Are Your Portfolio Sales Reps Making These Mistakes?

Kathy RiveraExecutive Assistant

November 22, 2023 in Sales

“Their first availability is in two months.” Now that’s an impressive gatekeeper! It’s also not uncommon to hear when working to schedule a meeting with a company’s decision makers. Unfortunately, two months out isn’t going to help a portco’s BDR hit their numbers for the quarter.

As a private equity leader, your own gatekeeper likely keeps your calendar in tight shape. Still, you’re stretched thin across portfolios, with due diligence assessments, finding the right leaders, and more. In the end, we all have just 24 hours in each day.

The same can be said for the decision makers at any company. No one has enough time, especially a leadership team. Memes and jokes about meetings that “could have been an email” are funny because they hold some truth. Time is our most valuable commodity, making the act of reaching decision-makers difficult and important all at once. Quote kathy

I’ve spent over 15 years as an Executive Assistant (EA) supporting C-suite and management in companies large and small. In that time, I have observed proven approaches to earning time in a decision maker’s day. My job is to help an executive get as much out of their meeting time as possible. That means not only keeping people “out”, but also letting the right people “in”.

Being one of those right people can be a challenge for a sales team. A Harvard study on how CEOs spend their time revealed 72 percent of their work time is meetings. Executive outreach, the art of cracking into that schedule, requires sales professionals to become a student in the art of C-level engagement.  

Some RevOps strategy analysis on connection rates often discovers that BDRs aren’t making the appointments needed for success. If that’s the case in one of your portcos, forward this article to your sales reps. Below are this gatekeeper’s top three proven strategies to secure part of a decision maker’s 72 percent. If you’re wondering how to connect to a CEO, start here. (I’ve shared three things to avoid, as well!)

DO go through the gatekeeper

EAs get a bad rep as an annoying hurdle to the access you need. It’s in your best interest to utilize their knowledge and make them an ally. EAs often have a high EQ (emotional quotient), sensing when someone is treating them like an obstacle. Conversely, they know when you are authentically working with them as a key part of the C-level team. 

Executives value their EA as a trusted advisor. We’re often the only person between them and a week of solid 7am-7pm meetings. EAs also know more about what’s happening behind the company’s scenes than most people. The CEO/C-level considers their EA as a dependable guide – shouldn’t your company’s sellers? Those who are trying to reach decision-makers often make this mistake, treating the EA as trivial, when they’re one of the most crucial parts of the team.pull quote

The hit TV series Suits features the main character (decision maker) leveraging the EA as a screen for candidates being interviewed. The EA serves as the tipping point directing him to his new hire. It’s fun in the show and consistent with real life. The show does a nice job of revealing the crucial role of an EA and why sellers should embrace their role. 

Even if you have a relationship with the decision maker, it’s best practice to go through the EA. I once had someone reach out with the times a CEO had given him to meet. The problem? The executive actually had no availability at those times, requiring me to start the process over anyway. 

The EA often knows the decision maker’s mandatory commitments better than the decision maker themself. Start the dialogue by speaking with that understanding. If you got the decision maker on the phone, what would you say? Say that same thing to the EA. Reaching decision-makers becomes much easier once you get this perspective in mind. 

If you’re trying to make a new connection, it’s even more important to go through the gatekeeper. Often they’re listed right on the company’s website, or are a relatively easy find through some LinkedIn investigation. Even if you only have the executive’s email, always include the possibility of an assistant. Close with something simple like: “If you have someone who manages your calendar, please let me know.” Usually the EA is screening the executive’s inbox anyway – this acknowledgment can ingratiate you a bit, as it shows that you’re considering the human side of the interaction.

DO your research

Treat the decision maker (and their EA per DO #1) as you would any marketing prospect. You want them to “buy” your offering – a meeting with you. Do some research. Find out if your offer is a fit before you reach out. What is their pain point? If and when you get your meeting with a higher-up, are you going to know how to talk to a CEO about the pain point and your solution for it?

Learn about them and their company on LinkedIn or via a quick Google search. If they’ve just shared a post celebrating their new website, and you’re a website designer, move on. Reaching out to them only makes you look like you don’t know anything about them or their company.

Researching can also help you find mutual connections. Share that you both worked for a certain company, attended the same (or rival) colleges, or know a certain person. Better yet, see if you can get that mutual connection to make an introduction on your behalf. Anything to make you a bit more human can make your request worth a second glance.

DO offer value

Another marketing tenet is to offer value to your prospect before they’ve spent a penny with you. This absolutely is true for getting in front of a decision maker. Prove the benefit of meeting – especially if they or their EA knows nothing about you or your company. Reaching decision-makers only happens when you have a tangible amount of value before you even walk in the door. How can a meeting with you help alleviate one of their pain points? 

If you’ve done your research (see DO #2) you should have some idea of knowledge you can offer. Share that with them in the initial request. BUT make it genuine! Help is not a link to the Services page on your website. It can be an article or podcast episode speaking to something the executive posted on Twitter or LinkedIn. And here’s a secret – I can probably count on 2 hands the amount of times someone has done this over the years. But if they do, and if it’s quality value, I’ll make sure they get that meeting.

And what about the Do NOTs?

Do NOT automate (without human review)

I’m a huge fan of automation for businesses and delegation for managers. However, when you are trying to connect with someone holding decision making power, a personal touch is required. We’ve all received those emails that signal automation by saying Dear <Insert First Name>. If you can’t even get the First Name merge field right, you won’t be getting a meeting.

To save time in your outreach, it’s fine to use email templates or delegate emailing to an assistant. That said, be sure to adjust with true personalization. I’ve received meeting request emails with words copied and pasted directly from my company’s website. That doesn’t show research, it shows laziness. Trust me, emails like that get deleted by the EA before the executive even thinks about opening it. Your value should shine through in every interaction you have with them, and this should be the backbone of your executive outreach.

Do NOT follow up the wrong way

Yes, you need to follow up, but do so with the Dos and Don’ts in mind. These decision makers, and their assistants, are busy people. Do not email 24 hours later with “Did you see my last email”. Give at least 48 business hours, my preference is closer to 72, before you follow up. Reaching decision-makers is often about timing, and showing impatience upfront means that they’ll be less likely to be in favor of meeting in the first place.

Remember DO #1 and continue to offer value in your follow up. A particularly annoying follow-up is to send ‘thoughts?’ as the messaging. Adding a relevant blog or podcast is good, or even a simple schedule update is helpful. For example: “My calendar has changed since I first reached out, so I’ve included new times below.” Recently I did this in a follow up. It turned out the other EA had been sick and had an inbox she was trudging through. She welcomed my follow up with new dates so she didn’t have to sift through old info. You may also run into scheduling issues with newer CEOs or those in Interim C-Level Leadership positions, as they acclimate to the company itself, meaning you must be even clearer about the value you bring to the table.

Do NOT forget your manners

This last item should go without saying, but you’d be surprised. Whether you’ve connected with an EA or the decision-makers themselves, you’ll get much further being polite. Use a salutation, a closing, and some please and thank yous thrown in for good measure. As my grandma used to say, you catch more flies with honey than with vinegar.

Next Steps

Connecting with a CEO or other decision-maker can take some time and effort. Keep the Dos and Don’ts in mind, work with the gatekeeper, do your research, and offer value. Knowing how to talk to a CEO is only part of the equation, be sure you’re ready for EAs and other potential gatekeepers. These proven strategies will ensure the highest probability of success. 

Need some value to share in your next connection? Sign up for Cortado Group’s blog Insights to receive regular thought leadership to thrive and resolve Go-to-Market challenges.