Episode 9: How to prep for meetings with execs

👋 Yo! Welcome to the next episode of How to Negotiate where you learn how to grow your career and income with better negotiation strategy in less than 5 minutes. 

In honor of International Women’s Day, I wanted to dedicate this episode to a question from a female reader about a) how to get the confidence to reach out to the executive team b) how to figure out when it’s worthwhile to share vs. not.

While the question was from a female reader, I focused on strategies that anyone can use.

💰️ Lessons I’ve learned the hard way

I spent so much time early in my career worrying about ‘getting in the room’ - i.e. meeting/driving conversations with the executive team (CEO + Directs), but I was always too afraid to do anything about it.

For one, I had no idea how to decide what to say. I knew these individuals had more experience than me, so I had assumed there was nothing I could tell them that they didn’t already know.

I was also plagued with imposter syndrome which meant I was constantly worried that even if I did meet an exec, they would quickly realize I had no idea what I was doing.

Finally, I was also worried about my boss and potentially my boss’ boss in how they would feel if I had a relationship independent of them.

These mistakes led to me:

• being passed over for promotion because I was overly reliant on my manager (and usually their manager) to articulate my value to the business

• (^related to above) creating the perception that I needed oversight because I constantly asked for ‘approval’ from my manager

• feeling jerked around in strategy because I was already going down one path when I heard that we were told by executive team to do something totally different

• losing control of the room to side conversations whenever I did get an audience with the executive team to the point where we didn’t even get to the ‘so what’

• (^related to above) realizing that I would almost always ‘bury the lead’ by spending way too much time on context and not being clear about the ‘so what’

Now these things may seem overly critical or small relative to other issues, but it’s these little things that compound over time that truly separate good performers from great.

💎 Here’s what helped me gain the confidence

1. Execs are people too. What I mean is they also struggle with balancing work + life, knowing if the decision they made is the right call, and have fears and dreams. Each of these are opportunities to connect on a human level which helps focus less on the title / your feelings associated with that title and more on the person.

2. Expertise is relative. One of my mentors helped me reframe my imposter syndrome with this statement — you likely spend more time than anyone else at the company looking at x, therefore you are the expert. It doesn’t matter if you feel like you only understand 10% of it. It is likely 10x more than anyone else, so you still have something to offer.

 🎯 Here’s exactly how I prep for exec presentations today

Pressure test with someone who spends more time with execs than you

Especially if it’s your first time, it can be really scary so one tip is to get feedback from someone who spends more time with the exec team (e.g. a Director or VP). Even if it’s one person they spend time with, practical tips like the format of the pre-read or content (slides vs. docs), typical dynamic in the room (who asks a ton of questions vs. who will likely be on your side), and any other general advice can be very helpful.

Give one person on the exec team a pre-read and ask for feedback

My goal is to find out who will likely have the strongest opposing feelings to what I’m presenting and meet with them beforehand. In a 1-1 setting we can have a much more productive dialogue that will result in a) me sharpening my argument b) me changing my argument c) me changing their minds. All are favorable outcomes and worst situation I know what kinds of questions to prepare for even if I don’t convince them of my perspective.

Context is key - no one has as much as you

The downside to no one spending as much time as you on a problem is that they also have no way to size how hard of a problem it is to solve and why. For example, I often am talking to execs about our win/loss data — i.e. why we win and lose. Without context it seems pretty straightforward — collect all the data and find the trends for each bucket. The nuances of this are important though — e.g. relying on a salesperson to fill out a field that informs why we lost when they are at their peak emotion (for losses) automatically has a bias on their willingness to share details let alone anything at all. Therefore not all data is equal and we have to supplement with surveys or interviews with the customer.

Don’t shy away from bad news

A VP once told me that they crave constructive criticism about themselves or the team because in their experience the higher in the org they got title-wise, the less candid, clear, and constructive feedback they received. While it’s not a great feeling to tell the CTO or VP of Product that people don’t like the product, the best execs will separate their personal feelings from the product and appreciate the feedback because they can actually do something to fix it (most of the time).

Sometimes the basics are all you really need

I used to rack my brain looking for the deep, complex nuance that was leading to less revenue / some other metric that mattered to the business but 90% of the time it’s because we are missing first principles. Going back to those basics like - how much our opinion is validated by real customers, are we honest about where our product is today relative to the market, and what’s the willingness to pay can seem like the easy answer but often the one you actually need.

 🤔 How to figure out what’s worthwhile to share

My recommendation to you is just ask. Every exec is different and what they care about will change based on the needs of the business/pressures of the market or Board. Ask in a 1-1 setting what might be helpful to share and give some specific suggestions/options for them to choose from. It’s natural that your updates will become more refined over time.

Building my own relationship with executives individually is exactly how I got my most recent promotion. It was those relationships that helped me understand the power dynamics in play, where I had advocates vs. detractors, and how I ensured that even when I’m not in the room my story was still told the way I wanted it to be.

If you’re feeling stuck on how to start - i.e. which exec or what your first conversation should look like grab some time here.

As always, feedback is a gift and I welcome any/all feedback on this newsletter - good or bad. See ya next week 👋 

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✨ Special thank you to Gigi Marquez who suggested I start this newsletter 🙏