5 Essential Strategy Questions I Ask of All My Clients

Tired of investing in new marketing efforts that were supposed to transform your business, but somehow fell short of delivering real results? 

In this episode, I reveal the five strategy questions that any good strategist should be asking you—questions that cut through surface-level solutions and get to the heart of what your business actually needs. 

You'll learn what these essential strategy questions are, why they matter, and how the answers can completely transform your approach to business growth.

 
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EPISODE 154.
Read the show notes and view the full transcript here: https://erinollila.com/five-strategy-questions-episode/

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

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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 to get started right away
• Visit Erin's website to learn more about her business, services, and products

Transcript

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The easiest way for a strategy session to get completely derailed is starting with a question like, so what brings you here today? This isn't a counseling session, and it's not my client's responsibility to. Share their entire history up until this point of the information that I might need to know in order to help them make strategic decisions for their marketing. Which is why it's my job to make sure I start and move through all of my strategy work with clients in a very detailed and organized way. And I do that by incorporating a few specific questions into all of my strategy work, so that I can get my clients really to hone in on the heart of the matter, what needs work, what I can help them with, and how we can move through things. These questions have saved my clients. A ton of time and potentially even misguided investments, pursuing strategies that would've never worked. And today I'm gonna share that with you. Hey friend. Welcome back. Last week we talked about what happens in a strategy session. If you haven't listened yet, I highly suggest going back to check it out after this so you understand, not only, the options you have for strategy sessions, but how to get the most of them when you are really ready to be more strategic with your business. Today we're staying on the topic of strategy, and we're gonna go a little bit deeper into it by talking about five specific questions that I ask every single client. And I, I really do mean all of my clients, whether they are just starting out, whether they're running seven figure businesses, whether they are, , coming to me for a one-off strategy session or for some longer more intensive strategy work together, or if. Strategies just baked into a different project, like website copy as an example. Here's the thing. In my experience, finding the right solution isn't jumping to quick fixes. It's about asking the right questions that reveal what's really going on beneath the service. And before we begin with those questions, I wanna talk about why they matter. Have you ever had someone come to you saying something like, I don't know, maybe you're a website designer and they say, oh, I need a new website. Or if you're a social media manager, they, come to you and they're like, oh my gosh, I totally need to be on TikTok. My audience is on TikTok. If any of those rules are familiar with to you? What happens is when you dig deeper with these leads, you discover that what they're coming to you for is not necessarily what they need. And that's because we all have a tendency to focus on surface level solutions. We see what others are doing, or let's say we fixate on the most visible problem and we jump straight to a solution without understanding the full picture. I see this all the time., it could be an , entrepreneur, rushing to invest in solutions that, hmm. I see this happen all the time with leads, with my clients, with colleagues, even in myself. I've done this, but what's happening is it's like taking ibuprofen for a raging toothache. Sure. It could provide you temporary relief, but it's not gonna fix a cavity. Adv, Advil's not gonna give you a root canal. It's just like a bandaid over what's currently happening. The right questions are gonna help you cut through all the noise and reveal what's going on and what needs adjusting. They help us understand context constraints and true objectives. They show us where gaps are, and most importantly, where opportunities lie, and the magic of good questions is that they're not just giving you information, they're creating clarity. So these five questions that I'm sharing, let's look at each one individually. I always start with what is actually working right now and for good reason. Because before we can figure out what needs fixing, I need to know what's already working well. There's a natural tendency to focus on problems. You know, people don't generally book a a one-off strategy session, let's say, because they wanna celebrate their wins. They're booking the calls because they know that there are things that are broken, missing, or just underperforming. But starting our conversation with strengths gives us several advantages. First, it creates a more positive framework for the conversation. Instead of immediately diving into what's wrong, we can acknowledge what's going right, and this sets a really good constructive tone for the entire process. Second, it prevents us from fixing what isn't broken. I can't tell you how many times I've seen businesses abandon practices that were actually working well for them because they're distracted by shiny new tactics. Knowing the wins, knowing these things helps us kind of decide how we move forward. And before I forget, there's another reason why celebrating what's working is important from the beginning, and that's because your current successes are. They have clues about your own unique advantages., maybe your email open rates are through the roof and your social media. Yeah, it's struggling, but you have super high open rates, awesome. Click through rates and , an email list with people on it who actually respond to you. Knowing this tells us something important about where your audience engages with you, and that's just one example. But again, we find this out by celebrating what's working. And when I ask this question, I don't wanna just hear about like, obvious metrics because it's important to really like push deeper to find out, , , what channels may be bringing their best clients. Not just the most clients, but their best clients, the ones they loved working with., what offers do they actually like doing? That is key. And I cannot tell you how many website copy projects have been adjusted after we've gotten started because in conversations about their services or their group programs or whatever it is that they offer, they admit to me that they hate doing whatever that particular service is and. Because I think this is an important point. I'm gonna pause here for a second. If you don't like something, you do not have to do it. And I know that sounds so obvious, but I think we, as business owners, neglect sometimes the most obvious things. Um, other things to dig deeper. Where are you getting positive feedback? What parts of your business just feel absolutely effortless? And it's my job as the strategist to look for patterns in these answers. My clients are telling me where their natural strengths lie, and that's pretty precious information for building a sustainable strategy. I. You know, so many people ask copywriters like, how do you, how are you able to write in my voice? Well, we're good listeners and we're good pattern grabbers, so if you can provide us quality information, we can hear your voice, we can hear these patterns and then implement them on our own. All right, let's move on to question two. We've spent en enough time in question one. The next question is, what specific results do you need? And it might sound obvious, but it's really amazing how many people struggle to answer this question clearly because when I first ask this, I think what what tends to happen is I get a lot of vague responses. Like, oh, more sales. I need more sales. Or, you know, I'd really love more engagement. Or,, I just wanna, I just wanna be more visible. But those aren't. Specific results. There are directions, let's say. So for example, if you're coming to me and saying you need more sales, well, how many more sales of what type?, and what are the parameters? Such as like. Buy when or during what timeframe?, , let's say maybe another thing we could dig deeper on is what type of engagement matters to your particular business model. You know, if you are a service provider, you know it doesn't make a difference how many reals you film and keep filming them. If you love making reels, no shame for you. But it does not matter about virality on reels if you're not getting clients from Instagram. So we don't even need to pay attention to that level of engagement when we're talking marketing. If you are not getting the engagement or the leads that you need from that channel., off of that soapbox, you know, what happens with this question of like the specific results that they need is it forces clarity. It, it just forces them to like stop being fuzzy and start getting concrete targets. And the process of answering the question often reveals what they thought they wanted is not actually what they need, you know? For example, social media is a good one. You know, so many of my clients will say things like, well, now that the website's done, like I really need to double down on my, , Instagram following, or I need to, you know, really go heavy on LinkedIn. And when we discuss the specific results, what they're actually looking for is to convert more of their existing audience into paying clients less. About follower account, less about, you know, likes and clicks and comments and more about the conversion factor of marketing, especially 'cause they have an audience that's already there. You know, it's just that they need to do better of a job of getting that audience to become a paying customer. And I think the other critical aspect of the question before we move on . Is timeline, are we talking about results that you need today? This quarter, this year, or for long-term sustainability because timeline dramatically changes approach. You know, if you need, let's say more sales and more sales fast, you might need to throw money behind, social media ads as an example. Or if you're looking for long-term sustainability, just opposite sides of the spectrum, that's when you double down on SEO. And again, this is not prescriptive advice. This depends on each strategy that is being developed, but knowing the results that they need is the only way we're able to come up with those answers, and finally, before I move on to question three, we just wanna ensure that whatever the desired results are, that they align with. Available resources. And that leads, that leads me to my next question, , which is, what have you tried before? And I, I don't know why, but from what I'm told, like this question is so overlooked in strategy discussions with other providers or one-on-one with themself. If, if they've been doing all of their own strategy, the previous attempts, whether they were successful. Unsuccessful or somewhere in between. They all contain crucial data. They tell us what resonates with the audience, whether they are, you know, a cold audience or your nurtured one. They tell us what implementation challenges you might face, and they tell us what hidden obstacles exist. When clients tell me what they've tried before, here's what I'm listening for. I wanna hear patterns of success or failures across different attempts, , consistency as it relates to implementation. Did they give their strategies enough time? Because, , that is one thing that I see all of the time is that people do not give the strategy the legs that it needs to to go on its own and survive. Before they can make decisions about whether the strategy worked. But back to what I'm listening for, some other things are external factors and, and if those external factors have influenced results., one of the, the clients I work with actually a few years ago now, we talked about how a launch that she had done, , twice a year. Had been extremely consistent, actually impressively consistent in sales, had a major flop and she, we talked through so many things that related to the flop, you know? Did she change things within the launch? What did she add to the launch? What was different with timeline approach? You know what? You know what it was? It was the fact that she was pregnant and exhausted \ and she, I guess maybe she didn't give herself the grace or , the,\ , perspective to look outside of the actual business, to look at the external factors of you being pregnant, physical changes in her body, emotional changes, and how that influenced how she was able to show up. And, I'm sorry, what am I talking about? Things I listen for. Oh, internal resistant points, because. Sometimes things work, but they don't feel good, so you don't want to replicate that as well. Asking the question about what they've tried before prevents us from repeating mistakes. If it's something that you tried and you, again, maybe it doesn't feel right, you don't want to do that again, it's so much better to know that upfront rather than have me propose it to you as a strategy. But beyond avoiding repetition, understanding past effort really helps you build on what came. So maybe a strategy wasn't completely wrong, but it needs refinement or it needs a better execution or a longer timeline., one pattern I see a lot is that sometimes clients will have tried the right strategies. I mentioned this, but what I see very frequently is people, they might've tried the right strategy, but they didn't stick with them long enough to see measured results. They don't take the time to compare actual data. And what happens is this, it tells me we need to build more realistic timelines, , or , better systems for getting the consistent implementation. And sometimes it's a mindset thing. Sometimes clients just need,, reinforcing ,. That they need to be patient, and that's okay. I need reinforcing that with my own business stuff from outside sources. That is why we hire strategists. That is why we hire service providers to step into their own zone of genius so that we can do the work that we need to do for our own businesses. So if you do hire a strategist and they push you and some of it feels a little uncomfortable or you're, makes you feel a little anxious. One, never do anything that you don't feel good about. That's not what I'm suggesting here, but, but maybe just sit with it for a second and, and ask yourself whether that anxiety or that uncomfort is a good thing, if that's what you need. And if you can recognize that, just go with it.,I'm, I'm taking up more time than I thought with these questions, so we're gonna move away from question three and into question four, and that is what resources do you actually have? Ugh. What a way to bring your conversation back to reality. Because strategy without resources, it is just wishful thinking, there's often a huge gap between the resources that we wish we had and what is truly available. And being honest about constraints is not a negative thing. It is a necessity, right? It's so important to create a strategy that is going to work in the real world. And we need to assess more than one type of resource first time. Set a timeline, but also determine when are those hours available and how they're distributed next though, you need to think about budget. You know, what can you actually invest right now? What return do you need to see to justify that spending? Third. Team capacity, or if you're a solopreneur, you know your own capacity. Who, who's gonna do this, this work? After we develop a strategy, who implements it? You know, what are their skills, availability, their current workload? Even the best strategy, it's gonna fail if there's no one there to execute it, which is why for me, as the business owner who does strategy, it's so important that all of my strategy, or almost all, is tied to a deliverable. You need your website copy updated. Great. Let's do strategy first, and I will write it for you. Do you need content for your business? Are you looking to rank online as as it relates to SEO? Great. I can write it for you or I can do the SEO research for you and create content briefs for your own team to run with. But knowing what capacity you have, I have your team has is, is extremely important, which brings us to skills and knowledge because you have to have capacity, but you could have all the capacity in the world if you don't know how to do something, you are wasting your time, your budget, and your, and your capacity, one of the ways that we talk about skills and knowledge as it relates to resources, you know, with clients is what can they do in-house and what needs to be outsourced., is there an in-between for any of that? And the answers to these questions are, gonna help you get that reality check. They will help you design a strategy that is able to be implemented within those resources and the final question, and I will probably say, I think I word this differently almost every time, but one of the more common questions is what is stopping them or like, what is. Why can't they move forward?, because again, often I get surface level answers here. Like, oh, I just don't have the time, but when we dig deeper, it's, it's a lot more complex. Very often it's things like fear of failure or fear of success.. Uncertainty about the right approach. Maybe they have like a circle of spinning ideas in their head about how they could approach things in many ways and they just don't know what to choose. It could be competing priorities, perfectionism, , analysis paralysis. Lord, do I suffer with analysis paralysis? But everything, , past disappointment, it could be, , just overall like not knowing what the next step is and. I think it's important to talk about them., again, we started with a positive and I, the reason I try to frame this. Differently than the way that I described it is.'cause I don't want this to be a negative thing. I don't want us to do such great work and then all of a sudden we have to have like a pseudo , therapy session on , their fear of failure. Right. Or, you know, their stressors of success. But when we can identify, what's holding them back, it's easier to, take that issue away. Because the strategy has to address them directly. Because what will happen if I'm not addressing this with my clients is they'll keep hitting the same walls. The beauty of this question is that it often reveals the real starting point for our work together., sometimes my clients don't need complex marketing strategy, but they need permission to focus on a few smaller things, or they need confidence that they're moving in the right direction, or they just need an outside perspective to organize things for them so they can work on the complex. Ideas that they have, and I think that's what they get. All right, so now that we've explored those questions, I want to talk about what you can do with the answers. You know, if you're DIYing your own strategy just from this podcast episode, look for patterns. Do the same themes keep emerging., if lack of time keeps reappearing as a resource constraint and a primary obstacle, it's telling you something important about where to focus., watch for red flags. is something misaligned. Do you have a gut feeling about something? Those are important. You know, I'm not one to ignore gut feelings. If, if something doesn't feel good or it feels off or you feel uncomfortable, you shouldn't be moving forward with that. And then, use the answers you've come up with to prioritize your next steps. I'm not suggesting you can listen to one podcast episode and suddenly become your own strategist, but I do think that if you do the work you can, , review your thoughts, let's say, and start to. Take what you've come up with and, and parcel it out as work to be done in the future. And if you do that, you know, make sure you set some realistic timelines for yourself or make sure to, , build some accountability in here so that you can check in on yourself or have a, have a true accountability buddy to help and check in on you. And if you. Want to be a little bit more serious about it, then hire a strategist. I'm hireable., , we've talked about this in the past couple episodes. You can hire me for a one-off strategy session. You can hire me for a strategy within a larger project like an SEO. Project or a website, coffee project, you can hire me for a VIP intensive. That is, either completely on strategy or one part strategy, one part implementation. You don't have to do this alone. I mean, I would absolutely argue that you should not be doing this alone. I understand that, , sometimes if, if you are new to business, if you are pivoting, if you are just anxious to put something in someone else's hands that , it might not be the right time for you, but. Strategy still needs to happen. And the goal here is not to create a perfect plan. It is to create a workable plan. Something that moves you forward, something that gives you meaningful results and some in a way that you can do it with the resources that you actually have. So that's it. There you have it. The five questions that I, I believe I ask most every client that I work with. What's working, what results do you need? What have you tried before? What resources do you have and what's stopping you from, , moving forward? I encourage you to take some time this week to answer those questions for yourself., you might be surprised on what you discover and the clarity that can emerge from honestly answering those questions. Next week on the show, we're shifting gears just slightly, and we're gonna talk about refreshing your website as part of your spring cleaning . Again, as a reminder, now is the time to get on the wait list for the annual spring Clean your website challenge. If you are on the wait list, that will be your one opportunity to join us at a discounted rate the dates will be announced very soon, so,, don't hesitate , but in our slight shifting, next week we're gonna talk about some signs that show you how your website is working against you.'cause we wanna make all of those spring cleaning changes now so that we can just forget about them and move forward with more exciting marketing goals. You know, once we've done our spring cleaning efforts. All right, friend. That's it. Thank you for listening, and I'll see you next week where we'll keep talking. Copy.