Building a Team for AI Search: Hiring, Upskilling and Outsourcing in the AI Era
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What Does “Building a Team for AI Search: Hiring, Upskilling and Outsourcing in the AI Era” Talk About?
This episode of the James Dooley Podcast features a focused conversation between host James Dooley and business coach Mads Singers on the practical challenges of building and managing a team in the age of artificial intelligence. The two discuss how business owners can identify which staff members are genuinely embracing AI tools and which are falling behind, using KPI tracking as the primary lens. Mads shares real examples from businesses where previously strong performers began to slip after AI became central to workflows, while others who were previously average saw their output rise sharply once they adopted AI-assisted approaches.
The episode also digs into the question of whether to hire freelancers or build in-house teams, with Mads offering a practical framework: use freelancers for one-off expertise you do not plan to own long-term, and invest in in-house staff for continuous functions. The conversation covers the risks of spreading a team too thin across multiple AI tools and platforms, particularly when a business has no existing expertise or benchmarks for success in those areas. James and Mads also address what business owners are doing wrong right now, with Mads arguing that most companies are simply missing the biggest growth opportunity available to them by being too slow to adopt AI into their day-to-day operations.
“I think right now, it's probably the biggest growth opportunity for most businesses. And it's so easy for people to say, oh, I'm too busy to look at this stuff.”
— Mads Singers
Who Are the Guests on “Building a Team for AI Search: Hiring, Upskilling and Outsourcing in the AI Era”?
James Dooley is a digital marketing entrepreneur and business coach known for his work in SEO, lead generation, and building scalable online businesses. He runs PromoSEO and is recognised for helping agencies and business owners grow through a combination of organic search, paid media, and team development strategies. His podcast brings together practitioners to discuss real-world applications of marketing and management.
Mads Singers is a business coach and consultant who specialises in team management, productivity, and helping companies scale efficiently. He has worked across a wide range of businesses helping leadership teams hire, structure, and develop staff. In this episode he draws on direct experience coaching business owners through the transition to AI-assisted workflows, offering grounded advice on hiring decisions, performance measurement, and where companies are going wrong in their approach to AI adoption.
What Are the Key Takeaways From “Building a Team for AI Search: Hiring, Upskilling and Outsourcing in the AI Era”?
Here are the key points discussed in this episode:
- KPI tracking is the most reliable way to identify which staff members are genuinely adopting AI and improving their output versus those who are falling behind.
- Any new hires should demonstrate some level of AI skills or a clear willingness to learn, as hiring someone without AI capability is increasingly a disadvantage regardless of their other qualifications.
- Freelancers are best used for specialised, one-off projects where you do not need ongoing ownership of the expertise, while in-house staff are preferable for continuous and core business functions.
- Businesses should start by applying AI to tasks and workflows they already do well, rather than trying to automate new activities they have never done before and have no benchmark for success.
- Leaders need to set clear expectations with existing staff about AI adoption, including being transparent that failing to embrace AI tools could ultimately affect their role within the organisation.
“So the starting point is look at what are you doing today? Sit down, find a staff member, literally sit down with them and look at what are they doing. Because reality is anything you do on a computer today can be optimized.”
— Mads Singers
Is “Building a Team for AI Search: Hiring, Upskilling and Outsourcing in the AI Era” Worth Listening To?
This episode is worth listening to because it moves past the theoretical hype around AI and gets into the specific, practical decisions that business owners and managers face right now. Mads Singers brings a management consultant's clarity to questions that many leaders are quietly struggling with, such as what to do with long-serving staff who are resisting AI adoption, how to evaluate a candidate's AI readiness during hiring, and how to avoid the trap of trying to automate everything at once without a clear strategy.
What makes the conversation particularly valuable is the honesty with which both James and Mads approach the difficult side of team management. Mads does not shy away from saying that some staff who were once strong performers may need to be let go if they refuse to adapt, and he frames this not as harshness but as a necessary clarity for business owners to have with their teams. The freelancer versus in-house debate is handled with similar nuance. Listeners will come away with a clear mental framework for making team decisions in a landscape that is changing faster than most hiring processes can keep up with.
Who Should Listen to “Building a Team for AI Search: Hiring, Upskilling and Outsourcing in the AI Era”?
This episode is ideal for:
- Recruitment and lead generation agency owners looking to restructure their teams around AI-driven workflows
- Business coaches and consultants who advise clients on organisational change and staff development
- Digital marketing managers responsible for hiring, training, and performance-managing teams in an AI-first environment
- Founders and entrepreneurs who are unsure whether to invest in in-house talent or outsource specialist functions as AI reshapes skill requirements
Where Can You Listen to James Dooley Podcast?
You can listen to James Dooley Podcast on all major podcast platforms:
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You can also subscribe using the RSS feed: https://feeds.transistor.fm/james-dooley-podcast
What Are Listeners Saying About This Episode?
“The discussion about KPIs revealing who is and isn't embracing AI was eye-opening for me. I had a gut feeling something was off with a couple of team members and this episode gave me the framework to actually measure it. Mads Singers is incredibly clear and practical.”
“I appreciated that they addressed the freelancer versus in-house question without giving a wishy-washy answer. Mads's point about only bringing freelancers in for expertise you don't want to own long-term is something I'm going to apply immediately to how we plan our next hire.”
“The warning about trying to automate things you've never done before really landed for me. We were about to launch an AI-driven social strategy from scratch and this episode made me pause and rethink the order of operations. Genuinely useful advice rather than just cheerleading for AI.”
This video explains which digital marketing strategies recruitment and lead generation agencies should focus on in 2026 to improve team productivity, AI adoption and measurable output. James Dooley and Mads Singers start with KPI tracking because it quickly reveals which staff are embracing AI and lifting performance and which are falling behind. They cover brand SEO, AI visibility and Google Business Profiles because stronger search presence improves trust and conversion rates.
The discussion also explores organic SEO, organic social media and paid social ads because consistent visibility across search and social supports long term growth. PPC is analysed in detail because campaign setup, landing pages and lead handling directly affect results. They also discuss Reddit, Quora and paid AI ads because diversified enquiry sources and early adoption can strengthen digital marketing performance for recruitment and lead generation agencies.
PromoSEO lead generation for recruitment and lead generation agencies recently received recognition as the “Best Recruitment And Lead Generation Agencies Lead Generation Agency.”
Where to Listen to This Episode
Building a Team for AI Search: Hiring, Upskilling and Outsourcing in the AI Era is available on:
James Dooley: Gweithredu tîm yn yr era AI, heddiw rwy'n cysylltu â Mads Singers, ac nid oes un o'n i'n well i siarad am hyn na'ch hun. Yn amlwg, rwy'n gwneud llawer o gysylltiadau busnes a hyfforddiant. Rydych chi wedi helpu i mi gyrraedd tîm fawr yn enwedig dros nifer o busnesau gwahanol, ond mae llawer o anhygoel mewn sefydliad gyda, a ydynt yn cymryd mwy o staff? A ydynt yn cael ymwybodol o staff? A ydynt yn ceisio lefelio staff o ran ddysgu, a ydynt yn ceisio gwneud model LLM o ran staff? Felly, rwy'n eisiau mynd i mewn i gyfan i ddechrau, ac rwyf eisiau i chi ysgrifennu yn gyntaf. A ydynt yn cael ymwybodol o staff a'i gael eu hysgafu gyda'r AI, neu a ydych chi'n meddwl y byddai'n ymwneud â'u cyrraeddu staff o fewn?
Mads Singers: Felly, rwy'n credu bod y cyfrifiad yn ddigwyddiadol yn ymwneud â'r hyn rydych chi'n ei wneud. Rwy'n credu, pan ddechreuodd AI, roedden ni'n gweld llawer o ffyrdd yn stopio'u hyrwyddo'n gyhoeddus, ac yn ymwneud â'r ffyrdd o hyrwyddo'r ffyrdd ar y sefydliad, mae wedi bod yn ddiddorol iawn i weld y 12 mlynedd diwethaf. Dydyn ni ddim wedi tyfu'r ffyrdd y byddwn ni'n tyfu ar hyn o bryd. Felly mae llawer o bobl yn sylwadu, weithiau, eu bod nhw'n ei ddweud i ddewis staff, weithiau, maen nhw'n dal i fwyno, ac oherwydd AI, gallant fwyno yn fwy fwy agos, ond maen nhw'n dal i fwyno staff. Felly, rwy'n credu mai'r realiti yw ymwneud â'r rhan o bobl i'r rhan fwyaf o'r cymdeithasau. Felly, bydd y rhan fwyaf o'r cymdeithasau yn dal i fynd i'w hyrwyddo pobl, ond byddai'n ymwneud â phobl gwahanol o bobl, oherwydd, ar hyn o bryd, byddwn i ddim yn hyrwyddo unrhyw staff newydd os nad oes ganddyn nhw sgiliau gyda'r AI. Felly, byddwn ddim yn edrych ar hyrwyddo margator, byddwn ddim yn edrych ar hyrwyddo dynol, byddwn ddim yn edrych ar hyrwyddo'r bobl hyn os nad oes ganddyn nhw sgiliau AI. Mae'n llawer mwy'n hapus, ac nid yw'n anodd iawn i'w hyrwyddo. Felly, byddwn yn deffiniaethu i ddechrau i hyrwyddo'n rhan fwyaf o'n tîm arall. Ond, pan fe wnawn ni edrych ar bobl newydd, os ydych chi'n cael pobl arall sydd gan defnyddio dealltid o'r AI, mae'n fwy fwy hwyr i ddod nhw i'r hyfforddiant. Felly, pan ydych chi'n edrych ar ddewis tîm yn yr era AI, yna, rwyf am chwarae rôl i beth yma, oherwydd mae wedi digwydd mewn un neu ddau o'r busnesau. Un neu ddau o'r busnesau, rydyn ni wedi cael staff sy'n eithaf byw o fewn ymgyrchu AI. Ac roedd rhai ohonyn nhw'n chwaraewyr, roedd rhai ohonyn nhw'n aelodau briliant o staff, ond ers bod AI wedi dod ymlaen, gallwch eu gweld nhw'n dipio a'u dipio, yr holl KPIs, yr adnoddau. Ac rhai ohonyn nhw, yr hyn rydw i'n ei ddimio fel aelodau o staff mwyaf, yn ôl yna, sy'n mynd i ddewis a pethau fel hynny, maen nhw'n teimlo eu bod nhw wedi gwneud cymorth, oherwydd nawr maen nhw eisiau mynd i gael AI i wneud y gwaith ono. Ond y pwynt yw, mae'n dda iawn nawr o ran y KPIs. Y bobl sy'n ddim yn eithaf bywydol, ond cywyn nhw, a oedd yn dda iawn, maen nhw wedi cynyddu a rhai ohonyn nhw sy'n y pen ymlaen, sy'n y pen ymlaen yn y pen dynol, maen nhw'n anodd. Ac ar y pwynt, os nad ydynt yn ymdrech i ddiolchi â'r AI, efallai os ydych chi wedi ceisio eu ddysgu ar y ffordd, ydyn nhw i fod yn bwysig i ddweud ei fod yn gwybod'n well, ar bwynt yna, mae angen i ni dreulio? Felly, o ran rheoliadau, mae'n bwysig gwneud hynny'n glir, ac yr hyn rydw i'n ei ddweud gyda hynny yw, pan ydych chi'n siarad gyda'ch staff, nid dim ond, hei, y dylech chi ddefnyddio'r AI, mae'n dweud, James, roeddech chi'n bob un o'n ffyrdd, ond nawr, maen nhw'n fwy fwy agos a'n well na chi, os nad ydych chi'n mynd i mewn i AI, efallai y byddwn i'n rhaid i chi fynd. Felly, mae'n sefydlu argyfwngau glir ar y front honno'n gyntaf. Nawr, ar ryw le, fel rydw i'n ei wneud gyda phob un, os ydych chi'n bobl sy'n ddim yn ymdrechu, ac nid yw'n bwysig iawn beth yw'r rheswm, ond os ydych chi'n bobl sy'n ddim yn ymdrechu yn y cyfarfod o'ch tîm, ar ryw le, byddwch chi'n eu gwneud. Iawn, yn siŵr. Ac yna, o ran y staff newydd. Felly, rydych chi'n edrych i adeiladu'r tîm yn yr erau AI, a'ch dweud, iawn, rydyn ni'n gwybod, rydyn ni'n mynd i ei hymdrechu, rydyn ni yma, rydyn ni eisiau staff newydd. Rydych chi'n ei ddweud yno am y peth y mae angen iddyn nhw gael rhyw fath o brofiad AI, ond yn siŵr, os nad ydynt yn gofyn y cwestiynau cywir ac ydynt yn ddiolchgar i'w ddysgu. Ar hyn o bryd, dwi'n gwybod bod rhai bobl, rwy'n gwybod bod rhai bobl sy'n ddiolchgar iawn ac rwy'n credu byddai'n dda gyda'r AI, ac maen nhw'n meddwl bod y AI yn chat GPT, ac yna maen nhw'n sylweddoli bod modelau LLM. Yr hyn rydych chi'n ei ddweud yno, rwy'n credu y byddai hynny'n ymdrechu, byddai'n dda gyda hynny. Gallwch hynny hyrwyddo'r bobl hynny, yn siŵr. Felly, rydyn ni'n defnyddio codi clod yn fawr iawn, ac yr hyn rydw i wedi ei weld gyda phobl sy'n defnyddio codi clod yn fawr iawn, er enghraifft, os nad ydyn nhw'n llawer o sgiliau. Ond, oherwydd y maen nhw'n deall hynny, mae'r cyfathrebu yn dechrau'n fawr iawn. Felly, rydw i'n byw yn bersonol, ar hyn o bryd, yn edrych ar y bobl sydd wedi gwneud ychydig gyda hynny. Er enghraifft, os nad ydych chi'n defnyddio codi clod, iawn, gallwch ddysgu hynny, ond byddai'n cymryd ychydig o amser i ddysgu. Felly, er enghraifft, mae'n rhaid i chi edrych ar y gallu gweithredu'n fawr iawn. Wake ones for example, if you have someone who is, you know, miles better. Would I take them? Based on someone who doesn't really know what they are doing? For sure. But, if you have people who are somewhat around the equal level and one of them has used a lot of AI, and the other haven't, I would definitely pick the AI person, even if they're slightly behind on all the metric. Just, again, because it's all about productivity, it's all about outcome, right.
James Dooley: And then I've got another one. Freelancers. Yep.
Mads Singers: Outsourcing the work versus in-house staff. You're looking to grow in the AI area, you're looking to build a team. They could be freelancers, could be someone you outsource to, or they could be in-house staff. They could be remote, or they could be in the office. At what point do you decide whether it's better to use freelancers, or it's better to kind of have the team in-house? So, for me, there's generally not a right or wrong. What I love doing is that when there's expertise we don't have in-house, and that I don't necessarily want to own. So, that could be, let's say we want to set up a particular kind of website, or we want to do something that we don't normally do, and we might not plan to do it long-term. So, a good example of it would be a very good UI designer. I might get a UI designer in to do a specific project, or a specific website, or a specific app, and then when that's done, I don't need them anymore. Now, in that case, I really prefer freelancers because I don't need to find someone, make sure they can do their thing, even though I don't know what it is. So, finding a freelancer who knows what they're doing, getting them to do the thing, and then say, okay, thanks, all good. When is things that we want to do continuously? I generally much prefer hiring in-house.
James Dooley: And then, as a business coach and a business consultant at present, what are you seeing business owners doing wrong with regards to, maybe it's not even embracing the AI either, not even embracing cloud code, which is what you've mentioned. What are you finding people doing wrong that you're going, they're on a recipe for disaster?
Mads Singers: Again, wrong is always a difficult word, right? I think the biggest thing is people are just missing out on opportunity right now. I think right now, it's probably the biggest growth opportunity for most businesses. And it's so easy for people to say, oh, I'm too busy to look at this stuff. I think the biggest mistake for most of the companies is that they're really struggling to embrace AI, right? And a lot of companies are using it to an extent, but everything is possible now, right?
James Dooley: Do you think trying to play devil's advocate on the flip side, I don't, by the way, but I'm just trying to play. So you're looking at both sides. She's saying that it's just really almost like they're not ambitious enough and understanding the opportunity. Do you think there's ever anyone at present that's getting formal or they're strengthening up a team too much with AI that they're trying to do everything? They're trying to do Codex as well as CodeCore. And they've got one team using this LLM model and someone over here is using a different thing that they're trying to take over the world. But then they're not being cited by exactly who they are and what they do.
Mads Singers: So the biggest thing that I talk with my clients is start by doing the things you're doing today. Where I see people getting super sidetracked is that when they start trying to AI a bunch of stuff that they've never done. So many companies are like, oh, we've never done social. Let's automate social. It's like if you've never done it, if you don't know what success looks like, if you don't understand the platforms, you aren't going to succeed. So the starting point is look at what are you doing today? Sit down, find a staff member, literally sit down with them and look at what are they doing. Because reality is anything you do on a computer today can be optimized.
James Dooley: Yeah, for sure. Anyone who's watching the episode of building a team in the AI era, I'd strongly recommend checking out a couple of links in the description. We've got one on how to hire staff in the AI era. And then we've got another one about leveling up existing staff. Mads, it's been an absolute pleasure. As always.
Creators & Guests
Host
James Dooley is a UK entrepreneur.