August 18, 2020
Updated: September 4, 2020

Sales enablement shouldn’t automate bad practices — it should replace them

Sales enablement shouldn’t automate bad practices. Our topic today is why that’s an issue and how to do it better. Before we go into that, let me summarize what we’ve covered so far in this series for executives.

You learned three critical success factors, enablement’s role when it comes to digital transformation, the role of change management and why you should lead this change process and how to scale your enablement efforts.

The blog post on digital transformation is a great foundation for our discussion here. One of the statements I made there might be a good starting point: “Be aware that a dysfunctional process remains dysfunctional, even if digitized.”

You’re likely saying, “Wait a minute, shouldn’t I automate my processes and practices? Isn’t this what I was told for many years? And now that all these AI tools are available, I shouldn’t use them?”

I hear you. It isn’t an either/or situation. It’s about developing the sensitivity to wisely leverage technology where it makes sense, instead of using technology just because you can across the board without looking into the details and potential negative impact on your prospects and customers.

What are bad practices in sales? Those that create more damage than value. Automating those only amplifies the problem.

Let me give you a few examples. The worst of bad practices happens in the prospecting phase, sometimes processed by marketing, sometimes by sales. For potential buyers, it doesn’t matter what the source is; how the message is perceived is the only thing that matters. From a prospect’s perspective, the message can be perceived as relevant, valuable, tailored and respectful; or — and this happens way too often — as an irrelevant product pitch that wasn’t on target at all. Often without even saying hello. Let’s look at a few examples:

“Hi, nice to e-meet you,

I know time is of the essence, so I want to be short and to the point.

My company specializes in …..”

No name included or even an attempt at personalization. What makes it even worse is the fact that the message is only about them and their product. After “my company…” the sender went on and pushed their products.

The shortest and the worst example:


Do you buy oil and gas?”

Really bad. Clumsy. Ungraceful. In addition to that, you will have a hard time making any connection between my various current roles and buying oil and gas.

“Hello Tamara,

I’d like to invite you to our new platform XYZ. We help people to make highly valuable business connections. We would love to have your network on board.

Check out our website, it’s all explained there.


No, I won’t check it out. Why? The message is only about what you want. My network. Why would I ever do that? Explain to me in one or two sentences why this idea should be relevant and valuable for me. And again, no other relation to my profile other than my, apparently, attractive number of followers. Bad practice, except from saying hello and using my name.

“Hello, thank you for the confirmation of contact and I hope you are well in these special times. Short question: Do you currently have a crisis management and alerting solution in use in your company with which you can alert emergency services and / or employees in an emergency? I would like to talk to you briefly over the phone. How about you next week? I look forward to hearing from you, Best regards …. 

Also a practice that doesn’t work, a push message with a lack of research and preparation. Poor automation, as not even my name was included. No effort was made to format the message. It would be so much easier for the recipient to receive a well structured message. To be fair, it was at least polite.

I didn’t react because the message is absolutely irrelevant to me, which would be apparent to the sender — if they had looked up my profile. None of my current roles on my LinkedIn profile could have anything to do with alerting solutions. I mention this one as it was clearly automated, as the automated follow-up landed soon after in my LinkedIn inbox. I won’t share this one, as it was a simple product pitch, again without even making the attempt to connect with me as an individual, as a human being and, most importantly, with any of my current roles.

This one started targeted and personalized, but didn’t end so well:

“Hi Tamara,

Fellow vegan professional here. Thought it’d be nice to connect 🙂

OK, personalized, and the person obviously did some research and found out that I’m vegan. So far, so good. I appreciate this. It’s referring to a shared experience, such as the same university, the same previous employer, etc. The person did some research and that’s positive. I answered and said yes, happy to connect.

The next message ended in a kind of a product pitch. Not so good, unless I was interested in learning more about losing five pounds or more. It’s a challenging topic to address, but in that situation I’d suggest asking questions as a next step to learn more if this is even a challenge for the person, rather than offering a weight loss fitness program right out of the gate.

Without even giving me some time to respond (as this was a message of no relevance to me) that I’m happy with my body and not focused on losing weight, the person kicked himself out of the game by sending me this not even two days later:

“Friendly reminder”

Seriously? You killed it yourself. No, you don’t have to remind me of anything. Absolutely not.

Bad practices have three things in common: irrelevant to the prospect, not targeted or personalized and poor product/company pitching.

“But I get some responses, some demo bookings, etc.” That’s the answer I usually get. I then ask how many messages were sent and what the response rate was. The numbers are usually devastating, something like 1% to 3% response rates that include negative responses as well.

The question to ask is what damage was created for the 97% of your addressable market. You created at least no value for them, which is neutral. But for a percentage that’s usually a multiple of the 1% to 3% response rate, you created some sort of damage.

This damage ranges from killing your own credibility as a sales professional all the way up to tarnishing the reputation of the company you represent. It depends on how bad the message was whether I’d ever consider engaging with your organization again.

Don’t focus on the response rate only. Think also about your addressable market and don’t burn it!

To make this transparent: If you send out, for instance, 5,000 bad automated messages with a 3% response rate (150). Let’s assume that 100 (2%) of those were interested in one way or another, and you have actually created leads, and the other 50 have responded negatively.

Your focus should also go to the perception you created for the 4,850 recipients — the remaining 97%. Why would you risk burning your list or addressable market for no reason? Why not choose a better approach in the first place?

By the way, do you really think that a 3% response rate is a good result? It is not. With the right messaging approach, you can achieve better response rates that also drastically reduce the potential damage to your addressable market.

Do you know what messages your SDR and BDR teams are currently automating? Does your enablement leader know?

With automation tools available at people’s fingertips, you might be surprised how many of your salespeople create their own automation cycles and probably suboptimal messages with nobody overseeing these activities. That means your addressable market gets burned without your knowledge. This is where sales enablement comes into play. You need some sort of structure, process and guidance around all things automating sales practices.

Automating bad messages falls under the false perception that efficiency (doing things right) matters more than effectiveness (doing the right things). If you automate questionable efficiency goals, you multiply the damage and hurt your effectiveness goals. I hope you can see that this perception can lead to suboptimal choices, to say the least.

Define your effectiveness goals first, then drive efficiency towards your effectiveness goal.

Now, let’s discuss how to fix this problem and how to ensure that there is a “method to the messages” and some structure and process as well.

Three principles enablement leaders should follow right now — and your executive support empowers them

Let me share three practices you should ask your enablement leaders to focus on to optimize prospecting messages and their automation processes.

#1: Create messaging templates that stick for your sales force

This isn’t rocket science; it just has to be done properly. Ask your enablement team to create highly relevant, valuable and differentiating messaging templates. If you have no copywriting talent on your enablement team, make sure they hire an excellent outside resource.

Focus on creating these templates per role and industry. If you outsource this process, make sure that you have 100% control of the messaging being used. The following criteria might help you to evaluate the quality of the services you signed up for:

  • Personalize with their name (I shouldn’t even have to name this here, but as you could see in the examples, there is a need to do so).
  • Tailor to the targeted role and industry: It’s mission critical that your enablement team knows the business challenges of your targeted roles per industry and can speak to these challenges eloquently and to the point.
  • Offer insights: Your marketing, product or research teams should be able to come up with solid data that support the challenges you refer to and connect the dots to the improved results your services can help to achieve. If you are new as a business, refer to data you can find in the market. If you already have clients, it’s always powerful to share how relevant clients have solved similar challenges. Relevant clients is the important detail.
  • Bulletproof messages with these three questions:
    • Is it relevant to the targeted role in that industry?
    • Is it valuable enough for them to give you some time or do what you want them to do, see your CTA?
    • Is it differentiating; does it stand out from the crowd?
  • Include a reasonable call to action (CTA)
    In such a message, you want to provide some evidence that you know what you are talking about and that you can support your statements with insights and data. Then, you want them to do something: respond to your message, download an asset, register for an event, sign up for a newsletter, etc. Is the balance OK? Would you click on that CTA yourself?

#2: Create a messaging and automation framework

As mentioned above, anyone can theoretically use some sort of email or LinkedIn automation without you knowing about it. So, it’s important that you create awareness across the sales force that effectiveness comes first, before efficiency. Ask your enablement leader to come up with a framework of templates, automation tools and processes for getting started.

You should definitely avoid that various members of your SDR team, for example, message the same target roles in parallel at the same time. In such a case, and I’ve experienced this several times, my perception would be that this is totally disorganized and would immediately stop following.

This step cannot be done without your sales managers. Even if your enablement leaders have implemented the best framework, it won’t make any difference unless your sales managers are on the same page.

Your leadership is required to change the narrative from efficiency to effectiveness and from quantity to quality.

#3: Last but not least: Test before you automate

This principle cannot be mentioned enough. Time and time again, I see really bad messaging sequences, often with technical errors, flooding my inboxes, LinkedIn and email, and I can only ask myself if they ever tested it before pushing the automation button.

As stated in my digital transformation blog post, and quoted earlier here:

“Be aware that a dysfunctional process remains dysfunctional, even if digitized.”

So, design a small pilot, run the sequence manually and learn from these experiences and the responses you are receiving. Adjust your messages, and then you can automate good practices. This way you avoid bad practices being amplified.

I hope I made clear that the more technology we use, the more wisely we have to design our approaches to get the most out of technology rather than damaging our potential clients.