Products
Integrations
Services
Company
Let’s be honest. Nobody likes awkward moments in meetings.
The “let’s circle back” line. The silent nods. The polite smiles that mean absolutely nothing.
It’s all part of the game, but it’s time we change how we play. One of the biggest misconceptions in investment sales is this: follow-up happens after the meeting.
But if you’re waiting until after, you’re missing a massive opportunity.
I’m talking about asking the Two Tough Questions. And the truth is, you should ask them right there during the meeting.
Now, I get it. Asking these questions might make you cringe a little at first. But if you want real answers and a clear path forward, these two questions are the ultimate guideposts.
Not only do they help you know where you stand, but they also give the prospect a chance to be honest about whether there’s any real traction.
In this article, we’ll discuss why you need to start asking the two tough questions in the room and how they can be a game-changer. By the end of this, you’ll have a better idea of how this will save you time and money.
Let’s clear this up right now: follow-up isn’t something you figure out after the meeting, in the Uber on the way back, or when you’re drafting your “thanks for your time” email. Too often, people leave the meeting feeling confident thinking, “That went well!” – without any idea of what the client is actually thinking.
That’s why we implemented a mandatory follow-up technique that doesn’t happen after the meeting, but right there in the meeting. Here’s the approach:
As the meeting winds down, I’ll turn to the prospect and say:
“Susan, I really enjoyed our meeting today. Do you mind if I ask you a few quick questions? We’ve spent an hour together, and I think you have a good understanding of our strategy.”
Then comes the first of the Two Tough Questions:
1. “Do you see our strategy fitting into your asset allocation model for your clients?”
If the answer is no, you know what the follow-up is: add them to the mailing list, stay on their radar, and move on. But if the answer is yes, then you’re onto the second question.
2. “If that is the case, do you anticipate conducting a search in our asset class within the next twelve months?”
If they say no, it’s the same follow-up as before: mailing list and periodic updates. But if the answer is yes, now we’re getting somewhere. I’ll follow up with:
“What would be the next steps we could take to begin to better familiarize you and your team with our strategy?”
If you’re marketing a private fund with closing dates, just tailor the second question slightly. Instead of asking about the next twelve months, ask, “If that’s the case, do you think you would be able to make the March 31, 2030, final close?” The follow-up logic stays the same, but you’re being specific about timing.
These questions aren’t just polite formalities; they’re strategic probes designed to gauge genuine interest and potential next steps. Most importantly, they help us avoid the trap that many salespeople fall into post-meeting: The Unknown. By asking these two questions right there in the meeting, you’re not walking away without knowing where things stand.
These two questions may be tough, but they’re designed to cut through the guesswork. Here’s why they matter.
1. The First Question: Do You See Our Strategy Fitting Within Your Asset Allocation Mix?
This one is critical. You want to know if there’s a fit, right here, right now. This isn’t about getting a “yes” on the spot. It’s about clarity. If they say yes, you know you’ve got a green light to keep the conversation moving forward. If they say no, that’s actually valuable too because now you’re not wasting time chasing a dead end.
This question isn’t about being pushy; it’s about respect for both their time and yours. People respect directness, and they appreciate it when you’re brave enough to ask this right there in the room. If the answer is no, you know it’s time to shift gears, thank them for their honesty, and consider a long-term nurture strategy instead.
2. The Second Question: Do You Anticipate Doing a Search in the Next 12 Months?
If they see a fit, your next step is to get specific about timing. This question is golden because it moves the discussion from hypothetical interest to a more defined timeline. Are they actually planning a search in the next 12 months?
If they say yes, now you know there’s something real to work with, and you can start figuring out what needs to happen next. If they say no, you’re not left hanging, wondering if you’ll be circling back for months on end. Either way, you leave the room with a much clearer idea of the path forward.
You might be thinking, “Can’t I just follow up with these questions in an email after the meeting?” Sure, you could, but I guarantee you won’t get the same results. When you ask these questions face-to-face, you’re putting the ball in their court in real-time. There’s no hiding behind an email, no polite delay in responding, and no guessing on your part.
Here’s the beauty of it: when you ask these questions in person, you’re giving them permission to be upfront. It’s like opening a door for honest feedback, which isn’t just valuable – it’s priceless.
I can’t tell you how many times I’ve left a meeting where I didn’t ask the Two Tough Questions, only to realize later I had no idea what the client was really thinking.
And then?
I’m spending weeks, maybe months, on follow-ups that go nowhere. Asking these questions on the spot saves you from the endless loop of “just checking in” emails that often follow a meeting with unclear outcomes.
Don’t get me wrong, I know these questions can feel a little bold. The last thing you want is to come off as aggressive. But remember, you’re not asking these questions to pressure anyone; you’re asking because you respect their time and your own.
Here’s the key: approach it with curiosity, not expectation. You’re simply trying to understand where they stand so you can be as helpful and efficient as possible.
This isn’t about forcing an answer or making anyone uncomfortable. It’s about creating clarity in the conversation, so you’re not left reading between the lines later.
Investment sales isn’t just about pitching products, it’s about creating clear paths forward. By asking the Two Tough Questions right there in the meeting, you’re treating the prospect like a partner, and you’re showing that you’re serious about finding a fit (or recognizing when there isn’t one).
So the next time you’re in a meeting, remember: follow-up doesn’t start after you leave. It starts in the room. Ask the Two Tough Questions, get the clarity you need, and leave the guessing game behind.
Trust me, once you make this a habit, you’ll wonder why you didn’t start sooner.
Written By: Gui Costin, Founder, CEO
Gui Costin is the Founder and CEO of Dakota.
January 30, 2025
September 24, 2021
March 31, 2022
925 West Lancaster Ave
Suite 220
Bryn Mawr, PA 19010
Tel: (610) 642-1481
© Dakota 2024 | Terms of Use | Privacy Policy | California Privacy Policy