Steer into the Objection — A Simple Persuasion Hack

Saumil Mehta
5 min readApr 2, 2018


The meeting featured 15 people at Square across different organizations. Going into the meeting, the presenters likely knew that one of the key stakeholders had specific and major concerns. In response, they had prepared extensively and built models, data tables and a 15 slide deck that they hoped would bring the diverse audience up to speed and propose concrete solutions to the problem at hand.

But by the time they got to the third slide, the key stakeholder had latched onto an innocuous point as a way to express their concerns. This opened the floodgates for everyone else in the room to jump in and start driving the discussion, myself included. After an hour of discussion, the presenters had gotten through five slides. The painstakingly prepared narrative had gotten unceremoniously blown up within minutes.

As I walked out of there, I was once again reminded of Reid Hoffman’s LinkedIn Series B pitch deck for Greylock to help entrepreneurs with fundraising. While the whole thing is great, what I remember the most is a pithy statement that applies to fundraising but also so much more — “Steer into your investors’ objections”.

Over the years, I’ve used this myself but also seen it help others in the persuasion business — managers, marketers and product managers. It has, um, rarely steered me wrong so I share it here.

Simply put, “Steer into the objection” refers to the idea of anticipating and addressing well-understood objections and challenges both proactively and also as early as possible in a presentation or discussion. As Reid says, “There will be one to three issues that are potentially problematic for your financing — address them head on. You have the most attention from investors in the first couple slides. Most investors arrive with questions, and if you proactively show you understand their principal concerns, you earn their attention for the rest of your pitch.”

After helping several people shape their presentations, I realized that this happens to be counterintuitive for most presenters, especially former Engineers like yours truly (heavy emphasis on former). The natural tendency is to let the narrative unfold in a linear fashion — first a throat-clearing agenda slide, then more table-setting, then a detailed description of the problem with supporting data, then the solution with supporting data, then resources required, then the milestones to measure success. Then death by PowerPoint.

This is a standard-issue deck that is presented every day at companies small and large. It’s vanilla but it’s fine most of the time when giving updates, presenting largely un-controversial content etc.

But this can easily blow up in your face when the presentation is meant to truly persuade a potentially skeptical audience to a different point of view. Or in meetings where a decision-maker needs to pull the trigger a particular way based upon the presentation. Especially if the decision-maker is highly opinionated, pressed for time and not highly aware of all the details — aka most executives.


Because a skeptic or even a well-prepared decision maker will literally hear “WHEN ARE THEY GOING TO GET TO X?” in their head the entire time you’re droning on and table-setting. That is their burning issue and until the itch is scratched they may hear you but they sure as shit ain’t listening to you. I used to think this was mostly about VCs who say no for a living and yet see hundreds of pitches every year.

I was wrong. After 2.5 years at a bigger company where the meetings-per-capita is naturally higher than small startups, I’ve now seen many different combinations of people have good meetings, great meetings and meetings that went off the rails within minutes. A highly common feature amongst the train wrecks? The decision-maker in the room jumped in during the first 5–10 minutes and took the conversation hostage to discuss their main concerns, pretty slides and linear narratives be damned.

The decision-maker steered into the objection because the presenter didn’t. And if that decision-maker is your boss or a person of real positional authority, good luck recovering from that during the meeting. It’s probably best to abort and try again.

Metaphorically speaking, of course

The better approach is to disarm the decision-maker by, at minimum, acknowledging their likely objections early on and promising to get to them later in the narrative. This quiets the loud voice in their head — temporarily! — and makes them feel like you’ve been listening. The more patient ones will then let the presenter follow the prepared narrative and the impatient ones will ask to just go straight to the part they care about. Either option is better than getting sucker-punched on Slide 3.

The truly ninja approach, of course, is to be able to fully address the concerns head-on, up front. In the case of LinkedIn’s Series B, Reid focuses up front on how LinkedIn will eventually generate revenue. The slide itself doesn’t foresee that they’ll do it by annoying the hell out of everyone with poorly written recruiter InMails but that’s a different rant. In the meeting I attended, the presenters could have shown a clear but high-level proposal addressing the decision-maker’s concerns and said something to the effect of, “This is our proposal for addressing what we understand are the key issues here — we’ll now explain the problem statement in more detail and explain why we arrived at this solution”. To be candid, I’ve personally found this much harder to do at all times but when it works — well it’s a thing of beauty watching victory being snatched from the jaws of likely defeat.

LinkedIn’s early revenue plans

A final point — you may wonder how you can even know the full list of objections before the meeting. To that I have a simple answer — ask them! I’ve had good luck sending an email a few days prior to the presentation and telling the key decision-makers the set of concerns I intend to address in the meeting. If I’m off base, they’ll quickly correct me and feel heard regardless. If I’m right, I’ve already bought myself goodwill walking in the door.

As I said before, this is counter to people’s natural tendencies so the first time will be a bit uncomfortable but I hope you’ll like the results nonetheless. Try it and watch yourself avoid steering off the rails by steering, instead, into the objection.

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Thanks to Kate Brennan for reading a draft and helping to shape this post.



Saumil Mehta

EVP and GM at Square (leading Point of Sale, Ecommerce, Workforce Management, Payments Partnerships). Former entrepreneur. Opinions obviously my own.