Lessons From the Sidewalk

Oakland, California. 1999. A sport coat. A briefcase stuffed with paperwork about "the worldwide web." And a green CitySearch rep threading past spatulas and knives to reach the owner of a kitchenware shop on Piedmont Avenue, who was in the back crunching numbers on a notepad.

I interrupted him. I introduced myself. I told him I loved his tongs. Then I pitched him on getting his store online, because the internet was about to be big.

He looked up, smiled, and said, "This sounds really interesting. Why don't we walk through the store and you tell me a little bit about how you'd be promoting this. I've had a prominent spot in the Yellow Pages for 25 years. Walk with me."

So the walking started. So did the pitching. And by the time the scene came into focus, the sidewalk was underfoot and the owner was saying, "Look, dude, take a hike. I got your worldwide web. Just keep walking."

Twenty-seven years later, that guy was right. A stranger had barged into his day, pitched a future he hadn't asked about, and ignored the fact that his current marketing was working fine. The sidewalk was earned.

Doug Landis recently asked for the most unforgettable sales story of a thirty-year career on his Sales Stories Podcast, and the kitchenware owner came back first. But so did everything that came after him. Thirty years, eight companies, a lot of doors opened and a lot of doors closed in the face. A handful of lessons have kept the work upright through all of it.

Here they are, for anyone earlier in the climb.

People First. Process Always. Never One Without the Other.

Across UPS, CitySearch, Ticketmaster, Elsevier, InsideView, Achievers, ServiceNow, and now Kahua, two things haven't changed. People and process.

People without process is chaos. A warm, well-liked team that can't forecast, can't scale, and can't tell you why deals won or lost. Process without people is a different failure. A machine that hits activity targets and loses deals nobody understands, because nobody built a relationship strong enough to hear the truth.

The job of a revenue leader is to keep both plates spinning. The job of a seller is the same thing in miniature. Follow the process. Care about the person on the other end of it.

Technology Doesn't Replace the Basics.. It Amplifies Them.

Thirty years ago, sellers had a phone, a rolodex, and a territory. Today they have CRM, sales engagement platforms, intent data, conversation intelligence, enrichment, AI copilots, and whatever tool launched last Tuesday. Every one of those tools is a force multiplier, which is both the gift and the warning.

Good relationships and real problem solving scale beautifully with a stack behind them. Bad messaging and skipped discovery scale too. The prospect on the other end can always tell the difference. The stack is not a place to hide from the craft. It is a way to extend the craft.

Four Things Worth Hiring SDRs For...

After hiring and coaching a lot of sales development reps, four attributes rise to the top. All four matter, not three:

1 - Coachability. Can this person take feedback and change something by next week?
2 - Work ethic. Are they disciplined and consistent, not just on good days?
3 - Curiosity. Are they asking real questions about the business, the buyer, and the market?
4 - Competitiveness. Is there a fire in their belly that makes losing hurt?

Any three without the fourth hits a ceiling. A coachable, hardworking, curious rep without competitiveness plateaus at "pretty good." A competitive rep without coachability tops out the minute they decide they've figured it out. The combination is what compounds over a career.

Rejection Is Data, Not a Verdict!

Rejection at CitySearch came constantly. Phones slammed down. Doors closed. One memorable escort to the sidewalk. For any SDR building the muscle right now, there are four ways to hold it:

It is not personal. A "no" is almost always about the prospect's situation, timing, or priorities, and almost never about the seller. The moment rejection gets internalized as a verdict on self-worth, the flinch starts before the dial does.

Bounce back fast. The best sellers aren't the ones who don't get rejected. They're the ones who get rejected, breathe, and pick up the next call without carrying the last one into it.

Learn from it. What actually happened? Was it the message? The timing? The target? The opening line? Every rejection has a lesson inside it for anyone willing to look.

Celebrate the wins. When a meeting books, when a reply lands, when a deal moves, make a deal out of it. Rejection carries negative weight on its own. Positive reinforcement has to be manufactured on purpose.

People for Others

St. Ignatius College Prep in San Francisco had a motto that shaped every career decision that followed: people for others.

In leadership, it looks like giving context before giving direction. Telling the team how a decision feels and why it's being made, then trusting them to run. Being vulnerable and candid at the same time, which is harder than it sounds.

In selling, it looks like what many leaders have long called servant selling. Tell the customer the truth, even when the truth costs the deal. Point them at a better fit when you're not it. Remember that their business isn't a quota. It's their livelihood.

Servant sellers don't get walked out of kitchenware stores. They don't barge in. They ask what's working, they listen, and they earn the right to make a suggestion.

One More Thing

If you take nothing else from this piece, take this. The kitchenware owner was doing a favor that day. Every "no" landing in your inbox this week is doing you a favor too, as long as you're paying attention.

Read the room. Serve the person in front of you. Trust the process. Celebrate the wins. And if you ever find yourself on a sidewalk wondering what just happened, laugh about it now so you can tell the story later.

The walk out was a gift. It taught more than a dozen closed deals ever could.