What Happens in a Strategy Session?

Ever booked a strategy call and wondered if you just wasted your money? 

Or hesitated to book one because you weren't sure what would actually happen?

 In this episode, I'm sharing my exact process for strategy sessions - from the questions I ask to what you should walk away with. No more mystery, just a clear roadmap for getting real value from your strategy time.

__________________________________________

EPISODE 153.
Read the show notes and view the full transcript here: https://erinollila.com/what-happens-in-a-strategy-session/

______________________________________________

Join the waitlist for Spring Clean Your Site 2025: https://erinollila.com/opt-in-spring-clean-your-website/

______________________________________________

Here's info on your host, Erin Ollila
Erin Ollila believes in the power of words and how a message can inform – and even transform – its intended audience. She graduated from Fairfield University with an M.F.A. in Creative Writing, and went on to co-found Spry, an award-winning online literary journal.

When Erin’s not helping her clients understand their website data or improve their website copy, you can catch her hosting the Talk Copy to Me podcast and guesting on shows such as Profit is a Choice, Mindful Marketing, The Power in Purpose, and Business-First Creatives.

Stay in touch with Erin Ollila, SEO website copywriter:
• Learn more about my VIP intensive options or just book a strategy session right away
• Visit Erin's website to learn more about her business, services, and products
• Come chat with Erin on Threads, Instagram, or LinkedIn

Transcript

0:00

Have you ever booked a strategy call and then immediately wondered if you simply had just wasted your money, or maybe you've considered booking one, but you've hesitated because you weren't really sure what would actually happen during the call, or worse if you'd walk away from the call with anything useful. I get it. The idea of paying for someone's brain for an hour can feel like a gamble, especially when you're not even sure what questions to ask, how the process works, or if you're just feeling overwhelmed. Today, we're gonna fix that hey friend. Last week we talked about the different ways to build a strategic foundation, whether that was hiring out for an integrated project to simply scheduling an individual strategy session, or you know, even VIP days or the marketing month as a mix of all of those, and. What was really exciting was that I got so many great messages from people like you who asked about what actually happens during a strategy session. So I decided to actually interrupt my previously planned content schedule and. Create an episode today that talked about the interior of a strategy session. In full disclosure, it's coming to you a tad bit late because I was trying to do too much with it., I wasn't sure if I should address things from strategy overall or an individual one-off call. So a lot of what you hear today is about independent strategy sessions, though I will point out a few things about strategy in the larger picture, like if you're doing a website copy project or you've hired me for a VIP intensive. And don't worry, you know, I'm not gonna give you just the theory here. I will share as best as I can, my exact process, the questions that I ask, and how to make the most of the time. Here's the caveat. It depends, like I say all the time, it's, it depends on your business, what happens in a strategy session. They are so custom that. I can't give you the exact questions or the exact outline because really it develops per call, per person, per project. But I think what I've created here is a comprehensive enough guide to get you to understand the beauty of strategy sessions and how they can really benefit your business. So let's start with the very beginning, and that actually happens before the call. Great strategy sessions start with preparation. You risk spending so much time on a strategy session, getting up to speed if you haven't kind of prepped before the call. And this goes both for the strategist and for the person who's hiring it out. Um, for example, if you hire someone to do a strategy session with you and they aren't asking you any upfront questions, all of that. Information needs to get gathered once you get on a call. Similarly, if the copywriter or other strategist hasn't reviewed the answers to your questions, they're wasting your time by getting up to speed. So no real progress is getting made. For me specifically, when clients book that strategy session, they're immediately receiving a focus questionnaire, and it is not just busy work. It's short, and it helps me understand their business, their goals, and any current challenges they're facing. More importantly, it gets them thinking about what they want them to really accomplish in our time together. The questions on this short form are designed to uncover things like, , where they're stuck, you know, or where they're confused, what type of solutions that they've tried, what's actually working in their business right now, whether or not there's something very specific they'd like to address, especially for a one-off strategy session. Obviously there are different short forms based on the type of strategy we're doing. If it's a website copy project, it's happening within an overall project guide where my clients know what to expect before the call. And if it's a VIP day, let's say, you know, we, we've already designed the project that we're going to do together and what we'll cover during the VIP day, so they don't need to provide as much detail. If it's a one-off strategy session, then yeah, I need to know a little bit more before we get on a call so I can be most effective. It is also really helpful for my clients to get this done right from the booking process because it gives me time to review their answers, to look at any assets that they've provided to me and to start mapping out our approach. Sometimes I think what people forget, I. About individual strategy sessions is they see a time marker on the call. Let's say it's a 60 minute call and they assume what they're paying for is 60 minutes of your time. When in truth that's not actually the case. The call itself may be only one third or one fourth of the time. You know, in some instances, yes, it could be, you know, only half of the time, but. What happens usually is the upfront work of reading through questionnaires, sometimes reading through long surveys, checking out research, doing some, uh, competitive analysis. Then there's the actual time spent on the call, and then there is the follow-up process, which can include very simple stuff like, you know, preparing transcripts and, and saving the video call to a Google Drive. Two, writing out recommendations, developing strategy, and then sending that over. So don't be fooled by the amount of minutes that the call takes, because there's a lot more that goes on behind the scenes. But I don't wanna start a ran here. So let's just jump back into again, what's happening before the call. That form is really helping to also set clear expectations. No. But so that I don't rant here, let's talk about what needs to happen before the call. In addition to the quick questionnaire I'm asking of my clients. And one of those things is setting expectations. I want my clients to understand that we realistically can and cannot. I want my clients to understand what we realistically can and cannot accomplish in our time together. So again, if I have the form or if I've had earlier conversations with you to understand about what we're going to talk about, it's so much easier for me to set priorities and prep to make sure we stay on pace during the call. Because a strategy session, especially an individual one, isn't gonna solve every problem or map out an entire business plan and you know, the processes, then the copy and content that needs to go with it. It can provide incredible clarity on a specific challenge, or as I mentioned, you know, in the earlier episodes, just the opportunity to get unstuck when there's too much on your head. So what should you bring to a strategy session? Honestly, your job is to come prepared with questions, your goals, and an open mind. It's also to come prepared to be able to either make decisions or provide feedback, because again, I'm saying this again when I've said this in a previous episode, but. While a strategist can help you design a plan, you also need to help us, , be a decision maker, or to give, you know, really important feedback based on the strategies we're suggesting. The more specific you can be about the things you want to accomplish, the more valuable the session will be. All right. We've covered everything that happens before the call. Let's talk about the actual session structure. So I've found that a clear structure really does make all of the difference between a productive strategy session and one that. Feels scattered, so I have a clear structure for what happens during my strategy sessions. This helps me stay on track and it helps my clients feel like they're getting the best out of the call. As most are 60 minutes. What we're doing is we're starting with the first 15 minutes max, I should say. Sometimes we go through this very quickly,, but maximum of 15 minutes is focused on the current situation and the vision. And I want you to think of it like we're using this time to get our bearings. You know, where are you now? Where do you wanna go? And I ask things of my clients like, , what are your primary revenue streams right now?, who is your target audience or your ideal client? How long have you been working with clients or let's say, selling products in this capacity?, what's working well in your business right now? What specific challenges are we hoping to solve today? What have you already tried? And you know, what was that like after you tried it? And then finally something like, what's your capacity for implementation? Because we can come up with some strategic plans, but those plans need to match the capacity to actually implement them when the call's over. And that's not an extensive list, and they might even seem basic, but it's really important. To cover those bases because you know, you can jump into solutions if you, without clearly defining the problem first. Or I could suggest things that make sense. To the problem that they're experiencing, but they don't make sense to their actual business if I don't know, things like what their clients are looking for or the type of people that they serve, or again, if they've already tried these things in the past, it's really all about not wasting time and uncovering any hidden obstacles or opportunities that we might not have considered or they might not have considered. I think one of the biggest benefits of working with a strategist is getting that outside perspective. You know, when you're deep in your own business, it's incredibly difficult to see the forest for the the trees. You might be so close to the work that you miss. Obvious opportunities or challenge challenges that someone with fresh eyes can spot. Immediately as your strategist, I can ask the questions that you might not think to ask yourself, and I can bring objectivity, which is really the most important part to your decision making process. So after those, that initial setup time is done, whether it takes five minutes or 15, we really have to move into the meat of the session, you know, and this is about 45 minutes of strategy development and action planning where we, let's say, , brainstorm potential solutions, evaluate options against whatever those specific goals are. Create concrete action steps. Prioritize what needs to happen and what needs to happen first, to address potential roadblocks and to map out a realistic timeline for all of this to get done. And here's what makes this part different from just chatting with a business friend or potentially even with a coach. I'm bringing the structure and the strategy to the conversation because we're not just throwing ideas around together. While I do obviously hope that our conversation can feel like talking to a friend, what we're doing is we're systematically working through options and creating a plan that you can actually implement. That's the key. Let me think of an example I had a client somewhat recently who joined me for a VIP intensive day, so I wanna point out here, this gave us extended strategy time. What she wanted to do was to launch a new service but wasn't actually sure how to position it alongside her current offerings. It was closely situated to what she was doing, but it had its own. It was, it was still different. So during our time together in our initial strategy session, we mapped out her customer journey. We identified exactly where the new service fit, like how to bring it up to her audience because she didn't, I. Actually launch it to her entire audience as if it were like, you know, one cohesive launch. It was launched to a specific segment of her audience., and then the rest of her audience got presented with it alongside something else at a different time after the initial launch. And then we also work together to come up with some key messaging facets that. Could differentiate it from the other options, but we still had that full implementation part of the VIP intensive that we could spend together. So while she originally thought that she would be hiring me to do some writing in the VIP day, we, we, during the strategy session, pivoted to make it more of a collaborative VIP experience where we could go beyond the actual planning. We created her launch content, which means we drafted up the, I would say, an overwritten outline of her sales page. We mapped out an email sequence that she was then able to write after our VIP intensive on her own because it had bullet points for everything that needed to get said in all of the emails, , and direction for what to say, and she could say it in her own voice because she was a great writer. And we even talked about some of the ways to take that and repurpose the content from the sales page that we had outlined. From those ideas we had for the email sequence to use on social media. So by the end of our full VIP intensive, that strategy session and our day together, she was really excited to launch with confidence. And I will say I was very, very impressed with the copy that she created. It was a hundred percent written in her voice and she was very pleased, even though she, excuse me, even though she originally thought I would be doing a lot of the writing for her. She was so pleased with how easy it was because it was like, , what did she say? I think she was the one who called it like, mad lib style. Like, fill in the blanks to anything that was unfinished and just touch it up. And I reread it all before she launched it. And honestly it was just, it was great. I was so excited for her. Again, that's just one example, which is why I should, you know, reiterate here that the specific content of a strategy session is gonna vary widely and be completely dependent on what you need. So let's. Let's look at what we could do during some of the common focus areas and what we might cover. You know, for website strategy, we might be focusing on site structure and user flow., if there's any key conversion points that need to happen and where to put them. Content hierarchy, messaging, consistency and, and the updating of that, , SEO integration. For email marketing, you know, we could tackle things like list growth opportunities, , email sequence development, automation opportunities as they relate back to the sequences, nurturing strategies. I. For content strategy, we can cover things like content types and formats. Um, content brief creation, or content calendar creation, content repurposing strategies, the actual content creation specifically if they're tied to a VIP day, you know, we could strategize on what to write and then I can write it for you., let's see. Launch strategy, kind of like my example, we could talk about timeline planning, asset development, audience warming. And speaking of audience warming, I have an excellent early episode of the podcast on, , with Ash Chow about her pre-launch framework and how she takes clients with that. I'll link to it in the show notes. So again, those are just some varied examples for you. I really wanna reiterate that that's not the only thing you can do on a strategy session. The beauty of a focused strategy session is that we can adapt it to exactly what you need. Some clients may come with a very specific question like, you know. How do I structure my services page? Or others might have broader challenges like, Hey, my content isn't converting. What am I missing here? Whatever the focus, the goal is the same, to give you the clarity in a concrete plan to move forward. Speaking of moving forward, here's something important to understand. A strategy session is only as good as what you do with it, so let's talk about how to make sure you get real value from and after the experience first. Either take good notes or record this session if you have permission to do that. My strategy sessions have all of them. They're all recorded, they're all transcribed, and usually I'm the one taking notes, , that I give to my clients. But you are welcome to take notes alongside me if you'd like. Let me tell you, your future self will. Thank you for doing this. During each session, you're gonna be processing a lot of information and making a lot of decisions, so it's easy to miss important details. But if you have something to reference later, you know, that's really invaluable. Next, let's plan your implementation time. One of the biggest mistakes I see is that people have a great strategy session and then they do. I. Absolutely nothing before a session even ends. I like to ask clients to look at their calendar and block time for implementation, ideally within the next week, so that those ideas are fresh and they can take action. However, I also think it's important to prioritize, which is a completely different approach, instead of blocking out the time. If we've talked about a lot of different things, sometimes the important thing to do once the call ends is just outlining and listing them in the order of priorities that they can get done. So it's kind of more like just ticking tasks off versus like creating one block of time to do everything that you need to do. And you know, it's important to be like realistic about what you can accomplish because you know, if you try to implement everything at once, you're gonna get overwhelmed. Period.. What could work, well again, many different approaches here is to identify quick wins and then, you know, roll with those quick wins or maybe take the biggest action item and the something that will have the biggest impact and start there. That's something we can figure out together, or whoever you work with during a strategy session. And someone should be helping you with this. You know, it's not like let's talk strategy and then sign. It's really important for your strategist to kind of help you figure out how to do this. And then finally, you know, when we're talking here about how we want to make the most of this, you know, one part of that is just recognizing potential roadblocks and, you know, doing that before they derail you. You know, we'll talk about what might get in the way of the work that you need to do, whether that's things like technical limitations, , time constraints, knowledge gaps, and we'll make a plan to address those challenges. Sometimes you have to call in a website designer to help you fix things. Other times you might need to have like an email strategist or someone who does tech stuff within your email stack. Again, great episode to listen to. Here would be Bev Feldman's email tech episode. So you can hear things about like segmentation and tagging and all of that stuff. Because if that comes up and you're not familiar with it, at least you'll be able to know, A, who you can hire, or B, what skills you need to take that next step forward. And that's not it, because our work doesn't end when the call does, in fact, what happens after the session could just be as important as what happens during it. After our call, you'll receive from me a detailed action plan according to what we discussed. Again, this is like my notes, and this isn't just a simple recap. It could be, depending on what we talk about, a step-by-step guide., it could be. Tasked organized into immediate actions, short term projects, longer term goals, so you know exactly where to start. You'll also get access to the video recording and the transcript so you can go back and review anything that you are a little cloudy on or you just need, you know, like really reminding to get you to take that action. And then, you know, one thing I've learned is that accountability can make a huge difference in implementation. This is why I recommend, you know, one, setting specific check-in points for yourself, like dates when you'll reassess your progress, or you may adjust your approach.. Some people might find having an accountability partner, , is important, or even just schedule a follow-up strategy session with me to stay on track. And this is one of the biggest benefits to the Magic Marketing month. You know, I talked about that briefly in the last episode because it's not just a one-off strategy session with the month long commitment you are getting built in accountability, support, and strategy with me throughout. The planning and the implementation process. We start with strategy and I'm there as you put the like pieces together. So for many clients, this ongoing support makes all the difference because it's, you know, not just that plan that lives in Google Drive and you say you're gonna get to it one day, but you're doing the action in real time to transform your copy or your content or whatever it is related to your business. And you know, even if it is a one-off strategy session, you know, sometimes when they're done, what happens is that my clients realize they actually want or need more support than they initially thought, which is why I offer the option to roll a strategy session into a VIP intensive at a special rate if they're booking within 30 days of their strategy call. This gives us time to not just plan, but to actually implement. So let's say we get on a call where we're doing a website review., actually one, one of the ways I see this happen most often is a website review for someone who has DIYed their website. I. We get on a call and we walk through all or as many pages as possible during the strategy session, and I take them from top to bottom of the page suggesting what's working well, what's not working well, and the actual improvements that they can make to either reorganize or adjust messaging to make their page more conversion friendly. Now what happens is we just talked about a lot on that call and some people can absolutely take the recording and then make the edits in, you know, real time. Once the call ends and, and do it on their own. Other people are like, yeah, wow, there's a lot. So, , can you do this for me? I can then roll them directly into a VIP day where I then take all of those things we talked about, do copy rewrites for them. I. Do you know, outlining adjustments of their pages, create specific buttons for calls to action that maybe weren't there. You know, talk about site navigation, suggest anything new that we might have talked about and, and implement it so they don't have to do the follow-up work. Because, you know, even just the decision making process in a strategy session is a lot. It can be heavy and overwhelming. So having someone to do the work for you, it's a blessing. So there you have it. Friends. That's really, I hope a good look inside what's really happening during a strategy session. And I hope that I answered questions., well, I know I answered the specific questions that were asked of me, but I hope that if you are wondering these things yourself, it gives you a good idea, , of what to expect from a strategy session and how valuable they are remember, the most important part is not just the session itself. While that's absolutely valuable, it's what you are doing to prepare and then what you do later with the insights and the plan that you develop a strategy session is really just meant to be the beginning of a positive change, not just an interesting conversation. So next week I'm gonna be talking about strategy specific questions, why I use them in all of my strategy work and why they're so important. And more importantly, I think what they reveal about what's needed based on the answers. Thanks for being here, friend. See you next week where we'll keep talking. Copy