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Sales Outreach Tips and Best Practices

Let’s imagine for a second that you’ve received a message via LinkedIn messenger, or an email, or via any other numerous channels. It’s yet another sales outreach message, you’ve seen 20 of similar messages this week alone, but this one is a bit different from the rest. You keep reading it, and you actually find yourself intrigued.

This email doesn’t have your name in a weird font that stands out. It’s well written as if a person on the other side has actually done some homework. And this one doesn’t try to play make-belief as you are old pals and it doesn’t go out of its way to seem funny. After finishing reading the message, you are open to the idea of contacting this person and hear what they got to offer, and who knows, maybe even doing business together.

Unfortunately, that doesn’t happen too often. Sales outreach via digital channels such as email, in 9 cases out of 10 (that’s a generous stat), is poorly executed. Although today all the necessary tools are available to businesses, only a few know how to leverage them. Sales reps often lack understanding and skills in lead generation that marketers would have. This is especially true for SMB-type companies, where salespeople do their own sales outreach.

It’s understandable that a small business will not always be able to support such a campaign with a dedicated marketing team and execute it at a high level. However, the absence of a marketing professional doesn’t mean that your sales outreach letter should be the one that people will engage with.

So today we are going to look at 10 simple tips and best practices to help you elevate your sales and marketing plan above a mediocre crowd and stand out. By the way, some of the mistakes that we are going to discuss are not exclusive to small businesses. Many large companies suffer from the same problems and could really boost their open and conversion rates. We will cover high-level concepts of how to build a connection with the client as well as talk about actual technical mistakes.

So, without further ado.

Top Strategies for Small Businesses to Improve Their Sales Outreach

Sales Outreach Tips and Best Practices Image

1. Establishing a Connection Rather Than Selling

Probably the biggest mistake that most companies make when launching a sales outreach strategy, is trying to sell too hard right away. Initiating a real dialogue and engaging with a prospect from the perspective of their business is a craft. And like any craft, it has a certain skill set required in order to succeed. It’s easy to learn but hard to master. The real problem – most don’t even learn it.

Nothing creates a bad first impression, and nothing creates a worse association with a word salesperson like someone who starts selling right away. A simple search on Google will not tell you much about the prospect’s business and their needs. So instead of pushing your product or service in the first email, try to start a conversation that a potential client might be interested in.

2. Focus on the Prospect’s Business First

We all heard the phrase “Mind your own business”. Well, in case of sales outreach, you have to throw that idea out the window. Client’s business and their needs should always come first, and your offer should come as a solution specifically tailored to those very needs.

When utilizing sales outreach engagement platforms and email automation software, it is essential to invest time and resources into personalization. Today, in the digital age, we all can recognize an email template, so creating a subject line that will not turn away a prospect is of paramount importance. Nothing kills sales like the prospect’s feeling like just another item in your database. So don’t treat them like that!

Make sure that you include the name of your prospect, the name of their company and a brief intro on how you may help them. Try to show your own enthusiasm for the possibility of talking to them.

3. Engage with Their Vision

Another common mistake for even experienced salespeople is the inability to see beyond deliverables and goals and to recognize customer vision. Facts and numbers are relevant but they are not the deciding factor. People buy with their emotions and rationalize it with their logic.

So when conducting your sales outreach plan, you should try and recognize the prospect’s vision, stand behind it and show how your product or service can help them achieve it. And in order to convince them that you are the right company for their business, you back up that vision with facts on how together you can solve an actual business challenge.

4. Control the Flow of Conversation Through Questions

This is a useful practice for both sales outreach and just negotiations on the phone or in person. The person who asks the right questions guides the flow of conversation. This practice comes back to the idea of understanding the prospect’s vision and learning about their business requirements.

Instead of having all the answers and writing long emails about how great your product is, it is much better to ask a question.

Free sales tip: any salesperson has encountered a prospect, who goes right to the bottom line, without hearing out with “How much will it cost?” catching you off guard. Chances are good no matter what you will state, their response will not be positive. In an account-based selling, it’s much better to simply ask “It depends on what you need and what’s right for your business. May I inquire you to tell me more about your goals for the next month\quarter\year?” From there, you can start listening (or reading, in case of email) to prospect’s needs and provide them with a solution they need.

There are always some questions for engaging a prospect, so practice your sequences and refine this skill.

5. Avoid Impatient Words

Don’t say things like “Quick call”, “Fast meeting”, “It’ll take no more than 15 minutes” in your sales calls and emails. If you are not ready to dedicate as much time to the prospect as needed, then it’s not worth their while at all. You are talking about doing business together, possibly for years to come, and there is no way you can convince them that fast! Even if it is a “Quick meeting”, treat it as if it will be the most important one.

6.  State a Clear Roadmap

A salesperson needs to appear professional in order to command respect and trust of the prospect. A professional always has a plan. You should have a few default scenarios of further engagement ready as part of your sales outreach strategy. Each should have blanks that can be filled in with the prospect’s data and requirements. Remember, you don’t sell promises, you sell solutions.

Each follow-up needs to start precisely where you left the conversation, and each conversation needs to end up with a clear action list. This way you don’t risk going off track and miscommunicating with a prospect.

Free tip: you can use this tactic even after the sale was closed, moving forward to working with the client and potentially launching an upsale outreach campaign.

7. Don’t Write in CAPS!

Here is a free and straightforward tip: throw the idea of all CAPS in your sales outreach subject line away. This is simply unprofessional. Using caps has a negative effect on your read-through rates, which means that by only making your email appear “LARGER” you lose prospects. A subject line is one of the deciding factors in your open rates, so make sure you nail it. A study by Convince & Convert has gathered some interesting statistics regarding how people in the US engage with email marketing.

8. Make a Calendar and Stick to It

Practice makes perfect. And sales, like any other skill set, require a lot of practice as well as strong discipline. Map out your activities for each month and follow them. Even if your first attempt would not prove as successful as you’ve anticipated, failures can be valuable data in your sales analytics software. Collect information, see what works and what doesn’t, adjust your sales strategy by adding value and make data-driven decisions.

9.  Don’t be Afraid to Ask for a Reference

When did asking for reference ever hurt your relationship with a prospect or a client? Even if the prospect tells you that they are not interested, it is still a good practice to thank them for their time and ask them if they know of anybody else who might be interested in your offer. In the worst case scenario they say no, and you move forward. In the best case, you might get a prospect who is more likely to convert.

Same goes for existing clients and upsale activities in your outreach. You are not going to lose existing customers just because you ask for a reference.

10. Ask Your Best (and Worst) Prospects for Feedback

When talking about sales outreach ideas, there is no better data like an opinion of your customers. Just like with references, it wouldn’t hurt you to ask for honest feedback. If you receive a rejection, don’t be afraid to ask for feedback, what worked for the prospect, what didn’t. Same goes for converted prospects, just because you’ve closed the deal doesn’t mean that the execution was perfect.

Free sales tip: you can always ask your colleagues to tag a prospect and ask for their opinion on your performance. People rarely want to be rude to a salesperson, and most probably they will not give you a full review. But they can share feedback with somebody else.

Grow Your Business

Sales Outreach Tips and Best Practices: The Best Guides

In the end, sales outreach can be an excellent tool for your business. If done right, it will allow you to engage with new prospects and grow your operation. It takes practice, but if you follow these guidelines, over time you will be able to craft outreach messages that capture your prospects’ attention. You’ll see a funnel drop off rate decreasing, and will be able to send a more confident, impactful message to your prospects.

Brad Banyas Headshot
Brad Banyas
CEO and Founder at

Brad Banyas is a successful entrepreneur, investor, executive and technology strategist with over 20 years of experience in high-tech solutions development and deployment. Brad started his career in software sales in 1991. He then started, and subsequently sold, Output Solutions Inc. in the mid 90’s, and since founding OMI in 1999 Brad has been a successful innovator in cloud-based platforms and solutions.

OMI is the go-to resource for emerging mid-size companies that embrace CRM, marketing automation and sales enablement platforms to grow and dominate their niche.