Routines Reap Rewards
- Dan Greenberg

- Feb 19
- 6 min read
We finished last weeks post talking about resilience and routine, so let’s put some more meat behind that conversation. I want to be clear here, picking up a phone book and dialing random people is not the answer. Obviously that is hyperbolic, but when I talk about cold outreach, I am not talking about the type of cold outreach that more traditional sales teaching was talking about in the 80s and 90s. This is because of all of the barriers that buyers have built up. We have mentioned in previous posts about how buyers are skeptical and jaded, and therefore cold outreach in the absence of research, targeted material and inbound signals is a tremendous waste of time and a resource suck.
The story of Chet Holmes is well known in the sales literature world, but it is basically the story of how Chet Holmes was hired by Charlie Munger (Warren Buffett’s business partner) to head up a large and struggling media sales organization. A couple of years into his time leading sales he was asked by Munger, “Are we lying, cheating, or stealing? I’ve never seen sales numbers this good”. The answer is that he was doing none of the above; he attributed his success to one important strategic decision. He had taken a list of 2,000 prospects, trimmed it to the 167 best potential clients and focused 100% of his team’s energy on those 167 clients.
This story is well known, and not new, but it teaches us a very important lesson, 10 well informed, targeted, tailored outreaches are better than 100 spray and pray outreaches. The time that you spend on cold outreach should not be spent on volume and tallying as many calls, emails, and messages as possible, it should be spent on research, tailoring of information, and crafting of messages that fit. The messages don’t have to be witty or perfect, they just need to speak to the person you are speaking to.
Many sellers are scared by this idea. They think to themselves; “what if I focus my list but accidentally leave off potential clients who really were interested and now will never buy from me?’ Sure, this is a slight risk but the real calculation is the value of all of the lost time that you will spend reaching out to clients that will be wasted because your messages are not targeted and don’t elicit a response. You are not a call center, you are an executive, and your job is to solve problems for specific clients that you select that are worthy of the time you will spend on them. That mindset is important when it comes to how you develop a prospecting plan.
Once you have wrapped your mind around that idea, then it is time to set a routine. Resilience is not some magical phenomenon or idea that is fundamentally built into the personality of a good seller by nature. Resilience is simply the setting of routines and the discipline to adhere to that routine without succumbing to the desire to avoid it. Routines need to be set because they contain the things that we don’t want to do. My favorite fortune cookie I ever opened was very simple; all it said was, “Winners do what losers don’t want to do”. This is very simple and true because there are very few competitive advantages in the world anymore. Given the flow of information and the sheer volume of people, there are just not a lot of completely unique skill sets or knowledge sets. But one area where you can differentiate is simply doing things that others don’t want to do. The good news is that being successful does not require sitting down and making 100 phone calls a day like a drone, as it used to.
The world has changed, we have more information and we can use that information to make our jobs more enjoyable and more fruitful. Information allows us to research, tools allow us to target and tailor, and platforms allow us to communicate in more effective ways than in the past. This means that instead of being a mindless drone and making the same phone call 100 times, you get to be an investigator for a while and figure out the best prospects. Then you get to be a researcher and learn about them and their companies. Then you get to be a marketer and tailor material that makes sense for each of them, and then you get to be a seller and send the messages and make the calls. Sure, you may not like every piece of the work, but it sure beats doing the same thing over and over again all day.
The key is to set time blocs and stick to them. Make sure that the time blocs make sense within the goals that you are trying to achieve, and that you are setting the right amount of time aside for the right activities, but treat those time blocs as close-to-sacred so that you are sure to do all of the activities that you can control and that lead to your success.
The last important thing to realize when thinking about prospecting is that inbound signals are very important. Depending on your organization, your marketing team may help with some of this work, but tailored messages to targeted individuals within researched organizations will elicit some responses. Sometimes these responses are direct message responses, sometimes they are visits to a website, or signups for a blog, or maybe even requests for information, but they are happening, and they are the strongest signal you have of potential opportunity. In outreach, familiarity is key, and the more times a client sees your name and your company name, the more familiar they become, so when you get a response, that is a client indicating to you that they are familiar with you, and that they have engaged their conscious brain in thinking about you and your company. There is no reason to spend a single minute with the best prospect in the world who has not yet indicated interest, if you could rather spend that minute with a qualified client who has sent some version of an inbound signal.
If your marketing team has set up systems for tracking inbound signals, that is good, but not enough. You should be doing the same thing with more targeted outreach that you are doing to your prospects. If you reach out to a client 5 or 6 times and don’t receive any inbound signals of their interest, add them to a group that you will put on hold and then reach out to again in 3 to 6 months. I see so many sellers try 5 times, decide a lead is a bad lead and then send it back to the marketing team. If you give a client a 3–5 month break, and then message them again, most will lose track of the circumstances of the original outreach. They won’t remember if they didn’t respond to you because you were annoying them, or because they weren’t interested, or because they liked your competitor better. They likely won’t remember any of that, but what will last is the familiarity and that will trigger them to pay just a bit more attention to your outreach.
The point is that the battle in outreach starts with visibility, moves to familiarity, and then to solution association. Your client needs to notice your outreach, then become familiar with you and your company, and then associate you and your company with the problem you solve. This can take months, and sometimes double digit outreach, which is why I started this section by talking about routines. You can’t sell anything to anyone until they are receptive to listening, so all of the commercial teaching, discovery, presenting, social proof, and everything else that we have talked about in past posts, and will continue to talk about, cannot start until you have crossed those three hurdles. The client has to notice your outreach. The client has to recognize your name and your company name. The client has to have a general idea of how you can help. The only way to make sure that is the case is to set a routine for yourself and to continue to take the actions necessary to drive those outcomes.





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