The Art of Follow-Ups: Timing & Messaging Tips

by | Objection Handling & Follow-Ups, SDR Consulting

The Art of Follow-Ups: Timing & Messaging Tips

In the time-starved world of sales and business development, almost no opportunity worth exploring is killed by a first ‘no’ – it is usually the resounding nothingness that follows that chokes the life out of all but the most robust leads. As a seasoned sales professional (or an entrepreneur growing your relationships, or a marketing expert nurturing leads) the act of following up (or not following up) can be the difference between success and failure. Research continues to reveal that even though at least 80% of sales involves between 5 and 12 follow-up contacts to close the sale, fully 44% of salespeople throw in the towel after only one follow-up. This disconnect between what works and what most people actually do is one of the greatest missed opportunities in business today. The truth is: good follow-up isn’t about being a pain in the you know what or calling someone every single hour on the hour, every single day (some people may even call that harassment); it’s about proving worth, having a professional relationship and showcasing to your prospect or contact that you are serious about helping and that they are more than a number at this point.

Why Most Follow-Up Strategies Fail Miserably 

The emissary approach founders largely due to misconceptions about timing, message and the psychology of the prospect. While the latter one would immediately kill the conversation, the former would leave things hanging, as if you were just poking to remind them it’s been a while since they heard from you. These copy-paste tactics immediately alert the recipient that they haven’t earned the difference-maker’s attention, and what they are seeing is just one name on a list, not a valued prospective partner of whom the sender has tried to understand the needs and struggles. Another mistake is following up too early, which can be interpreted as too needy or pushy, or too late, which opens the door to a competitor or prospects lose interest. The penalty for these rejected methods not only cost you deals, it also tarnishes your name, breaks trust with prospective clients, and brands you as the “ugly source.” If you make them feel like you’re harassing them, they’re going to view your follow-ups as spam, and may tell others about how often you follow up, which can shut doors for any future opportunity in their network.

What Science Says about the Best Time for Follow-Up

Knowing the psychology and the numbers behind when to follow up can revolutionize the way you respond and convert. According to sales psychology though, the best times for follow up tend to actually be during normal working hours – i.e between 10am and 2pm from Tuesday to Thursday – because this is generally when they (hopefully) have their business hats on – not wanting to ruin their week on a Monday, or being all too ready to kick off for the weekend on a Friday. But timing isn’t restricted to day and hour. You also need to know how long you wait between follow-ups, and you should follow an escalation and patience pattern that reflects your prospect’s intuitive schedule instead of your own. When it comes to your initial follow-up after a proposal or presentation, the sweet spot is often 2-3 business days as it shows you’re keen but not needy, and after a few of these it becomes a weekly knock and that evolves into bi-weekly and then monthly touchpoints. According to industry research, response rates plummet when follow-ups are sent after hours or on Monday and Friday, as individuals are more likely to be in focus-and-finishing mode. The trick is understanding that timing is also going to be industry specific, audience specific, particularly specific to the complexity of the decision that you’re asking your prospects to make (enterprise B2B sales cycles are going to take longer by nature than e-commerce checkout and purchase).

How to write follow-up emails that actually add value

The most successful follow-up sequences are premised on a simple (and compelling) idea: every message you send should be valuable to your reader, whether or not they decide to opt in to your offer. This value-first strategy turns follow-ups from cold-call sales pressure into actual business development – and you into a trusted advisor rather than some other vendor begging for a little attention. Effective follow-up messages will usually involve some sort of relevant industry news or analysis, useful resource, referrals to important connections, or ways to solve the pain point the prospect raised in previous dialogues. Instead of leading with “just checking in” or “following up on my previous email,” lead with specific, value-added statements, such as “I found this case study that gets at the efficiency issues you mentioned” or “In consideration of our conversation on budget restrictions, I found three cost-saving strategies that may be of interest to you.” The real trick is to show that you’ve really been thinking about their particular situation and that you did something, no matter how trivial, to aid them in their success — even if it wasn’t with you. Personalization isn’t just inserting their name or company either — it’s identifying particular pain points they’ve shared, addressing the challenges in their industry, and making it clear you know where they are positioned in the market.

Strategic Sequencing: Know When to Advance and When to Retreat

Creating a good follow up sequence is a be delicate balance between being persistent and respecting your prospect’s time and path to make a decision. The best sequence is typically 5-7 touch points over a 3-4 month period, with frequencies that build to not overload very busy professionals while ensuring continual visibility. Your second follow-up should be after 2-3 business days, and concentrate on addressing any remaining questions or issues that have arisen since your initial pitch. The second follow-up, usually about a week later, could bring additional new information or value that wasn’t included in your original proposal, and the third follow-up could take a completely new communication approach, like a LinkedIn message or a short call. Multichannel sequencing works so well because it allows for varying communication preferences and maximizes your chances of being seen when the time is right. It’s also important to use each channel effectively—emails are perfect for detailed information and resources, phone calls are great for urgent issues or complex clarification, and maintaining visibility on social media can remind the beneficiary that we are present without appearing to invade their space. The secret is knowing when to turn up the heat and when to back off, discerning subtle indications from prospect behavior, such as email open rates, response times, and engagement, to modulate your pursuit.

Template Library – Pre-Written Follow Ups for all scenarios

 A good set of tried and true follow-up templates can help you be more consistent and effective while still being able to tailor your message to your prospects’ individual wants and needs. In the case of post-demo follow-ups, a good template would start out with thanking the prospect for their time, a reiteration of the main points that stood out during the discussion and resources related to particular questions or issues that may have come up. A powerful post-demo follow up might say: “Thanks for taking some time to discuss how our solution could meet your team’s productivity problems. As you were asking about ease of integration I’m attaching our Technical Overview which explains exactly how we’ve been able to get companies like yours up and running with our system with minimum fuss.” When it comes to follow-ups on proposals, effective templates are all about pushing your decision maker closer to making a decision with the help of addressing any concerns and using social proof from like clients. Post objections, effective follow-ups respect the prospect’s preferences, present them with more evidence or options that cater to these concerns and shift the conversation back to your mutual interests, not your product’s features. When encountering a case of radio silence, the most effective templates should not be focused on selling at all, instead finding a unique way to serve, sharing useful lessons or resources without asking for anything in return and re-engaging those conversations that have been swamped or sidetracked elsewhere.

Advanced Tactics: When Non-Response Becomes Feedback

The moment the pipelines go dark and you’ve gotten no response in over a month all means the same thing: It’s a breakaway that you can win back and learn from. The ‘final attempt’ email is a killer re-engaging tool because it says, “we understand you’re busy” and “clearly what we’re discussing doesn’t matter to you because I haven’t heard back, but I wanted to offer one last attempt to work together and learn together”. It works because it takes the pressure off and appeals to most people’s inherent need to be helpful or to provide closure. There is the really smartly written last effort message which could read something like: “I’ve realized that maybe we’re not the best option for you now and I surely want to respect your time and choice. Instead of pounding on you, I’d like to ask for 60 seconds of input on what led to your decision, or what timeline, if any, starts to make sense in managing these obstacles.” For the most part, it gets responses because it separates you as a player who respects boundries and really wants to make things better for the two of you. A lot of them will give you some real feedback about budget limitations, when they need solutions, who they are comparing you against in the market, etc that will build your role play more consistently against similar prospects. And even if prospects don’t respond to feedback requests, the polite, respectful close leaves a good impression and may even make it more likely for a person to refer your or work with you in the future, when they are in another situation.

Leveraging Technology and CRM Tools for Consistent Follow-Up Excellence

Strategically leverage today’s CRM and sales automation solutions For going above and beyond the plain and simple tactics, modern day CRM and sales automation applications, when deployed strategically, can make all the difference when it comes to both the consistency and effectiveness of your follow-through. The answer is to find a balance of technology and to augment, but never replaced, with genuine relationship building while using automation as way to give us more time to do what we do well as info brokers and add personal touches to show a genuine interest in our prospects’ success. Using CRM effectively is having those little automated reminders about the right time to follow up, monitoring engagement metrics with your emails or messages to help tailor your messaging strategy, and storing detailed notes on prospect preferences, objections, decision making criteria. Smart salespeople leverage CRM data to spot trends in their most effective follow-up sequence, and to figure out which messages get the highest response rate, are sent in the best time interval, and lead in the most deals. Email tracking technology can be incredibly useful in offering insight into how your prospects are engaging with your email and when the emails are opened, what links are being clicked, and even the amount of time they spent going through it. Of course, what is important is that this is to be used ethically and transparently to gain a deeper understanding of the prospects dicovered rather than to manipulate or pressure in making decisions. The best approach is a mix — automated scheduling with personalized content, such that every touchpoint feels timely and relevant, yet remains human in order to foster trust and relationships.

Common Mistakes To Avoid That Disrupt Your Success

As much as it is important to know what you should do in your follow-up communications, knowing what not to do is just as crucial as some mistakes can kill the rapport you’ve been working to create. One of the most detrimental missteps is apologizing too much for the follow-up, which starts your message off as an unwanted pest, rather than a productive business meeting. If you send a halfhearted follow-up saying, “Sorry to bother you again” or “I hate to be a pest,” you undermine your credibility and signal that you don’t even believe you’re entitled to a reply. Another deadly sin is to evoke guilt, or other pressure tactics, to try to trick prospects into responding (e.g., “I’m disappointed you haven’t responded” or “Can’t seem to figure out why you’re ignoring my emails”) and just about quickens their retreat into radio silence. Many people also make the mistake of not updating their follow up scripts with real-world results, and continuing to use messages that have poor response rates just because it makes the sender feel good, or is easy for them. This suggests you haven’t really taken the time to learn about their unique concerns and circumstances, and in an era of little free time, verbose messages frequently end up in busy decision-makers’ delete folders, rather than their keepers. The most effective follow-up tactics sidestep these traps with professionalism, deference to the prerogatives of prospects and iterative, empirically-driven improvements to approaches that consider what actually works rather than what theoretically ought to work.

Measuring and Optimizing Your Follow-Up Performance

The only way to continually increase your follow-up effectiveness is by constantly testing and improving your communication methods. Begin by measuring metrics trigger rates, meeting booking rates, conversion rates per follow-up message type and time interval: The most successful salespeople keep up with which subject lines get the most opens, which message structures produce the most responses, and which follow-up sequences convert the best. Testing different styles A/B testing different styles with similar prospects can tell you exactly what engages your market so you can continue to craft your message based on data instead of a shot in the dark. Quality feedback is crucial here too – hear the tone and content of prospect replies to learn what follow-ups are seen as valuable touches versus irritations. Top producers also measure some longer-term factors like referral rates and repeat business from prospects who initially declined, knowing that business follow-up techniques can yield value that far surpasses individual deals. “We’re trying to provide a systematic procedure that can be transferred and improved rather than just sort of magical communications that result in unpredictable product.”

Building Long-Term Relationships Through Strategic Follow-Up Communication

The point of mastering follow-up communication is not simply to close deals, but to develop lasting business relationships that are continually valuable to everyone involved. When executed right, follow-ups establish you as a helpful advisor whom prospects come to inform them about their industry, guide them in their strategy, and solve business problems with — even if they’re not currently in the market for something you sell. This is a relationship based strategy, so you must change from thinking short-term sales to long-term value — constantly feeding them helpful content and tools that are helping them to reach their business goals, whether buying from you or not. Savvy relationship builders leverage follow-ups to pass along timely industry news, introduce prospects to useful connections, for offering market intel — market insights or strategic advice that’s grounded in experience that spans their entire business, for all that. Eventually, this process builds a web of professional connections that results in referrals, repeat business and collaboration that is orders of magnitude more valuable than a single transaction. The trick is to remain genuinely interested in your prospects’ success, while ultimately showing the experience and reliability that makes you an important business partner; the kind your prospects can rely on it in the long run beyond being just another “vendor” in their already full inbox.

 

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