Whether you call it a strategy session or a discovery call, this first paid conversation is how you move from guessing what a client wants to knowing exactly how to help.
What Is a Strategy Session?
A strategy session is a type of meeting where a company seeks to learn more about a potential customer’s needs and pain points. The goal is to understand the customer better so the company can sell them the right product or service.
A strategy session serves several primary purposes, including the following.
- To establish the reason for the project by diagnosing the business problem.
- To uncover hidden value for the client by understanding what it would take to make this problem go away for your client. I.e. Return on investment (ROI).
- To plot a path forward by prescribing a treatment plan to help end the prospect’s business problem
What Do You Need To Run a Strategy Session?
If you want to run a successful strategy session, you’ll need a few things.
First, you’ll need to have a clear understanding of what your goals are for the session. What do you hope to accomplish? What questions do you want to answer?
With a clear goal, keeping the session on track will be easier.
You’ll need to prepare some materials. Materials might include presentation slides, handouts, etc. Having something to refer to will keep the session organised. You’ll also want to ensure you take plenty of notes or ask permission to record the session.
Finally, you’ll need to ensure you take point as the facilitator, keeping the session moving, keeping everyone on track, and making sure the discussion stays focused.
How Do You Run a Strategy Session?
If you’re at the beginning of your WordPress developer journey, brush up on how to handle your first client experience.
Here are the steps you need to take to run a successful strategy session.
Step 1: Research Your Client and Their Pain Points
A strategy session is an excellent way to learn more about your client and their specific pain points. By doing your research ahead of time, you can be sure to ask the right questions and uncover areas that may need further exploration.
Some tips for researching your client before a strategy session include.
- Reviewing the client’s website and any relevant marketing materials.
- Checking out their social media presence.
- Searching for their company name online.
- Reading any available customer reviews.
- Talking to other businesses in the same industry
By taking the time to research your client before meeting with them, you can ensure that the strategy session is productive and informative.
Step 2: Prepare Your Strategy Questions
Prepare your questions to get the most out of the strategy session.
Some example questions you may want to ask include.
- What is currently working well for you, and what isn’t working?
- What are your main pain points? ← Starting to “Go Wide”
- What is the source of [pain point]? ← Starting to “Go Deep”
- Why hasn’t [source of pain point] been addressed before ← “Go Deep”
- What are your primary goals?
- What’s stopping you from moving forward?
- What is your timeline?
- Who is your decision maker?
- What does success look like to you?
- What would that do for you if you could overcome the challenges you mentioned and achieve [outcome]?
- How does the current situation make you feel?
- How would you feel if the problem were to go away?
- What solutions have you tried before that did/didn’t work?
- What is your timeline for making a decision?
- What is your budget for this project?
- Are you willing to meet us at our price if we can deliver the solution and excellent service?
Asking these questions will help you better understand your potential customer’s needs and how you can help them.
By preparing your questions, you can ensure that you make the most of your strategy session and ultimately close more deals.
Step 3: Create an Agenda
There is no one-size-fits-all strategy session agenda, as the content and focus of the session will vary depending on the project, the team, and the client’s needs.
Here’s a high-level agenda overview to get you started.
- Welcome (5 minutes)
- Describe the purpose of the session.
- Review the agenda and agree to move forward.
- Sequential Questioning (60 – 120 minutes)
- Ask your prepared questions.
- Record key points.
- Dig deep and wide using “Why?”.
- Meeting Close (10 minutes)
- Share key insights.
- Decide the following steps and communications.
Step 4: Book a Meeting With Key Stakeholders
A face-to-face meeting is essential, whether in person or via video conferencing. You need to be able to read people’s body language as well as listen to their verbal answers.
You will be asking some detailed and, at times, probing questions about the client’s business and operations.
In-person meetings work best at the client’s business premises. It’s an environment where the client feels safe and comfortable.
Ensure you invite all the key people with a significant stake in the project. The strategy session will be an excellent chance to get them all aligned and come to a consensus. It will also give you more information to work with when planning your strategy based on the information you get from the meeting.
Step 5: Introduce Yourself
Kick off the guts of the meeting by introducing yourself and any colleagues you have brought along.
Give a short elevator speech about you, your business and why you are at the meeting and allow the client to introduce themselves.
Introductions are a good icebreaker for new people.
Step 6: Ask Questions and Document Responses
Run through your prepared questions but be prepared to jump in and use the “Go Wide and Go Deep” method.
Going wide means you are covering a broad range of adjacent issues or problems that the client may not have brought to your attention and could have a bearing on the project. Going deep drills down to the issue’s root by exploring each vertical problem.
Sometimes a client will already have a solution in their head to an issue without digging around for underlying or related issues and problems. The Go Wide and Go Deep method should help uncover these and better understand the client’s issues.
If you completely understand the client’s problems, you’ll be able to craft a better solution.
Step 7: Discuss Challenges and Benefits
In your questioning, make sure to discuss challenging issues. Is it necessary to fix it? Does it need to be fixed right away? Can it be broken up into smaller chunks? Etc.
You don’t want to walk away from a strategy session wondering, “How am I going to do that?” The strategy session is the vehicle to help you answer those questions.
You also want to highlight additional benefits to your client’s business or operations, such as increasing productivity, possible automation, the number of hours saved per month, etc.
Step 8: Demonstrate Your Expertise By Discussing High-Level Solutions
If you want to demonstrate your expertise to potential clients, you need to be able to discuss high-level solutions, explaining complex concepts in a way that is easy for clients to understand.
It also means being able to provide concrete examples of how your solutions have helped other businesses achieve success.
Doing this will show potential clients that you are the best person to help them solve their problems.
You should only discuss technology at this point if the client insists. Keep your solutions conceptual and practical.
Step 9: Discuss Budget and Important Dates
Many WordPress freelancers are scared to bring up budgets and costs, but it’s a topic that you need to include, and a strategy session is an ideal time.
You and the client need to be on the same page as far as possible budget and costs for the project. You may not be able to give an exact figure right there and then, but as a seasoned web professional, you should be able to provide a ballpark estimate.
You also need to understand any critical dates in the client’s calendar. They may have unmovable marketing or launch dates you need to work into your timeline.
Step 10: Ensure Commitments From Key Stakeholders
Towards the end of the strategy session, confirm commitments from your key stakeholders. For any web project, the client will have a list of tasks to complete to keep the project moving forward.
Client tasks may include.
- Supply branding guides.
- Supply images, audio and video assets.
- Supply written content.
- Grant access to data systems.
- Grant access to internal systems.
- Grant access to company personnel.
- Perform reviews and submit feedback.
Ensure that the client understands these commitments and that the right person has the time and resources to deliver.
Step 11: Set Clear Expectations for the Next Steps
At the end of a meeting, it is vital to set clear expectations for the next steps. All parties having a clear anticipation of what lies ahead will ensure everyone is on the same page, knowing what to do next.
Here are some tips on how to set clear expectations.
- Summarise key points discussed.
- Be clear and concise in your expectations.
- Make sure everyone understands their commitments.
- Set some S.M.A.R.T. goals.
- Set a deadline for the next steps.
Once you’ve set expectations and a deadline for the following steps, you can thank the key stakeholders for their time and conclude the strategy session.
Step 12: Follow Up and Present Your Proposed Solution
The last step happens after the strategy session has concluded.
Gather all your notes and information discovered during the client session to hone your proposed solution. Outline the main pain points you found, how your solution solves them and what benefits it delivers to the client.
What Should You Deliver After the Strategy Session?
A well-conducted strategy session should culminate in a tangible deliverable: a Digital Roadmap.
This document serves as a strategic plan outlining:
- The client’s primary goals and objectives
- Recommended website features and functionalities
- Technical requirements and integrations
- Content and asset needs
- Proposed timelines and project phases
- Suggestions for ongoing maintenance and future enhancements
For those starting out, a concise roadmap focusing on immediate project goals and basic maintenance plans is sufficient. As you gain experience, you can expand this into a comprehensive 12-month Digital Roadmap, detailing quarterly objectives, advanced features, and long-term growth strategies.
Providing this roadmap not only showcases your expertise but also offers the client a clear path forward, whether they choose to proceed with you or not.
FAQs About a Strategy Session
Knowing When To Diverge During a Strategy Session
When it’s clear that your client’s objectives do not align with the scope of the questions you have prepared, consider stopping and rescheduling a follow-up session to get back in alignment.
When this happens, it’s usually a symptom of your lead qualification system.
Great Strategy Sessions Help You Close More Deals
If you run a successful strategy session, you should have all the information you need to write the best proposal your client will ever get for that problem. The client wants to avoid going through the strategy process again, and if everything ticks the boxes, you will land the deal.