Why Great Salespeople Focus on Decisions, Not Deals

When was the last time a salesperson helped you make a truly confident decision? In this episode of the Sell by Being Human podcast, Alex Smith sits down with Mark Kosoglow, Chief Revenue Officer at Deutsche Bank and former CRO at Catalyst Software, to talk about what selling actually looks like when you strip away the scripts. From selling shoes as a teenager to helping scale Outreach to $250M, Mark’s journey is anything but typical, but his core idea has stayed the same: great salespeople help others make confident decisions.

They get into what that looks like in practice. Mark shares why letting passion lead often creates better conversations than trying to sound polished, how his early experience with consultative selling shaped the way he works today, and why honesty and vulnerability matter more than most people think, especially when you’re asking teams or customers to embrace change.

They also dive into storytelling, the role of metaphors in making ideas stick, and the problems that come from unclear expectations. Throughout the conversation, Mark makes a strong case for being yourself, not as a slogan, but as a real advantage in both sales and leadership.

If you’ve ever felt like selling forces you to be someone you’re not, this episode will change how you approach every conversation.

Key Takeaways

Help people make confident decisions, not just hit numbersLet passion show instead of hiding behind professionalismTreat “no” as a step that moves you closer to yesFocus on understanding the problem before offering solutionsBuild trust by being transparent about intentions and mistakesGive direction, but avoid control to unlock creativityAct, learn, and adjust instead of over-planningPrioritize clarity and ask questions instead of assuming

In This Episode:

[00:00] Mark’s core motivation for selling [01:00] Welcome & introduction to Mark Kosoglow[02:05] Dan Pink’s To Sell Is Human and personal connections[05:05] What “sell by being human” means to Mark[06:03] Helping people make confident decisions (the 2-out-of-3 rule)[08:15] Early days: Selling shoes at The Athlete’s Foot & learning consultative selling[11:45] Telemarketing lessons and embracing “no”[14:21] Leading through change and the weight of asking people to shift how they work[16:05] Balancing control with freedom and creativity[18:46] Admitting failures and iterating quickly (self-sourcing example)[22:28] Revenue Kickoff reflections and the power of in-person connection[25:32] Using metaphors