Ten habits for better prospecting
Outcomes
Watch sales expert George Leith on what it takes to keep a funnel full.
A full funnel beats a big deal
You have seen it happen: someone crushes every record one month and is scraping the bottom of the leaderboard the next. It is almost never that they got worse at selling. It is that they stopped prospecting while they were busy servicing the deals they just won — and the funnel behind them went empty.
Prospecting is not the thing you do when you have spare time. It is the thing that determines whether you have a next month at all.
Keep the funnel full: ten habits
Ten habits separate the reps who always have a next month from the ones who do not. Open each to see what it looks like in practice.
The five-before-nine, nine-after-five rule
If you work a standard nine-to-five, make five prospecting calls before 9am and nine after 5pm. The logic: your buyer is doing their actual job during business hours. You want to reach them when they are doing their own admin and planning, when they are more likely to pick up.
Even on days this feels arbitrary, the discipline of doing it keeps prospecting as something you think about every day, not something you get to eventually.
Automate the outreach grind
Everything above is a discipline. The next part is a tool. A sales engagement platform like Yesware plugs into Gmail or Outlook and takes over the mechanical side of outreach, so you spend your time on conversations instead of the busywork around them:
- Track — get a real-time notification when a prospect opens your email or clicks a link, so you know exactly when to follow up. This is the respond-when-engaged habit, automated.
- Search — pull verified contact data (phone, email, social) for new leads in a couple of clicks instead of hours of manual research.
- Standardize — build reusable, personalizable email templates once, instead of rewriting the same email every time.
- Automate — schedule multi-touch outreach across several days, so the fourth and fifth touches actually get sent instead of quietly forgotten.
- Analyze — see which campaigns, cadences, and follow-up counts actually produce replies, so you stop guessing.
None of this replaces the habits above. It removes the manual grind around them so more of your day goes to actually talking to people, which is where the 60/30/10 rule says most of your time belongs anyway.
Pick one prospect you have not followed up with this week. Write the headline version of your outreach — one sentence of value, one question — before you write anything longer.
Put your AI Workforce on the funnel
Two AI Employees do real work around prospecting, and it is worth being precise about which part each one takes.
Works the top of the funnel. It answers website visitors around the clock using your knowledge base and website content, and it collects a name, phone number, or email so you have someone to follow up with. That is habit 4 running without you: someone is engaged right now, and something is responding right now instead of tomorrow morning.
Works behind the funnel. After a meeting is recorded and analyzed, it updates the CRM records that came out of that conversation and creates activities from the action items, so a commitment you made out loud becomes something on a list. You can also ask it about your pipeline in plain language, such as "What opportunities are currently open in my pipeline?" or "What action items came out of my recent meetings?", instead of building a report.
When you are ready to put a Chat Receptionist on your site, this guide walks you through setup. The AI Sales Assistant is part of CRM AI and needs a CRM AI Standard or Pro subscription; the AI Sales Assistant guide covers what it updates and how to control it.
Both of them work on conversations that arrive at you or have already happened. Going out and finding someone who has never heard of you is still yours, and the six habits above are how you do it.
Do it, delegate it, or buy it
- Do it — build your own outreach cadence and templates by hand. Free, but the most time.
- Delegate it — have an SDR or junior rep own the prospecting-volume side of the funnel while you focus on live conversations.
- Buy it — a sales engagement tool to automate tracking, sequencing, and reporting. The fastest path to more outreach without more hours.
Knowledge Check
Four questions on why funnels run dry, and the habits that stop it.