Driving Executive Engagement

Seth Martinez, PhD
9 min readJul 19, 2020

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Over a 16 month period I had been recruited for a range of learning and development roles across a number of tech companies in the SF Bay Area. Invariably during the interview process for each role, I would be asked about my ability to manage up and influence leadership. For example, a common question was: “Can you explain how you drove executive buy-in and engagement for a past project you’ve worked on?” Additionally, last fall I was invited to speak in a session of a Customer Advisory Board conference hosted by an external partner company. The topic on which I was asked to speak? Driving executive engagement. My presentation led to a warm and fruitful discussion. Afterward, several people asked for a copy of my deck. As a result of this pattern, I want to share the substance of my presentation that day, which is essentially my answer to the frequent L&D interview question “How do you drive executive engagement?”

It is no secret that if you polled 10 executive leaders (i.e., VP level) about the importance and impact of employee learning and development programs, you would hear a variety of answers. Some executives believe strongly in the value of employee training, while others, if not most, require much more convincing. That is just the way it is. So the onus falls on the L&D pro — you and I — to make it easy for the executive or senior leader to join us in the effort to realize the potential impact we envision, regardless of the executive’s standing. And to do this, it is essential that L&D professionals embrace the role as driver. In my experience, driving executive engagement consists simply of building equity with key senior leaders and knowing when and how to cash-in that equity.

I. Building Equity with Executive Leaders

What trait do all executives and senior leaders share? They have very little time and even less interest in the minutiae of an L&D professional’s life. This places the responsibility on the L&D professional to gain the trust of executives— trust that becomes equity. To build trust (i.e. accumulate equity), you and I must ensure that we are methodical with these three principles: (1) know your stuff; (2) do due diligence to gather feedback and data; and (3) draft a plan or strong recommendation that is based on said feedback and data.

Do I know my stuff thoroughly? The first question to resolve is whether you have comprehensive knowledge and awareness of all relevant aspects of the training program, namely the particular aspects that are to be in discussion with the executive.

You are the expert of the program, and executive stakeholders are looking at you to be exactly that. It is therefore imperative that you know all you can. It is also essential to anticipate the likely concerns or questions that the executives may pose. What is the learning experience? What do SME’s say? What feedback do the participants offer? What are the numbers and statistics? What is your interpretation of all of the above? Once you are comfortable and confident in your command of the relevant facts, only then should you begin to formulate a plan for interaction with the executive.

Is my plan based on data, information, and experience? As you form a plan, you should base your conclusions on data, information, and experience. If you fall short, then you should spend the time and effort to obtain more data and information. Send out a survey, conduct several interviews, or put together a focus group. Often, I’ve had to do all three before arriving at a firm game plan. Ask yourself: “What does the data show? What is the story here?” Once your plan is grounded in sound facts, then it is wise to also test your thoughts.

Have I pulsed my ideas internally for feedback before raising to senior leaders? Getting a quick reaction from your manager, teammate, or colleague is an invaluable way to obtain impartial feedback. As I have done this over time, I have consistently received nuggets of information that improve my plan even just 1% more. And make no mistake, when dealing with executives, you want every last bit of help in refining what you present them.

II. When & How to Cash-in Equity

The least common denominator approach is a safe guide in working with anyone senior to you. That is, are you taking your plan to the lowest level possible needed to get the green light you seek? If not, then you must absolutely not waste the executive’s time. That is the fastest way to burn equity. If the answer is yes, terrific. Now that you’ve done your diligent preparation and have a plan worthy of discussion, it’s time to meet with the executive leader. And because their time is precious, after 1–2 minutes of small talk, it’s time to get right to it.

It is always helpful to start off with a brief preamble of the meeting’s purpose. A very common introduction to my meetings with senior VP’s is, “Today I’d like to provide an update of training program X, provide information concerning topic Y and get your reaction, to then hopefully arrive at a decision for Y and/or Z.” From here, there are only three options for you during the substance of your interaction: (1) you tell, (2) you pose a question or scenario for discussion, (3) or you ask for something that requires their blessing.

Why only those three options? Because the executive leaders trust you more when you are so purposeful and intentional that you have every second accounted for. You are either telling, discussing, or asking…the end. Anything outside of that and you want no part of it. In fact, I consider it a bonus (dare I say a “win”) to end a meeting slightly early and say “Ok great, well that’s all I have for today. I will give you 5 minutes of your time back. Thanks a lot for your help today. Bye.” Get on the stage, say what you need to say, and get off the stage. That bears repeating: start the meeting, be direct and say what you have to say, and then end the meeting and get out of there. Bam! Unlike a manager or even director, an executive leader just has minimal room for small talk — assume that they carry too much responsibility to have time for that. The executives will only appreciate you that much more for the complete and total respect of their time.

*Note: the types of meetings you can engage with executives will vary. Some meetings will be solely to provide an update; others will require you to report a situation that needs executive guidance; occasionally you will need to ask for an approval or more funding. Regardless, while you have their audience, your behavior and language towards them needs to be 100% direct and intentional. To do so, I suggest you always start off by telling.

Tell. It is wise to take the initial portion of the meeting to walk the executive through the latest status and feedback-received of the relevant training program. “OK first, a status update on program X.” This could very well be the entire meeting if providing an update is most important. But if you have several purposes, then dedicating the initial portion to a state-of-the-union is best. Reciting facts and details from memory is a simple way to show you know and own your stuff. When they pose questions, you have anticipated them and have answers and appendix PPT slides prepared and ready at your disposal.

Discuss. After providing a status update, the bulk of the meeting should focus on the purpose for the meeting. For example, if you need their input to make a decision: “Regarding Y, there are multiple good options, I’d like to discuss the pro’s & con’s of each as I see them, and get your reactions and guidance to arrive at a decision.” You would then walk them through the variables at play — what are the pros, what are the cons, why each are what they are, etc. Once you have done this you should include your thoughts as well. “Based on all of this, it is my recommendation that we do the second option. It would allow us to achieve (insert desired goal) without the pain of (insert undesirable cost). Now, I want to get your thoughts.” And therein the discussion portion begins.

*Note on when: until now I have not mentioned the “when” of cashing-in equity. There are two reasons for this. First, providing updates and leading a discussion to arrive at a decision are two fundamental activities that often must occur with executives regardless. These are primarily equity building activities; that is, these are opportunities for you to shine, to demonstrate your thorough preparation and competence…these establish and build trust. Second, really the only time the “when” to cash-in equity comes into play is for making requests or asking. Throwing more money at a problem cannot be your first response to crucial situations. It just can’t. While unstated by the executive, the truth is that you have to earn the right to ask. Think of it like this: in the executive’s mind you have to demonstrate worthiness of granting additional funds or approvals. Thus, the level of your ask should match (or at least approximate) the level of trust you’ve earned. For example, early on in your interactions the likelihood of a VP approving an expensive net-new request is very low. Conversely over time, say one year or more, after you’ve consistently demonstrated your competence through success (and therefore, demonstrated your trustworthiness), the chances of making a convincing recommendation for an enhancement to a training program that costs a considerable amount more and still receiving approval is much higher in comparison. It’s true — I have experienced this exact phenomenon. Now, how do you make the ask?

Ask. Likely the most challenging part of interacting with executives is when you need to make the request for something you need in order to advance the program or increase its success. But this is why you have spent so much energy building up equity — you are prepared for this. You might tell the executive, “In order to achieve X, we’ll need A.” But that is the easy part. To be clear, the single most important part of making a request to executives is your explanation of the logic behind the request. Why should they approve more funding? Why should they approve a new direction? Why should they grant a request-for-proposal? Regardless of the ask, what alternatives have you considered, and why is this specific request the superior option to any of those alternatives? Your prepared remarks that answer these questions will likely determine your fate. But fortunately, you have already considered all the options and vetted each and are preemptively sharing this information before the executive even thinks to ask. The more you are in sync with your senior leaders, the more you will be able to anticipate their questions and prepare thorough answers. In fact, if done properly, you should be able to prepare enough to almost expect a green light approval from your executive leader. Your thorough preparation will fill you with confidence, if not near certainty. In this way, because of your trust-building up to now and your thorough preparation for this specific request, the ask then becomes quite simple for you.

As this process plays out over time, you will find the trust of the executives increasing. With more trust, they will be warmer to your updates (tells), more thorough in answering your questions (discussions), more receptive to your requests (asks), and not surprisingly more engaged with your efforts with the program. And therein the trust-engagement cycle perpetuates. You will also find the nature of your interactions will improve; that is, meetings with executives that initially felt more like transactional exchanges will, over time, transform into true, warm discussions between respected peers. Now certainly the intuition and process I have described above does not guarantee success. However, applying the concepts I have shared has greatly increased the responsiveness I’ve received from executive leaders and my success rate with them. I hope these ideas can increase your efficacy as well.

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Seth Martinez, PhD

Senior learning strategist at Facebook by day. Author & scholar of cognition, learning, & performance improvement by night. https://www.sethaaronmartinez.com/