Selling to senior executives demands more than a strong solution and value proposition. It requires a deep understanding of senior executives, business strategy, risk mitigation, industry trends, and much more—along with the ability to communicate effectively at the highest level.
With 85% of sales leaders reporting challenges in dealing with multiple decision-makers, mastering executive sales has become crucial. Yet, executive-level buyers find only 20% of salespeople meet their expectations and create value.
To help sellers address this gap, RAIN Group has developed the STRATEGIC model. This framework is comprised of nine key principles to elevate your executive sales approach.
In this infographic, we explore these principles and provide actionable tips to boost your competence and confidence in executive sales conversations. Whether you're new to executive sales or looking to refine your skills, these insights will help you succeed in high-stakes sales situations.
Click the infographic to enlarge.
Tips For Each Principle of Executive Sales
Scrutiny
Sellers must be prepared to face scrutiny from senior executives.
1. Prepare Thoroughly
Do your research in advance on:
- The executive, including their goals and priorities
- The organization
- Industry and market trends
- Current challenges and opportunities
- Your value case and how your solution addresses their situation
2. Anticipate Objections
Senior executives tend to be more skeptical than other buyers—slow to trust and quick to raise potential concerns.
Identify likely objections in advance and be prepared with evidence. Build a thorough knowledge of relevant case studies and be prepared to share numbers (including ROI and KPIs) related to your proposed solution. Be prepared to communicate how the solution applies to the executive’s challenges and priorities.
3. Focus on Accuracy
When you bring data to senior executives, it should be defensible. If it isn’t, they won’t give you the benefit of the doubt. Validate and confirm in advance all data you share and claims you make. Where appropriate, use third-party data to support your claims.
4. Demonstrate Reliability
Build trust by delivering consistently accurate and relevant information. When you say you’ll do something, do it within the timeframe promised. By doing so, you build trust over time.
5. Emphasize Risk Management
Perceived risk can sour a senior executive on your solution. Some sellers try to avoid talking about risk for this reason. However, if you try to downplay risk too much, you may alienate buyers.
Instead, be proactive when it comes to discussing areas of risk, and address how your solution mitigates risks they’re concerned about. Done well, conversations about risk can build trust with buyers.
Time
Senior executives value their time and expect you to do the same. If you don’t respect their time, you’ll be less likely to land another meeting.
6. Be Concise
You have a limited window to make your case to senior executives. While you should be prepared to answer questions, distill your research into key points and communicate them clearly and quickly.
7. Front-Load Information
If you’ve done your research, you should have an idea of what will resonate with a senior executive and what might get their attention. Be upfront with your intentions, what you’re offering, and why an executive should work with you.
8. Respect Their Time
If you’ve scheduled a half-hour meeting with a senior executive, plan for that. A meeting should only go over the allotted time if the executive explicitly asks you to continue. Pay attention to your own schedule and agenda, keep executives engaged, and stay on track.
When you stick to the schedule you’ve set out, executives are more likely to perceive you as trustworthy and reliable.
9. Use Time Wisely
It’s important to build time for collaboration into your sales meetings. However, in any meeting with a senior executive, it pays to focus on decision-critical information that moves the sale forward.
Build in time for rapport-building, but understand that some executives will prefer to get straight to the point.
10. Prepare for Quick Pivots
Senior executives won’t hesitate to share their own ideas or concerns. Don’t railroad the conversation; be receptive to pivoting to topics of interest to them.
In fact, part of your research and preparation should involve informed speculation on where an executive might divert from your planned conversation. If you’re caught unprepared, it could derail the conversation.
Results
Senior executives are focused on driving high-level results for their organization. You’ll need to persuade them that you can help achieve their goals.
11. Showcase Tangible Outcomes
When finding case studies and results to demonstrate competence, focus on measurable success. Even if you’ve been successful with other clients, executives will want to know that your results are consistent, repeatable, and impactful. Outcomes should have hard numbers associated with them that you can share.
12. Quantify Benefits
Many sellers struggle to communicate their ROI—and this can be a huge issue for senior executives.
The expected ROI or performance improvements should be customized to the buyer, demonstrate a knowledge of their situation, and be tied to the broader impact of your solution.
13. Align with Their Goals
When you understand the challenges senior executives are trying to overcome, you can tailor your solutions to support their specific business objectives.
14. Set Clear Expectations
In your executive conversations, you should be able to define success and communicate how it’ll be measured. Come prepared with KPIs and metrics to quantify what success looks like for your solution.
15. Know Their Hurdle Rate
Demonstrate how your solution will surpass their hurdle rate. This is the minimum threshold of impact necessary for an executive to move forward on any project or initiative.
To find a senior executive’s hurdle rate, ask them or other contacts in their organization. Do this before your meetings with them, if possible.
Approach to Meetings
Top-Performing Sellers are 62% more likely to lead highly effective meetings with senior executives.
Senior executives expect sellers to be prepared for and lead meetings that are focused, strategic, and highly specific to their business.
16. Start Before the Meeting
Don’t be afraid to ask questions beforehand. Going into a meeting with a strong grasp of an executive’s priorities and challenges allows you to focus your time and attention on satisfying their needs, collaborating, and moving the sale forward.
17. Set a Clear Agenda
Establish the agenda from the start and communicate it in advance. Make sure the executive is clear on the purpose and structure of the meeting. Proactively drive your own agenda and build in time for collaboration.
18. Engage Early
Start your meetings off strong! If you lead a meeting with a new idea or perspective the executive may not have previously considered, they’re more likely to pay attention.
Come prepared with a compelling point that sets the tone for the rest of the meeting.
19. Involve Them in Conversation
Senior executives will likely be upfront with their own ideas and objectives. If you can get them talking about their needs and listen actively, you’ll be more prepared to customize a solution that resonates with them.
Collaboration starts by asking strong questions that invite input and change buyer thinking.
20. Close with Action
Reserve time at the end of your meeting to set clear next steps. Give them a good reason to continue the conversation.
Transformation
Senior executives often focus on driving organizational transformation and reserve their time and attention for high-level issues.
21. Focus on Innovation
Organizations must stay competitive, but established practices can hinder transformation.
To counter this, present ideas that drive significant organizational progress. Bigger changes are more likely to meet the executive’s hurdle rate.
22. Link to Strategic Initiatives
How does your solution drive an executive’s transformation goals? If it doesn’t relate, you’ll have a much harder time convincing them to move forward. Communicate how your solution fits into their broader goals.
23. Demonstrate Long-Term Impact
Your impact case should excite senior executives and highlight the long-term benefits of working with you. Show how your solution will help drive sustained growth or efficiency for their organization.
24. Highlight the Competitive Advantage
No organization exists in a vacuum. Position your solution as something that will set them ahead of their competitors, in their industry, and in the market.
25. Showcase Adaptability
Senior executives will be much more interested in hearing you out if they believe your solution is scalable and adaptable.
To that end, don’t just present your solution as a one-and-done fix. Share how your partnership might evolve over time if an executive chooses to work with you.
Elevate
Top-Performing Sellers are 91% more likely to develop enterprise-level relationships.
Selling to senior executives means speaking their language, understanding their priorities, and demonstrating expertise in solving their complex business challenges. You must adopt a different mindset for executive sales.
26. Discuss Big-Picture Impacts
Understand and communicate how your solution relates to the company’s long-term strategy. Demonstrating holistic knowledge of how an executive’s business functions builds your credibility and gives your solution focus.
27. Avoid Tactical Details
Conversely, don’t get bogged down in minor technicalities unless asked. Early in executive-level sales conversations, you aren’t selling the specifics—you’re selling the vision of how you can help a senior executive and their organization.
28. Speak Their Language
In conversations with executives, use terminology and concepts that tie in with their industry, business, and priorities. You’ll be more likely to resonate.
29. Build Executive-Level Relationships
The goal for an executive-level relationship is to position yourself as a trusted partner. At this level, you’re considered essential to the executive and the organization. If you’re not there yet—maybe you’re considered a supplier or even a preferred or strategic supplier—there are specific actions you can take to develop strong enterprise-level relationships.
30. Outsell Your Competition
Your mindset is a key differentiator in executive-level sales. When you plan your conversations with executives around the STRATEGIC framework, you differentiate yourself from less prepared sellers.
Gravitas
Top-Performing Sellers are 40% more likely to inspire confidence with executives.
Senior executives want a partner to drive initiatives forward, someone who can be trusted, is respected, and is an authority figure in their own right.
31. Demonstrate Executive Presence
Project confidence and speak with authority about your solution in your meetings with executives. Stay composed and purposeful. If you’re missing these qualities, executives will notice.
32. Be Decisive
Part of gravitas is displaying your own leadership capabilities. You’ll gain the respect of executives when you take the lead and make strong recommendations rather than leaving decisions entirely up to them.
33. Manage Your Reactions
Maintain your composure and professionalism under any circumstance. For example, if an executive raises an objection, avoid getting defensive and instead turn it into an opportunity to learn more and move the conversation forward.
34. Establish a Peer Dynamic
Many sellers are nervous to sell to senior executives, believing that they’re out of their league. This leads to them becoming overly deferential, undercutting their authority.
If you’ve built a foundation of strong executive sales skills, you have everything you need to refine your approach and engage with executives. Internalize the STRATEGIC framework and have confidence in yourself and the value you offer.
35. Build Credibility
Your expertise, the reputation of your organization, your level of research, and your insights all contribute to your credibility.
Wherever possible, build credibility among others in the executive’s organization. Referrals from a trusted decision maker come with a level of implicit trust you may not have as an outsider.
Insight
Top-Performing Sellers are 88% more likely to inspire buyers to reach out for advice.
Capture the attention of senior executives with fresh insights that address their challenges in innovative ways.
36. Offer Unique Perspectives
When selling to senior executives, you need to bring fresh ideas or analysis .
The idea is to move the buyer out of their comfort zone and open their mind to change. You do this by introducing new ideas and asking questions that lead them to consider alternatives.
37. Use Data to Tell a Story
When providing strong evidence and support for your solution, data is your friend. But share it in a way that clearly reveals new opportunities. Whatever the details of the story you tell, it should follow a similar structure: that change is undeniable, and your buyer can make meaningful change with your help.
We call this the Convincing Story framework and it makes your story and evidence more compelling. And compelling evidence is even more important with executive-level buyers.
38. Challenge Their Thinking
To engage with senior executives as peers, you should be willing to question their assumptions or offer alterative viewpoints. Do this by:
- Disrupting their thinking by questioning it or offering alternatives
- Reframing their thinking by encouraging them to look at ideas or problems differently
- Directing their thinking by guiding them toward better options
39. Provide Strategic Advice
Be a valuable resource to executive-level buyers beyond your offerings. If you’re proactively providing insight into broader business issues, executives will be more likely to later seek you out for your opinions and recommendations.
40. Stay Informed
You can’t drive value and insight without staying informed! Stay ahead of industry trends and use what you learn to lead relevant and valuable conversations with senior executives.
Concise
Stay organized, clear, and brief in your meetings and other interactions with senior executives.
41. Be Succinct
Don’t let the details get in the way of the message you’re trying to communicate. Focus on the essentials of your message and organize it in as few points as possible.
42. Read the Room
Stay flexible in your conversations with senior executives. If they’re curious about a certain point, be open to elaborating on it. Be aware of how long you speak for and know when to get to the point.
43. Lead with the Most Important Information
Lead with the key message. What’s the conclusion or benefit you want to communicate? For example, in a meeting, start with the main point so you can spend the rest of the meeting solving a problem or capitalizing on an opportunity. As they say in journalism, don’t bury the lead.
44. Eliminate Fluff
Too much complexity or detail can undermine your message. While using relevant terminology is good, don’t rely too much on jargon.
Senior executives want to know about the big picture. Save the fluff.
45. Prepare for Follow-Up
Even if you’re not planning on covering it in conversation, have information prepared that you can share, if needed. Anticipate specific questions, be prepared with broad-based knowledge to handle questions you might not expect, and send follow-up information after the meeting if it’s called for.
Applying These Tips
Sales with senior executives are complex and you have a limited window of time to make an impression and capture interest. To succeed with executives, you need to go beyond fundamental consultative selling skills. Executive sales requires a different approach that starts by recognizing the ways executive sales conversations are different and adapting accordingly.
Identify how the 9 Principles of Selling to Senior Executives—each part of the STRATEGIC framework—match your selling style and refine your skills in each area.
