Navigating Sales meetings with senior leaders: how to make the most of their presence
Hopefully...
During your career, there are moments that can trigger either an immense sense of gratitude or a deep feeling of “solitude”. One of those moments? When you’re in a customer meeting and senior leaders decide to join the conversation.
As a Salesperson, there are times when you find yourself in meetings with customers, and a manager - sometimes even a senior leader like your CEO or someone from a parallel function - joins the conversation. These meetings can vary greatly depending on the senior leader’s attitude and level of involvement. Their engagement can significantly impact (one way or the other) your success in the meeting and, ultimately, your relationship with the customer. Let’s explore some common scenarios that arise when senior management joins a sales meeting and how you can leverage them to your advantage.
Disclaimer: All resemblance to real-life senior leaders, customer meetings, or sales scenarios is purely coincidental. No senior leaders were harmed in the making of this article.
A. The different scenarios
1. The engaged supporter: the ideal scenario
In the best-case scenario, the person joining the meeting is fully briefed and has a clear understanding of what the customer’s needs are and what you’re hoping to achieve. This is the manager or senior leader who actively asks you to brief them about the customer, the meeting's objectives, and what specifically you expect from them. They come into the meeting prepared, ready to listen, and contribute in a meaningful way.
During the meeting, they engage thoughtfully, provide valuable insights, and give you credit where it’s due, helping to position you as the key driver of the relationship. The customer sees this collaboration as a sign of your credibility, and your manager’s participation only enhances your standing. Afterward, the organization highlights your role in managing the customer, reaffirming your position and emphasizing your success.
In a previous experience (US listed company), I’ve had the opportunity to set up meetings for our CEO during his visit to the country. He specifically asked to be briefed about every meeting and the people he would meet, along with our expectations and objectives. As a co-founder of the company, he was very knowledgeable technically and had a clear vision. Though he was the type of person you could listen to lecture for hours (he was a professor, after all), he always made sure to listen to the customer and praised the local team in front of them.
This is the golden scenario—a clear win for everyone involved, particularly for you as the salesperson. It exists. It’s rare, but it does exist.
2. The passive observer: when silence can be gold
There are times when the senior leader’s involvement is more of a formality. They’ve been in the game for so long that they feel they know the customer or the business inside out. They might not ask for a briefing beforehand, nor do they seem to take the time to understand what you’re aiming for in the meeting. Instead, they show up to “be there” and listen in.
In these cases, your best course of action is to remain focused and take the lead. Ideally, they stay quiet, allowing you to drive the conversation and manage the customer’s expectations. Their presence is still valuable, though, as it gives you additional credibility. Your customer might feel reassured that leadership is involved, even if the senior leader doesn’t actively participate.
This scenario could be even more beneficial if the dynamic of the meeting is discussed and agreed upon beforehand, and if, after the meeting, you have a debrief to receive feedback. This debrief can serve as a coaching session, providing you with valuable insights.
In this case, the key is to manage the meeting while subtly positioning yourself as the expert. At the end of the day, their silence speaks volumes - they’re backing you up without overshadowing your role.
And if you want their feedback, don’t wait for it; ask for it. This can be a valuable learning opportunity.
3. The disconnected leader: when they take over
In the less-than-ideal scenario, a senior leader might attend the meeting without asking for much input beforehand. They come in and immediately take control of the conversation, often without consulting you first. They have the credentials, the stripes on the shoulders, so everyone should listen to them - even the customer. They may start talking about irrelevant topics, diving into their own agenda, and disregarding your prepared strategy. Instead of elevating your role in the meeting, they may unintentionally undermine it by dominating the conversation.
Is it time to plant your head in the ground and wait for the rain to pass? No, in this situation, it’s essential to stay calm and assertive. Politely redirect the conversation if necessary, emphasizing the customer’s needs and the objectives you set for the meeting. Don’t be afraid to interject and bring the focus back to where it should be. If your "invitee" isn't asking questions, try to ask them on their behalf. If you see your customer withdrawing from a monologue from your peer, ask questions to bring them back into the conversation.
It’s important to maintain an active role in the meeting to help refocus the conversation and keep the balance of engagement between both parties. Though it can be frustrating, try not to let their behavior detract from your professional image. The customer is still looking to you for leadership.
4. The unprepared visitor: when they are unaware
Sometimes, the most challenging scenario is when a senior leader shows up without any preparation - either failing to ask for a briefing or not making an effort to understand the customer’s background. This might happen if they decide last-minute to take an active role in the meeting or if you’ve assigned them a part to play in the conversation. They enter the meeting unprepared, asking questions that feel out of place or offering feedback that doesn’t align with the discussion. This lack of preparation can be detrimental, especially when the customer expects valuable insight from leadership.
The best way to handle this scenario is by remaining flexible and taking charge of the room. Gently guide the conversation back to the customer’s priorities. If possible, suggest topics for discussion, subtly steering the meeting toward the objectives you’ve set. I’ll admit, it’s much easier said than done.
I recently found myself in a meeting like this, and it wasn’t pleasant to watch the situation unfold in the worst possible way. We lost the deal - one of the significant ones. A flood of negative emotions hit me during and after the meeting. But remember, you win as a team, and you lose as a team.
While this may not be the type of meeting you'd prefer, it’s a valuable opportunity to learn how to handle these situations more effectively in the future. Even if it’s uncomfortable or counterproductive to your immediate business goals, treat it as a chance to develop your social and leadership skills.
5. The over-confident veteran: when they think they know everything
Sometimes, senior leaders enter a meeting with the mindset that they've seen it all before. This “over-confident” attitude can be tricky. They may talk over you, dismiss your insights, or even disregard the customer’s perspective in favor of their own. This can disrupt the flow of the meeting and make it feel like your expertise is undervalued.
I’ve experienced this firsthand while covering a multi-country region for a US-listed company. The Presales Director, who was responsible for a much larger region, would visit us once a year. During these visits, I was asked to arrange meetings with key customers, usually at a senior level. Unfortunately, everything I feared came true - no interest in the customer, no questions asked - just a one-man show.
In situations like this, it’s important to stay respectful and patient. Let them speak, but don’t hesitate to assert yourself when needed. Politely but confidently offer your insights, reinforcing the customer’s needs and the strategy you've set in place to address them. With time, you’ll build the tact needed to balance their confidence with your own expertise, as well as the authority to decline setting up the call if an agenda has not been shared.
B. How to handle each scenario
1. Preparation is key
No matter who joins the meeting, make sure you’re always well-prepared. Brief your invitees on the customer, their needs, and the meeting objectives, even if they don’t ask. Even if they don’t ask you directly, send them a note before the meeting with key points you want to address—your expectations, the objectives, and the context. At the end of the day, your preparation sets the tone for everyone else, so make sure you’re on top of it. As we discussed in one of our articles about Culture, every action you take contributes to positive changes within the team and the overall work environment.
2. Take the lead
It’s easier said than done, especially if you’re early in your career or new to the organization. Whether your senior leaders are passive or active, you’re still the primary point of contact for the customer. Stay in control of the conversation, guiding it toward the desired outcome. Don’t forget: this is also a learning opportunity.
3.Use Their Presence to Your Advantage
Even in challenging scenarios, the mere presence of senior leadership can enhance your credibility. Keep your focus on the customer and let their position work for you.
4.Adapt and be flexible
Every meeting is different, and you’ll encounter different dynamics. Be ready to adjust your approach based on the situation and the individual you’re working with.
C. Now You
Yes, YOU.
Since we’ve discussed the value that senior leaders might bring into your meetings, isn’t it time to reflect on what you bring into others’ meetings? Sooner or later, you’ll be seen as someone with influence or authority, and others may need your presence in their meetings.
Be honest with yourself and ask: which scenario best describes your attitude in these meetings?
Educate by example, and you’ll influence the culture of your team or extended network. If your practice and behavior are positively received and perceived, people will follow your example. This is how you become a leader - by creating followers.
Conclusion: don’t forget – YOU are the product
While the presence of senior leaders in a sales meeting can sometimes be unpredictable, understanding the different scenarios and knowing how to navigate them will ensure you maintain control of the conversation and position yourself as the key driver in the relationship. No matter the level of involvement from your senior leaders, your ability to stay composed, assertive, and focused on the customer will always be your greatest asset.
By managing expectations, guiding the conversation, and using their presence to your advantage, you’ll continue to build strong relationships with both your customers and your leadership team.
Always try to be proactive and provide context, the agenda, and objectives before the meeting. If you don’t provide them with the necessary information, remember: you can’t win the lottery unless you first buy a ticket.
Keep an eye on the bigger picture, and treat these situations as opportunities for personal growth. It’s tough because we’re talking about your customer and your potential deal—you have more “skin in the game” than anyone else. However, don’t forget that the product you’re selling is yourself. By learning from these situations and improving how you handle them, you’re investing in your own success in the long run.