Driving Executive Outcomes as an Individual Contributor

Do you feel empowered during executive engagements and confident in driving outcomes, or do you feel the familiar pull to go more in-depth to prove value? Executives are increasingly involved in software sales meetings, but their priorities differ from those who manage or will be adopting new solutions. A budget line item may be in question, or a better understanding of where your solution meets organizational goals are just a few reasons executives are joining SaaS sales conversations. 

Whether you are a contributor in a customer success role looking for a renewal, an account executive, or in solutions, moving your desired outcome forward with an executive requires a different tact, skillset, and plan. When you engage with an executive, you do not want to miss the opportunity to increase your deal velocity with executive buy-in.

Grow Your Confidence in Executive Interactions

Executives are People, Busy People 

Executives are everyday people with excellent business track records, different priorities in engagements, and are busy. If you are unaware that an executive will join a sales meeting, keep this in mind to overcome the feeling that you are not good enough to present. (Read more on Imposter Syndrome here.) Remember that in every engagement, your priority is to meet them where they are. In the case of executives, they may be operating in a specific mode, which we will outline; time constraints may bind them, and they may need higher-level discussions at that moment.  

A typical meeting for SaaS software sales with operational and middle leadership stakeholders may run something like this. You confirm everyone has the time allotted for the meeting, then launch an opening story with an impact statement. Then, you discuss topics or actions, close the story, connect actions to the following steps, and obtain the buy-in for the next steps. Executive meetings should be structured differently. When we change this structure, we more easily meet executive priorities. 

Intel, Intentionality, Organization 

How do you spot the executive modes in advance? Can you plan for unexpected shifts in a conversation? When should you talk about you, and when should you lean into customer concerns? Being able to think on your feet in executive engagements is the result of careful preparation and practice in spotting shifts in topics of conversation, executive mode, and changing your speed. Preparing for an executive engagement, including research and creating an executive summary and plan, helps you keep pace with shifts and influence the conversation towards a buy-in. 

Building an Executive Summary 

Your executive summary is the focal point in the information you deliver in the engagement. The key components are aligning with their priorities—relationships, vision, results, or data, and knowing the executive mode. Start with the outcome, define it concisely, and present the overarching business impact. Focus on measurable values, financial implications, efficiency gains, or risk reduction, avoid unnecessary details unless requested, and then support them with key insights or evidence.  Keep it short and direct. 

Preparation for Executive Engagements 

You have to set your intention to get into the driver's seat in an executive engagement. Is this meeting meant to educate, advise, share, or inform? Are you looking to align or urge an outcome or validate a viewpoint? Or are you coming in to convince, surprise, persuade, or challenge? Define your intention and the outcomes you hope to achieve, and make sure to also have a fallback plan. Next is your plan of action.  

Your plan of action should be executive-centric. Lead by ascertaining their current position, shift to the desired outcome or what you believe they need to achieve your intended result, and then deliver an impact statement. The impact statement is carefully crafted to shift the executive's perspective and depends on the intention of the engagement. You may be challenging or discussing a goal to change the executive's mind and obtain support. 

Risk mitigation and a fallback plan are the final components of the executive engagement preparation. Suppose you are still looking to move the needle forward but encounter opposition that requires more time or additional points of view. In that case, how can you keep the conversation moving and the deal alive? Risk mitigation is preparing materials and viewpoints that address uncertainty, how accurate your preparation was, and where you could not have known certain information. A fallback position is the best outcome for establishing another meeting to discover the unknown or an alternative next step.  

Know the Modes and the Shifts

Three types of shifts can occur during executive engagements. Shifts in executive modes, shifts in time constraints, and shifts in topical conversation. Connecting with an executive and winning them over as an advocate begins with understanding the possible modes an executive may be operating in and predicting the shifts that can occur in executive engagements. Our Winning with Executives course teaches methods for shifting your tact to meet executive priorities. 

We teach how to recognize and respond to the most common modes an executive may be operating in. There are commonalities to these leaders, such as how they must function to be effective. Whether they lead passively or are more direct, a contributor should be aware and prepared to meet these modes and know their priorities. The mode shifts have subtle signifiers to be on the lookout for, to be able to shift your executive plan accordingly. The modes we identify are amiable, expressive, driver, and analytical.  

Amiable: Relationship-oriented, collaborative, and focused on harmony. Prefers teamwork and consensus-building.

Expressive: Enthusiastic, persuasive, and vision-driven. Values creativity and big-picture thinking.

Driver: Results-focused, decisive, and action-oriented. Prioritizes efficiency and directness.

Analytical: Detail-oriented, logical, and data-driven. Emphasizes accuracy and structure. 

To be successful, you should meet an executive in their mode and notice when modes shift. You must be able to spot the shift and address their concerns or expectations to redirect the conversation back to your desired outcome or fallback plan. Ultimately, you are seeking support from the executive. Still, the speed with which you obtain the support can be increased if you recognize shifts and modes and adapt the conversation accordingly. 

Time shifts can occur suddenly, so having a concise structure and plan is critical to successful engagements. Your executive summary, followed by areas of impact, as defined by moving up and down the value pyramid, and then asking for closing support, should be able to take place in 5 to 30 minutes. While you are in the impact portion of the engagement, you may also encounter topical shifts in conversation. How might these look? We define the topical shifts as customer-centric or me-centric. There are times when both are useful and impactful. Customer-centric in the executive summary and impact and shifting to me-centric in the closing is common. 

How to Lead Executive Conversations

Leading the conversation, Smooth Selling, Asking for Support 

You can lead a conversation to a desired outcome when adhering to your executive summary, practicing active listening to look out for shifts in mode and priorities, and discussing strategic impacts. The key to smooth executive selling is making an executive feel that you are meeting them where their objectives are, keeping pace with their time constraints and mode, and inviting them to engage and participate topically according to their purpose of the meeting. Whether you have clarified positions and addressed concerns or will need  gather more information, when you finally ask for support or to continue the engagement if you have followed these guidelines, you will likely meet with acquiescence. 

But! To get support, you will need to ask for it. By far, the biggest mistake all sellers make is failing to ask for support. If you have established that you are in their mode, have responded to their questions, and restated your executive summary, they will be able to give you a reply. 

Learn more here if you want to learn our precise methodology and how we train individual contributors to drive executive outcomes.