Winning with Executives

Connecting to Stakeholders 

The Value Pyramid 

Understanding stakeholder motivations allows you to deliver value that speaks directly to their needs. This is particularly useful in navigating executive engagements because executive motivations differ from those of managers and front-line staff. 2Win uses the concept of the Value Pyramid to visualize the differing motivations of stakeholders occupying three distinct levels in an organization; operational users, managers, and executives.

At the base of the Value Pyramid are the operational impacts that result from using your solution. The people who care the most about these impacts and who will be motivated by them are front-line staff and operational users. To win approval with this group, you should discuss the benefits of a solution in terms of how it will positively impact their day-to-day activities.

In the middle of the pyramid, we have departmental impacts. Managers are the stakeholders motivated by departmental impacts. When you have management in the audience, they will resonate with impacts such as increased productivity, improved visibility, time or budget savings, etc.

We have strategic initiatives and impacts at the top of the value pyramid. This is what executives care about. To resonate with an executive you must be able to quickly demonstrate alignment with their strategic initiatives. Can you articulate how your solution will result in, say, increased market share or reduced churn?

Flipping the Script with Stakeholders 

When you enter into an executive engagement, you are on a different playing field with new rules of engagement. The secret to winning is understanding how to connect with the executive's strategic initiatives. This may require flipping the script you would use when presenting to managers and operational users. Rather than building a case of how operational impacts could lead to departmental impacts, connect first to the strategic initiatives your solution will help achieve and then add value by discussing departmental impacts. You want to stay high in the value pyramid. Discuss departmental value when needed, and try to stay out of the operational impacts unless requested to do so. If you cannot communicate with executives about the things they find valuable, you will find yourself being directed down in the organization.

Executive Mode and Space 

In all our engagements, we need to understand the mood and mode of the people we engage with. Executives are no different. They may operate in either an assertive or a collaborative mode of discourse. Winning with Executives explores four common modes, amiable, expressive, analytical, and driver, and provides tactics to adapt your approach to them specifically. Part of the preparedness for an executive conversation is learning to observe certain traits, body language, and tones of voice that indicate shifts in energy and emphasis in an engagement. Because executive engagements have different goals, it is important to know what mode the executive operates in to present value similarly. 

Diligent in Preparation

Adaptive in Execution

Being prepared for an executive engagement helps you be adaptive in the moment. This preparation includes knowing who will be in the room, understanding what the current organizational objectives are, from operational to strategic, and which stakeholders may have objections that an executive will be taking note of. Get to the best understanding possible of your position and identify your desired result for the end of the meeting. From this place, develop a plan of action and craft an impact statement that connects the executive's strategic initiatives to your intended outcome.

This plan of action will need to adapt to the executive's mode and should identify who will be delivering the key points of impact, whether that is the sales engagement team or an account executive. Get very clear on the information you have moving into the engagement. Ask the big questions. Do you have support? Does your contact have support for your solution? Being adaptive here is very important because there are variables on the buyer side that you may not have visibility for. Along with the plan of action, plan for a fallback position, and plan for potential risks. You may need to come back with more information or learn new priorities. Learn the specifics if you find that you have to pivot.  

Timing, Questions, Themes 

In your plan of action, you should schedule time accordingly and check that the executive still has that amount of time available, have prepared questions to lead with, select themes that are relevant to their specific industry, and have discussion topics prepared around the solution you are representing. This will allow them to open up and share their perspective. You will want to “float your agenda” first to be sure that they are comfortable with the position you are presenting. You also give them the option to discuss what matters to them the most first. 

When you can address an executive with the right information that speaks to their strategic initiatives, you give yourself an edge in moving the conversation forward in your plan. You intend to prove how the departmental impacts lead to strategic objectives. The conversation needs to center around their priorities. In your preparation, consider the questions they may ask, depending on their mode as an executive. When you plan these topics, be prepared to answer questions. Encourage engagement and keep asking questions to keep it conversational. 

Closing Summary, Recognizing Shifts, Pivoting in Response to Shifts 

Your closing summary should include two things: requesting the next steps in your plan and making your final impact statement. We have the most important tip: ask for support to move forward. Actually, ask. Listen to their response and establish a reason to meet again. If you sense the executive is not with you, you can move to a fallback position. What we have discussed up to this point does not account for pivots and shifts. 

When preparing for executive meetings, we must factor in dynamism in our engagement style and be poised to pivot. We have to listen intently and respond with purpose. Shifts will be signaled by body language and words. Review our active listening skills. Clarify, paraphrase, and be able to test the pivot before committing to take the conversation in a different direction. Repeat the process until you feel you are comfortably on the right path. There are three common shifts. The first is a time shift, which means you might have less time. Second, they can shift modes. The third is a topical shift. The project can be about something different. This is where it is so important to be customer-focused and practice active listening and responding to adapt the pivots. Continuing to adapt to the executive with presence and asking questions will help you overcome these unexpected shifts. 

Winning with Executives 

Successful executive interactions and winning executive buy-in are among the greatest skills for a seller. It shortens your sales cycle and is one of the most important engagements you can have with a client. Where the stakes are so high, investing in preparation and learning is well worth it for an organization and an individual. Beyond understanding how to speak to strategic initiatives through selling departmental impacts, you need practice and exercises in reading the executive mode and shifting priorities deftly. Winning with Executives was developed precisely to provide a platform for this training. There aren't many chances to win a deal after you have lost or performed poorly in an executive engagement. Learn more about how we work below. 

These are some of the precise exercises we teach at 2Win. 

• Defining Your Executive Engagement

• Identifying Executive Modes

• Preparing for Executive Engagements

• Connecting to Executive Priorities

• Pivoting in an Executive Engagement

• Choose an Engagement 

• Build an engagement plan 

• Plan of action 

• Executive Summary 

• Conversation Topic

• Closing 

• Measure your performance