Group Coaching Questions

Following are questions that have been answered in my group coaching program:

Questions from 2019-02-21 session

I'm trying to get myself onto stages and in front of people to help build my reputation/authority but haven't done much in the way of speeches since school. Do you have any resources you would recommend for helping with both talk creation and presentation? (timestamp: 1m 18s)

I've made the decision to stop taking on new implementation projects so I can focus on building out a niche and my own products. Some of the clients will easily transition to working with my friend, but he only takes on high-value projects. As for the rest, I want to see them succeed and I don't want to burn any bridges, but I just can't continue to do hands-on dev work for them. Any recommendations on how to gracefully end the dev relationship with the remaining clients? (timestamp: 21m 13s)

Ideally I’d be prospecting to those making $1m+/year BUT feel like I’m maybe not “good enough” or experienced enough to be an attractive option. Any suggestions? (timestamp: 32m 29s)

I have a potential client who I proposed a 'Preliminary Strategy" session online prior to the Brand Strategy because she's creating a new lifestyle category and has tons of ideas. I wanted to narrow down her ideas on a phone call or webinar to pinpoint her desired state, so going into the strategy session, we would have a clear direction. I'll also be collaborating with a financial strategist during this session (timestamp: 51m 32s)

Questions from 2019-02-07 session

Is there ever such thing as additional scope on a value-based project? If the client pivots their whole business model mid-project which requires significant changes/revisions, do you just keep working under the original price? (timestamp: 1m 53s)

I'm working on a product ladder and debating how to price the various rungs. Is there a strategy or is it pretty subjective? Trial and error or is there some research I can do to dial it in? (timestamp: 19m 17s)

I'm hearing the advice of setting up a product ladder but am struggling with coming up with options. My Mercedes offer is typically a custom backend system ($30-$100k), and I offer an audit/strategy report ($5-$10k). My "sawdust" would be frameworks etc which I dont see my clients wanting. Am I thinking inside the box too much on this? Do you have general suggestions on products categories to kickoff brainstorming? (timestamp: 36m 20s)

When do you know to go all in on specializing? Does it ever make sense to just have two businesses? (timestamp: 47m 34s)

Follow up to my first question if you have time: if you work down from the top of the product ladder, how do you effectively generate leads for that next rung down? (timestamp: 55m 6s)

I have been developing a software application for a company for the last 18 months. When I took over the project was dead. Now it has gone nuclear, getting traction in the org. This is a big win for me and the team I’m working with. They want to expand it to other depts and are asking me to lead the effort (more assumed that I will), their desire is to hire me, my desire is to go from hourly to value, ugh, I feel like I might have to move on (timestamp: 60m 26s)

Questions from 2019-01-24 session

Is it ever okay to work on an hourly basis? (timestamp: 1m 49s)

I sent a cold email to a potential client, in the email I listed the things I can help with, here is the response I got "I'm not sure how to use your service. I would love if you could tell me something you could do for us, like a project/optimization you see us needing? If that's possible. " it seems that they need me to look into their business for free, what's the proper way to get back to them? (timestamp: 14m 46s)

If I only have one url to direct people to, lke a "work with me" type page, what should I make sure is on it? Only the fixed price things? Only custom engagement process? Both? (timestamp: 25m 36s)

When does it makes sense to look for a business partner? Or is it better to keep going solo? (timestamp: 41m 53s)

Questions from 2019-01-10 session

When offering a bug-free guarantee, how do you handle or explain bugs that come from vendors/OS/browsers and not from our code? (timestamp: 1m 51s)

Do you have any advice on metrics to look for with a start up for evaluating value? Is there anything unique about a startup that would cause you to change your approach to pricing/proposal/etc? (timestamp: 17m 20s)

Does using different language like "promise" instead of "guarantee" make it less effective in your opinion? To us in Canada the word "guarantee" sounds a little Walmart. It seems to us that a guarantee is somewhat implied in the value pricing... (timestamp: 27m 38s)

Do you have any advice on what to do if your conference talk proposals get rejected fairly often? I'm not really sure what to do next, other than perhaps write a different talk to pitch next time, since there's not much feedback. I live in area with very few meetups and such where I can trial/tune the talks much. (timestamp: 40m 35s)

if there's time left, can you tear down my landing page? (timestamp: 61m 43s)

Questions from 2018-12-27 session

I am about to complete an hourly based project. It, shockingly, went about 15% over the estimate. The client is happy with the results, but not that the cost was higher than estimated. I'm writing a case study for the project and was wondering if you have any recommendations on presenting a case study where everything isnt a win? (timestamp: 1m 9s)

I'm getting ready to launch a new productized service, any general advice on how to price it? I've primarily done the work in the past as an FTE, so I'm a bit uncertain on pricing. (timestamp: 15m 20s)

I’ve built a team around me where we can execute on 3-4 big projects at a time. These projects typically last 3-6 months as they are fairly big. My issue is that I’m still very much in the center of it all. I don’t have revenues to support the hiring of talent to replace me yet. How do I bridge growth? (timestamp: 34m 24s)

Questions from 2018-12-13 session

Via email: I asked my client how would you measure the success of this project (after the work has been done), and they replied with the fact that they were happy with the "outcome". Meaning the work was done, but couldn't measure success in a dollar value. The work I provided was Brand Identity. In speaking with the founder and their staff, they all felt excited with the new look and feel of the brand. What am I missing here? (timestamp: 1m 12s)

Via email: Could a corollary to "If you're worried about bugs, you're not charging enough" be "If you are on thin margins you should invest more in quality assurance so there will be less bugs"? The issue here is pricing of QA services. Rich clients don't fear bugs so don't need QA, and poor clients fear bugs but can't afford QA. Bummer... So how do you value price QA or other risk-control services? (timestamp: 14m 9s)

Via email: I am a 20 year old designer that is currently studying design at university. I have had paying clients but nothing over £2000 yet. My question is, how do I show the value I bring to them without having the “professional” experience? (timestamp: 46m 10s)

When a prospect asks, “how do you price your services?” I “try” to do 10% of estimated annual hard dollar ROI outcome as long as its head and shoulders above time and materials cost now. I’ve tried to “mix in” perceived value for unmeasurable stuff as part of that value calculation based on gut, but can’t tell a prospect that. So how would you handle that question? (timestamp: 23m 52s)

Can you do a teardown of my site (timestamp: 51m 42s)

Questions from 2018-11-29 session

I'm building an audience with my side hustle, with the long term goal of turning that into my core business. I don't have a clear idea of what products I can create and sell to that audience yet, I'm just focused on delivering value for now. Do you think not having a plan about a product ladder during these early stages is ok? (my feeling is that the products will reveal themselves as I have more conversations with my audience). Or does that sound naive? (timestamp: 1m 32s)

When you write daily emails, come up with products or podcasts episodes etc., do you have one person in mind who you "speak to"? i.e. a person who is your ideal target audience? Or are you more generic i.e. speaking to an imaginary person who ticks certain boxes? (timestamp: 7m 51s)

I’m interested in potentially getting royalties from my clients’ skincare or cosmetic products. My clients are in the beauty industry, and I’m curious about the pros and cons for both parties, and how and when I would approach the convo. I want a passive income and if I’m invested that would show that I’m committed for the long haul, right? But I also don’t want to screw myself over or give off a money-hungry, selfish vibe. A previous lead wanted a similar arrangement with me, shark-tank style, but it turned out that they just didn’t have any money 🤦🏼‍♀️ so we never ended up working together anyway. Thoughts? (timestamp: 17m 0s)

Can you please teardown my website: (timestamp: 24m 12s)

Questions from 2018-11-15 session

How do you deal with the fear that comes from various marketing and sales activities (e.g., niching down, public speaking, launching something new, presenting premium prices)? (timestamp: 1m 33s)

What are your thoughts for offering referral commission for other consultants/agencies referring leads? (timestamp: 28m 33s)

When you value price a project to a specific problem/solution and find out problem is more extensive than you thought, how do you handle seeking scope change vs saying, "Okay I can eat into this profit, learn, and move on" ? (timestamp: 30m 27s)

Any advice on how to qualify leads? I had a lead recently, he seemed that he had a budget for the work though after exchanging emails I found out that he is looking for cheap service, I'd like to avoid such leads in the future, is it possible? If so, how? (timestamp: 35m 48s)

Any advice to stay motivated, positive, and focused? (timestamp: 40m 3s)

I can't stay on the call, and feel free to answer anything else first but otherwise you can rip into my newly separated niched sites. FoxPro specific and Rails specific (timestamp: 48m 23s)

Questions from 2018-11-01 session

When building a proposal, I find it hard to figure out what should go in each option. I always ensure Option 1 solves their core problem, but struggle with where the "home run" should land. I've been treating option 3 as the "home run", but that starts to feel a bit like options 1 and 2 are the dodgy non-options. (timestamp: 1m 24s)

I became self-employed about 2 years ago. Since then work has been a "Roller Coaster"! Some months projects are coming-in and life is good. Other months it's completely dry. Based on your experience how can I have sustainable business? (timestamp: 9m 1s)

Is it important to to figure out "why am I doing this?" being self-employed I guess. I heard recently that I need to find my "why?". When I think of my "why" it always comes down to this: pay the bills, provide for family, live a comfortable life – one day hopefully – and never work for anybody else ever again, am I getting this "why" thing wrong? (timestamp: 18m 6s)

I’ve got a 30 minute call with my ideal customer next week (CEO of funded startup). My idea : “I help startups with Devops”. This is a ‘I want to find out what your problems’ kind of call. I’m worried the conversation will dry up. What are some good questions to keep him talking? (timestamp: 26m 0s)

The question I plan to ask my target demographic for our conversation is "When it comes to growing your business, what is the single biggest challenge, frustration, or problem that you've been struggling with?" In your experience, would a question like this sounds an alarm in a business owner's mind? In other word, how should I rephrase this question to make it more tactful? (timestamp: 31m 8s)

I'm just starting out, and don't have any business connections, how can I present myself to my target demo as credible and not trying to sell them anything, in order to get them on the phone for a conversation? I'm working a full time job, so all my social media accounts are all about my work experience as an interpreter, so there would be a disconnect between what I'm doing now and what I want to be, which is a marketing consultant. (timestamp: 40m 11s)

If I need to put in some work prior to reaching out, what are the things I should put together to show them that I'm credible, and not just a random spam in their email accounts? (timestamp: 43m 30s)

Client wants to start project tomorrow that was set to start on the 9th. How would you respond to this? The reason for urgency is a bug they want fixed right away. The project is a 2-month optimization project to get their web app stable for projected growth in January. I had not anticiapted having to fix urgent bugs from day 0. How would you manage expectations here? (timestamp: 45m 27s)

just bc you have a few minutes - you said don't work on portfolio/case studies? (we're updating that stuff now) why not? can you elaborate? (timestamp: 56m 55s)

Questions from 2018-10-18 session

At the moment I'm an eCommerce development consultant. I'd like to transition into an eCommerce growth consultant so besides development work I'd like to offer services that covers digital marketing & conversion rate optimizations. I can do it though as of now I don't have track record of it. Is it possible? If, so are we talking months or years? What would be the best way to approach this? (timestamp: 1m 28s)

I've a prospect (B&M) that needs help with digital marketing and Shopify store management. At the moment the store is doing pretty bad 0% conversion and traffic is pretty low, on the other had they are making $250K-$1M/year. I need help pricing this? (timestamp: 21m 11s)

I started off as a consultant with fixed pricing (sort of value), and have been pushed to go back towards a hourly rate as the client is trying to do some of the work themselves and are looking more for short interventions and are hesitant when I try to point out what the outcome is and how I can help (when they believe they've done 70% of the work). How do you suggest I handle these conversations? (timestamp: 28m 49s)

I started working with a well funded but frantic startup with a real deadline (conference) and need last minute help. I don’t want to gouge them or encourage the frantic behavior because they will be interesting/profitable future projects, but had no idea how to price small but not trivial work. How would you go about it? (timestamp: 40m 10s)

Questions from 2018-10-04 session

Do you believe that the path to thought leadership must always pass through the phase of expertise first? (timestamp: 2m 1s)

How much time I should be spending on growing my business per week or month? I find myself always prioritizing client work which I think on the long-term is hurting my growth rate. I'm not sure how to balance! Please advice, thanks. (timestamp: 6m 17s)

What do you think of paying for Ads to generate leads? From your own experience what generated most leads for you this year? (timestamp: 11m 57s)

What do you think about this LFPS? "I am a DevOps expert, who helps startup CEOs achieve their business goals by shipping better code faster. Unlike my competitors, I understand the needs of both business and tech." (timestamp: 20m 4s)

I'm doing a Keynote at the local Devops Days next month "DevOps: Why the Startup CEO should care and how to convince them with numbers". What would be a good lead magnet to have ready? (again, this jumped in my lap before I've done the prep for it..) (timestamp: 27m 52s)

When you’re new to pitching fixed-price expensive-problem: what makes sense as an initial project/product to a prospect who has approached you? I plan to have a product ladder ranging from the low-price-low-touch book/course, up to the very expensive done-for-you service. This prospect has approached me before I’ve thought it all through. (timestamp: 35m 3s)

Questions from 2018-09-20 session

In a recent proposal, I mentioned time to deliver since I know there is urgency to the project. But they used it against me: If it only takes X days, why does it cost $XXX? Did I make a mistake mentioning time? How can you communicate the added value of a quick turnaround without it backfiring? (timestamp: 1m 28s)

I’ve started a productised service creating digital annual reports, and aiming to sell to the renewable energy sector (basically, annual reports published as microsites, I have sold two in other verticals). I know a bit about the R.E. vertical, can speak about benefits over features etc, but can def learn more. Would like to get a landing page up - any thoughts on what this first landing page should aim to achieve at the start? Eg: lead capture, sales, something else? Happy to play the long game (timestamp: 8m 24s)

I get all my clients through referrals, which is good but I feel like a hostage. At any time those referrals could dry up and there is nothing I can do. I started putting effort into my website and social media. I paid a copywriter for website content and blog articles so it reads professional. I also did few Facebook (and Instagram) Ads to promote my blog articles, Facebook page, and website. I spent around $400-500 and I got 0 leads out of those campaigns. How can I create my own sales funnel? (timestamp: 20m 19s)

From Slack: I am having trouble connecting the dots between my skills and solving expensive problems. I have recently started instigating conversations with a market segment that I want to serve, in order to understand their problems. I am trying to be genuinely curious. But when they mention problems unrelated to my area of expertise, the conversation languishes. I already have clients who are getting value from what I deliver, so I know there’s appetite. Is this just a case of persevering? (timestamp: 34m 33s)

Questions from 2018-09-06 session

Can you give a good example of what a weekly habit of "optimizing for conversations" might look like? I'm particularly interested in using LinkedIn like you described on the BOA episode. (timestamp: 1m 6s)

As a solo consultant with a steady stream of referrals, I've always neglected building a site. Next month I'm bringing on a friend to join me, so I'm thinking more about the sales funnel and attracting leads. I hope this isn't too broad, but what good resources can you point me at for building a site focused on attracting leads? Or is this the wrong thing to focus on for lead generation? (timestamp: 31m 22s)

Had a good why conversation, all boxes checked, sent them a proposal (told them I was the expensive option ahead of time), response “price point for this is higher than I anticipated”, “At a price point of $90k, I would expect more of a fully developed system”, my take, they are thinking cost+ pricing, not the value they are getting. Any suggestions on where to go? I don’t want to push, am fine with moving on (timestamp: 47m 36s)

Questions from 2018-08-23 session

I was referred by a client in the coworking industry (my niche) to their industry association. Apparently the association needs help with their marketing but don't really have a budget. They want to grow the number of members and have several hundred already who pay a small annual fee. They also have a conference. I think the idea might be to get exposure to their network of coworking space owner/operators. I usually don't work for exposure, but this feels different. Thoughts on this situation? (timestamp: 1m 32s)

If I'm just getting started with a new consulting business, and I've thought of a problem I think is worth solving, what should I be doing as a next step? (timestamp: 19m 12s)

What should I do if a prospect balks at my pricing? (timestamp: 35m 13s)

Questions from 2018-08-09 session

I'm feeling a bit stuck. As a contract developer, I'm essentially a fulltime employee. That means all my work time is committed to that employer, leaving very little time to work "on" my new business. have any ideas or thoughts on a good transition plan for someone like me, to be able to free up some time to get the flywheel moving? How have other students been able to do this? (timestamp: 1m 36s)

Can you tear down my landing page at (BTW, I don't have the registration button wired up yet.) (timestamp: 10m 29s)

I have an awesome client, currently an hourly arrangement. A few months ago they had a super busy month coming up, and I suggested a higher-priced, fixed cost retainer which they accepted for that month. It worked great, and they went back to hourly after that thinking it would quiet down again, but it hasn’t really. I’d like to bring the retainer up again, and I think they’d be open to discussing, but they are quite price sensitive so not sure how to bring it up. Extra background: I started out doing creative work for them (brand design, brochures, signage etc) but am now more of a brand manager for them. I’ve become their first stop for advice on how to start/run/do most marketing projects, and am now about 50% project management and 50% creative work. I’ve created systems and dashboards for them to manage our work together and they’re always open about how happy they are, so each passing month gets smoother (ie, I’m making their lives a lot easier). (timestamp: 32m 27s)

Can you do a teardown of my homepage targeted at messaging / websites for professional service firms? I'm trying to balance how much to pigeon-hole my homepage. I'm considering niching it down to target only B2B CPA firms. I'm planning to run linked in messaging campaigns for specific consulting offerings geared just towards CPAs. Right now those are their own Landing pages , not my homepage. (timestamp: 46m 31s)

Questions from 2018-07-26 session

I help prof. service firms w/ customer experience/messaging strategy. Most of my clients don't have a dedicated marketing function so we're starting from scratch. I've found that clients want access to me to guide their strategy and activities, but quickly ask me to oversee or source a team that is also producing deliverables. Do you have tips on how to delineate and set boundaries between 'advisory retainers', 'coaching services' & 'done-for-you' service lines? (timestamp: 2m 18s)

I am wanting to move away from doing implementation work and more towards strategy consulting. What would be the best way to get started and how can I convert existing clients to do this? (timestamp: 11m 26s)

You suggested that I continue to reach out to Tennis Directors, to get connected. I can do that for some, via LinkedIn. For the ones that aren't on LinkedIn (but that I have an email address for), what's a good template to use, to connect with them? What's the correct approach and CTA to use? (timestamp: 18m 4s)

Would it be too niche to specialize in helping multi-location coworking spaces with their marketing (as a consultant/advisor)? And have an intro tier for coworking spaces aspiring towards multi-location? (timestamp: 25m 25s)

I have a long standing client on a retainer, where the work load has gradually declined. At this point they're paying me every month but they never call. It's not a huge amount of money for me. Should I just keep quiet and see if they notice that they're not using me? Should I suggest they stop paying me? Should I proactively reach out and try to increase the level of engagement? [I have a conflict so am not on the call, sorry] (timestamp: 30m 25s)

I'm interested in offering 3 pricing tiers on a proposal. In the past I've always offered a single, flat rate, but I'm wondering about the best approach to differentiate the offerings. I usually think in terms of features or amount of work to be done, but I've also heard about removing risk to the client as you move up the tiers. Just curious about some examples you could give on how this could be presented. (timestamp: 36m 37s)

I haven’t done any strictly advice based consulting before, usually I do discovery/implementation, but was asked during a networking event if I would come in to advise a company . We got cut off and he left before we could flesh out details but I plan to follow up. Do you have any advice on pricing this? (timestamp: 47m 38s)

From Slack: 1. Should I consider increasing the scope of work that Videobites delivers? 2. Is only creating “training” videos hindering the opportunity? 3. Or will diversifying my service reduce my expertise and value? (timestamp: 61m 13s)

From Slack: Sales conversation transcript teardown (timestamp: 78m 7s)

Questions from 2018-07-12 session

I have a lead who wants to hire me to help advise them on a fairly large capital purchase (somewhere in the $200K-$500K region). I'm an expert on both the technology and the vendor they're probably going to select. They want advice from an unbiased expert to make sure they purchase the right equipment and services for their plans. How would you approach pricing something like this? (timestamp 2m 2s)

What can I do on my website since I don't have any good testimonials yet for social proof? (timestamp 14m 56s)

Can you review my LinkedIn tagline? (timestamp 31m 15s)

Do you have any recommendations for long term support of a custom software solution for clients. Specifically, on-going small (low value) tweaks, small tweaks with high value and planning/pricing version x+1. (timestamp 42m 19s)

I've got a client that I had a roadmapping session with, followed by a $75K proposal. This is a company looking to increase monthly revenue by $100K by doing online marketing (they currently only sell offline). They said the price was high but they were still interested and would get back to me last week. I followed up with them on Monday but still haven't gotten a reply. How can I try to salvage the deal at this point? (timestamp 48m 34s)

Can you provide any suggestions on implementing and pricing GDPR compliance for clients (news sites, blogs, recruitment agency). Not sure if there is anything I can learn and do as a web developer or if I should be referrring them to a lawyer/GDPR consultant. From what I'm seeing online, it looks like lots of sites are going halfway and are not really fully compliant. (timestamp 62m 43s)

Questions from 2018-06-28 session

In light of the list of potential offerings you posted in Slack, what should I do next? (timestamp: 3m 23s)

Had a "no-show" call with a referral yesterday. Is there a good system to weed out the tire kickers that I ought to implement? (timestamp: 31m 4s)

I am doing a lot of specialty consultant work for my clients but I am trying to figure out how to move away from actually executing the work. How do you delegate this? (timestamp: 36m 35s)

In my specialization direction “sales funnels for thought leaders with digital products” i’m finding its still not specialized enough from convos with bigger names (there are a lot of funnel guys out there) so I think I either need to 1) further specialize skill wise e.g. top of funnel, brand building or 2) further specialize industry-wise, e.g. behavioral science, etc., do you have thoughts there? (timestamp: 42m 25s)

I mainly build internal tools to help automation of business processes. The easiest place for me to look at for the value I provide is savings in labor hours vs doing the process manually, ie 10 hours saved by 10 engineers a week times 50 dollars an hour is $5,000 a week saved. Are there other general areas you would consider when looking at internal tools for estimating the value of an engagement? (timestamp: 49m 29s)

I started my consulting business a year ago, but intentionally delayed building a website to prevent myself getting distracted before landing some paying clients. Now that I've proven the concept, I did a website build to create a presence that provides social proof, authority, and makes it easy/enticing for clients to start a conversation with me. Can I get a teardown of the website, with a focus on the value prop/concincingness/calls to action? (timestamp: 56m 5s)

Questions from 2018-06-14 session

As you know, I'm bouncing back and forth with my vertical specialization idea. I see it's potential, have made some progress, but I'm concerned that it's just an opportunity and not something I am necessarily passionate about. Wrapping my identity around it exclusively feels awkward. You mentioned needing to feel some degree of passion, and I wonder if I'm just facing "the resistance" or to what degree it matters that I'm not ultra-passionate about the industry. (timestamp: 1m 41s)

I'm a marketing "consultant" with a whale client problem. Basically an employee as my retainer is for full time hours. I would like to become a real consultant so that I don't have to trade all my time for money. I recently read TFR and like the idea of productizing a service. I'm introverted and not keen on creating a personal brand, doing speaking gigs, podcasting, etc. Is it unrealistic to think I can position myself as an authority without doing these types of marketing activities? (timestamp: 22m 33s)

I’m struggling with how to connect with additional people in my target market. They have very expensive problems that I am interested in, but I’m not able to find associations/conferences that are in common to them, to allow me to easily get in front of them. Any suggestions on channels to tackle for starting specialization. (timestamp: 34m 3s)

Can you please do a webpage teardown (timestamp: 41m 13s)

Due to your latest podcast I decided to finally publish this page. Not perfect, but could use your insights. (timestamp: 55m 50s)

Questions from 2018-05-31 session

I'm considering broadening my positioning from focusing on coworking spaces to specializing in helping subscription/membership/recurring revenue businesses with marketing and retention. My approach would be to focus on optimizing the 5 stages of the member/customer lifecycle (my own idea). Then still targeting coworking (and others) with industry and problem-specific landing pages/blog content/conference talks. Am I making a poor choice, is this too general? (timestamp: 1m 30s)

This might just be a “yes” question but, in slack someone mentioned a $450k project (going for “hell yes” value I think) and my question is, would you still ask for that as upfront? Would you ask that expecting they would come back with x payments over y months? (timestamp: 10m 34s)

I sell consulting services today and will be selling products later on. My marketing strategy is focused on content marketing. I am building out my website and I wanted to know what are some key tactics for your homepage layout? (timestamp: 21m 24s)

I currently do fixed prices for projects but have struggled to genuinely value price. I'm working with telephone companies and I'm usually talking to (e.g.) Director of Operations about a network upgrade (to put it in IT terms). My clients motivation to make changes usually comes from problems with current equipment or End-of-life situations. They need to do these projects to maintain their current status quo - but I find it hard to really assess value. Advice? (timestamp: 33m 38s)

I currently price by sprint and want to switch to value based. I do interact with the “CTO” role typically. I am meeting with a client to start discussing v2.0 of their system and plan to approach this value based. I plan to direct the conversation towards objectives/measuring success/value as opposed getting a list of todos and present a 3 option proposal etc. Is this the course of action you would recommend for transitioning? Is there any additional advice or strategy you would recommend? (timestamp: 43m 43s)

You've been a FileMaker developer before. I am, still. My primary skill, and source of new clients, relies heavily on my identity with that market. What "productized" services should I first focus on as I seek to rely less on selling solutions? (timestamp: 51m 11s)

Questions from 2018-05-17 session

I'm a bit stuck - my "generalized" consulting practice is approaching multiple 6-figures with only a handful of clients, and my foray into specialization in coworking spaces is proving to be a big demand on time and mental bandwidth. My hunch is that I'm not solving an expensive enough problem and the road to profitability on that front is long. Should I focus on my more lucrative consulting and reconsider my vertical specialization? Or keep pushing on my daily emails until something clicks? (timestamp: 2m 11s)

I have never tracked my time. I can see how this is maybe unnecessary for value priced or strategy projects, but I'm very much focused on implementation currently and am thinking it might be a good idea to start! What are your thoughts and have you any tips on successfully doing this? I'm concerned I'll spend too much time remembering to track the time rather than doing the work. Cheers, Ant (timestamp: 21m 36s)

My client paid for a project 6 months ago and never got around to doing the pre-requisite work. He is done now, can be very pushy and everything is urgent for him. I pushed back on him because I did not want to him to control my time even though the specific task was small. What's the best approach for handling client expectations like this? I am having trouble organizing my time better with multiple clients. (timestamp: 27m 23s)

How would you structure content marketing if your product is technical but the purchaser is probably nontechnical? Example: I'm looking to provide backups for SaaS apps as a productized service. I could write about how I would back up a MySQL database, or how I would help you design a disaster recovery plan (understandable by nontechnical folks). Some people have said devs will refer you to their boss, others have said "that never happens." (timestamp: 42m 4s)

I’m starting to write daily to see if this is something that works for me. My thoughts are pretty random right now and what I’m writing seems to be all over the map. I have identified my target audience, so that helps, but still, it feels like I have very little continuity. Any tips on finding a voice? (timestamp: 56m 7s

Questions from 2018-05-03 session

I decided to position myself to help salesforce powered businesses be more efficient. Clients have signed up for custom software development that integrates into their salesforce so that all the data is in one place. With a positioning focus around technology, should content and articles be more technical focused or business focused? (timestamp: 1m 37s)

I'm struggling to keep up with a daily email writing habit. Mostly because it's taking be over an hour to write something. Should I try to simplify my emails or do you have a mindset I should take into account when writing them? (timestamp: 15m 39s)

How would you recommend making the most of a speaking opportunity to my ideal audience but on a topic that is not my area of expertise / the service that I sell? (timestamp: 24m 10s)

For our new "info product sales funnels for influencers" page I'm building a quiz as the call to action that will generate a report based on user inputs related to marketing/product dev sophistication, revenue/list size and their personality. Am I getting too complex with this? Would you recommend just starting with something simple like classic sales copy + "schedule a call" or "view pricing" (for productized service) ? (timestamp: 33m 0s)

I am still on the fence about the proposal/roadmap document. What's your latest thoughts about it: single page vs. 50 page? Does it depend on how much they paid you for it? (timestamp: 41m 2s)

I am wondering if you could provide me with direction as a photographer. I tried to set up my website in a different way from other photographers, but think it's potentially over the top. I have a couple ideas on what to offer as an intro email series as I want to do email over blog. Website is (timestamp: 50m 46s)

Questions from 2018-04-19 session

Can you talk a little about creating and implementing an introductory email series as a call to action on a home page? No specific questions, as I’m just starting, but anything that might help make it more effective and avoid common pitfalls. (timestamp: 3m 32s)

Would you recommend selling a productize service and roadmapping side by side, or should they be standalone to avoid confusing the situation? (and maybe create another personal consultant style website where I do offer strategy?) (timestamp: 15m 26s)

How do I migrate from one specialization to another? I want to continue accepting customers in the old focus, but start driving customers to the new one. (timestamp: 23m 33s)

I'm a software developer and I've fired my biggest client then realized that I only have about 2 months of runway and I don't have a lot of past clients to reach out to. What would be your next steps to secure revenue with the right clients quickly? (timestamp: 32m 42s)

I’ve been doing daily emails for a little over a week now and have had good success so far. People are clicking, opening, and replying to my emails. Remind me, why do you send live daily emails instead of creating an evergreen workflow that every subscriber goes through? And would you recommend having them onboard with a series of 10 or so emails to get them “indoctrinated” into my way of thinking? (timestamp: 50m 33s)

Curious on ideas to make website maintenance worth my while. I know it's not high-value, but wondering different ways to propose it so it's not billed as hourly. My clients are used to this method, but curious of what I can do for future clients. (timestamp: 53m 7s)

How to find what are the pressing problems of your target customer and which you can solve with your skills (timestamp: 57m 13s)

Questions from 2018-04-05 session

You have mentioned recently how the first financial engagement with a client will always be the most profitable and then it's "downhill from there". Can you speak more about this? In a recent situation with me, my profits with one client have gone up because they've developed more trust (so there's less resistance to payment) and also because I've practiced the work it is quicker for me to deliver and therefore I have higher profit margins.

I have been freelancing for 3 years. Things are moving in the right direction but business is still maturing. I know I should focus on one thing at a time, but I am considering starting another business at the same time. The plan would be to spend a few hours a week on it. What is your advice on growing a second business whilst focusing primarily on a main business?

Feedback On: Delivering simple, accessible, data-to-people solutions to leverage your PI System Here is the bottom line: Your data is stuck in PI, it requires expertise to access and share, which is causing you to miss a huge opportunity. Subject matter experts, the people making key decisions, need to use and visualize your PI Data. This must be as simple as possible, not requiring training, or special tools. It should be as easy as opening a browser or mobile device and seeing the answers.

I'm considering sending daily emails to my small but growing email list in my niche market, but I don't know where to begin, and I am also somewhat concerned about whether I will have the discipline to keep it up over the long term. You have given lots of great advice on the subject already, but wondering if you could get specific on first steps and your mindset when you started doing it.

From our discovery calls, the common thread so far is “I have to do it all, I’m not a marketing expert so i need confidence to know what to do next” We want to do a catch-all online sales process audit with recommendations as our initial productized service but $1799 seems VERY low for the value. Are we shooting ourselves in the foot? Is there a better approach?

Questions from 2018-03-22 session

I have settled on a horizontal focus (i.e., software training videos for SaaS owners) but I'm not getting a lot of leads. What should I do next? (timestamp: 2m 23s)

If you could promote one thing (a remote service, digital product, etc.) to a niche audience, what would it be? All of your podcasts, content, etc. would promote this one thing for all of your income (ideally recurring revenue, low ongoing stress). (timestamp: 22m 41s)

Do you have any tips for finding where a target market is talking online? (timestamp: 38m 3s)

Questions from 2018-03-08 session

When your proposal is rejected but you're close to 100% sure they should take it, what's a polite way of saying "Your loss, I'm here when you need me"? I don't want to try and 'convince' these guys that they need me, but I want to suggest the alternative is doing things the hard way (I know the alternative they're considering, and it's totally the hard way). (timestamp: 1m 52s)

Questions I have are: 1. Do you have a Project propsal template? (not the retainer one) 2. What are your typical steps after the proposal is accepted? Do you create a spec and give to the client for approval or How do you define the scope details? 3. How do you handle support/maintenance? If you give a 6m/1yr support/maintenance as part of the proposal, what after that time frame? (timestamp: 7m 7s)

I've recently landed my first coaching client. I wasn't really considering coaching before, but I love it. I'm billing a fixed price for 2 hours coaching per month with unlimited email contact, with discounts for 3 months payment. What advice do you have for a budding coach, particularly around building a pipeline of prospects? (I'm going to be a litle late joining, so don't choose this as the first question!) (timestamp: 21m 45s)

Is it so bad to have a horizontal positioning? My main gig is digital strategy consulting for $5mil+ companies who prefer to have a hybrid internal/external team vs. a full-service agency. It’s a unique service model for reasons not mentioned. I know it’s harder to market myself, but I only need 3 clients to break 6 figures (I have that already) and 10 clients to break multiple 6-figures sustainably. Is it simply “the fear” making me hesitant to jump into a vertical with 2 feet instead of 1? (timestamp: 31m 9s)

How do I persuade leads to see the value of fixed-price offers when they are too used to hiring via staff augmentation? Like the habit to estimate a hourly rate based on the proposal and deciding on that and not the value they get. (timestamp: 38m 43s)

When trying to get work from past clients or more work from existing clients or new (super busy) prospects, we often get pressured to just send a proposal. That ends up needing to be revised or gets rejected because we couldn't/didnt do enough discovery/educating them for the value - do you have any tips for how to manage/insist on having enough discovery in that process to get to the desired outcome in these type of situations to get it right the first time and maximize chance of acceptance? (timestamp: 42m 29s)

I've been doing some web dev work for an agency who just went bankrupt. Yes, I lost some money but there is a chance to work with their client directly. It seems like a chance to move the project toward a fixed price approach. But I have no idea what that client's budget was/is. Any recommendations on how I can get some insight on the $ that's on the table? (timestamp: 51m 7s)

Questions from 2018-02-22 session

I've found a problem I can help solve. My ideal client has a "hero" office staffer with lots of processes that go through him or her. (I have tools to analyze and visualize this stuff quickly and easily in a way that empowers them and clarifies the picture.) How can I turn that into a vertical? (timestamp: 1m 5s)

Is it too vague or confusing to say you're a "Marketing and growth consultant for X industry?". The Growth part allowing me to branch into strategies for client retention, experience, etc. (timestamp: 22m 34s)

i have a 2 part question - 1. How would you go about targeting thought leaders (like yourself) for direct sales outreach? linkedin, open doors by trying to be helpful, etc? 2. How would you suggest I go about trying to generate inbound type leads? e.g. how would you personally go about looking for an improved online sales related solution (timestamp: 44m 31s)

Questions from 2018-02-08 session

As a designer I produce a lot of annual reports which I enjoy and would like to do more of. Can it be worth focusing on a (sometimes commoditised) service seeing as I would be looking to specialise in it - ie, could that eventually move me away from being commoditised? (timestamp: 2m 22s)

Follow-up question - I currently do most annual reports for the insurance industry which really doesn't interest me. I'd love to work with the renewable energy sector instead, but I have no contacts there. Should I bother trying to crack a completely new market? My process would be similar, and I could probably address the advantages and outcomes more to that sector than to insurance. (timestamp: 6m 14s)

I'm about to start a 6-month DevOps contract with the Scottish Government. I plan to use this experience to explore whether it's possible to sell online training courses to them once I've left; any thoughts or suggestions about how I can use this 6 months to maximise my credibility and opportunity afterwards? (timestamp: 13m 56s)

Also, thinking about my LFPS, I currently have this "I am a DevOps & Python expert, who helps large companies ship better code faster. Unlike my competitors, I have decades of experience that you can learn from." I'm thinking about changing the end part to "Unlike my competitors, I have extensive hands-on experience with large companies like the BBC and the Scottish Government. Thoughts? I'm trying to get over that doing things at scale is different to just knowing the syntax for the tools. (timestamp: 18m 26s)

When signing an NDA and maintaining privacy in general, where is the line between sharing what could be considered "competitive intelligence" and what is my own "intellectual property"? (timestamp: 32m 20s)

I’ve taken a first pass (with much anxiety) at a positioning statement and was wondering if you had any feedback? Is the vertical or service offering too broad or unclear? > We create content assets to help personal brands in performance related fields improve their sales velocity. Unlike competitors, we guarantee a specific result by taking inventory of the entire sales funnel, and then use the findings to focus on one point in the sales funnel at a time. (timestamp: 38m 58s)

What are your top tips for discovering a niche's expensive problems? We're currently researching online (reading blogs, following influencers and competitors) and reaching out to potential clients to try and book research calls. Got other practical tips? (timestamp: 56m 50s)

I'm going to be proceeding forward with doing some CFP submissions this month. Any suggestions for getting the best chances for being accepted? Is it strictly a numbers game? I'm looking to apply to general business as well as tech conferences, or any really that could look like it would work. (timestamp: 63m 4s)

Questions from 2018-01-25 session

Based on your advice and recommendations, I'm building a website that is 100% focused on my target market's industry. My plan is to build an audience first with nothing to sell, then determine products and services for them later. Would you advise for or against creating a free community (using something like or Slack) if I plan to later create some kind of paid membership later? Would it cannablize the paid group or help it? Thanks! (timestamp: 2m 1s)

I'm putting together some online training for the DevOps stuff I do; the online course provider has just added a Pay-What-You-Want option. I'm going to give this a go, but do you have any advice or experience to offer on this pricing options? (timestamp: 9m 18s)

If we have the time: How is the credit union outreach going? (timestamp: 16m 31s)

I have a couple of clients in a similar demographic who have a similar bundle of "basic needs" (keep the server running, administer email accounts...). In both cases grabbing that contract work through a job posting has turned into more interesting opportunities. I figure there are more of these out there. How might I go about marketing such a "basic needs met" package as a productized service? (timestamp: 28m 27s)

You've done conf. talks, have books, do podcasts, have magazine articles (read yours in .net mag). Have you found that any one in particular was more beneficial to you than others for landing new business? (timestamp: 40m 0s)

I'm sitting on the fence of working my niche (elite sports clubs/ski teams) and looking for a "job". Thinking about moving the niche to ski resorts. I have a 3-5 year goal to have 6 SaaS subscription products and a job might enable me to have the 4+ hours a week to work on these products. When I'm hunting for work or doing work, I have not time for my product development. I'm in a position right now where a good client is a paying client. . . (timestamp: 51m 5s)

5 minute answer please- i see recently alot of agencies and lead services for agencies totuting linkedin- my question- im an agency owner and im never on linkedin- so my question is this- if you are to use linkedin as a prospecting tool - its seems like the only people you can reach on linkedin are companies that are also using linkedin to prospect- is this true assessment? (timestamp: 63m 10s)

I've had a couple of interesting online and offline conversations this week about collaborating with other independent folk. What are your thoughts about whether this is a good way to amplify the mutual opportunities? Any warnings about what not to do? (timestamp: 66m 47s)

Questions from 2018-01-11 session

I've been reading Badass Your Brand and just had this epiphany. . . I can build most MVP web applications in about 6 weeks. So, why don't I start with an offer like 25KApps. Here's my prototype: Thoughts? Once again I find myself being the professional horizontal finder while never finding the vertical. (timestamp: 2m 57s)

I'm taking your advice and focusing on the coworking industry. I currently get a few sparse leads from my small niche website. However, what I want to do is marketing advisory and consulting, and not done-for-you work, and I do this successfully already as a generalist. The problem is they can't afford those services. Do I change my offer? Sell group coaching? Create info products instead? Or only focus on multi-location spaces? (timestamp: 23m 27s)

I currently have one consulting client in my target market. How do you do content marketing without feeling like you're giving away their intel? They are onboard with me specializing in their industry but I fear the idea of leveraging the experience gained with them and giving it away to potential competitors, making them upset. (timestamp: 32m 8s)

My SaaS business has acquired about 100 subscribers organically, but I have a strong sense that I need to start doing direct sales. Sales is not one of my strengths. Could you talk through the right approach? Example scenario: We sell training videos and want to get Heroku’s team of frontend engineers signed up. (timestamp: 40m 19s)

I don't have experience dealing with larger firms; my experience in my own business has been with smaller clients. Can you compare and contrast the experience of selling to clients with larger budgets with selling to smaller clients? (timestamp: 46m 10s)

I read and appreciated your emails about your LinkedIn outreach to credit unions. Have you got any "Wish I knew that before I started" or additional points to share now in retrospect? Thanks! (timestamp: 52m 59s)

I'd like to ask for your feedback on the following LFPS attempt: "I help infosec companies to protect high-speed datacenter-to-datacenter Ethernet networks". Now with the 'unlike my competitors' part I am struggling to fit the following options/benefits: a) help to go through a complex certification process b) eliminate vendor-lock by releasing full source code and design materials c) using hardware accelerated cryptography to deliver a higher-margin products. (timestamp: 57m 48s)

We have 1200 email subscribers, and I’ve been bad about forming a community with them. One of my goals this year is to email them more regularly and frequently. I’m having difficulty getting folks to engage - to write me back, tell me their frustrations, etc. What are some techniques or strategies to help me engage with my audience so I can understand how best to serve them? (timestamp: 67m 4s)

I want to try out a new productized service and I have a client in mind who could beta test it. It’s similar to your slack room, where me and my business partner would make ourselves available to help out an engineering team with UI development questions they have. How should we go about piloting this, and discovering the price? (timestamp: 72m 52s)

Questions from 2017-12-28 session

How do you deal with value pricing customers in a relatively close knit industry when you know there is differential value for different customers? What if the customers talk to one another? Do you have thoughts on this? (timestamp: 2m 2s)

What way do your credit union customers go in your funnel for getting on your most expensive retainer? Do you know them personally before? Have you worked with them before? (timestamp: 6m 58s)

You recently talked with Kevin in Slack about your writing process, and I appreciated the discussion. In the early days, did you ever struggle with what Philip Morgan calls The Fear? I imagine your "sun" could have been any of dozens of topics - how did you commit to one central area of expertise, and resist the temptation to change direction before you had an audience? (timestamp: 15m 13s)

I currently work with a small team of devs to deliver projects. Projects typically last 2-9 months. I'm acting as the salesperson, project manager and product manager for all projects. I'm getting to the point where I can't handle the client facing stuff all on my own. How do you think about team structure as you grow the business to handle more projects at once? How would you structure the team? (timestamp: 30m 59s)

When someone goes silent for months like that, do you ping them? or do you just sit and wait? Do they feel like they've been ripped off after they remember they have you? (timestamp: 39m 7s)

Do you have suggestions for how to determine the value of (specifically) design work to clients so as not to be taking mildly educated guesses, or is that just the reality of this approach to pricing? (timestamp: 47m 13s)

Questions from 2017-12-14 session

I'm really having a challenge converting existing clients from hourly billing to value-based billing. I know you cover this in some of your content, but any tips? (timestamp: 1m 34s)

Any tips for when running projects where your team is also outsourced / sub-contracted onto a project? Do you move them over to value-based billing? (timestamp: 8m 29s)

I struggle with how to word an invitation to chat about a businessperson's problems/felt needs. Can you give me some context about why this would be an appealing request for someone, what they might get out of it? (timestamp: 15m 24s)

Earlier this year, a real estate broker hired me to write software to consolidate his various tools into a more streamlined workflow. His two goals at the beginning were to serve more clients and to attract new employees. But later, he talked more about spinning off the IP into a new tech company, finding investors, etc. Eventually the budget ran out, and the tool was never used. He wants to meet again to talk about "finishing the software". How would you approach revisiting a project like this? (timestamp: 23m 18s)

I currently advise on and/or manage digital strategy for clients in a variety of industries. My best client is in the coworking industry, and I have considered going into that niche to specialize. My concern is I will limit my earning potential or I will need to work with a high number of clients, even though the one client I have pays well. I feel like they are an exception to the rule generally. Am I looking at this the wrong way? (timestamp: 27m 41s)

we are considering offering paid discovery / marketing plans for clients that come into our funnel- we design websites and manage marketing - is there a framework that we can follow on how to offer paid marketing plans/ strategy sessions -what to offer in them & how to do this correctly so we can move our client into our marketing plans- breenan dunn offers something like this, but are there others that have a good framework for this & what are your thoughts on having clients pay for these (timestamp: 38m 27s)

How do you deal with the scenario where you are selling to mid-managers and they need to sell to their senior managers? I can help uncover value with the mid-manager, but they often fail to convey this upward to their managers. The obvious answer is to try get in front of senior manager, but this is not always possible. Are there some hacks to help the mid managers sell the value-based price upwards on your behalf? (timestamp: 46m 3s→)

How do you say "no" to prospects? My filtering process is not working yet and most times I am in a meeting with a new prospect I quickly realize it's not going to work with them. Like there's no way to implement a value pricing in their project (for various reasons). However they don't see any issues and usually are keep asking for making an estimate for their project. Would you recommend saying "no" right there in a meeting? Or maybe start talking about paid road-mapping session? (timestamp: 51m 31s)

Questions from 2017-11-30 session

I started moving to tech training around building APIs, mainly in a specific tech. Now I was thinking of moving to advisory consulting in this field but with a different audience. Our previous exchange made it clear to me that the audiences (tech managers and biz people) are too different and have different needs, fears, etc. When focusing on building apis for business people, it is still horizontal? Should I add a vertical too? (timestamp: 1m 41s)

We're having difficulty pinpointing our ideal client. We've done a lot of implementation work this year and want to avoid that next year. We're considered experts in our programming language/framework, so we're trying to find products/services we could work on for our audience - thinks like trainings, building teams styleguides or libraries, Slack mentoring rooms, etc. What should we do to identify this? Email our list? Experiment with a product idea for someone we know? What's the next step? (timestamp: 13m 8s)

Do you have any tips on making the decision between two audiences less hard? Personally, I love training and also advisory consulting but have a hard time deciding between them. The only clear thing is that I don't want to code for someone else :-) (timestamp: 18m 12s)

We've helped a lot of companies this year but they seem to take our work/their product and move in a bad direction. We've tried hard to have conversations to get them to ask the right questions, but "business needs" pressure them to move quickly, and we see them just plow ahead into the unknown. Are these bad clients? Should we just break up with them? How do we get them to follow our strategic advice? (timestamp: 23m 28s)

Hi Im new to the group- we are a 15yr old webdesign and marketing management agency "generalists" and have seen the light in regards to specializing and niching we are currently looking at a few niches now so my first question is this- is there a step by step framework that exists that we can follow to effectively evaluate and research a niche? (timestamp: 31m 30s)

Investor have awesome expertise in target market but zero experience managing a development of a complex hardware product. External dev team (startup) is failing to deliver. Partly because they don't prioritize this funded project for themselves and use invested money to cover their own struggling business needs. Investor has already started to micro-manage everything (it doesn't help though). Are there any options to help this project to succeed (preferably with value pricing approach)? (timestamp: 40m 3s)

If you sign a client on a strategy advisory retainer (marketing in my case), but they don't already have a formal strategy, is the best approach to advise them on building pieces sequentially or should I create a detailed roadmap/strategy up front? (timestamp: 51m 33s)

I'm looking at religious organizations for my niche as I've built church conference level fund accounting systems. I've also coached soccer and ski racing for 15 years (in a previous life)--membership organizations. What would be a "niche" in the scope of large churches or upper level organizational units in non-profit/religious I'm also thinking along the lines of membership organizations? Am I being silly trying to link religious/non-profit with membership organizations? (timestamp: 57m 9s)

Advice on moving from implementation work to advisory consutling would be great. (timestamp: 63m 51s)

Questions from 2017-11-16 session

What do you think of this LFPS? “I’m a Python expert, who helps large companies with an old Python codebase get the best ROI from their dev team. Unlike my competitors, I (<)still working on this bit…)” (timestamp: 1m 54s)

How would you approach a situation with an "ex-startup" that positions itself not being able to afford a consulting services from an ex-employee? (Yes, "we're broke" discount request). A little twist: they owe me mid-five figures and agreed that I don't release all the source materials to them until that amount is fully paid. I think about releasing everything anyway to get to the point where they are technically not dependent on me anymore. (timestamp: 14m 16s)

The first part of my LFPS is "I help information-security companies to ship a state-regulatory approved carrier-Ethernet encryption appliances". What would you suggest for a second part of LFPS when companies are only developing these sort of products internally (those who think they can spend years without any output and others don't even try). (timestamp: 19m 22s)

I have three tiers of consulting services: 1- reactive advisory 2- proactive advisory + access to freelancer Rolodex (implementers) 3 - done for you digital strategy management (virtual CMO kind of role). My home page copy speaks to the highest tier almost exclusively. Would you advise softening it to include something like "I advise on or entirely manage your digital strategy for you" or was I right to lead with and focus on my highest tier of service? (timestamp: 30m 44s)

Assuming you've already narrowed down to a niche market and validated it, what marketing strategies would you suggest when switching from doing mostly subcontract work to getting clients directly? (timestamp: 35m 21s)

How do you enter a new vertical where you have no case studies to show you are an expert and don't understand the problems and pain points that exist? What is the best way to approach / cold email contacts in that market and ask them to have a conversation to explore the opportunity? I'm completely cold going in to this market but have a huge amount of passion and interest. (timestamp: 41m 23s)

Is there such thing as a "big fat check" that will drive you away from your LFPS area for a year or two? (timestamp: 47m 9s)

I'm trying to decide whether to hire an in-house sales rep / marketing manager to find more leads vs. a 3rd party marketing company who only manages online ads and lead magnets. What factors should I consider when making this choice? (timestamp: 53m 40s)

Questions from 2017-11-02 session

“Most of my clients have been entrepreneurs who are starting off. They have an idea and I help them succeed with getting there. This is an incredibly challenging audience to target however. Nobody on LinkedIn says "Aspiring entrepreneur". They have a full-time job typically or occasionally another business (in which case they are CEO). How would you go about positioning yourself when your audience is hard to reach? Or would you position yourself for another audience?” (timestamp: 2m 31s)

“Typically we work with clients who are experts in their domain. Because they're experts, they can answer all of our "Why" questions. But we end up building software with a list of features for the client that they themselves have more or less defined. Often the software doesn't solve their problem, so we deliver software that is not valuable, and then the client pivots and tries something else. How do we properly get to the underlying "why", so we can discover the business goal?” (timestamp: 8m 21s)

“I find it unexpectedly challenging to tune in to clients' yearly calendar (busy/less busy seasons; when various decisions are made by whom). Do you have ideas on when and how to get this information?” (timestamp: 50m 39s)

“If someone emails us about a low-risk/productized service (e.g. a training), should we have a "why" conversation to see if it's a good fit, or find out what the goal is?” (timestamp: 52m 26s)

“You mentioned you think of training as a productized service. Do you think training is a good way to get away from time-based consulting? We run a SaaS company but use consulting to bootstrap our business. Could trainings be a better way to fill out our service offerings & fund our company?” (timestamp: 56m 14s)

“I’m still having to rely on hourly freelance gigs to earn money until I make the transition to value pricing. Is it even worth mentioning value pricing in the context of responding to calls for freelancers who always ask your hourly rate? (Sorry I can’t attend the session today - I have a call with someone looking for a freelancer lol)” (timestamp: 58m 58s)

“I work with sensor data, e.g. like from wind farms, to bring value to the business. This usually involves creating management or executive web-based dashboards that are easy to access, understand, and in real-time (updated in seconds). I work with a specialized database, that my customers already have. It is usually difficult for those outside of operations to easily digest this data. I feel this is very general, any suggestions in how to boil this down to an expensive problem, easy to convey?” (timestamp: 61m 21s)

“I sell a highly commoditized service: Outsourced web development for web designers and agencies. My question is what would be the one marketing task that I can focus my attention on to generate leads. Would you recommend linkedin propecting, blogging, or something else? I have a fulltime employee doing the actual work. I've never marketed my services until recently when I started a blog and publishing content on freelancing, outsourcing, etc...” (timestamp: 69m 0s)

“Would you be willing to share your tool box list for all the tools you use in your business...crowdcast... hosting. Email. Payments. Etc? You have many landing pages and microsites as well and they all seem to gel together. Extremely valuable to hear the tools of the trade.” (timestamp: 80m 3s)

Questions from 2017-10-19 session

“You've talked about how to move up the altitude of involvement and sell strategy. You've also mentioned a strategy engagement (like a roadmap) might be 5% of overall project (say, 5k). Given that implementation is very expensive (and thus brings in a lot of revenue), if we start successfully selling strategy only, how will we make as much revenue as when we were doing implementation?” (timestamp: 0m 52s)

“With value based pricing, I need to determine what the overall value is for the client. Is it realistic to get value based pricing for implementation work? Example: Let's say that I'm able to figure out that the product's value is worth around $5 million in revenue for the client. What is a reasonable percentage to figure for how much I should charge? 5%? 10%? 5% would be $250k. Where as the hourly priced implementation might only be $50k worth of development if outsourced. Thoughts?” (timestamp: 7m 29s)

“I realize this positioning statement needs work, but can you tell me what areas you would seek to improve? "I'm a virtual CMO who helps time-strapped CEOs win back their time by managing their company's digital marketing for them. Unlike my competitors, I work for a fixed monthly fee and guarantee my work."” (timestamp: 12m 43s)

“We are considered experts in our chosen technology, and it's how we get lots of consulting leads. Is it possible to value price horizontal specialization? We've tried thinking about things like training, mentoring and coaching but haven't cracked the value pricing nut for these yet.” (timestamp: 34m 40s)

“In a why conversation, one way to discover the value for a client is to find out how much would an employee cost/take to do the project instead. Are there any other techniques (other comparisons one can ask the client to make) to estimate the price of the project that the client would consider acceptable?” (timestamp: 40m 14s)

“Right now I'm spending most of my time on implementation tasks (coding) for clients, because it's helping me build up a cash reserve. It's good to be busy, but I want to free up some time and mental energy to think about the future. Would it help to try delegating to junior developers, or will that just create new problems and more work? Do you have any more general advice on how to start freeing up time without cutting off too much short-term revenue?” (timestamp: 45m 45s)

“When a project is finished, it doesn't generate revenue (and profit for the client) immediately, but over time... When estimating the value of the project for the client, do you take a look how much profit they would make in a year (let's say 1 mil) or in 2 years (let's say that would be 2 mil) or in 3 years (3 mil) as that's a 2x or 3x difference to how much you could price the project?” (timestamp: 50m 8s)

“I have developed a layer on top of an open source platform (Drupal) that significantly reduces the time it takes to build a website and offers other enhancements for content management tasks. Since the time taken to produce sites is dramatically reduce, hourly billing makes no sense. Are there key factors to consider when working out value-based billing for production services based on open source technology? (I.e. where there is not full control of the IP.)” (timestamp: 51m 48s)

“I find it challenging to think clearly about dollar amounts at the scale that businesses larger than mine operate at. I've had a number of 5-figure projects over the years, but it's hard for me to internalize the fact that a business could justify spending half a million dollars on something. I've talked to potential clients who couldn't afford a few thousand for software development. How can I develop better intuition about the amounts of money that larger businesses are operating with?” (timestamp: 55m 57s)

Questions from 2017-10-12 session

“Hi! What would you do if you were working remotely from a country with lower salaries for a client in US and they'd expect a rate that's standard to that country (and much lower than US rates)? Hope the question makes sense. Thanks” (timestamp: 2m 41s)

“Should a prospect initially balk when I tell them my rate?” (timestamp: 9m 26s)

“If you're doing outreach and have several (or many) conversations going across email, Slack, LinkedIn, etc. How do you manage them without getting overwhelmed?” (timestamp: 15m 0s)

“I've done quite a bit of thinking on the best vertical for me to hone in on ... this feels like a difficult decision. Can you revisit the industry vertical / horizontal specialty and what questions to ask yourself when focusing on a niche area?” (timestamp: 20m 39s)

“Do you ask the client how much profit they make on each customer? This could come up in an attempt to explain how much value your work is going to be for the client. For example you can expect 10% increase in customers with your work, therefore you will make XYZ profit after paying for your work.” (timestamp: 35m 4s)

“Value based pricing in public sector (working for municipalities, governments ...) Can it work? Any tips?” (timestamp: 49m 17s)

“In reference to the $12k weekend project, would you say that it will only take you a weekend? Can a short time frame undercut perceived value?” (timestamp: 51m 33s)

“what's your email signature? how do you convert your initial outreach into clients?” (timestamp: 55m 40s)

“Verticals: if you want to focus on multiple verticals, is it best to have separate marketing/websites for each? I would assume so, since that's how you operate it ( = software devs, = mobile / credit unions)” (timestamp: 59m 14s)

“How do you determine if a client is a good fit?” (timestamp: 60m 54s)

“What is a compelling communication strategy to over come existing perceptions of what I ‘should' cost and get conceptual buy-in from not only my client contact but also their VP and CEO BEFORE providing a proposal? I want them to accept my higher rates and not feel like they need to consider another consultant.” (timestamp: 63m 48s)

“Is the outreach campaign you have been reporting your entire marketing strategy? Or are you advertising?” (timestamp: 68m 0s)

Questions from 2017-10-05 session

“I’m setting up a productized service for SEO / internet marketing companies where I’ll “health check / tune-up” their new clients’ websites (as part of their on boarding process). I have a flat rate price. What do you suggest on offering bulk discounts? For example - a 5 pack of tune ups at 25% off each?” (timestamp: 3m 5s)

“I noticed you exclusively offer productized services on your website ( Four questions: 1) Is that how you value price? 2) Don't you feel like you leave money on the table in some cases? 3) Do you find these easiest to sell? 4) Do you ever do custom engagements? Thanks!” (timestamp: 6m 17s)

“I've been offering Roadmapping Services with our software consultancy and our deliverables have always been tied to the implementation of tools so we never needed to put together a report. Now, I've recently incorporated the services into our web development business and I'm curious what type of format/info you provide. If you have a sample or a template you wouldn't mind sharing - even better :)” (timestamp: 13m 5s)

“Many of my family, friends, and colleagues are not people who make decisions to purchase services such as I might offer. Will this limit the effectiveness of my "magic wand" interview with them?” (timestamp: 21m 38s)

“I’m struggling with managing my time. I have a couple of ongoing hourly customers and with dead-lines etc.. I’m seeing the reality that at the rate I’m going, moving off of hourly feels like it is going to take a very long time. Any suggestions or tips on how to overcome this?” (timestamp: 29m 51s)

“Do you find that there is really a minimum company size, whether it be head count or yearly revenue, necessary to offer our services, otherwise, it's not worth the time and energy?” (timestamp: 36m 18s)

“Is it possible to do retainers for implementation work without falling into the hourly trap again? Or should implementation work typically be value-based?” (timestamp: 42m 14s)

“I do digital strategy consulting and advisory. One target market is $5-50mil+ companies looking for the equivilant of a digital marketing manager/advisor, and my other target market is small businesses who tend to DIY more of their marketing, and need guidance on where to focus, what to do, and how/where to find freelancers to help when needed. Do you think it's confusing to both groups if I target two very different markets like this?” (timestamp: 47m 44s)

“I'd given up on moving a couple of my clients off hourly, but Tricia reports success. "I moved off hourly billing almost overnight with customers I have done business with for the previous 10 to 15 years. It's the best thing I've ever done." Do you have ideas on switching existing clients to value pricing?” (timestamp: 56m 58s)

“How do you respond to the 'But what happens when you're hit by a bus' objection? Particularly when selling a large project with some amount of support required down the road.” (timestamp: 64m 53s)

“What do you think is one or some of the best ways to get street credit for any given industry?” (timestamp: 68m 16s)

Questions from 2017-10-05 session

I’m setting up a productized service for SEO / internet marketing companies where I’ll “health check / tune-up” their new clients’ websites (as part of their on boarding process). I have a flat rate price. What do you suggest on offering bulk discounts? For example - a 5 pack of tune ups at 25% off each? (timestamp: 3m 5s)

I noticed you exclusively offer productized services on your website ( Four questions: 1) Is that how you value price? 2) Don't you feel like you leave money on the table in some cases? 3) Do you find these easiest to sell? 4) Do you ever do custom engagements? Thanks! (timestamp: 6m 17s)

I've been offering Roadmapping Services with our software consultancy and our deliverables have always been tied to the implementation of tools so we never needed to put together a report. Now, I've recently incorporated the services into our web development business and I'm curious what type of format/info you provide. If you have a sample or a template you wouldn't mind sharing - even better! (timestamp: 13m 5s)

Many of my family, friends, and colleagues are not people who make decisions to purchase services such as I might offer. Will this limit the effectiveness of my "magic wand" interview with them? (timestamp: 21m 38s)

I’m struggling with managing my time. I have a couple of ongoing hourly customers and with dead-lines etc.. I’m seeing the reality that at the rate I’m going, moving off of hourly feels like it is going to take a very long time. Any suggestions or tips on how to overcome this? (timestamp: 29m 51s)

Do you find that there is really a minimum company size, whether it be head count or yearly revenue, necessary to offer our services, otherwise, it's not worth the time and energy? (timestamp: 36m 18s)

Is it possible to do retainers for implementation work without falling into the hourly trap again? Or should implementation work typically be value-based? (timestamp: 42m 14s)

I do digital strategy consulting and advisory. One target market is $5-50mil+ companies looking for the equivilant of a digital marketing manager/advisor, and my other target market is small businesses who tend to DIY more of their marketing, and need guidance on where to focus, what to do, and how/where to find freelancers to help when needed. Do you think it's confusing to both groups if I target two very different markets like this? (timestamp: 47m 44s)

I'd given up on moving a couple of my clients off hourly, but Tricia reports success. "I moved off hourly billing almost overnight with customers I have done business with for the previous 10 to 15 years. It's the best thing I've ever done." Do you have ideas on switching existing clients to value pricing? (timestamp: 56m 58s)

How do you respond to the 'But what happens when you're hit by a bus' objection? Particularly when selling a large project with some amount of support required down the road. (timestamp: 64m 53s)

What do you think is one or some of the best ways to get street credit for any given industry? (timestamp: 68m 16s)