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SalesGrowth MD, Inc. | Denver/ Englewood, CO

Why should a salesperson prospect?

The answer to this question always connects with the nature of the job for which we hired the salesperson. Many salespeople don’t prospect simply because they are not required to do so in their role; those who are required to prospect do it to varying degrees of success – and some of those salespeople struggle. An effective daily prospecting routine will be more important than ever in 2023. So: as sales leaders planning for a new and potentially challenging year, how can we support team members and help them to prospect more effectively? 

When it comes to building and supporting a prospecting approach, we at Sandler believe that the critical word for sales leaders to bear in mind is ownership. As in: Who owns the goals?  People will always work harder for their reasons than they will for ours. It follows that, in the realm of prospecting, they will connect more, achieve more, earn more, and contribute more once they: 

  • Conclude for themselves that the prospecting regimen they are following is getting them where they need to go in life – and  
  • Resolve to reach that destination sooner, rather than later.  

As leaders, we can help and support them on both fronts, but we cannot expect to persuade them to follow our prospecting plan. We can only collaborate with them as they design and follow their own plan. This brings us to… 

Critical Takeaway #1: Set Up a Template That Can Be Individualized

Consider developing templates that suggest a variety of types and levels of activities and a variety of sequences that can then be tailored by the owners. Don’t just dictate the numbers you want them to hit.

Remember: If we are the only ones who own the behavioral and performance goals, our team’s prospecting performance will be mediocre. If they own the goals, performance will be optimal. Once a salesperson assumes full ownership of a behavioral goal that connects to prospecting, we’re no longer pushing uphill as the leader of the team.    

Critical Takeaway #2: Find Out What They Want

Many leaders make the mistake of believing that money is what salespeople want. . What an individual salesperson plans to do with the money they earn is what you need to figure out. That means you, as the leader, have an obligation to invest the time, attention, and respect to conduct a private, one-on-one conversation that includes a question that sounds something like this: “Just out of curiosity – if you got your bonus this year, what would you do with it?”

Here’s the tricky part: The salesperson may not know what they want! That means you may need to continue this conversation over multiple sessions, do a lot of listening, and find the best way to support the salesperson as they connect all the dots. Time-suck? Not really. You will save massive amounts of time, energy, effort, and personal bandwidth by working this out with each individual member of your team. Once they (and you) figure out what they’re working toward and why – a trip to the Caribbean, the opportunity to take better care of an aging parent, time to write the Great American Novel, whatever – you will have flicked the “on” switch. Their passion to achieve that goal is what transforms a mediocre performer into an accountable, responsible, self-correcting rock star. That’s who you want on the team, right?

Once you know what the salesperson wants most in life, your job as the leader is to connect your business goals to their personal goals. Translate the financial quota into a meaningful goal that the salesperson will buy into at a visceral level – and prospect for.    

Critical Takeaway #3: Create Clarity on Where They’ll Be Hunting

Just figuring out what the salesperson wants most in life and then intoning the words “Go forth and prospect” is not going to get either of you where you want to go. The conversation needs to go a bit deeper. You both need to know where they are going to be hunting.

Maybe you’ve had this experience: you know the person is prospecting… but you find that they keep unearthing leads you don’t really want them investing precious time pursuing. If you and a salesperson on your team are out of alignment when it comes to prospecting, it’s highly likely that’s because you haven’t had a clear one-on-one conversation about the kind of business you are both committed to developing. Solution: Schedule time for what we at Sandler call the KARE discussion.

This is a critical planning session that begins with an understanding of four categories, each of which connects to a type of account that you wish to grow. KARE profiling is a powerful strategy component in territory management that tags each of your prospects, clients, and opportunities with one and only one designation: Keep, Attain, Recapture, or Expand. Here’s the breakdown on each:

Now, we are talking about prospecting, so I’m going to assume that the Keep category is not your main priority in your planning session with this salesperson. But what about the other three? What percentage of the salesperson’s time, effort, and energy should be invested in Attaining new business? What’s the percentage that you want them to invest in Recapturing previous partners? And what’s the percentage you want to see them putting toward Expanding your business with current major clients? More to the point, how much income do you each want to see arising from each of these categories?

Those last three elements of the KARE diagram each represent potential prospecting activity – but note that they are very different sales discussions, taking place in very different contexts. Be sure that both you and the salesperson are on the same page when it comes to the priorities and time investments that connect to the A, the R, and the E of KARE. If you don’t have this kind of planning discussion, what’s going to happen is that the salesperson is going to default to the prospecting routine they are most familiar with and most comfortable with. That default setting may not support either the team or the salesperson.

You will probably want to avoid “assigning” a time-and-effort priority you want to see from your own personal KARE analysis. It’s usually best if priority you have in mind lines up with the salesperson’s capacity, their skill set, and their driving personal goal. After all, what matters is that they own what comes out of this discussion.   

Critical Takeaway #4: Co-create a Cookbook

Now that you both agree on where you’ll be hunting, what mix of outreaches makes sense? What behaviors is the salesperson going to execute on a daily, weekly, and monthly basis? In other words, what is the behavioral plan?

Many sales leaders lose sight of the reality that there needs to be a unique written behavioral plan, or cookbook, for each person who reports to them. If you have eight people reporting to you, you’re going to want to co-create eight separate plans.

Here again, ownership is what matters most. If you hand someone a cookie-cutter plan with X number of phone calls, X number of InMail outreaches via LinkedIn, and X number of multi-platform responses to leads they receive from Marketing, that’s not going to deliver the same results as a plan that is glove-fitting to the individual, with activity targets that make sense for them and support their personal income goals.

There’s not enough space here for me to describe all the possible behavioral mixes that could go into an effective behavioral plan for someone on your team, but here are a few insights we’ve seen from, and shared with, leaders of effective teams in various industries. Some of them may be relevant to your world. 

  1. When in doubt, ask for a referral. Every positive interaction, whether it results in an active opportunity or not, is an opportunity to request an introduction to someone in the other person’s circle who could benefit from what we do. Make sure your team is taking advantage of that opportunity. 
  2. Don’t forget about phone calls. Lots of sales teams consider phone prospecting to be part of a bygone era; we see it as one of many tools in the multi-platform toolbox, and one that may be appropriate to build into the behavioral plan if it’s used with appropriate, carefully designed follow-through. Yes, it’s true that cold calls are probably going to go to voicemail nowadays. What’s also true, though, and too often overlooked, is that the people we’re calling are very likely to be wondering about who just left a message! Many of them will be looking with some curiosity at a text transcription of the voicemail message we just left. That means that, if we design that message properly and speak clearly as we deliver it, we can leave a “touch” that makes a future conversation more likely. 
  3. Leverage InMail. InMail, of course, is the internal messaging function for LinkedIn users. In our experience, decision makers and influencers to whom we are already connected on LinkedIn, but not currently doing business with or in conversations with, are more likely to respond to appropriately targeted InMail messages than they are to cold emails. We could probably do another deep-dive article on this topic alone; for that matter, we could also do a full-scale article on the potential advantages of buying LinkedIn’s Sales Navigator Tool for your team. For now, though, the moral is a simple one: Get your team to use InMail responsibly – meaning tailoring the message to the individual with whom they are connected – and you will generate conversations that identify opportunities and move the sales cycle forward. This behavior may well belong in each rep’s personal cookbook. (Our own salespeople have certainly made it part of theirs.) 
  4. Include multiple modalities. We live in a multi-platform world. If a given team member’s cookbook is too heavily focused on a single behavior (sending out cold emails, say), you can create deeper ownership of the behavioral plan by helping the salesperson to see how reaching out on multiple platforms with complementary messages can improve the quality of their pipeline.

One great way to elicit ownership of the cookbook is to ask the salesperson to create the first draft of the plan, and then schedule time to review it together. You might say something like this: “Can you give me your thoughts, in a Word doc or spreadsheet, of what you think the daily activity level would be that supports the income results you want? And what would be happening each day?”   

Critical Takeaway #5: Co-Create the Ideal Customer Profile and the Relevant Buying Personas 

Do you and the salesperson both apply the same definition to the phrase “our ideal prospect”? Many sales leaders fall into the trap of believing that they’ve created an ideal profile when they say something like this to a salesperson: “You’re going to be calling VPs of Operations. Go for it.”

That’s not enough information, and it certainly won’t instill a sense of ownership of the prospecting plan. You want to collaborate on an ideal prospect profile that clarifies all the organizational criteria of the prospects the salesperson will be targeting. What verticals do these companies operate in? How fast are they growing? Where are they located? How many employees do they have? And so on. These are the kinds of questions that help you to build a usable profile.

In addition, you will want to answer all of the following questions. They will help you to develop what we call Pain by Persona.  Based on deals we have closed before… 

  • What are the likely job titles of a primary contact at an organization that buys from us? (Note that one job title is never enough.) 
  • What is the ONE biggest problem this person is likely to face that we can solve? (Go into as much relevant detail as you can.) 
  • What is the short- and long-term impact of leaving that problem unsolved for this organization? What is the typical financial impact? What is the possible impact on mission orientation? What is the impact on customer relationships? What is the impact on employee retention for the buying organization? (Go into as much relevant detail as you can.) 
  • What is the short- and long-term  impact of leaving that problem unsolved for this person? What are the possible career implications? What are the quality of life issues? (Go into as much relevant detail as you can.) 
  • What terminology does this buyer typically use to describe this problem and its impact? (Spend some time on this. Remember that terms and descriptions that are familiar to us may sound like a foreign language to the buyer. The buyer’s language is the language we want to speak.) 
  • Using the buyer’s terminology, what are three to five concise pain indicators that connect to this ONE problem? (You’re looking for the “bullet points” that will, when mentioned, cause someone to lean into our conversation, rather than away from it.) 

Repeat the six questions above as often as necessary to address other problems you can solve that typically face this contact and their organization. 

  • What is another department, team, or influencer likely to be impacted by this problem and/or by a decision to work with us? (Even if this is a “C-level” decision, other people and teams are inevitably going to be impacted. Identify the most likely constituency, and the most likely players within that constituency.) 
  • What are their pain indicators likely to be? (Expect them to be different from those of your primary contact.) 

Repeat the above two questions as often as necessary to identify the likely cast of characters and their major pain indicators. (By the way, the powerful list of questions you just read comes from Sandler Executive Vice President Bill Bartlett.)

Take the time to lead a conversation that covers all these issues. Share the results with the other members of your team, so you can get their feedback, too.   

Critical Takeaway #6: Do a Skill Check

You’ve gotten buy-in on the goal. You’ve gotten buy-in on where they’re going to be hunting. You’ve gotten buy-in on the behavioral plan. You’ve gotten buy-in on the buyer profile. Surely that’s everything, right?

Not quite. An important part of your job as the leader of the sales team is to identify any gaps that may exist between this salesperson’s skill set and the behavior plan that supports their activity and performance goals.

One extremely common mistake is to assume that everyone on the team has basically the same skill set. (They don’t.) Another is to assume that, since skill X feels like second nature to you, it must feel like second nature to someone on your team. (It may not.) Neither assumption supports your relationship with this salesperson; neither promotes their personal ownership of the prospecting plan. If we ask people to do something we haven’t yet trained them to do, there’s going to be a disconnect! If that disconnect isn’t remedied sooner rather than later, buy-in will evaporate.

Many sales leaders have a blind spot in this area. It’s all too easy to deceive ourselves into believing that someone has skills that we have perhaps mentioned and discussed, but not yet trained and reinforced properly.   

Critical Takeaway #7: Do an Attitude Check  

Conducting an attitude check means you as the leader separate the willing-and-able from the unwilling-and-able.

There is a classic Sandler rule that states, “You don’t have to like prospecting – you just have to do it.” Is everyone on your team following that rule? Do they compartmentalize prospecting in the same way they compartmentalize, say, doing time on the treadmill at the gym? The attitude in both situations needs to be: I may not enjoy this, but it’s something that has to happen, so I’m committed to doing it. Those who don’t adopt that attitude tend to stand out.

Your job is to notice the people who stand out.

If you’ve gotten full buy-in on the goal, the type of buyer, the behavioral plan, and the client profile… and if you’re certain the person has the prospecting skills required to perform in this job… but you see that the results are consistently not showing up, then you’ve got a leadership responsibility to fulfill. It is time to take action. The best action is based, not on what you wish were happening, but on the facts on the ground. If someone is able to prospect, but right now they’re not willing to prospect, there is an ownership failure.

There could be any number of reasons for that failure. The person might be having problems at home that you don’t know about. They might be in the wrong job. They might have reached a point in their career where they need to focus on different types of buyers than the ones you want to focus on. Or they might not be cut out for a sales role. You really won’t know what the obstacle is until you put on your detective hat and conduct the (tactful, private) conversations necessary to find out.

Once you do know for sure what’s keeping the right behaviors from happening, it’s your job to make a decision that supports both the organization and the individual. Sometimes, that decision is to set up a transition to another position. Sometimes, it’s to support the person while they’re going through a tough passage. Sometimes, it’s to invest time, effort, and energy in the coaching necessary to help them take out their head trash. And sometimes, the right decision is to part company. Only you can make the final determination of what’s really going on in this person’s world and what the right response is.   

Critical Takeaway #8: Identify and Monitor the KPIs… Together 

If you’ve done the seven things I’ve shared with you thus far, the final critical prospecting takeaway pretty much takes care of itself.

Lead a one-on-one discussion that identifies what you both believe to be the most meaningful metrics that connect to behaviors in the rep’s personal cookbook. For instance, you and the salesperson might identify Total new voice-to-voice conversations with VPs of Operations as an important leading indicator of revenue production. That’s just an example; I don’t know what the right metrics for you to monitor with a given salesperson are. But I do know that a conversation with a salesperson who owns their own process is a great way to uncover them.

Once you’ve identified two or three such metrics, once the salesperson owns them fully and commits to recording them, and once you make those metrics a recurring agenda item in your weekly check-ins, you will see improvement in the prospecting numbers, and in the revenue figures that connect to them. We have seen it happen time and time again: salespeople who assume full ownership of the process consistently overachieve on their business development targets.

One word of warning is in order: The figures you’ll want to discuss most during these brief weekly meetings are the leading indicators: the prospecting and sales process behaviors that make movement through the sales cycle, and revenue, possible. Those metrics are the ones you both want to pay close attention to in coaching sessions. It’s not as constructive to focus your meetings on lagging indicators like closed or about-to-close deals. A qualified professional salesperson has far less control over those numbers… but they always have total control of, and ownership of, their personal behavior plan!

In our experience, the most effective sales leaders are those who are personally committed to supporting the members of their team in a way that empowers them to consistently overachieve in the strategically important realm of prospecting.


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