High Stakes Presentations — The Path from Anxiety to Absolute Confidence!

High Stakes Presentations

Dealing with high stakes presentations

Presenting and influencing in high stakes meetings, especially to an executive level audience – Is this a natural talent or does it take years of practice for you to develop this skill? Is there a formula or a set of best practices that can be used ?

I started recalling all of the unsuccessful presentations over the course of my career vividly. I also remembered how sweaty and nervous I used to get going into every presentation. It eventually dawned on me that I no longer feel nervous for important meetings and high stakes presentations. Instead, I tend to feel excited throughout the entire process! How did this happen? How did I get from crippling anxiety to confidence? I’ve broken down the guidance into three parts for those of you dealing with similar challenges in your career.

Part 1: Re frame unsuccessful meeting outcomes as learning opportunities

Early on in my leadership career, I was asked to help onboard a new CEO by showcasing our product road map and accomplishments. This was when I used to think that every executive meeting was a contest. And while this belief drove me to work extra hard for high stakes meetings, it also became a constant source of anxiety and stress. Halfway through this on boarding meeting, I started feeling hot and sweaty. The CEO was asking a lot of questions that none of us had answers for. In my head, I marked this meeting as a failure and started to think that I was surely going to get fired. I noticed one of my colleagues sitting quietly next to me, taking notes with a beatific expression on his face. After the meeting, I pulled him aside and asked what was running through his mind while we were being “grilled” alive? He said, “We weren’t being grilled, we were learning a tough, but important lesson. Aren’t we lucky to have a smart leader to point out the things that we haven’t thought of?” His reply stunned me into silence. I never thought about executive presentations in this way. In my obsession to gain acceptance, I had closed my mind off from the possibility of listening and learning. This event motivated me to start thinking about high stakes presentations in a new way. Instead of expecting to achieve a “predetermined” outcome for these types of meetings, I practiced keeping an open mind and focused on learning something new.

In my experience, high stakes meeting outcomes and associated learning typically come in three forms: A) Instant Validation, B) Additional Questions and Eventual Decision, C) Rejection

A. Instant Validation: We get instant validation when our pitch is met with immediate approval or acceptance. I used to expect this as the only acceptable outcome after my presentations. I have since learned (after countless occurrences) that this is not only rare, but not always preferable. First of all, the desire for instant validation is driven by a need for perfection on the first attempt, which then creates a great deal of pressure and leads to delays in feeling ready for important meetings. And during the meeting, every question raised feels like a challenge and personal attack creating a ‘me versus you’ dynamic between the presenter and audience. If you do get instant validation and acceptance upon the first attempt- that is great! But remember that this is not a realistic expectation to have every time.

B. Additional Questions and Eventual Decision: Most of the time, high stakes decisions are never made in the very first pitch meeting or presentation. Usually a presenter ends up receiving additional questions and follow-ups that require more meetings before a decision can be made. The higher the stakes, the more questions and challenges one can expect. Earlier, I used to consider this outcome as a personal failure. However, now, I have grown to see this meeting outcome as an important learning opportunity, and have even started respecting the high stakes decision making process faced by executives.

C. Rejection: Perhaps the hardest type of outcome and learning comes in the form of “No” AKA rejection. I now realize that some of my best and most life-altering meetings have been the ones where an executive has said “No” to me. Saying “No” is a difficult thing to do and requires a lot of thought and deliberation. However the simple act of saying “No” eventually leads to more focus and greater excellence. And this realization has made me stop cringing at the possibility of rejection”. It still hurts, but thankfully it doesn’t hurt as much or for too long.

Regardless of the shape or form in which learning comes to you, you become a better presenter by leveraging this acquired knowledge for your next meeting. I will say that it requires a great deal of awareness and practice — no matter how many times I’ve done it, I still need to steer my expectations away from obtaining ‘Instant Validation’ toward learning.

Part 2: Remember that it’s not personal

Your CFO probably woke up today with a headache and is struggling to get through her day. Your meeting attendees may have just finished a previous meeting which didn’t go well. The point is you never know what your colleagues are going through or struggling with. And regardless of what your meeting outcome is, it’s important to remember two things: 1) Senior leaders are as human as you or me, and 2) Meeting outcomes are rarely personal. Let me illustrate these lessons with an example :

I was scheduled to present a resourcing proposal at an annual finance review meeting with my executive team. I worked tirelessly with my team for weeks to create what I considered was a “flawless” proposal. We had beautiful slides, interesting research and compelling data as well as buy-in from several leaders on the executive committee. I had practiced and perfected my voice over narrative endlessly. The only acceptable outcome at this time was a resounding “YES”!

As I delivered my final slide with supreme smugness, one of the key decision makers (let’s call him D) spoke up. He referenced other teams that had made almost identical presentations that day and explained that he could not possibly approve all these requests. I immediately got defensive and marked D as a detractor in my mental list of ‘supporters’ and ‘detractors.’ I pointed him to the deck, and tried to answer his questions. I felt a familiar nervous energy rising through my body while a whiny, defensive tone started creeping into my voice. I could tell from his body language that no matter what I said or how hard I pushed, he was not getting convinced. Luckily for me (and my career), my boss (let’s call her T) spoke up and asked D if there were any additional details that we could provide to help him make a decision.

I realized that my preconceived idea of success for this meeting had closed my mind to other potential outcomes. Once I stopped pushing and gave D some space, he went on to ask some very thoughtful questions and eventually suggested that we schedule a follow-up. After the meeting, T pulled me aside. I was expecting some strong feedback for my ‘excessive passion’ in the meeting. Instead, she acknowledged how I might be feeling and then gave me a life lesson that I will never forget. She said: “We are all people (even those in C-suite) who are trying to do their best to make good decisions. Stop labeling people as “good” or bad”. Their job is to be objective and ask questions and oftentimes say no. It’s not personal. Similarly, your job is to not be ‘right’ or ‘wrong’ but instead to ask questions and do what is needed to get us to the finish line. So even though some meetings feel like personal rejection, they are actually an opportunity to make progress.”

For the next meeting, we went prepared with the answers to D’s questions and also shared alternative resourcing proposals. Most importantly, I went into the meeting with a learner’s mindset. We got our original proposal approved with some slight modifications and we also set up regular check-ins with D to provide ongoing progress updates. D not only ended up becoming one of the strongest advocates for our team, but he also became a valuable personal mentor to me.

Part 3: Prepare, Anticipate and Constantly Optimize

In addition to the above, I advocate for extreme preparation and practice to set yourself up for meeting success. Other important tools include preemptive anticipation of questions and the desire to get better each time you present (constant optimization).

A. Preparation: Typically, I work with my team to iterate through multiple drafts until the narrative feels just right. I always leverage data to substantiate my proposals. I practice the narrative in my head constantly and often do rehearsals with trusted peers and colleagues to get feedback before the final meeting. Finally, I try to send a pre-read in advance of the meeting to give a chance for executives to ask their questions ahead of the meeting.

B. Anticipation: One of my favorite tactics is to anticipate as many questions as possible in advance of the meeting so that I can have the answers ready. Pre-meetings with some meeting attendees is a great way to get early buy-in and even better understand what may be top of mind for executives.

C. Constant Optimization: As I mentioned in Part 1, every meeting will result in one of three outcomes. And in each of these three outcomes, it is never personal. So why not learn how to lead your meetings even better the next time around? During my meetings, I watch every subtle nuance in people’s body language, expressions, reactions and listen intently to the things they say and do. What questions are they asking? Which parts did not seem clear to them? Which parts required multiple people to jump in and offer explanations? These observations yield fascinating insights into how executives think and make decisions during these meetings. I also directly ask meeting attendees for feedback to help make improvements for next time.


So, in summary: A) Have a learner’s mindset, B) recognize that it’s never personal, and C) Be extremely prepared and be open to improving more each time. I truly wish I knew this earlier in my career. But now that I am armed with this knowledge, I’d like to share it with the world!

Check out the post on handling Tough Feedback and Tears by me in this context as well and feel free to reach out to me on Workplace related issues and challenges.

Head of Trust and Safety at Airbnb | [email protected] | Website

Nabarupa is an accomplished professional in the area of Business Intelligence, Product Management, Integration, Agile Methodologies, and has led cross-cultural teams across the US. She has worked with big conglomerates like Walmart and AirBnB. She loves building powerful product and operations teams driven to deliver innovative, customer centric solutions. An avid reader and artist,she raises a family of 5 amazing kids while juggling her professional responsibilities.

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