Every experienced sales professional has been there: your deal is progressing, you have a great relationship with your contact, but you can't get access to the people who actually influence the purchase decision. Your contact is helpful and well-intentioned — but they're not empowered to say yes, nor are they making introductions.
This is one of the most common reasons complex deals stall or disappear. The seller accepts the level of access they've been given rather than working to expand it. But assuming that the person you're talking to is the right person is a dangerous assumption in complex B2B sales. According to SBI research, the typical B2B buying group for a complex solution involves six to ten decision-makers. Engaging more decision makers in the sales process dramatically increases your chances of winning.
The good news: you don't need to bypass your contact or go around them. You need to work through them, using the right approach at the right moment. But before you pursue access, you need to know who you're pursuing and why.
Engaging too few stakeholders too early in the sales process is one of the most common reasons complex deals are lost — broader access improves win rates, shortens cycle times, and increases deal value.
Mapping the buying organization before pursuing access — tells you who the right people are, how much influence each person has, and which relationships to prioritize.
Every complex deal involves four types of stakeholders — economic decision-makers, technical evaluators, end users, and influencers — each with a different relationship to the buying decision and a different engagement need.
Your existing contact is the path to the stakeholders you need, not an obstacle — the right approach turns them into facilitators rather than gatekeepers.
Being presumptive — framing broader access as being in the buyer's interest — consistently outperforms asking permission.
Most sellers understand that getting in front of senior decision-makers is important. A lower-level contact is often responsive, engaged, and easy to get time with, so there's a natural pull to continue that relationship rather than risk it by asking for higher-level access. The meetings feel productive. The deal seems to be moving. And so, the seller keeps scheduling time with someone who can't make the final buying decision.
This is the convenience trap. Deals that seem to be progressing with a single lower-level contact often stall, get deprioritized, or collapse at the approval stage — when stakeholders who were never engaged introduce new objections, change the requirements, or don't recognize the value of a solution they've never been part of evaluating.
Breaking out of the convenience trap requires two things: knowing who the right people are, and having a practical approach for reaching them without damaging the relationship you've already built.
Before you use any of the four access tactics below, take time to map the buying organization. This means identifying who is likely to be involved in the decision, understanding each person's role, and assessing how much influence each has over the outcome.
Most complex B2B deals involve four distinct types of stakeholders, each with a different relationship to the buying decision
Here are four tactics for gaining broader access through your existing contact. They're presented from least to most direct because the right tactic depends on how far you have developed the relationship with your lower-level contact. Each of these tactics can give you a natural segue to asking for a meeting with a more senior level contact.
Before any meeting, use LinkedIn and other publicly available sources to identify who is likely to be involved in the decision. Then test your assumptions in conversation: "Will Jill and Dave also be involved in this decision?"
This approach is non-threatening — you're checking your own research, not asking for introductions. It signals that you understand how complex buying decisions work. And even if your assumptions are wrong, your contact will typically correct you by sharing who is involved. Either way, you learn something useful, and your stakeholder map becomes more accurate.
Once basic rapport is established (see here for the Ultimate Guide to Building Rapport), ask directly: "Who else besides yourself will be involved in this initiative? Can you help me understand who the final decision-making committee will be? What other departments need to be represented?"
Lower-level contacts will answer honestly when asked in a genuine discovery context. You're not being intrusive — you're trying to understand the buying process so you can serve the account well. Frame it that way, and most contacts will help. The answers fill in your stakeholder map and give you a clearer picture of who you still need to reach.
As you deepen the relationship, ask business-focused discovery questions that go beyond what your contact can respond to — questions about strategic priorities, financial impact, or senior leadership's objectives. When a contact genuinely can't answer a question, the natural next step is to involve someone who can.
If trust has been established, your contact will often suggest the meeting themselves. If they don't, be presumptive: "We are most successful in helping our clients when we ensure our solution is aligned with all of the business stakeholders. When can we set up a meeting to address these questions with the broader team?"
This frames broader access as being in the buyer's interest, not the seller's. You're not asking to meet the boss — you're ensuring the solution will work for the organization. Most contacts respond positively to that framing.
Lower-level contacts are often unaware that other departments will be pulled into the decision at the last minute. Help them anticipate it: "We typically see stakeholders from departments such as IT, Finance, Marketing, and Legal involved in this type of initiative. Is that the case here? Can you share who those people are so I can keep track of their names and roles?"
This positions you as a seasoned partner who has navigated this before. It gives your contact a practical reason to share the broader org structure. And it frames the access you're seeking as being in their interest — helping them avoid the last-minute complications that derail internal approvals.
Once you've mapped the organization and expanded your access to other stakeholders, you now must prepare for a more complex meeting. Before any multi-stakeholder meeting, revisit your stakeholder map: confirm each person's priorities, anticipate their concerns, and set a meeting objective that works for the group — not just your primary contact. Open by creating shared context that connects everyone in the room, rather than building rapport only with the person you know best. Follow up with every stakeholder individually after the meeting, not just the person who arranged it.
To understand how to sell to key executives, see Mastering the Art of Selling to the C-Suite: Strategies for Success and Want To Win Large Deals? Follow the RAMP Method.
Winning complex deals requires engaging more senior level stakeholders. Start by mapping the organization — identify the economic decision-makers, technical evaluators, end users, and influencers involved, find your Customer Coach, and assess each stakeholder's commitment and influence. Then use the four tactics discussed above to expand your access through the relationship you already have.
Is your team leaving complex deals in the hands of contacts who can't say yes? SBI works with sales organizations to build custom sales training programs that help sellers map buying organizations and engage the right stakeholders. Schedule a consultation to learn how we can help your team win more complex opportunities.