Why You Should Keep Sticking With Persistence
Whether you source opportunities for an investment strategy, or close tickets in the IR and marketing team, part of your role is sales, convincing a counterparty to pick you, your team, your “product”, over the competition. Great salespeople know (and academic research confirms) that success requires persistence, but many worry that they might come across as too pushy.
What can we do to remain persistent, without damaging relationships?
THE SCIENCE BEHIND THE COMMON SENSE
A recent academic paper showed how relying on a salesperson’s interpretation of verbal cues underperformed an AI-driven methodology (“stopping agents”). The researchers found that salespeople in the study overweighted expressions of disinterest, quitting their outreach too early.
In a relationship‑driven industry like ours, it’s natural to be sensitive to approaches that are sustained and recurring, but structured, ongoing outreach is necessary. Research across multiple disciplines shows that large deals require multiple touchpoints before meaningful engagement even occurs, yet many choose to move on from potential opportunities after just one or two unanswered attempts. In private credit, fundraising, deal sourcing, and hiring, the majority of meaningful conversations do not begin with the first outreach. They begin with the follow up. The lesson: If the person hasn’t explicitly said “no,” the opportunity is still alive.
Disciplined follow‑up approaches consistently outperform ad‑hoc (or abandoned) outreach, especially when decision cycles are long and transactions are complex. In environments like private markets, where context and opportunity shift constantly, measured persistence is a core competence.
TIPS FOR PROFESSIONAL, EFFECTIVE PERSISTENCE THAT AVOIDS OVERSTEPPING
Here’s how I think about staying in touch without stepping over the line:
1. Let them set the timeline and then stick to it
If someone tells you to follow up in a month, follow up in a month. Not three weeks, not six weeks, and definitely not never. That demonstrates good organization and reliability (and that you respect their time). You should always treat your counterparty’s timeline like a deadline.
2. Make the follow-up worth their time
People are busy. They don’t want to be “checked in on”. They want to know why you’re reaching out again, so I try to offer something that could be valuable to them:
A new opportunity: “I know we were talking about [x], but I hear that [y] was happening and I thought that could be interesting for you…”
A nuance to the story: “You probably saw that [x] acquired [y], but did you hear why it happened in the first place? Well, when…”
A helpful read on the market: “We’ve noticed an interesting trend in strategy extensions in Europe that I think might be making its way over here…”
Each of these can work really well in the right situation and keeping a note of intelligence you pick up is always a good use of time.
It doesn’t need to be ground-breaking, just relevant: Give them a reason to pick up, next time you call.
3. Don’t confuse silence with a “No”
I see this all the time: someone doesn’t respond, and we assume they’re not interested. But non-response is not a response. It just means they haven’t decided it’s worth their time…yet. I keep going until someone tells me no. Not because I’m pushy, but because I know that timing and context change. And when they do, I want to be top of mind.
If you have more junior staff that are reluctant to persevere with contacts that are hard to reach, help them to really understand what is going on by uncovering examples in their lives where they have been glad that someone reached out right when they were looking for support.
4. Use your network to break through
If I really want to talk to someone, and I’m not getting traction, I don’t just keep hammering them directly. I go sideways. I ask people they trust to make the case for me. That third-party credibility is often what moves the needle. It’s not just about being persistent. It’s about being strategic. Who has their ear? Where can I find an easier way in. Networks take time to build, of course, but making sure you always have something useful to share with people in your market will help accelerate the process.
5. Show progress, not just persistence
If all you’re doing is following up, people tune out. But if you can show that your side of the story is evolving, that the deal has sharpened, the team has grown, the market has shifted, they will start to see value in staying engaged. I try to make every touchpoint a chance to move the conversation forward, not just keep it alive.
6. Never apologize for doing your job
If you’re being thoughtful, relevant, and professional, then you’re just doing your job, and the people we’re trying to reach? Whether it’s investors, entrepreneurs, borrowers or candidates, they all know how this works.
If you show up the right way, at the right time, with the right message, there’s no need to be sheepish about it.
FINAL THOUGHT
Persistence is about timing, relevance, and trust, not piling on pressure. In our industry, showing up consistently, respectfully and thoughtfully is often what turns a quiet prospect into a closed deal.