Summary
Why your deals keep getting stuck with middle management
Your proposal looks solid and the technical team loves your solution. Yet weeks pass, meetings get postponed, and you find yourself stuck in an endless loop with procurement officers and project managers who keep saying they need to “check with their boss.” Meanwhile, your competitor somehow gets a meeting with the CEO next Tuesday.
Sales representatives and negotiators instinctively gravitate towards the people who respond to emails quickly and attend meetings regularly. These contacts feel safe and manageable. They understand the technical details and never make you feel uncomfortable with challenging questions about strategy or budget authority.
We all like to stick to what we know and what works for us. In negotiation, this is true as well. Many representatives on the seller’s side feel uncomfortable engaging decision-makers on the buyer’s side. The discomfort can stem from a lack of experience or the fear of talking to someone higher up the ladder. Relying on someone else to engage and convince the decision-maker is a risky move you should avoid.
The people who engage easily rarely have decision authority.
The problem is that comfortable contacts are rarely the people who can actually say yes to your deal. They might be enthusiastic advocates, but they lack the authority to commit budgets or override objections. You’re essentially asking them to do your negotiation for you.
The Consequences of Avoiding Direct Engagement
Avoiding direct engagement with decision-makers will cost you deals. You risk losing revenue and experiencing severe delays. The immediate loss is painful, but the long-term damage to your reputation and future opportunities is worse.
When you negotiate through intermediaries, your message gets filtered and diluted as it travels up the organisational chain. The procurement manager who seemed enthusiastic about your proposal presents it to their boss as just another vendor option. Your compelling business case disappears entirely.
Every filtered message loses impact. Talk directly to those who control the budget.
You also lose control of the negotiation timeline. Decision-makers work on their own schedules, not yours. That “urgent” deal you need to close by quarter-end sits on someone’s desk for two weeks because your contact doesn’t have the authority to create urgency at the executive level. When questions arise, they get filtered back down through the same slow chain, turning a five-minute clarification into a week-long process.
Your competitors face the same organisational barriers, but the smart ones find ways around them. They build relationships with senior executives before they need them. They position themselves as strategic partners rather than vendors. When decision time comes, they’re already in the room while you’re still trying to get your contact to schedule a meeting with their boss.
Perhaps most damaging, you become associated with indecision and bureaucratic delay. Decision-makers begin to view your deals as “complicated” or “requiring too much internal selling.” They start to question whether you really understand their business if you can’t navigate their organisation effectively.
Six Steps to Successful Negotiations
Next time you negotiate, follow these six steps to ensure success:
1. Identify the Decision-Maker Early On
Before you even start the negotiation, know who holds the cards. It’s crucial to identify the decision-maker as early as possible.
The person with the biggest title isn’t always the real decision-maker. The CEO might delegate all technology decisions to the CTO. The procurement director might only execute decisions made by the finance director. You’re looking for the person who controls the budget, sets the timeline, and has the authority to override objections from other stakeholders.
The highest title isn’t always the real decision-maker.
Direct questions work better than assumptions during your discovery calls: “Who typically makes the final decision on investments of this size?” or “When similar projects have been approved in the past, who was involved in that decision?” Watch for body language and verbal cues. The real decision-maker is usually the person everyone else looks at when difficult questions arise.
Sometimes the official decision-maker is influenced heavily by a trusted advisor or subject matter expert. In family businesses, the founder’s opinion might carry more weight than the current CEO’s. In highly technical companies, the lead engineer might have effective veto power over executive decisions.
If you do misidentify the decision-maker, the person you thought had authority will keep deferring to someone else, or decisions get overturned by someone you’ve never met. Address this directly rather than pretending it hasn’t happened. Ask your contact to introduce you to whoever is really driving the decision. The relationships you’ve built aren’t wasted. They become your route to the actual decision-maker.
2. Know Your Routes to the Decision-Maker
Once you know the decision-maker, figure out how to get in touch. Does someone in your company already have a relationship with them? Use that connection.
Direct access is ideal, but not always available. You might bump into them at industry conferences, discover a mutual golf partner, find out your board members went to university together, or realise your IT supplier also handles their infrastructure. LinkedIn reveals shared connections you didn’t know existed.
Informal channels can be surprisingly effective.
Informal channels work surprisingly well. The decision-maker’s assistant controls their calendar and makes a powerful ally. Industry associations, conference speaking opportunities, or even social media engagement create natural conversation starters.
Senior executives get hundreds of outreach messages. To cut through the noise, reference a recent company announcement, industry challenge they’ve publicly discussed, or mutual connection who suggested you reach out. Lead with their business priorities, not your product capabilities. Make your subject line specific to them rather than generic: “Your comments on rising acquisition costs” rather than “Partnership opportunity.”
Focus on business challenges you know they’re facing. Check their recent earnings calls for mentions of cost pressures, competitive threats, or growth initiatives. Look at industry publications covering their sector for common pain points. If they’ve spoken at conferences or given interviews, note what keeps them up at night. Revenue growth, operational efficiency, regulatory compliance, and talent retention are safe bets for most executives. Frame your outreach around these issues, not around what your product does.
When executives decline or ignore your outreach, ask about timing rather than pushing harder on the opportunity.
3. Build Rapport with the Decision-Maker
Building a relationship over time works better than reaching out cold when you need something.
Relationship building works best when it starts before you have deals to close. Share valuable industry insights, invite them to relevant events, or introduce them to useful contacts in your network. You want to position yourself as a strategic resource rather than another vendor seeking meetings.
Their company’s news and achievements provide natural conversation opportunities. Meaningful comments on their LinkedIn posts or congratulations on business wins show genuine interest. Reference their recent interviews or conference presentations in your communications. You’re demonstrating attention to their business rather than pushing your own agenda.
Common ground beyond business builds stronger connections. Shared educational backgrounds, professional interests, or industry challenges make for natural conversation starters. Many senior executives become more accessible when discussing industry trends or strategic challenges than they are when discussing specific vendor proposals.
Patience and consistency trump intensity. Relationship building with senior executives happens over months, not weeks. Respect their time constraints whilst demonstrating ongoing value.
Some executives won’t engage no matter how thoughtful your approach. They might ignore LinkedIn messages, decline event invitations, or have assistants deflect all vendor contact. Don’t take it personally or keep pushing harder. Instead, focus on building stronger relationships with the people around them who do have their ear. The CFO’s deputy, the CTO’s trusted advisor, or the board member they consult regularly can become more valuable contacts than the unresponsive executive themselves.
4. Plan Your Engagement Strategy
Even the best proposal can fail if delivered at the wrong time or in the wrong setting. When and how you engage with the decision-maker matters as much as what you say. Timing can be everything.
Decision-maker conversations happen everywhere except formal sales meetings. Industry conferences, company events, or even brief encounters before board meetings often prove more valuable than hour-long presentations where they’re surrounded by their team.
Their communication patterns from public sources reveal preferences worth studying. Long, detailed LinkedIn articles suggest they want comprehensive analysis. Brief, punchy posts indicate they prefer executive summaries. Conference presentations show whether they speak at length or stick to key points.
Budget planning season opens doors that stay closed the rest of the year. Decision-makers are naturally thinking about next year’s priorities and strategic investments. A good proposal during budget season beats a perfect proposal submitted after funds are allocated.
5. Tailor Your Concession Strategy
Different decision-makers respond to different types of concessions. A finance director cares about cash flow whilst a CEO worries about competitive advantage.
Your concession strategy should revolve around what the decision-maker needs to justify internally. Board presentations require ROI calculations and risk mitigation plans. Budget approvals need clear cost comparisons and timeline commitments. Regulatory compliance demands documentation and audit trails.
Smart concessions cost you little but solve their biggest problems. Extended payment terms might be more valuable to them than a 10% discount if they’re facing cash flow pressure. Implementation support could matter more than pricing if they’re worried about internal adoption.
Concessions gain power when tied to commitments.
Concessions gain power when tied to commitments from their side. They want faster decisions? You want longer contract terms. They need public references? You need expanded user counts. They’re asking for flexible payment terms? You’re asking for executive sponsorship. Specify exactly what you need in return: “I can extend payment terms to 90 days if we can get approval by month-end” or “We’ll include free training for 20 users if you commit to a three-year term.”
6. Take Ownership of the Process
Deals get stuck when you create distance between yourself and the decision-maker. Every intermediary dilutes your message and weakens your ability to create urgency. Stop relying on others to sell for you. Take full ownership of your negotiation.
Your internal contacts mean well, but they have their own priorities and constraints. They’re not invested in your deal the way you are. They might forget to mention key benefits, downplay urgency, or simply lack the skills to present your proposal persuasively to senior leadership.
Multiple touchpoints with the decision-maker throughout your sales process beat saving everything for the final approval meeting. Early relationship building makes the final ask much easier. Decision-makers prefer working with people they know and trust rather than evaluating proposals from strangers.
Warning signs appear when decision-makers aren’t engaged directly. If they’re not responding to your outreach, not attending key meetings, or delegating all interactions to subordinates, your deal is in trouble. These situations require immediate attention, not hopeful assumptions that everything will work out through intermediaries.
Decision-maker time is precious, so make it count when you get it. Focus on business challenges rather than product demonstrations. Understanding their strategic problems and positioning your proposal as a solution creates more value. Save product details and technical specifications for follow-up meetings with their teams.
Why You Should Talk to Us
We’re an independent consulting business that doesn’t sell licenses or Cloud services. We do this intentionally to keep our advice unbiased.
Let Us Guide You Through Your Next Negotiation
If you’ve got an upcoming software or Cloud vendor negotiation, we’re here to help. Fill out the form below to tell us about your challenges, and let’s sort them out together.