5 Life-Changing Strategies for your Strategy Session

Written by: Jesi Wicks | Photo by Christina Morillo

Can you read minds? Wanna learn how? With the right strategy for your strategy session, your client will be blown away at how well you made their vision come to life. It is so incredibly satisfying. Let me tell you what I mean.

A strategy session is like fishing. You know what kind of fish your creative project is, you just need the right bait to reel it in. Luckily, if you are able to ask the right questions and create the right rapport, it’s really not that hard.

Most creatives fall short in strategy sessions because they equate it to a pitch. Stop trying to pitch and start trying to problem-solve.

Trust is what sells your product, and trust is not built in a fancy PowerPoint. Trust is built through listening, asking relevant questions, and troubleshooting problems in real-time. Give the client the satisfaction of knowing they were a part of creating the strategy for their own project.

In this article, I’ll give you seemingly simple tactics and tools you can implement today to make your process run smoother, save your precious time, and make you seem like a mindreader.

What a strategy session is NOT

Don’t confuse a business lunch or a sales meeting with a strategy meeting. Many creatives get frustrated because they have a “strategy” meeting where people are distracted or engaged with something completely other than giving you the information you need. Don’t schedule your strategy sessions over lunch. Don’t schedule your session with other vendors present, and please, don’t call the pitch or sales meeting a strategy session.

Whether you give away a strategy session for free or do it as a part of your package, schedule your meeting specifically for you and the sole decision maker** in a space that is distraction free.

Your goal should be to find little nuggets of what your client wants that can make you valuable to them. A strategy session is NOT a meeting where you tell them your strategy. It is where you uncover the strategy they need together!

Once you understand your purpose in this meeting, you can follow the tips below to make you client fall in love with you:

My first strategy phone call was my biggest lesson in strategy AND appreciating the humanity of our clients. The call went something like this:

The client got on the line and kindly said, “Hello Jessica, so nice to finally meet you. How are you?”

I said, “I’m great, thanks. I am super excited to share our ideas with you. The first thing I want to talk about is where we can improve your website…” and I went straight into the script I was given. I had planned so carefully and researched my clients website with precision.

After about ten minutes of me talking, he stopped me and said, “Are you finished yet? I have to go. Can you just send it to me in an email?” His kind voice had dissipated, and I wasn’t sure he was even listening.

Who has ever started a strategy session full force like this? I was so consumed with coming off as smart and researched that I forgot about the humanity of the project. I forgot that the person on the other line had way more insight and know-how about his own website than I did. I simply forgot to listen.

The strategy meeting is about your client — not you, your research, or your expertise. The best thing you can do to set your strategy is to ask some guided questions and then LISTEN at the top of the meeting. This does 3 things for you.

1. Builds rapport.

2. Creates trust that you want what is best for the client.

3. Gives you a truly better understanding of what they really want.

Forget what your client needs — that’ll be stated over and over. What you are looking for is what they really WANT. What are their wins? If you get them to talk about themselves in relation to your project, THAT is gold. Savor it. It is not just information you are collecting, it is their desire.

The first 5–20 minutes of the meeting is for you to ask pointed questions that get your client talking about themselves and excited about their project.

How are you feeling today? Are you ready to strategize?

How is your mom, dog, aunt, kid (what do you already know about them)?

Have you thought about anything else since we scheduled this meeting?

I’m really pumped to chat about the project. Before I get started, I just wanna know what you think it’ll look like in your head?

Or my simple favorite: How is your life?

These questions establish that you care about them on a personal level and you want their project to be successful on their terms, not your own. If they start talking and talking — that is great! AGAIN, LISTEN. They are giving you free advice on how to communicate and serve them. Now you have ammunition to write, design, or create in their voice and style without wasting time on choices they may never even consider.

So you do web design. Great! Do you also do graphic design, photography, copywriting, editing, app development, podcast production, social media, advertising, funnel marketing, and email campaigns? If you do, you are a very tired unicorn. Stop trying to wear all the hats. Instead, simply find the people who can support you. Share the project or ask your client to pay for another contractor while you are still in the strategy phase. Setting the expectation of your scope is so important for a happy client at the end of a project.

Look, you need to know what you do and what you don’t do. It seems like a simple request, but a lot of creatives get excited about an idea that involves work beyond what they enjoy or even know how to do. That is okay. You can still dream about a great project. Define exactly what you WANT to do, and promise yourself to stick to those things only.

Network and create a list of other amazing creative professionals who can support your business. Then, share the love. If additional services are needed, you can recommend or contract out that work to your client. You will get SO MANY referrals back to you if you send other people business. Trust me. Save your time and stop doing the things you hate to do. It is not helping you.

My favorite line to say to clients is, “Look, I would love to take your money, but… [here is what I think would provide you a better outcome than hiring me for this bit.] It’s honest. It saves you stress, and everyone wins. Nothing builds rapport better than saying you won’t take someone’s money cause you want the best for them!

Deciding exactly WHAT you want to do seems pretty simple, but most of the creatives struggle with picking just one (or five) things. They either pride themselves on being a jack of all trades or they simply fell into work that needed to be done. It may seem like good money right now, but in the long term, it deflates your drive and soils your reputation.

Now that you know exactly what service(s) you provide, it should be much easier to dig for the information you need. Be ready for this meeting with detailed questions about style, voice, and preferences.

Your strategy session should be less of a pitch and more of an interrogation.

Depending on what you do, the questions will be different. The purpose is to narrow down preferences so you don’t have to present million choices just to get started.

Logos and Branding: Show them clusters of brand boards or logos that represent several design styles. Let them pick 1–3 styles they want you to focus on for their logo. They are not picking one logo from the bunch. They are just identifying styles.

Voice & Tone: Read examples of copy that have different voices. Maybe one excerpt is analogy heavy and another is more story-heavy. Maybe one uses more questionable language and another is more conservative. Let them hear it and judge their responses.

For Websites: Print out site design examples for them to identify their style generally. Ask if there are any industry-specific colors or styles they want to stay away from to differentiate.

The idea is to identify their general preferences and rule out excessive ideas that may be floating around in your creative mind. You will come up with your favorite questions as you dial in your process, but know what you need to know from them to be confident in your creative process.

Once you have style figured out, take care of the logistics of your project to save LOADS of time:

Passwords needed (make them find the passwords before they leave)

Who should be on communications

Are there any existing style guides

Budgets

Relevant social accounts or links

Other housekeeping

Sure, this can all be done over email, but think of how much time you save when you never have to send those emails. If you can ask them to go in and find these before the meeting is over and wait for it then, you will save so much time waiting for them to get to that task later. Sometimes signing in to things takes two-factor authentication which can be a nightmare without the client’s full attention. Use your time to make sure you have all the little needs in check.

4. Take Notes In An EMAIL

Email notes give me so much street cred in the creative industry! I take all my notes in the form of email and edit them into a coherent message to the client after the meeting. Strategy sessions have so many ideas, info and action items attached to them. This method helps quantify an otherwise abstract session.

It would look something like THIS:

SUBJECT: Client + Jess Kelly | Notes from 10/14/2027 Strategy Session

Thanks so much for a great meeting. I love your idea about the golden eggs! Here are my notes from the meeting and our immediate action items:

JESS ACTION ITEMS:
1. Send over official proposal & contract (if not completed yet)
2. …
3. …

CLIENT ACTION ITEMS:

1. Sign contract and pay deposit to start work!
2. …

Deadlines and Important Dates:



Style choices:



Top priorities:



Let’s stay away from:



Quotes I love from client about XYZ:


Please let me know if I missed anything, or if you want to add something. I’ll check in with you on Friday for your action items. I can’t wait to get started.

Cheers, Jess

I do this for all of my client meetings now, but ESPECIALLY in the strategy session. It has so many benefits:

  1. Legal proof of what you talked about if there is a discrepancy later.
  2. Searchable notes to find ideas you only half remember.
  3. Clarity on direction and a written road map at the project start
  4. Clarity on next steps and who is responsible for what.
  5. Never lose your notes again by creating searchable subject lines

I did this once and never went back. Your clients will love you for this. You will love you for this.

Want to increase your value as a creative? Get in touch with your own energy.

Your client is going to follow your lead… if you are enthusiastic and responsive, they are likely to follow suit. Visualize how you want the meeting to go? See it in your head and rehearse it. You don’t have to plan it out in detail, but at least know how you want to feel and how you want your clients to feel when they leave. Then go in there with that same feeling. That energy doesn’t happen to you. You create it.

I find that having a transitioning routine helps me a lot. Before the client comes, and after I have put away my previous project, I take 30 seconds to transition in my mind:

1. Breathe deeply.

2. Make a conscious decision and visualize how you want the meeting to play out.

3. Let yourself have the feeling you want to have when the meeting is over by closing your eyes and pretending it already happened. Trust me, this works. Your brain can’t tell the difference.

4. Then, say the word, “release” out loud (if it is not weird). When you say release, let any other thoughts, worries, or anxieties you had from before your meeting leave your body.

Now you are ready to go in confident and curious.

It is time to get out your fishing pole and start fishing for the vital information you need to make your projects thrive. Strategy sessions can be some of the most invigorating and exciting parts of the project. It is where you get to brainstorm, dream, and problem-solve. Get curious about your client and enjoy the experience.

5 Life-Changing Strategies for your Strategy Session

Written by: Jesi Wicks | Photo by Christina Morillo

Can you read minds? Wanna learn how? With the right strategy for your strategy session, your client will be blown away at how well you made their vision come to life. It is so incredibly satisfying. Let me tell you what I mean.

A strategy session is like fishing. You know what kind of fish your creative project is, you just need the right bait to reel it in. Luckily, if you are able to ask the right questions and create the right rapport, it’s really not that hard.

Most creatives fall short in strategy sessions because they equate it to a pitch. Stop trying to pitch and start trying to problem-solve.

Trust is what sells your product, and trust is not built in a fancy PowerPoint. Trust is built through listening, asking relevant questions, and troubleshooting problems in real-time. Give the client the satisfaction of knowing they were a part of creating the strategy for their own project.

In this article, I’ll give you seemingly simple tactics and tools you can implement today to make your process run smoother, save your precious time, and make you seem like a mindreader.

What a strategy session is NOT

Don’t confuse a business lunch or a sales meeting with a strategy meeting. Many creatives get frustrated because they have a “strategy” meeting where people are distracted or engaged with something completely other than giving you the information you need. Don’t schedule your strategy sessions over lunch. Don’t schedule your session with other vendors present, and please, don’t call the pitch or sales meeting a strategy session.

Whether you give away a strategy session for free or do it as a part of your package, schedule your meeting specifically for you and the sole decision maker** in a space that is distraction free.

Your goal should be to find little nuggets of what your client wants that can make you valuable to them. A strategy session is NOT a meeting where you tell them your strategy. It is where you uncover the strategy they need together!

Once you understand your purpose in this meeting, you can follow the tips below to make you client fall in love with you:

My first strategy phone call was my biggest lesson in strategy AND appreciating the humanity of our clients. The call went something like this:

The client got on the line and kindly said, “Hello Jessica, so nice to finally meet you. How are you?”

I said, “I’m great, thanks. I am super excited to share our ideas with you. The first thing I want to talk about is where we can improve your website…” and I went straight into the script I was given. I had planned so carefully and researched my clients website with precision.

After about ten minutes of me talking, he stopped me and said, “Are you finished yet? I have to go. Can you just send it to me in an email?” His kind voice had dissipated, and I wasn’t sure he was even listening.

Who has ever started a strategy session full force like this? I was so consumed with coming off as smart and researched that I forgot about the humanity of the project. I forgot that the person on the other line had way more insight and know-how about his own website than I did. I simply forgot to listen.

The strategy meeting is about your client — not you, your research, or your expertise. The best thing you can do to set your strategy is to ask some guided questions and then LISTEN at the top of the meeting. This does 3 things for you.

1. Builds rapport.

2. Creates trust that you want what is best for the client.

3. Gives you a truly better understanding of what they really want.

Forget what your client needs — that’ll be stated over and over. What you are looking for is what they really WANT. What are their wins? If you get them to talk about themselves in relation to your project, THAT is gold. Savor it. It is not just information you are collecting, it is their desire.

The first 5–20 minutes of the meeting is for you to ask pointed questions that get your client talking about themselves and excited about their project.

How are you feeling today? Are you ready to strategize?

How is your mom, dog, aunt, kid (what do you already know about them)?

Have you thought about anything else since we scheduled this meeting?

I’m really pumped to chat about the project. Before I get started, I just wanna know what you think it’ll look like in your head?

Or my simple favorite: How is your life?

These questions establish that you care about them on a personal level and you want their project to be successful on their terms, not your own. If they start talking and talking — that is great! AGAIN, LISTEN. They are giving you free advice on how to communicate and serve them. Now you have ammunition to write, design, or create in their voice and style without wasting time on choices they may never even consider.

So you do web design. Great! Do you also do graphic design, photography, copywriting, editing, app development, podcast production, social media, advertising, funnel marketing, and email campaigns? If you do, you are a very tired unicorn. Stop trying to wear all the hats. Instead, simply find the people who can support you. Share the project or ask your client to pay for another contractor while you are still in the strategy phase. Setting the expectation of your scope is so important for a happy client at the end of a project.

Look, you need to know what you do and what you don’t do. It seems like a simple request, but a lot of creatives get excited about an idea that involves work beyond what they enjoy or even know how to do. That is okay. You can still dream about a great project. Define exactly what you WANT to do, and promise yourself to stick to those things only.

Network and create a list of other amazing creative professionals who can support your business. Then, share the love. If additional services are needed, you can recommend or contract out that work to your client. You will get SO MANY referrals back to you if you send other people business. Trust me. Save your time and stop doing the things you hate to do. It is not helping you.

My favorite line to say to clients is, “Look, I would love to take your money, but… [here is what I think would provide you a better outcome than hiring me for this bit.] It’s honest. It saves you stress, and everyone wins. Nothing builds rapport better than saying you won’t take someone’s money cause you want the best for them!

Deciding exactly WHAT you want to do seems pretty simple, but most of the creatives struggle with picking just one (or five) things. They either pride themselves on being a jack of all trades or they simply fell into work that needed to be done. It may seem like good money right now, but in the long term, it deflates your drive and soils your reputation.

Now that you know exactly what service(s) you provide, it should be much easier to dig for the information you need. Be ready for this meeting with detailed questions about style, voice, and preferences.

Your strategy session should be less of a pitch and more of an interrogation.

Depending on what you do, the questions will be different. The purpose is to narrow down preferences so you don’t have to present million choices just to get started.

Logos and Branding: Show them clusters of brand boards or logos that represent several design styles. Let them pick 1–3 styles they want you to focus on for their logo. They are not picking one logo from the bunch. They are just identifying styles.

Voice & Tone: Read examples of copy that have different voices. Maybe one excerpt is analogy heavy and another is more story-heavy. Maybe one uses more questionable language and another is more conservative. Let them hear it and judge their responses.

For Websites: Print out site design examples for them to identify their style generally. Ask if there are any industry-specific colors or styles they want to stay away from to differentiate.

The idea is to identify their general preferences and rule out excessive ideas that may be floating around in your creative mind. You will come up with your favorite questions as you dial in your process, but know what you need to know from them to be confident in your creative process.

Once you have style figured out, take care of the logistics of your project to save LOADS of time:

Passwords needed (make them find the passwords before they leave)

Who should be on communications

Are there any existing style guides

Budgets

Relevant social accounts or links

Other housekeeping

Sure, this can all be done over email, but think of how much time you save when you never have to send those emails. If you can ask them to go in and find these before the meeting is over and wait for it then, you will save so much time waiting for them to get to that task later. Sometimes signing in to things takes two-factor authentication which can be a nightmare without the client’s full attention. Use your time to make sure you have all the little needs in check.

4. Take Notes In An EMAIL

Email notes give me so much street cred in the creative industry! I take all my notes in the form of email and edit them into a coherent message to the client after the meeting. Strategy sessions have so many ideas, info and action items attached to them. This method helps quantify an otherwise abstract session.

It would look something like THIS:

SUBJECT: Client + Jess Kelly | Notes from 10/14/2027 Strategy Session

Thanks so much for a great meeting. I love your idea about the golden eggs! Here are my notes from the meeting and our immediate action items:

JESS ACTION ITEMS:
1. Send over official proposal & contract (if not completed yet)
2. …
3. …

CLIENT ACTION ITEMS:

1. Sign contract and pay deposit to start work!
2. …

Deadlines and Important Dates:



Style choices:



Top priorities:



Let’s stay away from:



Quotes I love from client about XYZ:


Please let me know if I missed anything, or if you want to add something. I’ll check in with you on Friday for your action items. I can’t wait to get started.

Cheers, Jess

I do this for all of my client meetings now, but ESPECIALLY in the strategy session. It has so many benefits:

  1. Legal proof of what you talked about if there is a discrepancy later.
  2. Searchable notes to find ideas you only half remember.
  3. Clarity on direction and a written road map at the project start
  4. Clarity on next steps and who is responsible for what.
  5. Never lose your notes again by creating searchable subject lines

I did this once and never went back. Your clients will love you for this. You will love you for this.

Want to increase your value as a creative? Get in touch with your own energy.

Your client is going to follow your lead… if you are enthusiastic and responsive, they are likely to follow suit. Visualize how you want the meeting to go? See it in your head and rehearse it. You don’t have to plan it out in detail, but at least know how you want to feel and how you want your clients to feel when they leave. Then go in there with that same feeling. That energy doesn’t happen to you. You create it.

I find that having a transitioning routine helps me a lot. Before the client comes, and after I have put away my previous project, I take 30 seconds to transition in my mind:

1. Breathe deeply.

2. Make a conscious decision and visualize how you want the meeting to play out.

3. Let yourself have the feeling you want to have when the meeting is over by closing your eyes and pretending it already happened. Trust me, this works. Your brain can’t tell the difference.

4. Then, say the word, “release” out loud (if it is not weird). When you say release, let any other thoughts, worries, or anxieties you had from before your meeting leave your body.

Now you are ready to go in confident and curious.

It is time to get out your fishing pole and start fishing for the vital information you need to make your projects thrive. Strategy sessions can be some of the most invigorating and exciting parts of the project. It is where you get to brainstorm, dream, and problem-solve. Get curious about your client and enjoy the experience.

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