Episode #346: Keep Following Up Buyers

Why do some companies stay top-of-mind with prospects for years?

A well-known Japanese recruitment firm has called me at regular intervals for five years. That’s not unusual on its own. What’s unusual is the consistency despite staff changes. The person calling me changes from time to time, yet the follow-up never stops.

Most sales organizations lose momentum when a salesperson leaves. The relationship “falls into a hole,” and no one sustains the outreach. But this firm clearly has a system that ensures continuity. Their persistence makes one key point obvious: follow-up isn’t a personality trait — it’s an organized process.

Mini-summary: Consistent follow-up over years doesn’t happen by accident; it requires a system that survives turnover.

This experience forces an uncomfortable mirror on us:

• How organized are we as a sales team?

• How organized am I personally?

Most companies suffer from “falling through the cracks” when people leave or change roles. It’s rarely guaranteed that a new salesperson can keep a buyer engaged at the same level as the previous one.

Sometimes it’s about effort. Sometimes it’s about chemistry. Either way, if we want to protect revenue, we must protect the relationship beyond the individual.

Mini-summary: Sales continuity is a structural challenge, not just an individual one.

Effort can be trained

Effort includes the habits and discipline that keep deals moving: tracking, timing, and repeated outreach. Yet in many teams, we’re dealing with the classic 80/20 imbalance:

• 80% of the team produces 20% of the results

• and often causes 80% of the problems

If that lower-performing majority inherits a key account, the client experience can turn into a rocky ride fast.

Chemistry is harder to replace

The outgoing salesperson may have built a close, personal relationship. When they leave, that bond breaks. The new salesperson needs to re-establish trust — and that doesn’t always happen.

It’s normal not to “fit” every buyer. Differences in personality, style, communication, or expectations can make retention difficult. The important thing is to distinguish:

• Laziness

• Stupidity

• Genuine lack of fit

Only one of those is acceptable.

Mini-summary: Effort is coachable, chemistry is fragile, and both must be managed deliberately during handovers.

What is “stickability,” and why does it decide who wins?

Stickability is the ability to stay with a prospect long enough to convert them into a client. Many studies suggest it takes around eight touches to close a deal. I don’t know the exact number for Japan, but I do know this:

Prospects get away easily when salespeople lack:

• organization

• time sensitivity

• sustained effort

Many salespeople stop after one or two touches. If it really takes eight, then no wonder deals don’t close.

Mini-summary: Deals often fail not because prospects say no, but because salespeople stop too early.

How do you run follow-up in Japan right now?

With Covid easing in Japan, networking has restarted in person. That changes the game. Instead of being trapped in online events, I can meet people face-to-face again, and then follow up while the connection is fresh.

I tell my team we need to keep at least 50 active relationships in motion at any time. Prospects fall into three groups:

1. those who will do nothing

2. those who will do something later

3. those who will do something now

We don’t know which is which until we push things along.

Mini-summary: A healthy pipeline in Japan requires constant human contact and disciplined follow-up.

Here’s the practical cadence I use:

Email #1 — initial follow-up

Send a clear, relevant message soon after meeting.

Email #2 — resend with the previous email included

If there’s no response, I copy the previous email into the new one.
It subtly pressures them to respond — not aggressively, but socially.

Timing matters:

• Send follow-ups at 8:30am or 1:00pm

• Avoid emailing after 4:00pm — it gets buried

• A 5:00pm Friday follow-up is basically insane

You want your email near the top when they start work or return from lunch.

Email #3 — short reminder

If email #2 gets ignored, I send a third follow-up.
I include both previous emails and ask one simple question:

“Any progress?”

Some will still ignore it. But others respond because:

• they were busy

• their need resurfaced

• guilt finally kicked in
  Even a “no thanks” is fine — at least we know where we stand.

Stop after three (sometimes four)

I usually stop at three touches, occasionally four.
I don’t want to damage my personal brand by being seen as unreasonable or spammy.

If someone complains about follow-up, I ask:
“How many times do you want your sales team to follow-up with prospects?”
They know the honest answer.

Mini-summary: Effective follow-up is simple, timed well, and repeated just enough to be professional — not pushy.

What systems should we use to make follow-up unstoppable?

The recruitment firm that keeps calling me proves the point:
systems create consistency, not individuals.

To avoid relationships dying when people change, we need:

• shared prospect history

• scheduled touchpoints

• clear ownership rules

• visibility across the team

That’s how you build follow-up that survives turnover — and builds trust in both 日本企業 (Japanese companies) and 外資系企業 (multinational companies).

Mini-summary: A sales system must protect relationships from human turnover.

• Stickability — consistent, disciplined follow-up — is a major separator between average and high-performing sales teams.

• Effort is trainable; chemistry is harder, so handovers must be structured carefully.

• Three well-timed follow-ups are often enough to get clarity without harming trust.

• Strong systems prevent prospects from falling through the cracks when salespeople change.

Founded in the U.S. in 1912, Dale Carnegie Training has supported individuals and companies worldwide for over a century in leadership, sales, presentation, executive coaching, and DEI. Our Tokyo office, established in 1963, has been empowering both Japanese and multinational corporate clients ever since.