Sales outreach: 25 best practices for today’s reps

“I hope this person responds.”

How many times has this thought crossed your mind before reaching out to a potential customer? You draft an email, send it, and wait. Days pass with no reply.

Reaching out on LinkedIn or the phone feels just as uncertain. Maybe you send a short note tied to a recent post, but the prospect never sees it. Maybe your cold call hits voicemail. You look back at each step and wonder what missed the mark.

Sales outreach is tough at times like this.

That’s true for both outbound sales teams working cold leads and channels and sales reps who depend on inbound-related prospect activity to move forward.

So, that begs the question: What exactly does good sales outreach look like, when inboxes fill up fast and prospects barely have time to respond to sellers?

Leaders from HSBC and Bain discuss how their go-to-market organizations have enhanced their sales outreach strategies using Highspot’s AI-powered enablement platform.

Breaking down what modern sales outreach strategies look like today

Good sales outreach comes down to timing, clarity, and personalization.

It’s all about grabbing a prospect’s attention with a tailored message, keeping messaging short and simple, learning about a given lead’s world, and using that awareness and related deal-activity metrics to better engage them over time.

Strong prospective-customer outreach also means knowing when to switch channels. Sometimes, personalized emails and seemingly well-timed phone calls get no traction from would-be buyers, but LinkedIn messages get a quick reply.

Selecting the right channels to engage prospects (and not attempting to connect with them multiple times via the same channel over and over) keeps you from wasting time. What’s more, when you have a versatile, coordinated, data-driven approach to engagement, you gradually increase follow-up response rates,

Above all, a good sales outreach strategy focuses not just on increasing engagement with savvy email sequences but also starting genuine conversations that moves the buyer’s journey forward—and improves your sales conversion rate.

What effective sales outreach looks like for today’s go-to-market teams

Effective outreach campaigns look different today than they did even a few years ago, especially with AI changing how teams work. This shift pushes sales organizations to rethink how they connect with buyers. Every new wave of technology raises the same question for sales reps: Is this the one that will take my job?

“Radio, television, and early information systems all triggered predictions of the salesperson’s demise, yet each wave of innovation redefined the job rather than replacing it,” principals at global professional services firm ZS recently wrote for Harvard Business Review. “Today, AI and digital systems are once again reshaping what it means to sell.”

Even with this shift, there are still tried-and-true habits—regardless of the technology being used by B2B reps—that should be a part of any sales strategy:

• Basic preparation to fully understand the ideal customer profile
• Speaking directly to a prospect’s industry, business, or challenge
• Keeping sales outreach efforts simple, brief, and right to the point
• Using simple engagement data like opens, clicks, and profile views to plan next steps and develop more impactful digital sales room and email templates
• Treating lead follow-up as a normal part of the sales process

When these habits become routine, sales outreach is more predictable. You know which prospects warrant another try and which ones can wait. You spend less time rewriting the same message and more time talking to actual people.

25 best practices for a more successful sales outreach strategy

Good outreach starts with sales readiness. When sales reps know the message, the buyer, and the plan, every touchpoint gets stronger. Use the following best practices to boost lead generation and improve your conversion rates.

1. Open strong with a hook that earns you the right to get (and keep) attention

Your first line determines whether a contact keeps reading or keeps listening. A simple way to sharpen that opener is some quick prep and a little help from AI.

“Rolling out a new pitch deck? Build rehearsal prompts to help reps internalize key talking points,” per Highspot’s 5 Ways to Help Sellers Win with AI Role Play Guide. “Prepping for Q3 planning calls? Create scenarios that speak to outcomes and urgency. Whether they’re learning new messaging or adapting to a new persona, AI role play helps reps build the muscle memory they need before a live call.”

These AI role play exercises—ones that reps can take part in using an AI-powered sales enablement platform like Highspot—make it easier to deliver a strong, compelling opening line that grabs a prospect’s attention, leaves them wanting more, and helps BDRs overcome objections and answer tough questions.

2. Personalize email templates so they sound more “you” and less “Mail Merge”

Email templates save time, but business leaders can spot canned lines instantly.

To personalize a message, pull one or two details from an ICP, then rewrite the message so it sounds like something you’d actually say to them in person.

For example, instead of, “I just wanted to take a moment to reach out regarding your current strategic initiatives,” try, “I saw your team just expanded your operations group. Congrats! How is that shift positively affecting your workflow?”

Use this same approach to create email subject lines that entice readers. Natural, human outreach is what builds trust and improves response rates.

3. Spark LinkedIn outreach with relevance, not recycled cold email templates

LinkedIn works best when your message fits the platform. Keep your notes to potential customers short, direct, and tied to something the buyer actually did.

Mentioning a mutual connection or reacting to a recent post works far better than pasting in a generic sales pitch. A simple two-sentence message tied to a lead’s perceived pain points often opens the door to new customer relationships.

4. Build rapport by asking smart questions before you overtly pitch anything

Good sales outreach starts with curiosity, not long-winded pitches.

Ask a short, specific question tied to something you noticed: a new product launch, a team announcement, a challenge their business posted about. Something like, “How is your team adjusting to that change?” feels far more natural than an overt pitch. Buyers respond better when the first touch isn’t salesy.

5. Write emails like texts: concise, warm, and impossible for leads to ignore

Most prospects skim your customer outreach. Keep your messages easy to read in one pass. Simple sentences, a friendly tone, and a clear point work best.

Think of how you’d text a coworker: direct and helpful, with no unnecessarily lengthy paragraphs. A quick line like “Saw your update about evaluating tools. Thought this might help.” will be far more effective than an exhaustive introduction.

6. Automate wisely to increase productivity, not robotically blast your list

Sales automation should remove busywork and cut through the noise. An AI sales assistant that factors in all sales outreach and lead engagement data like Highspot’s Deal Agent helps sales reps personalize quickly by pulling insights into their workflow.

It can’t be overstated enough: Using the right sales tools can help you consistently adjust your tone and augment your personalization efforts. The ideal AI-powered platform saves your sales team time and gives your sales leaders coaching help.

7. Trim your opener, as short intros pull prospects in faster than bios ever will

Before writing an email or LinkedIn message, ask yourself, “Would I actually read this if it showed up in my inbox?” Anything that sounds like a resume, pitch deck preview, or apology for reaching out only turns of would-be buyers.

A tight opener like, “Saw our recent post about scaling your team. I’ve got a quick question about how you’re doing it, if you have 5 minutes,” is likely to get more attention than a prolonged paragraph explaining who you are or what you do.

8. Research buyers’ companies and lead with something they’ll care about

You don’t need hours of deep research to write something relevant. A quick scan of a prospect’s website, their existing customers (via case study pages), recent news and press releases, and other digital channels can reveal valuable clues.

Maybe they expanded their business in new international segments, announced a new, AI-centric partnership, or got a new round of funding. Reference items like these to show you’ve taken the time to learn more about their organization and direction.

Buyers respond when they see a message written just for them.

9. Polish your formatting so your email doesn’t end up in their spam folder

To avoid the spam filter, keep your sales outreach emails simple and clean. This means short paragraphs, no giant images, no colored text, and minimal links. Use plain-text formatting (no need for fancy fonts) and focus on clarity. Avoid click-bait subject lines or email templates with messy formatting.

10. Write email subject lines that tease value without sounding like clickbait

Subject lines determine if a prospect opens your email. Something like, “Quick question about your Q4 shift,” or, “Saw your note on XYZ,” creates curiosity without hype. The best email campaigns deliver on what the subject line promises.

11. Follow up like a pro: Vary your timing, tone, and channel until they bite

Most prospects need multiple touchpoints to get going. If email gets no traction, try LinkedIn. If LinkedIn stalls, send a short follow up. Steady, no-pressure follow up will keep you top of mind as long as you focus on customer value.

“Not all touches are created equal,” RAIN Group‘s Mike Schultz wrote about sales outreach. “Standing out amidst the noise is critical for crafting an effective touchpoint, and factors such as timing, medium, and brand presence are all relevant. At its core, a quality touchpoint is built on buyer-focused value.”

12. Share content that resonates with leads, based on your engagement data

Good content grabs attention, keeps the conversation moving, and increases sales engagement. Highspot AutoDocs helps by creating relevant, polished materials from approved templates. Look at your engagement data to see which pieces sparked interest. Build from that rather than guessing what works.

13. Mention their business or product to prove you’re not spraying and praying

Buyers ignore messages that feel generic. One reference to their company size, product, or a recent update shows you put in some thought. Something simple like, “I saw you’re growing your support team rapidly,” or, “I noticed you just opened a new location,” is all it takes to increase response rates of your outreach efforts.

14. Target decision-makers with tailored messaging that passes the gut test

Senior directors, C-level executives, and other buying committee decision-makers skip jargon in sales outreach and skim for solely relevance. When crafting sales messaging, speak directly to outcomes they care about. Avoid filler. A direct line about a challenge they face helps them see why your message matters.

15. Leave room to reply by closing with a question, not a wall of bullet points

Prospects are often overwhelmed by the labor- and time-intensive process of researching, speaking with, and shortlisting prospective vendors and partners. That means they’re (far) more likely to skip reading emails that close with a list of assets to read or a time to schedule a demo or appointment.

Instead of going this route, give the leads you connect with an easy path forward. Simple questions like. “Worth a chat?,” or, “Want me to send a quick rundown?,” encourages movement and makes your sales outreach feel conversational.

16. Reengage leads that go cold with value tailored to where they left off

When a warm lead goes quiet, look at the last asset(s) they clicked or viewed or the last deal-related topic they asked about on a recent phone call by leveraging your conversation intelligence data in your sales enablement solution.

Then, use that data to inform the next piece of collateral you send them, whether it’s a new case study, article, or update that aligns with their buying needs.
Lead-nurturing tactics like this help them rejoin the conversation without effort.

17. Circle back with prospects when they’re seemingly more ready to buy

As with most things in life, timing is everything. Pay attention to small buying signals like team growth, job changes, product launches, or new investments.

Use your wealth of sales analytics from across your GTM tech ecosystem to surface these hints so you can reach out to buyers at the optimal moment.

18. Call with confidence, but have the right message ready to make it stick

Cold calling only works when sales reps are fully prepared to hear just about anything from net-new prospects. You don’t need a script, just a loose outline and one clear point. Highspot’s AI Role Play can help you prepare for conversations and practice tough questions so you’re ready for whatever comes next.

Our AI-powered selling tool improves sales outreach campaigns for inside, field, and partner sellers, empowering them to practice real-world selling scenarios they or their colleagues have experienced out in the wild before.

19. Speak directly to specific pain points so they’ll feel totally understood

Leads respond to thoughtful solutions to real problems they face in their day-to-day. Name their pain points directly: workflow gaps, missed handoffs, shifting targets—whatever they’ve shared in recent interactions in their B2B buying journey.

Using a line like, “I find that teams your size typically struggle with time-consuming manual tasks—do you?” shows empathy and builds trust quickly.

20. Drop compelling social proof that’s punchy, not generic testimonials

If your past customers solved a similar challenge to a buyer, share a short example. These real-life examples go much further than anonymous testimonials.

Highspot’s Digital Sales Rooms can help by pulling approved customer success stories, videos featuring key stakeholders at existing accounts, and examples of ROI in one organized space so prospects can see real business outcomes.

21. Prepare for phone calls with a loose outline, not a word-for-word script

Static sales scripts sound forced and insincere. Outlines open the door for genuine conversation. Before calling a prospect, jot down a few key points you want to hit: a quick reference, one question, a next step. If calls make you nervous, practice with a teammate or run a quick scenario using AI-based role play.

22. Reply to inbound leads within a few minutes to catch them while they’re hot

Quick replies keep momentum and aid with ongoing pipeline generation. You don’t need a polished message. Something like, “Thanks for reaching out. Want to schedule a quick chat?,” works well while you gather more information.

You’ve undoubtedly seen the stats that show the importance of rapid response to net-new leads. The difference between reaching out minutes after a buyer enters your B2B sales funnel and waiting hours could lead to lost business opps.

23. Test out message timing to see which periods get the most lead responses

Different audiences respond at different times. Try creative ways to get the best results. Experiment with mornings, afternoons, or early evenings. Test out times and days of the week to call or email leads. Track opens and replies to see patterns.

Over time, you’ll find a ‘sweet spot’ for engaging your ideal prospects.

(Pro tip: Liaise with your sales enablement and marketing teams to see what’s worked timing-wise with integrated campaign messaging in recent months.)

24. Use curated plays, not a bloated pitch deck, to better engage prospects

Utilizing comprehensive pitch decks slows things down, especially when they try to cover everything. Curated sales plays, on the other hand, keep things simple.

Consider Highspot, which gives reps access to targeted, enablement-constructed sales playbooks and shared resources inside their daily workflow. Instead of sending 20 slides, you can send the three things that matter most to the customer’s journey.

25. Highlight how your offerings can benefit their business in the long run

Buyers want to know what happens after the sale. Tie your sales outreach to the outcomes they care about: fewer manual tasks, smoother operations, clearer workflows, or faster delivery. There’s no need to make dramatic claims.

Just paint a clear picture of how you can help their business.