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Outreach With A Thought-Provoking Question Playbook

Updated: Apr 12




Send an email sequence to prospects providing a thought-provoking question. First, you will ask the question and then explain the value your product or service can offer the prospect. Follow-up emails will share additional helpful information to answer the question, best practices, success stories, and content to educate the prospect on your offering and help accelerate their buying decisions.


Email Sequence


  1. Introductory Email: Introduce yourself and ask them a thought-provoking question. Introduce your relevant offering and how it applies to the question you asked. Share case studies to help them see your offering's value and how it applies to the question. Ask for a meeting.

  2. Reminder Email: Remind them of your question. Provide additional case studies that may help out. Ask for a meeting.

  3. Referral Email: Ask them for a referral if they are not the right person. Provide a company overview that they could share with others introducing your offering. Ask if they know others from their company who may be coming to the event that you can meet.

  4. Final Invite Broad Email: Give them an overview of all your services if they may be looking to solve additional problems they may have that you did not discuss. Let them know they can reach out anytime.


Personalize <<personalize_tag>>: Contact First Name, Contact Company


Add content [[insert_content]]: Case Studies, Company Overview, and Overview Of All Services.


Email Best Practice


  • The subject line between 28 and 50 characters. Three to four words.

  • Email body between 50 to 125 words of text.

  • Remove extra words from the email body.

  • Make your email closing lines powerful and intriguing.

  • Personalize your email content and keep it conversational.

  • Answering three key questions—what are you offering? How will it help the reader? What should they do next?

  • Send out 2 to 5 emails per month.

  • Use 1 to 3 images.

  • Emails should be at a third-grade reading level.



Best Practices

  • Decide upfront on key industries you are targeting and companies you want to win as customers within those industries.

  • Find several prospects that have the same general problem and require the same skills. Build a prospect list. You may end up with several segments of prospects that have different needs.

  • You can use LinkedIn or the company website to identify the right team of people that will make a buying decision. Target multiple people in a company. Once you identify the people in a company, use a service to find their email address and contact information.

  • Create a list of segments of prospects and assign them to a particular salesperson or virtual sales assistant

  • Create a custom message for each segment, provide a thought-provoking question relevant to each segment, and provide relevant content that will interest companies.

  • Modify the following email sequence and tailor it to your message and content.

  • Launch multiple campaigns for each segment identified.



Get Started


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