: there's fortune in the follow-up. Kevin would absolutely agree.

What I'm Taking Into This Week

There was one constant message in Kevin’s thoughts: control what you can control. The market is uncertain. The job landscape is hard. AI is changing everything. But how curious you are, how prepared you show up, whether you have a real perspective, whether you know your own value, whether you respond when you say you will, those things are entirely in your hands.

Kevin closed by talking about the people he's most proud of in his career. Not the deals he closed or the revenue he generated. The people he watched succeed. The careers he got to be a small part of.

That's someone who knows their why. And it was a good reminder for the rest of us to figure out ours.

Go listen to the full episode. Kevin is the real deal. ☕