Success often hinges on more than just charisma, product knowledge, or closing techniques. Sometimes, it comes down to having the right person by your side—your wingman. While the term “wingman” might conjure images of fighter jets or nightlife dynamics, in sales, a wingman plays a crucial role in navigating the unpredictable and often awkward terrain of client conversations.
A wingman is your teammate in the room—someone who’s got your back during meetings, pitches, or networking events. They’re not just there to nod along or hand out business cards; their job is to step in when the conversation stalls, shift the mood when things get tense, and subtly steer interactions toward a more productive, positive outcome.
Breaking the Ice and Tension
Sales meetings can quickly become uncomfortable. Maybe your prospect is distracted, the conversation has hit a dead end, or you’ve accidentally said something that didn’t land well. This is where a skilled wingman shines.
They can shift the mood without it feeling forced or artificial. That’s a subtle art—and it’s incredibly valuable.
Moving the Conversation Forward
Sometimes a conversation just gets stuck. Maybe the decision-maker is hesitant or unsure, or maybe there’s been too much technical jargon and not enough human connection. A wingman can redirect by:
- Introducing a fresh angle or benefit.
- Asking the “dumb” question you can’t ask without losing authority.
- Looping in the emotional drivers behind the decision.
Because the wingman isn’t the lead, they often have the freedom to bring in new energy without seeming pushy. Their input can make the lead salesperson appear more credible by contrast—like good cop, better cop.
Creating a Dynamic Duo
A good wingman isn’t just a backup—they’re a strategic partner. When the chemistry is right, it creates a sense of momentum and trust that the client can feel. It humanizes the sales process, which can often feel transactional or impersonal.
Here’s what a good sales wingman brings:
- Emotional intelligence: They read the room and respond accordingly.
- Adaptability: They know when to step in and when to stay silent.
- Complementary strengths: If you’re the expert, they’re the storyteller. If you’re analytical, they’re intuitive.
Examples
- You blank on a detail. Your wingman fills it in naturally, making it feel like teamwork, not a fumble.
- The energy drops mid-meeting. They lighten the mood with a well-placed comment, question or humour.
- Client seems unconvinced. They share a success story from a similar client that hits the right note.
In a profession built on relationships, perception, and timing, having a sales wingman isn’t just helpful—it’s strategic. They’re your ally in the room, your support in the silence, and your escape route from awkward moments. Together, you create a more engaging, authentic, and ultimately more effective sales experience.
