Hold 'Em, Fold 'Em, Walk Away, Run

More and more people outside Sales are having commercially important conversations with customers. Engineers, consultants, customer success, support, product people, executives — anyone close enough to the customer to hear things Sales doesn't always hear first.

They might hear about a new problem. Discover a competitor. Meet someone who has influence over a buying decision. Spot an opportunity to expand an account.

And often, they're perfectly capable of having the conversation — they're just not necessarily equipped to recognise what the situation requires.

For example: an engineer gets asked a technical question, and he knows the answer. So he spends 25 minutes explaining it.

He showed his expertise. But did he find out why the customer was asking? Did he understand the business problem behind it? Was he talking to someone who could actually influence the decision? Was there a bigger opportunity? Did he know when to bring Sales in?

The mechanics vs. the moment

Traditional sales training teaches people the mechanics: prospect, qualify, discover, present, negotiate, close. It's good stuff. But customer-facing people often face a different question — not "where are we in the process," but what does this situation need from me right now?

Do I ask or explain? Challenge or support? Keep going or bring someone else in? Solve the problem or look for the bigger opportunity? Am I even talking to the right person?

They don't need a sales process in these moments. They need to make a judgement call. They need Kenny Rogers.

The Gambler had it right

Know when to hold 'em, know when to fold 'em, know when to walk away, and know when to run. Turns out that's not a bad description of commercial judgment.

Hold 'em. There's something here worth exploring. Don't jump straight to the answer. Stay in the conversation. Ask another question. Get curious about what's really going on. That engineer with the technical question? He needed to hold 'em — stay curious for one more question before diving into the explanation.

Fold 'em. What you're doing right now isn't working. Maybe you've been explaining when you should have been asking. Maybe the conversation has gone down a technical rabbit hole. Fold 'em is the in-the-moment correction: change direction, in this conversation, right now.

Walk away. Not every customer problem is an opportunity. Walking away is the bigger call — this isn't about redirecting one conversation, it's deciding the account or deal isn't worth the next three meetings, six emails, and half a day of engineering time. Walking away is a commercial skill too.

Run. You've spotted something. A change in the customer's business. A problem they haven't fully articulated. A new stakeholder. A potential expansion. Something bigger than the conversation you originally came to have. That's when you move — connect the right people and create momentum.

These aren't steps. They're judgment calls.

That's how we should be preparing customer-facing people.

Not by turning everyone into a salesperson — your technical people don't need to start carrying a quota and opening every conversation with "so, tell me about your pain." They need to recognise when a conversation has become commercially important, and know when to ask, when to explain, when to fold, when to walk away, and when to run.

The next generation of commercial capability isn't about teaching more people how to sell. It's about teaching more people when to hold 'em, when to fold 'em, when to walk away, and when to run.

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