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Troubleshooting outbound sales and prospecting: a comprehensive guide

Troubleshooting outbound sales and prospecting: a comprehensive guide
Stefan Kollenberg
Troubleshooting outbound sales and prospecting: a comprehensive guide
Troubleshooting outbound sales and prospecting: a comprehensive guide

Nailing your outbound sales and prospecting process can help you generate leads, acquire customers, and drive revenue growth. In this guide, we’ll share a step-by-step approach to troubleshooting each stage of your outbound sales campaign—whether you’re a new sales professional or a seasoned team leader.

We’ll cover how to check early campaigns, identify quality prospects, analyze insights from metrics, double down on well-performing sequences, and more, with detailed examples from our own experiences. You can use the table of contents to easily navigate to the areas that are most relevant to you.

How to set up your campaign up for success

Once you’ve launched your first sales campaign, you’re officially on a path to generating revenue! It’s important to evaluate your prospecting strategy as early as possible to see if you’re likely to book sales meetings that land customers.

Turning meetings into closed deals can take a long time, but you can quickly gauge if you're engaging the right people. Try using these guiding questions to hone in on your Ideal Customer Persona (ICP) and refine how you communicate with them.

  1. Are your prospects good fits? Use the MEDDIC framework (Metrics, Economic Buyer, Decision Criteria, Decision Process, Identify Pain, and Champion) to assess if your prospects are a good fit and improve your sales pitches.
  2. How long are your sales cycles? Track your sales cycles to monitor how much effort is required to move prospects through the sales funnel. Identify areas where prospects are getting stuck and make adjustments.
  3. How many people are no-shows? Track your no-show rate to make sure you’re not targeting the wrong prospects or failing to resonate with them.

Let’s go through each guiding question and metric in detail below.

1- Make sure your prospects are a good fit using MEDDIC

The first step to successful outbound sales is to target the right prospects. Salespeople who don’t qualify prospects upfront often waste time on unwinnable deals. Instead, you should qualify prospects early and constantly tweak your communication strategy based on what you learn from your meetings.

The MEDDIC (Metrics, Economic Buyer, Decision Criteria, Decision Process, Identify Pain, Champion) framework helps salespeople understand customer fit and close deals. Let’s review each part of the framework, including what to ask customers to gauge fit and how to adjust your pitch accordingly:

Metrics: Data that a prospect may use to measure the impact of your solution on their business.

  • Ask: What metrics do you use to measure the success of your business?
  • Action: Tailor your pitch to demonstrate how your solution can help them achieve their goals. For example, if a customer's metric is reducing customer churn, you can show how your product has helped similar businesses achieve that goal.

Economic buyer: The person in the business with the authority to approve the money spent on your solution.

  • Ask: Who is the person in your business responsible for making decisions about purchasing solutions like mine?
  • Action: Identify who has the authority to approve purchases. Focus your efforts on building a relationship with them.

Decision criteria: The criteria used by the customer's business to make decisions on a solution like yours.

  • Ask: What criteria do you use to make decisions on a solution like mine?
  • Action: Demonstrate how your product meets those criteria. For example, if a customer values ease of use, you can highlight how your product is user-friendly and can be easily integrated into their existing processes.

Decision process: How the customer's business decides to purchase a solution like yours.

  • Ask: What is the process you use to decide on a solution like mine?
  • Action: Anticipate objections and identify potential roadblocks. For example, if you're selling a project management tool to a large enterprise, you might ask how decisions are made and who is involved in the process. With this information, you can tailor your pitch to address the concerns of different stakeholders and anticipate any bureaucratic hurdles that might arise.

Identify pain: The customer’s current pain points that your product or service can solve.

  • Ask: What are the biggest challenges or pain points your business is currently experiencing?
  • Action: Position your solution as a way to solve these problems. For example, if you're selling a CRM tool, demonstrate how your solution can help solve a prospect’s issues with their sales process.

Champion: The person within the customer’s business who is invested in your success and pushes for you.

  • Ask: Is there someone in your business who is an advocate for my solution and is invested in its success?
  • Action: Build momentum to secure the sale by focusing on your advocates. For example, if you're selling a HR tool to a mid-sized business, tailor your messaging to the needs of the team member most invested in your success. Enlist their help in pushing the sale forward.

2- Analyze the length of your sales process

It’s important to think about which customers take the longest to convert, how big their deal sizes are, and whether they are worth pursuing. In general, outbound sales processes will typically take longer than inbound ones. This is because cold prospects have much less trust and context on you and your product when you start a conversation with them.

To track and improve your conversion times, you configure your CRM to track the following:

  1. Date of first marketing touchpoint
  2. Date of first sales touchpoint
  3. Date of first sales meeting
  4. Date that a deal moves between stages in your sales process
  5. Lead Source

These data points will help you understand how long customers take to move through the buying process and how that changes based on where the lead originated.

3- Reduce your no-show rate

If more than 20% of your scheduled meeting participants fail to show up without any explanation or attempt to reschedule, they’re likely unmotivated by your messaging or facing technical barriers (Close.com, 2023). Here are a few things you can do to reduce your no-show rate.

Remind prospects about the purpose of your meeting

Executives are busy and use their calendars differently. If your prospects aren’t knowledge workers, they may not rely on their digital calendars at all. Even people who live by their online calendars may not remember the purpose of every meeting they have booked, especially if they don’t know you.

Consider including a short agenda in the “meeting description” field of any calendar invite with your value proposition. Send a pleasant reminder email the day before that re-emphasizes the value proposition in your subject line or first line.

Here’s an example agenda for prospects of Volley, a company that helps B2B SaaS companies expand into new markets with confidence:

Meeting agenda:

  1. Discuss your revenue growth priorities & goals for Q2
  2. Overview of how Volley books you qualified sales meetings
  3. Align on next steps

When possible, use phone meetings

The best way to make sure a meeting happens is to make it a phone call. Ask for your prospect’s number once they confirm the meeting and send a calendar invitation with your agenda + their phone number in the meeting location field. You can send a casual text the day before to confirm the meeting too—you’ll notice that people are typically more responsive to texts than emails. When the time comes, simply call them!

Choose a compatible video conferencing software

Many companies use different default video conferencing software. If you’re not using your prospect’s default tool, they may face annoying technical hurdles when joining your meeting. From our experience:

  • Zoom is the most widely used and accepted, with a smooth onboarding for people who haven’t previously used it.
  • Microsoft Teams is broadly adopted in larger enterprises, but it has a clunky joining process for non-Microsoft users.
  • Google Meet may be blocked when meeting with banks. People who normally use Zoom or Microsoft Teams sometimes have audio/video problems when joining for the first time, especially if they don’t use Google Chrome as their default browser.

How to read and extract insights from campaign metrics

In our last post on creating the best outbound sales campaigns, we talked about the key metrics to track as part of your campaigns. In this section, we’ll provide some guidance on how to use those metrics to troubleshoot your campaign. First, let’s look at some benchmarks for what to expect from each metric.

1- Understand bounce rates

If your bounce rate is higher than 5%, ask yourself the following questions:

Have you verified that all prospect emails are valid before reaching out? Using lists of invalid emails will hurt your campaign and reputation. Use Zerobounce or another verification service.

Have you warmed up your email accounts? If not, it’s highly likely that your emails will go to spam and your domain health will get damaged. This damage can spread across your entire company, causing non-sales emails to land in spam. I recommend that you use Instantly to warm up your emails.

Are you monitoring the health of your email accounts to see if any are going to spam? If any of your emails are going to spam, should remove them from your outbound campaign and monitor email warming until they no longer go to spam. Instantly is also great for monitoring this.

Is your domain in good health? Emails from domains with poor reputations will often trigger spam filters. To look at your domain health, use a tool like Uptime. If your domain isn’t in good health, then don’t use it for outbound sales. Buy a new domain, set up new emails, and begin warming up those emails.

2- Understand open & reply rates

Analyzing your open and reply rates will help you understand what you need to adjust to get prospects to engage with your emails. Let’s go through a variety of scenarios and what you can do to troubleshoot them.

Scenario 1: Low open rates

If you’re seeing low open rates, check if your emails are going to spam, review your copywriting, and reassess customer fit.

Are your emails going to spam? Check your email warming report in Instantly. If needed, pause that email from launching so it can warm up and get away from the spam filters.

Are your subject line and first sentence catching people’s attention? Do your subject line and first sentence look like obvious clickbait? Adjust your subject lines so they catch attention, but don’t feel like clickbait or sales material. There are endless examples of good and bad subject lines. Here are two great guides from HubSpot that I use as a reference:

Are you A/B testing your subject lines? If not, start doing so using your email sequencing tool. If you are testing, then add a few more variations that use a different style. Try the different styles referenced in the HubSpot guide linked above.

Are the people you’re reaching out to active email users? Some types of customers just don’t actively use email.  A couple industries I’ve found to have very poor response rates to emails include non-digital service professionals, like healthcare or real estate, and labor-intensive industries like mining or construction. If you suspect that your customers don’t actively use email, test other outreach channels and compare how responsive they are.

Scenario 2: High open rate but low reply rate

This is a sign that your subject lines + first sentence are catching people’s attention, but the rest of your email is falling flat. Here are some questions to guide your review:

Does your subject line misrepresent the purpose of the email?

For example, a subject line like “Input Needed - Brand Project'' could be perceived as an internal email for someone working on a brand project. While this increases their chances to open the email, they will psychologically feel “tricked,” which will build distrust between you and the prospect.

Can your email be skimmed in 3 seconds and understood in 10?

Is there a clear & concise call to action?

Make it easy for your prospect to reply—don’t ask them to do too much. The goal of your email is to get a reply and start a conversation, not close a deal. Keep that in mind with how much you share in the email.

Is it clear how the prospect will get value by responding or booking a meeting with you?

Share your email with a friend. If they can’t immediately explain the value or purpose of your meeting, then you need to make it more clear. Here is an excellent infographic that goes through all the kinds of value that motivate buyers.

Are the pain points mentioned in your email relevant to this customer persona?

I commonly notice people mentioning day-to-day operational problems in an email to executives, or a high-level strategic problem in emails to more junior team members. You need to make sure that the problem your product solves is also the problem that this specific person in the organization is responsible for solving.

Does your email read like you’re a peer or someone the prospect can learn from?

Avoid asking questions or making comments that show a very generic level of understanding for their job, company, or industry pain points. Don’t use language that is “begging” or “hoping” that they will give you their time.

Does your email portray confidence, but not arrogance?

A confident, positive tone will show that you know what you’re doing and can make good use of the other person’s time. On the other hand, an arrogant tone, where you sound entitled to a meeting, will convey disrespect for the other person’s knowledge, experience and time.

Scenario 3: High open rate and high reply rate

This is a great place to be! Ideally, your replies will be converting to meetings—if not, you should analyze what prospects are telling you to see how you should improve your messaging. We’ll go into depth on this in the next section.

3- Understand different types of replies

There are various reasons prospects may be replying to your campaigns, but not converting to meetings. Let’s go through various reply types that you can address.

Scenario 1: Prospects are using an internal solution, a competitor, or not experiencing pain

If you have trouble converting prospects who seem to have a genuine interest in your product or service, you may be encountering one of the following barriers to conversion.

Your product isn’t differentiated enough: What do you offer that is uniquely different from your customers’ alternatives? Why should your customers care about that differentiation?

Your product is positioned inaccurately: Are you getting compared to the wrong type of solution?

The perceived cost to switch to your product is higher than its perceived value: How can you add value to the prospect in conversation? Can you avoid making the sole purpose of the conversation to be evaluating your solution?

You are reaching out at the wrong point of the buying journey: Is the problem not painful enough yet? Is the internal solution or competitor’s product good enough? Did they recently invest a lot of money into a solution for this problem?

Scenario 2: Prospects seem like the wrong fit

To assess whether your prospects are the right fit, go through each of these reflection questions and suggestions for action.

Do certain customer personas consistently tell you that they aren’t the right person to talk to?

If so, review your ICP criteria. Adjust those that are least valid, widening the scope of those that are too specific, and revisit your original assumptions. Here is an example of an analysis we did to identify which seniority levels for us to focus on:

Are prospects correctly understanding the problem you solve or what your solution does?

Your prospects may see the problem you solve as irrelevant to them or hard to understand. To solve for this, adjust how you describe the pain points or include different pain points you believe they experience. Does the prospect care about strategic priorities or day-to-day operations? Does your email add value? Check out this infographic covering different consumer needs for help.

Is your product servicing a new type of department within organizations?

If you are selling to a new type of department (e.g. Corporate Innovation or AI model development), prospect’s job titles are often not consistent from company to company, which makes it challenging to decide who to reach out to. Instead of relying on titles, identify key job responsibilities of the people you’re selling to and find those responsibilities within the summary of their LinkedIn bio or experience description.

Did you simply just reach out to someone who is not within your customer persona?

It’s possible that the data source you used pulled in people or companies that are not what you intended. Revisit the filters you used when building your prospect/account list and make them more specific.

Scenario 3: Prospects are uninterested or unsubscribing

If your prospects are uninterested in your outreach or unsubscribing from emails, your messaging and tactics may not be resonating. Take a step back and reflect on your approach using the following questions:

Is your sequence cadence too aggressive?

Consider adjusting your sequence cadence. Typically I will aim for this (in business days): Email: Day 1, Day 3, Day 6. New Thread: Day 10, Day 15. LinkedIn Engagement: Day 1, Day 5, Day 10.

Does your message lack thoughtful personalization?

It’s possible that your message feels very scripted and inauthentic. Consider adding personalized openers or PS lines that reference content you found online about the prospect.

Is the persona that you’re selling to bombarded too many cold emails?

I don’t do much cold calling since it’s time-consuming, but in some industries warrant calling if buyers are not responsive through digital channels. Once you start building out a sales org, cold calling can be a very powerful tool for your BDRs/AEs.

4- Dig into negative replies to adjust your strategy

Negative replies offer you the chance to learn more about your customers and process. Dig into the steps of your sequence to uncover where your rejections come from. Here are a couple of examples of analysis that we did on a campaign for a startup that was reaching out to procurement & sourcing teams in auto manufacturing.

We identified areas of improvement in the email sequence and did end up generating one very significant opportunity. In the end, however, our biggest realization was that these prospects needed to be called. They did not like to engage with salespeople by email or LinkedIn. In addition, the sales team needed to reposition their value proposition, as the ERPs that existed presented too high of a switching cost in comparison to their software’s value.

5- Test your email campaigns on yourself

We highly recommend testing your email campaigns on yourself to build empathy for your prospects and improve your copy. Send each email in your sequence to yourself and open them on both desktop and mobile. Here’s what you should do to reflect on your experience:

Review the email preview in your inbox

The email preview in your inbox should catch your attention amongst a sea of other emails. Make sure you have a clear reason why someone should open the email based on the text in that preview. Check out this guide from HubSpot on writing great subject lines for some great examples.

Review the full email inside your inbox

Your email should only take 10 seconds to read. Ideally, on mobile, you wouldn’t need to scroll down to read the entire email. Make it short and easy to understand what problem our client solves based only on the text in this email.

In addition, you should be able to uncover the reason for your outreach within 5 seconds of reading it. Put yourself in the shoes of a prospect: Would you give the person sending you this email 20 minutes of your time, based on your current schedule?

Use tools to categorize, store & manipulate outbound campaign data

Having the right tools to manage and analyze your sales data is crucial to your success. Let’s take a look at some of our favorite tools: HubSpot and Google Sheets, using Clay.

Hubspot reporting

HubSpot's reporting feature is a powerful tool, especially for Pro subscribers. It includes multi-variable reporting that covers all data across sales, marketing, and support. HubSpot keeps user activity, contact, company, and deal data lives in one place and automatically updates it.

One of the most useful features is the pivot table, which enables you to compare sequences side-by-side based on a prospect's progress throughout the funnel. This allows you to identify trends, opportunities, and areas for improvement, and make data-driven decisions that can help your business grow.

Google sheets reporting

In some cases, HubSpot won’t have the flexibility and control of a spreadsheet, so you’ll need to export the data to manipulate it. We often do this to compare sequence performance using percentages, analyze the step-by-step performance of sequences, or analyze and categorize prospect responses in bulk.

Let’s take a look at a response analysis we did for a company that was selling a document generation platform to the revenue department of global companies. We initially used a company’s size & industry as an indicator of fit. We assumed that larger companies that were professional services businesses would be more likely to compete for Request For Proposals (RFPs).

Clay is a tool that allowed us to collect data at scale about the size of our target companies’ RFP submission teams and add this to our analysis.

Here is how I set up the analysis:

  1. I categorized all email responses and I associated an action to take with each type of response.
  2. I grouped replies based on these actions and segmented those prospects based on the size of the company they worked for and whether their company had an RFP team.
  3. Looking at the output, I noticed that while our assumption about company size wasn’t inherently wrong. However, the presence of an RFP-related team had a more significant impact on whether or not prospects would respond with interest and book meetings.

How to optimize your campaign when things are going well

When you’re running a successful campaign that resonates with your ideal customer profile (ICP), do everything you can to maximize results from that segment before moving on. Here are some tips on how to find more prospects that fit your ICP, improve the way you handle responses, and increase the number of valuable interactions prospects have with your brand.

Find more prospects that fit your ICP

If you start with a lead database like Apollo, you will eventually run out of prospects. You can try supplementing multiple sources of data to find additional leads. One option we use is Clay, which sources LinkedIn, Twitter, Google, Google Maps, or scrapes any public directory or website. Another is LinkedIn Sales Navigator combined with Wiza or Phantom Buster to extract data.

Your prospects will constantly change company or role, so you should monitor for new people that fit your ICP as time passes. To do this, we recommend using Apollo list change notifications or LinkedIn updates from people you’ve marked as leads in Sales Navigator.

Send more effective replies

Nailing the messaging in your email sequences is just the beginning. Once you’ve gotten a response, it’s time to try to convert your email into a live meeting.

Prospects will often reply to your initial message with questions or concerns that may hold them back from booking a meeting. Your reply, in turn, will set an important tone for any conversations you have. Make sure to do the following:

  • Acknowledge any concerns and empathize with your prospect. Read the email thread they replied to so you know what they saw before writing their response.
  • Answer the questions your prospect asks. Use enough detail to answer their question, but leave some information for the meeting itself.
  • Ask them questions to better understand their concerns.
  • Demonstrate the value the prospect will receive if they continue to reply to or meet with you.

Track what kinds of messaging helps convert responses to meetings so you can identify patterns and adjust your sequence.

Increase the valuable interactions a prospect has with your brand

In order to convert prospects into customers, it's important to increase the number of valuable interactions they have with your brand. This can be achieved through nurture campaigns, marketing support, and retargeting campaigns.

Implement nurture campaigns

Nurture campaigns help build awareness and thought leadership for your brand. You’re not asking the prospect to book a call or learn about your solution, you’re just sharing valuable content, analyzing current events, etc. You can send these out to all contacts from old campaigns - but the best way to do it is to keep track of people’s reasons for not being interested - and factor that into the content you’re creating + sharing.

Add marketing support

Outbound sales is the “tip of the spear” in your overall growth. Once you find your ICP and nail messaging that performs well, it will be time to reach this ICP through more channels. That’s where your marketing operation comes in! We won’t go into detail about how to run a comprehensive marketing campaign here, but here are a few ways you can start.

  • Re-target campaigns during long sales cycles or highly competitive deals to keep your value top of mind to all stakeholders in your target account.
  • Create content to help prospects navigate their buying process, including blog posts, videos, tutorials, case studies, etc..
  • Run paid ad campaigns that are built around the pain points of this buyer

***

In conclusion, this article has provided you with a wealth of information to digest about running and troubleshooting outbound sales campaigns. Use it as your go-to guide as you tackle the process of building and launching outbound sales campaigns.

Keep in mind that this is only the start of your outbound sales journey, and you will continue to learn and grow as you progress. The most effective way to maximize your impact is by shortening the "learning loop" within your campaigns. Apply your newfound knowledge immediately to ensure your campaigns are continuously improving!

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